Italy

Dolce Vita, Eternal Stone & the Open Road: 101 Things to Do in Italy

101 Things Expert

Italy is the country that invented the good life and has been refining it for 2,000 years. Its contribution to human civilisation is so comprehensive that listing it feels like a catalogue of everything that matters: law, architecture, painting, sculpture, music, opera, cinema, fashion, and the food that the rest of the world has been attempting to replicate since the first Italian emigrant showed someone else how to make pasta. The country of Virgil and Dante and Leonardo and Michelangelo and Verdi and Fellini also produced the pizza, the espresso, the Ferrari, and the Vespa — objects so perfectly designed for their purpose that no improvement has been possible.

Italy rewards the traveller who goes slowly. Its greatest pleasures are not experienced at speed: the fresco in the side chapel of a church no one told you about, the glass of Barolo in a cellar in Piedmont, the hour on a ferry crossing from Positano to Capri when the Amalfi Coast shows you its full geometry in the afternoon light. The country is also vast and regionally diverse in a way that the Golden Route (Rome–Florence–Venice) barely hints at: the Baroque excess of Lecce, the cave cities of Matera, the Greek temples of Agrigento, the Romanesque cathedrals of Apulia, the wine valleys of Barolo, and the Dolomites are all as specifically Italian as the Colosseum — and are seen by a fraction of its visitors.

This guide covers 101 things to do across Italy’s 20 regions — from the Sistine Chapel to the trulli of Alberobello, from the Uffizi to the hill towns of Umbria, and the places that most visitors never reach.

Rome: The Eternal City

Ancient Rome

  1. The Colosseum, Roman Forum & Palatine Hill (UNESCO) — The most visited monument in Italy: the 50,000-seat amphitheatre of 80 AD, where gladiatorial combat, animal hunts, and mock naval battles were staged for the Roman public. The combined ticket includes the Roman Forum (the civic, commercial, and religious heart of the ancient city, with the Temple of Saturn, the Arch of Septimius Severus, and the Via Sacra) and Palatine Hill (the birthplace of Rome, the most dramatic archaeological viewpoint in the city). Book timed entry at least a week in advance; the underground and arena floor tours are the finest access experience.
  2. The Pantheon — The most perfectly preserved building of the ancient world: a circular temple with a concrete dome 43.3 metres in diameter (still the largest unreinforced concrete dome in the world, completed in 125 AD), with the oculus — a 9-metre circular opening to the sky at the apex — as the only light source. Stand in the centre at noon when the light forms a perfect circle on the floor. Entry is ticketed since 2023; the best experience is in early morning when the light is most direct through the oculus. Free on the first Sunday of each month.
  3. The Trevi Fountain — The most famous fountain in the world, completed in 1762 at the terminus of one of Rome’s ancient aqueducts: Nicola Salvi’s Baroque composition of Neptune in his chariot, with the triumphal arch of the Palazzo Poli as backdrop. The coin-throwing tradition (one coin for return to Rome, two for love, three for marriage) drains the fountain of around €3,000 per day, donated to charity. Best seen before 8am when the square is empty enough to hear the water; best photographed from the upper steps at the east side.
  4. The Vatican Museums & Sistine Chapel (Vatican City) — The largest art museum in the world: 54 galleries including the Gallery of Maps (the finest cartographic ceiling painting in the world), the Raphael Rooms (four rooms painted entirely by Raphael and his workshop, including the School of Athens), and the Sistine Chapel — Michelangelo’s ceiling (1508–1512, 12 principal figures including the Creation of Adam, the most replicated image in Western art) and the Last Judgment (1541, the most powerful single wall painting in Christian art). Book skip-the-line tickets months in advance; the early-morning or evening access tours offer the Chapel with fewer than 50 people.
  5. Piazza Navona & the Baroque Fountains — The finest Baroque public space in Rome: Bernini’s Fountain of the Four Rivers (1651) at the centre, with the obelisk and the four allegorical river figures, flanked by Borromini’s Sant’Agnese in Agone. The evening atmosphere — the restaurants, the street artists, and the quality of Roman light on the travertine facades — is the finest piazza experience in the city. Free; always beautiful.
  6. Campo de’ Fiori at Dawn — The Roman morning market in the square where Giordano Bruno was burned at the stake in 1600 (his hooded statue presides over the flower stalls): the finest neighbourhood food market in the historic centre, with the Roman women who have been shopping here every morning since the piazza was a meadow. Come before 9am; the market ends by noon.
  7. The Borghese Gallery — The finest medium-sized art museum in Italy: Bernini’s sculptures (Pluto and Proserpina, Apollo and Daphne, and David — three of the greatest sculptures ever made, all within 50 metres of each other) and Caravaggio’s paintings (six, including the Boy with a Basket of Fruit and the Jerome) in the 17th-century villa in the Borghese gardens. Entry is strictly timed and strictly limited to 360 visitors per two-hour slot; book as far in advance as possible.
  8. St Peter’s Basilica & the Dome — The largest Christian church in the world, with Michelangelo’s Pietà (1499, the only work he ever signed), Bernini’s 29-metre bronze baldachin, and the dome (the climb to the lantern — 551 steps, or the lift to the base and steps to the top — gives the finest view of the Vatican gardens and the Roman skyline). The basilica is free; the dome is ticketed. The Vatican Square at dawn, before the tourist buses arrive, is one of the finest open spaces in Europe.
  9. Trastevere at Night — The neighbourhood west of the Tiber: the cobbled lanes of the old working-class Roman district, with the Basilica di Santa Maria in Trastevere (its golden mosaics illuminated at night), the outdoor restaurants, the lively piazza life, and the quality of Roman evening that the tourist circuit north of the river rarely produces. Walk from the Gianicolo viewpoint (the finest panoramic view of Rome) down through the neighbourhood to dinner.
  10. The Appian Way (Via Appia Antica) — The ancient road leading south from Rome, lined with the tombs and mausoleums of Roman patricians: the Catacombs of San Callisto (the most extensive early Christian catacombs in Rome, with the papal crypt where 16 early popes were buried), the Circus of Maxentius, and the tomb of Cecilia Metella. Rent a bicycle at the archaeological park entrance; the Sunday morning closure to cars makes it the finest cycling experience in the city.

Florence & Tuscany

Florence

  1. The Uffizi Gallery — The greatest collection of Italian Renaissance painting in the world, in the U-shaped palazzo that Giorgio Vasari designed for the Medici’s administrative offices (uffizi): Botticelli’s Primavera and Birth of Venus (the two most important paintings in the Italian Renaissance), Leonardo’s Annunciation, Raphael’s Portraits of Leo X, Michelangelo’s Holy Family, and the complete arc of painting from Cimabue to Caravaggio. Book timed entry at least two weeks in advance. The corridor across the Ponte Vecchio to the Palazzo Pitti is open on guided tours.
  2. Michelangelo’s David at the Accademia — The 5.17-metre marble figure, completed between 1501 and 1504 from a block of Carrara marble that had been abandoned by two previous sculptors: the most celebrated sculpture in Western art, and the experience that rewards careful looking. The tension in David’s right hand (the tendons and veins visible as if in a living hand), the sling hanging over the left shoulder, and the expression — concentration, decision, the moment before the act — reward the time most visitors do not give it. Book timed entry in advance; arrive 15 minutes early.
  3. Brunelleschi’s Dome, Florence Cathedral — The dome that Filippo Brunelleschi designed and built between 1420 and 1436 without the use of external scaffolding, using a self-supporting herringbone brick pattern of his own invention: the greatest engineering achievement of the Renaissance, and still one of the finest architectural experiences in Europe. The climb (463 steps) passes through the space between the inner and outer domes, allowing visitors to see the mechanics of the construction. The Baptistery’s East Doors (Lorenzo Ghiberti’s Gates of Paradise) and the interior of the cathedral are free.
  4. The Oltrarno & the Artisan Quarter — The south bank of the Arno, less visited than the tourist circuit north of the river: the Pitti Palace (the Medici’s private palace, with seven museums and the Boboli Gardens), the Brancacci Chapel (Masaccio’s frescoes, the finest early Renaissance painting in any church in Florence), and the artisan workshops of Borgo San Jacopo and the surrounding lanes. Leather workers, jewellers, paper marblers, and frame makers still operate in the medieval buildings.
  5. The Ponte Vecchio — The oldest bridge in Florence (1345, rebuilt after the great flood of 1333): the only bridge in the city to survive the German retreat of August 1944 (Hitler reportedly ordered it spared because of its beauty). The jewellery shops that replaced the butchers and tanners in the 16th century (by Medici order) are still in operation; the view of the bridge from the Ponte Santa Trinità at dusk is the finest single image in Florence.

Tuscany

  1. Siena & the Campo — The finest medieval city in Italy after San Gimignano: the Campo (the scallop-shaped central piazza, the site of the Palio di Siena horse race twice each year), the Gothic Cathedral (with Nicola Pisano’s marble pulpit of 1268, the finest Romanesque-Gothic sculptural programme in Tuscany), the Palazzo Pubblico, and the Torre del Mangia (the view from the top is the finest of the surrounding Sienese hills). The city has been preserved in its medieval form, with no development permitted within the historic walls.
  2. The Palio di Siena (July & August) — The most intense public spectacle in Italy: a bareback horse race of 90 seconds around the Campo, run twice a year (2 July and 16 August) between the 17 contrade (city wards) of Siena. The race is preceded by days of medieval pageantry, the blessing of the horse in the contrada’s church, and a procession of medieval flag-throwers in historical costume. For the Palio itself, standing in the centre of the Campo (free but densely packed by 2pm) or watching from a paid balcony are the two options. The most specific cultural event in Italy.
  3. Val d’Orcia (UNESCO) — The landscape south of Siena that appears on every Italian travel poster: the rolling hills of clay and limestone covered in wheat and sunflower, the cypresses in single file along the ridge roads, the isolated farmhouses, and the walled hill towns of Pienza (the ideal Renaissance city, built by Pope Pius II in 1459), Montepulciano (for Vino Nobile), and Montalcino (for Brunello). A UNESCO Cultural Landscape; best photographed in May (green wheat) and August (golden harvest).
  4. San Gimignano: The Medieval Manhattan — The hill town of Siena’s province, with 14 surviving medieval towers (72 were originally built by competing noble families as status symbols): the finest preserved medieval tower-house cityscape in Italy. The Museo Civico’s Gozzoli frescoes and the view from Torre Grossa are the finest experiences; the Vernaccia di San Gimignano (the local white wine) is available at every bar. Best visited in the early morning before the day coaches arrive from Florence.
  5. Driving the Chiantishire Wine Roads — The road from Florence south through the Greve in Chianti to Siena: the Chianti Classico wine zone, with the black rooster (Gallo Nero) on the label of its finest wines, the farmhouse estates selling direct from the cellar, and the particular quality of the Tuscan landscape at vintage time (late September to October). The SR222 Via Chiantigiana is the finest single road in Tuscany.
  6. Lucca: The Walled City — The Renaissance walls of Lucca — a complete 4-kilometre circuit of 16th-century fortifications wide enough to be used as a promenade at the top — enclosing a medieval city of extraordinary quality: the Romanesque Cathedral of San Martino, the oval Piazza dell’Anfiteatro (built on the foundations of the Roman amphitheatre, its medieval houses preserving the exact ellipse), and the birthplace of Giacomo Puccini (a museum). The most personally scaled complete walled city in Italy.
  7. Pisa’s Campo dei Miracoli (UNESCO) — The Field of Miracles: the Leaning Tower (the bell tower of the Pisa Cathedral, begun in 1173 and listing from the third storey due to inadequate foundations — the lean is its reason for existence), the Cathedral (with Giovanni Pisano’s marble pulpit), the Baptistery (with its extraordinary acoustic — guides demonstrate it every 30 minutes), and the Camposanto (the monumental cemetery, with medieval frescoes damaged in the Second World War and incompletely restored). The Leaning Tower climb requires advance booking.

Venice & the Veneto

  1. St Mark’s Square (Piazza San Marco) & the Basilica — The finest civic square in Europe: the basilica (a Byzantine confection of five domes, golden mosaics, and the Pala d’Oro — the jewelled altarpiece), the Doge’s Palace (the Bridge of Sighs, the Golden Staircase, and the Council Chambers with Tintoretto’s enormous ceiling canvases), the Campanile (the view from the top — the city spread across the lagoon), and the Florian (the oldest café in Italy, operating since 1720). Book the Basilica’s Pala d’Oro and terrace access separately; both require advance booking in high season.
  2. The Grand Canal at Dawn by Vaporetto — Take the Line 1 vaporetto from Santa Lucia station to San Marco at 6am, when the gondoliers are taking delivery of supplies and the palace facades catch the first direct light: 3.8 kilometres of the finest architectural corridor in the world, with 200 palaces from the Gothic to the Baroque along both banks. The Ca’ d’Oro (Gothic, 1420s), the Rialto Bridge (the market area’s stone crossing, 1591), the Ca’ Rezzonico (Baroque, the finest palace museum in Venice), and the Salute church (Longhena’s masterpiece, 1631). Free with a vaporetto ticket; the finest urban water journey in Europe.
  3. The Doge’s Palace — The seat of Venetian government for 1,000 years: the pink-and-white marble Gothic facade, the Sala del Maggior Consiglio (the Great Council Hall, with Tintoretto’s Paradise — the largest oil painting in the world, 22m × 7m — on the end wall), the Bridge of Sighs (the enclosed bridge connecting the palace to the prison, named for the sighs of the condemned looking their last at the lagoon), and the State Inquisitors’ Chamber. The Secret Itinerary Tour (through the rooms not normally accessible) is the finest Doge’s Palace experience.
  4. Gondola Ride at Dusk — The Venetian gondola: a 280-kilogram flat-bottomed boat of extraordinary engineering (curved asymmetrically to compensate for the gondolier’s single-oar rowing stroke), navigating the narrow rio (smaller canals) away from the Grand Canal at dusk, when the water turns gold and the sound of conversation from open windows carries across the water. Standard fare is around €80–100 for 30 minutes (negotiable); the traghetto (the cross-canal standing gondola, €2) is the democratic version.
  5. Murano & Burano Islands — The lagoon islands accessible by vaporetto from San Marco: Murano (where the Venetian glassmaking industry was moved in 1291 to prevent fires in the city — the glass furnaces are still operating, with public demonstrations in the furnace halls) and Burano (the fishermen’s island of brightly painted houses, each colour registered with the municipality, with the finest lace-making tradition in the Veneto). The round trip takes half a day; come early and leave before noon.
  6. Peggy Guggenheim Collection — The finest collection of modern art in Italy, in the Palazzo Venier dei Leoni on the Grand Canal: the American heiress’s personal collection of Cubism, Surrealism, and Abstract Expressionism — Picasso, Dalí, Mondrian, Pollock (whose European career Guggenheim largely financed), Magritte, and Ernst. The terrace with the Marino Marini equestrian sculpture (the raised phallus of whose rider Guggenheim famously removed for visits by the patriarch of Venice) gives the finest private view of the Grand Canal.
  7. Venice Carnival (February) — The 10 days before Lent, when Venice returns to its 18th-century tradition: elaborate costumes and masks, the Festa delle Marie procession, the Flight of the Angel from the Campanile to the Doge’s Palace, and the balls of the private palazzi. The quality of the historical costumes at the Campo Santa Maria Formosa and the Gran Caffè Quadri is the finest visual spectacle available in February in Europe.

Verona & Lake Garda

  1. Verona Arena & the Summer Opera — The 1st-century AD Roman amphitheatre in central Verona, seating 15,000: the opera festival (June to September, the Verona Opera Festival) stages open-air performances of Aida, Nabucco, and La Traviata under the stars, with the audience’s candles illuminating the Roman stone in a pre-performance ritual unchanged since 1913. The most atmospheric opera experience in the world. Book the stone steps (bites sold at the interval) rather than the cushioned seats for the authentic experience.
  2. Lake Garda & the Gardone Riviera — The largest lake in Italy, between Lombardy, Veneto, and Trentino: the western shore (the Riviera Bresciana), with the Vittoriale degli Italiani (the extraordinary estate of the poet and proto-fascist Gabriele D’Annunzio — part folly, part monument, part madness — the finest heritage eccentricity in Northern Italy) and the town of Gardone Riviera (with its grand Belle Époque hotels). The northern Garda Trentino (Riva del Garda) is the finest sailing lake in the Alps.

The Italian Lakes

  1. Lake Como & Bellagio — The most dramatic of the Italian lakes: the Y-shaped lake between Milan and the Swiss Alps, with the villas (Villa Carlotta, Villa Monastero, Villa del Balbianello — used in the filming of Casino Royale and Star Wars) and the ferry connections between the towns. Bellagio, at the confluence of the two arms, is the finest town on the lake: the Passalacqua hotel (voted the world’s best hotel in 2023) is here. The ferry ride from Como to Bellagio in the morning light is one of the finest views in Northern Italy.
  2. Lake Maggiore & the Borromean Islands — The three islands in the northern section of Lake Maggiore: Isola Bella (with the Borromeo family’s Baroque palace and the ten-terrace garden — the most ambitious Renaissance island garden in Italy), Isola Madre (the most botanically diverse, with white peacocks in the garden), and the Isola dei Pescatori (the only inhabited island, with a working fishing community). The ferry circuit of the three islands takes a morning.

Milan & the Italian North

  1. Leonardo’s Last Supper, Milan — Santa Maria delle Grazie: Ludovico Sforza’s court painter Leonardo da Vinci completed the Last Supper (Cenacolo) on the refectory wall in 1498. The original tempera-on-plaster (not a fresco, which is why it began deteriorating almost immediately) is the most viewed painting in Italy for which timed entry is strictly enforced: 15 minutes per group of 25, in a climate-controlled room. Book six to eight months in advance; waiting lists apply.
  2. Milan Cathedral (Duomo) Rooftop — The third-largest church in the world and the most Gothic building in Italy: 135 marble spires, 3,400 statues, and the rooftop terrace where you can walk among the forest of pinnacles with the Alps visible on clear winter days. The cathedral took six centuries to complete (1386–1965); the most beautiful nave in Lombardy is inside. The rooftop access (via stairs or lift) is the finest view in the Lombardy plain.
  3. The Brera District, Milan — The artists’ neighbourhood: the Pinacoteca di Brera (the finest painting collection in Northern Italy after Turin — Raphael’s Marriage of the Virgin, Mantegna’s Lamentation of Christ, Caravaggio’s Supper at Emmaus), and the Brera streets with their galleries, jazz bars, and the street-side bookshops of the Via dell’Orso. The most culturally intense neighbourhood in Milan outside the fashion district.
  4. Aperitivo on the Navigli, Milan — The Milanese institution of the evening aperitivo: a cocktail (Aperol Spritz, Campari Soda, or a Negroni) accompanied by a buffet of small plates (olives, charcuterie, bruschetta) included in the price of the drink, served along the Naviglio Grande canal from 6pm. The Navigli district, with its canalside restaurants and bars, is the finest evening neighbourhood in Milan and the most specifically Milanese social ritual.
  5. Galleria Vittorio Emanuele II, Milan — The 19th-century glass-and-iron shopping arcade connecting the Duomo to La Scala: the finest shopping arcade interior in Italy, with the octagonal central space and the mosaics of the four regions of the newly unified Italy on the floor. The tradition of spinning three times on the bull’s testicles in the Turin mosaic brings good luck; the heels of Prada shoes have been destroying the bull for decades. Free to enter; entirely extraordinary.
  6. La Scala Opera House, Milan — The most celebrated opera house in the world: the Teatro alla Scala, opened in 1778, where Verdi, Toscanini, Callas, and Pavarotti defined the Italian operatic tradition. The season opens on 7 December (Sant’Ambrogio, the patron saint of Milan) and runs to July; the museum is open daily. Attending a production here — from Verdi or Puccini — is the most specifically Milanese cultural experience.
  7. Turin & the Savoia Royal Residences (UNESCO) — The first capital of unified Italy: the Residences of the Royal House of Savoy (a UNESCO World Heritage ensemble of 14 buildings including the Palazzo Reale, the Palazzina di Caccia di Stupinigi, and the Villa della Regina), the Mole Antonelliana (the iron-spired building that houses the National Cinema Museum), and the Egyptian Museum (the second-largest Egyptian collection in the world after Cairo). The most undervisited major Italian city outside the south.

Naples, the South & the Islands

  1. Pompeii & Herculaneum (UNESCO) — The Roman cities buried by the eruption of Vesuvius in 79 AD: Pompeii (66 hectares of urban archaeology — the Via dell’Abbondanza, the Forum, the Villa of the Mysteries, the brothel — the largest archaeological site open to visitors in Europe) and Herculaneum (smaller, better preserved, with original wooden furniture and organic materials surviving under the volcanic mud). The combined archaeological park ticket covers both; begin at Herculaneum for the better-preserved interiors and end at Pompeii for the scale.
  2. Naples: The Most Alive City in Italy — The city that invented pizza, gave the world the tarantella, and preserved more buried history beneath its streets than any other in the Mediterranean: the Spaccanapoli (the straight street that cuts the city in half, following the line of the ancient Greek-Roman decumanus), the National Archaeological Museum (with the finds from Pompeii and Herculaneum — the finest Greco-Roman collection in the world, including the secret room of erotic objects), the Catacombs of San Gennaro, and the Cappella Sansevero (with the Cristo Velato — the veiled Christ marble, the most technically impossible sculpture ever made).
  3. Pizza in Naples: The Original — The Associazione Verace Pizza Napoletana has 800 member pizzerias worldwide, but there is only one Naples. The Neapolitan pizza (a 00 flour dough, San Marzano tomatoes, buffalo mozzarella, fresh basil, and olive oil, cooked for 90 seconds in a wood-fired oven at 450°C) at L’Antica Pizzeria da Michele (founded 1870, two pizza varieties only: Margherita and Marinara) or Sorbillo on Via dei Tribunali is the most specific food experience in Italy and the definitive pilgrimage of any Italian food culture.
  4. The Amalfi Coast & the Drive from Sorrento to Salerno — The 50-kilometre coastal road that UNESCO lists as a Cultural Landscape: cliffs dropping 200 metres directly to the turquoise sea, white-and-pastel villages clinging to the rockface, lemon groves, and the towns of Positano (the most photographed village in the south), Amalfi (with its Arab-Norman cathedral), and Ravello (the Villa Rufolo and the Villa Cimbrone, with the finest garden terrace views on the coast). Drive westbound (Salerno to Sorrento) so the cliff-side windows face the sea.
  5. Capri: The Island of the Emperors — The limestone island in the Bay of Naples, winter retreat of Tiberius, playground of every international artist and socialite since Axel Munthe arrived in 1887: the Blue Grotto (the sea cave whose refracted blue light is the finest marine optical phenomenon in Italy), the Villa Jovis (Tiberius’s clifftop palace), the Faraglioni sea stacks, and the Piazzetta (the tiny square that functions as the social centre of the island, with a view of the harbour and the most expensive coffee in the south). Take the hydrofoil from Naples rather than the slower ferry.
  6. The Sassi di Matera (UNESCO) — The cave city of Basilicata: an ancient settlement of cave dwellings (sassi) carved into two ravines (the Sasso Caveoso and Sasso Barisano) above a river gorge, inhabited since the Palaeolithic and continuously through the present — a 2006 documentary found the final cave-dwelling family still in occupation. Declared a European Capital of Culture in 2019; the most completely unique urban landscape in Italy. The Murgia plateau opposite gives the finest view of the entire cave city.
  7. Alberobello & the Trulli (UNESCO) — The cone-roofed stone dwellings of the Itria Valley in Puglia: the trulli (singular trullo) are a building tradition specific to this corner of Apulia, with dry-stone conical roofs topped with a pinnacle symbol that was historically removed when tax collectors arrived (the houses could be disassembled without mortar). Alberobello’s Rione Monti district — 1,500 trulli in a single UNESCO-listed quarter — is the most other-worldly small-town landscape in Italy.
  8. Lecce: The Florence of the South — The Baroque city of the Salento peninsula at the heel of Italy: the finest Baroque architecture in southern Europe, executed in the warm golden lecce stone (pietra leccese) that allows a level of ornamental carving detail available in no other building material. The Basilica di Santa Croce (whose facade contains a full taxonomy of Baroque excess), the Cathedral, and the Roman amphitheatre (still visible in the central piazza) together make Lecce the most rewarding city in Puglia.
  9. The Greek Temples of Agrigento (UNESCO) — The Valley of the Temples in Sicily: the finest surviving ensemble of Greek temples outside Greece, with the Temple of Concordia (440 BC, virtually intact) and the Temple of Juno visible from the road 5 kilometres away. The almond blossom festival (February) turns the valley white; the temples at sunset turn amber and gold in a light that makes them look exactly as they did when the Greeks who built them were alive.
  10. Palermo: The Capital of Layered History — The capital of Sicily contains five centuries of overlapping civilisations in a single city: the Cappella Palatina (the Norman chapel with the finest Byzantine mosaics outside Constantinople, built by King Roger II in 1140), the Arab-Norman Cathedral, the Ballarò street market (the finest outdoor market in Italy, with the full range of Sicilian street food), and the Catacombe dei Cappuccini (the catacombs of 8,000 mummified bodies, dressed in the clothes of their burial — the most Gothic heritage site in Europe).

Umbria, the Marche & the Adriatic

  1. Assisi: The Basilica of St Francis (UNESCO) — The two-level Basilica of Saint Francis in the hilltown of Assisi: the Lower Basilica (with Simone Martini and Cimabue’s frescoes) and the Upper Basilica (with Giotto’s 28-panel fresco cycle of the Life of St Francis — the series that marks the beginning of the Western tradition of naturalistic painting). The most significant single decorative programme in Italian art history.
  2. Orvieto: The Tuff Plateau City — The hill city of western Umbria, perched on a volcanic tuff plateau above the valley: the Cathedral (the Duomo di Orvieto, with Luca Signorelli’s Last Judgment frescoes in the Cappella di San Brizio — the programme that influenced Michelangelo’s Sistine Chapel), the Pozzo di San Patrizio (the twin-helix well designed by Antonio da Sangallo for Pope Clement VII), and the underground city (the network of Etruscan tunnels beneath the modern city). The Orvieto Classico white wine is the finest in Umbria.
  3. Spoleto & the Festival dei Due Mondi — The hilltown of central Umbria, with a Roman amphitheatre (still used), the Romanesque Cathedral (with Filippo Lippi’s Life of the Virgin fresco cycle), and the Ponte delle Torri (a 14th-century 10-arched aqueduct above a wooded gorge). The Festival dei Due Mondi (Festival of Two Worlds, June–July) has been one of Europe’s finest classical and contemporary arts festivals since 1958.
  4. Perugia & the Umbrian Hill Towns — The capital of Umbria, with the Galleria Nazionale dell’Umbria (the finest collection of Umbrian painting, with Perugino and Piero della Francesca), the Fontana Maggiore (the finest Gothic public fountain in Italy), and the Corso Vannucci — the main pedestrian street that functions as a permanent passeggiata. The Umbrian Eurochocolate Festival (October) transforms the city into the finest chocolate event in Europe.
  5. Urbino & the Renaissance Court of Montefeltro — The hill city of the Marche: Federico da Montefeltro’s Palazzo Ducale (the most perfectly proportioned Renaissance palace in Italy, designed by Luciano Laurana in 1468), with the Galleria Nazionale delle Marche (Piero della Francesca’s Flagellation of Christ — the most analysed painting in Italian art history — and Raphael’s Portrait of a Gentleman). The most complete surviving Renaissance court in the world, UNESCO-listed, and entirely free of the crowds that descend on Florence.

The Italian North: Mountains & Plains

  1. The Dolomites (UNESCO) — The dramatic limestone massifs of the Eastern Alps: UNESCO World Heritage for their exceptional geological and scenic values, with the Tre Cime di Lavaredo (the three rock towers that are the most iconic image in Italian alpine photography), the Alpe di Siusi (the largest alpine meadow in Europe), and the Sassolungo group above the Val Gardena. Skiing in winter (the Sella Ronda circuit is the finest connected ski area in the Dolomites); hiking in summer (the Alta Via 1 is the finest long-distance alpine trail in Italy).
  2. Cinque Terre (UNESCO) — The five fishing villages (Riomaggiore, Manarola, Corniglia, Vernazza, Monterosso al Mare) on the Ligurian coast north of La Spezia: clinging to limestone cliffs above the Ligurian Sea, connected by the coastal path (the Sentiero Azzurro, partially reopened after erosion repairs) and the regional train. Best seen from the water (boat tours from La Spezia) to appreciate the vertical geography. Come in October for the grape harvest and the quality of autumn light; avoid July and August entirely.
  3. Bologna: The Food Capital — The city that gave the world ragù (called Bolognese abroad, never in Bologna), mortadella, tortellini, and the concept of serious food: the Quadrilatero market (the finest concentrated food market in Italy, with the pescheria, the salumeria, and the macelleria in adjacent lanes), the towers of the Garisenda and Asinelli (the leaning towers of the Middle Ages), and the university (the oldest in the world, founded 893 AD) give it the finest combination of food culture, architecture, and student life in Emilia-Romagna.
  4. Ravenna’s Byzantine Mosaics (UNESCO) — The city in Emilia-Romagna that contains the finest Byzantine mosaics in the world outside Istanbul and the Eastern Mediterranean: the Mausoleum of Galla Placidia (the oldest mosaic in Ravenna, 430 AD — the cobalt blue is unlike any other surface in Italian art), the Basilica of Sant’Apollinare Nuovo, and the Basilica of San Vitale (with the portraits of Justinian and Theodora — the most specific images of the Byzantine court in any art form). Dante Alighieri is buried here; his tomb is the finest plain monument in a city of extravagant decoration.
  5. Genoa: The Neglected Capital — The city of Christopher Columbus, of the Doria and the Grimaldi, and of the finest concentration of 16th and 17th-century palace architecture in Northern Italy (the Palazzi dei Rolli, UNESCO-listed): the Palazzo Rosso, the Palazzo Bianco, and the Palazzo del Principe (Prince Doria’s waterfront palace, with the largest Perin del Vaga fresco cycle in any private building). The caruggi (the medieval alleys behind the port, 90cm wide, dark, and entirely medieval in atmosphere) and the Mercato Orientale (the finest covered food market in Liguria) are the essential experiences.

Islands: Sicily, Sardinia & Beyond

  1. Sicily: The Island of Everything — The most culturally complex island in Italy: Greek temples (Agrigento, Selinunte, Segesta), Arab-Norman architecture (Palermo’s Cappella Palatina, Cefalù Cathedral), Baroque towns (Noto, Ragusa, Modica — the Baroque heart of the southeast), active volcanoes (Etna, the highest active volcano in Europe; Stromboli, which erupts every 20–30 minutes), and a food culture (arancini, pasta con le sarde, cannoli, granita) of exceptional specificity.
  2. Mount Etna Hike, Sicily — The 3,329-metre active volcano above Catania: accessible by cable car and 4WD to the 2,900-metre level, with guided walks to the summit craters (when volcanic activity permits). The view from the crater rim — the entire eastern Sicily spread below, the Strait of Messina, Calabria, and the Aeolian Islands visible on clear days — is the finest from any mountaintop in Italy.
  3. Noto & the Baroque Southeast, Sicily — The most completely Baroque city in Italy: rebuilt entirely after the 1693 earthquake in the golden limestone of the Iblean hills, with the Via Corrado Nicolaci (the finest single Baroque street facade in Sicily, with the balconies’ corbels carved as horses, lions, and mermaids), the Cathedral, and the surrounding towns of Ragusa Ibla (the finest intact Baroque centro storico) and Modica (with its famous chocolate, made to an Aztec-influenced recipe without heat).
  4. Sardinia: The Wild Island — The island of ancient nuraghe (Bronze Age stone towers — 7,000 survive, the finest concentration of prehistoric monument in the Mediterranean), the Costa Smeralda (the Aga Khan’s developed northern coast, with the clearest sea water in the Mediterranean), the Barbagia highlands (the most traditional inland culture in Italy — the Carnival of Oristano, the Sartiglia equestrian event, the Gennargentu massif), and the wild beaches of the Ogliastra.

Food, Wine & the Italian Table

  1. Espresso at a Roman Bar — The Italian espresso bar ritual: standing at the zinc counter, ordering with a single word or gesture, receiving a 30ml shot of concentrated coffee with a crema of precise thickness, consuming it in two sips, paying at the cash register rather than the bar. The price is €1–1.20 at the counter and €1.50–3 seated at a table. Sant’Eustachio il Caffè near the Pantheon, Tazza d’Oro on Via degli Orfani, and any bar in Naples are the essential encounters.
  2. Pizza Napoletana at Da Michele, Naples — Already mentioned (item 43), but the specific experience: the Margherita at Da Michele (queue outside, no booking, tables shared, service brusque, pizza perfection) in the context of the San Lorenzo neighbourhood of Naples at lunchtime is the most specific food pilgrimage available in Italy. The pizza arrives in 90 seconds; the experience requires the full context of the city.
  3. Pasta Masterclass in Bologna or Rome — The handmade pasta tradition of Emilia-Romagna (tagliatelle, tortellini, sfoglia — the thin egg pasta sheet rolled to the thickness of a gold ring on the statue of Neptune in Bologna’s Piazza Maggiore, by tradition) is taught in cooking schools throughout Bologna. A morning pasta-making class — beginning with the egg pasta dough, learning the sfoglia roll, and producing the first tagliatelle — is the most hands-on food experience available in Italy.
  4. Gelato at an Artisan Gelateria — The Italian ice cream made fresh each day with seasonal fruit, cream, and no air: the gelato culture requires specifying the difference between an artisan gelateria (where the product is made on the premises, stored in covered metal containers, and served with a flat-bladed spatula) and the industrial tourist-trap variety (stored in colourful piled towers, often containing food colouring and stabilisers). Giolitti in Rome (since 1900), Vivoli in Florence (since 1929), and any local gelateria with metal covered containers are the essential addresses.
  5. Barolo Wine Tasting in Piedmont — The King of Italian wines, from the Nebbiolo grape grown in the Langhe hills south of Turin: Barolo (and its cousin Barbaresco) require a decade of ageing to reach their full complexity, and the cellars of Serralunga d’Alba, Barolo village, and Castiglione Falletto offer tastings directly from the producers. The combination of a Barolo tasting and a Piemontese lunch (tajarin pasta with truffle, brasato al Barolo) in the October fog of the Langhe is the finest wine-and-food experience in Italy.
  6. Truffle Hunting in Tuscany or Umbria — The white truffle of Alba (Tuber magnatum pico, harvested October–December) and the summer truffle of Umbria (Tuber aestivum, June–August): guided truffle hunts with a trained Lagotto Romagnolo dog through oak forest, ending with a truffle-focused lunch. San Miniato (the finest white truffle market in Tuscany, November), the Tartufai of Acqualagna (Marche), and the truffle farms around Norcia (Umbria) are the principal centres.
  7. Sicilian Arancini & Street Food — The Sicilian street food tradition: arancini (fried rice balls with meat ragù or mozzarella filling, each Sicilian city with its own variant in shape and flavour — round in Palermo, pointed in Catania), pane panelle (chickpea fritter sandwiches in sesame rolls), pasta con le sarde (pasta with sardines and wild fennel), and the granita of Catania (the finest lemon granita in Sicily, served with a brioche for dunking). The Ballarò market in Palermo is the finest place to eat all of them in sequence.
  8. Cacio e Pepe & Roman Pasta at a Trattoria — The Roman pasta tradition: cacio e pepe (Pecorino Romano, black pepper, and pasta water — the simplest pasta and the most difficult to make correctly), carbonara (guanciale, egg yolk, Pecorino, and black pepper — without cream), and amatriciana (guanciale, tomato, Pecorino, and chilli). The Roman trattorie of Testaccio and Trastevere — particularly Flavio al Velavevodetto, Roscioli, and Da Enzo — serve the finest versions of the canon.

Festivals, Events & Italian Life

  1. Venice Carnival (February) — Already mentioned (item 29), but worth repeating as an event: the most spectacular urban festival in Europe, with the finest costumes, the finest city, and the finest weather window (cold, clear, before the spring tourist season begins). Book accommodation six months in advance for the most popular nights.
  2. Verona Opera Festival (June–September) — Already mentioned (item 30): the outdoor opera in a Roman amphitheatre is the most atmospheric classical music event in Italy. The June season begins with Verdi’s Aida and continues through August.
  3. Umbria Jazz, Perugia (July) — One of Europe’s finest jazz festivals, held in the piazzas and theatres of Perugia for ten days each July: international headliners, free outdoor stages in the Piazza IV Novembre, and the combination of jazz and one of Italy’s most beautiful medieval cities. The finest music festival in central Italy.
  4. Siena Palio (2 July & 16 August) — Already mentioned (item 17): the most intense civic ritual in Italy. Attending is free (in the Campo’s centre); the experience requires planning, early arrival, and complete surrender to the city’s collective emotion.
  5. Settimana Musicale di Stresa & Lake Maggiore (August–September) — The classical music festival on Lake Maggiore, with concerts in the Baroque palaces, churches, and gardens of the lake shore: the most intimate and the most scenically perfect classical music festival in Northern Italy.

Hidden Italy & Unexpected Discoveries

  1. Civita di Bagnoregio — The Dying City — A hilltop village in Lazio, accessible only by footbridge, that has been slowly eroding into the tufa valley since the 16th century: the last 12 permanent residents live in a medieval street of astonishing beauty above a landscape of collapsed tufa pinnacles. The most precarious inhabited settlement in Italy and the most melancholy heritage landscape in the country.
  2. The Sassi di Matera Cave Hotels — Sleeping in a converted cave dwelling in Matera: the sassi hotels (Sextantio Le Grotte della Civita, the Palazzo Gattini, and Corte San Pietro) have converted the ancient cave dwellings into the most atmospheric accommodation in southern Italy, with stone walls, terracotta floors, and the views from the room terrace across the ravine. The most specific hotel experience in Italy.
  3. Procida: The Island the Visitors Missed — The smallest of the Neapolitan islands, 40 minutes by hydrofoil from Naples: the pastel harbour of Marina Corricella (the most photographed harbour in southern Italy, used in the filming of Il Postino), the citadel with its former Bourbon prison, and the complete absence of the tourist infrastructure that has overwhelmed Capri and Ischia. Capital of Culture 2022; the most genuinely Italian island near Naples.
  4. Matera’s Rupestrian Churches — Beyond the Sassi themselves: the rock-cut churches of the Murgia plateau opposite Matera, accessible by a walking trail across the ravine, with medieval frescoes in cave chambers that have never been moved or restored. The Cripta del Peccato Originale (the Cave of the Original Sin, 9th-century frescoes, the finest Paleochristian painting in Basilicata) and the Madonna delle Virtù are accessible on guided tours.
  5. The Baroque Towns of the Val di Noto (UNESCO) — The eight towns rebuilt after the 1693 earthquake that destroyed eastern Sicily: Noto, Ragusa, Modica, Scicli, Caltagirone, Catania, Palazzolo Acreide, and Militello. Each rebuilt in a consistent Sicilian Baroque style over the following century, producing the most coherent ensemble of late Baroque urban planning in the world. The driving circuit of the Val di Noto (three to four days) is the finest heritage road trip in Sicily.
  6. The Cinque Terre by Sea — Approaching the five villages from the water (boats from La Spezia or from Monterosso): the vertical geography of the terraced vineyards, the villages embedded in the cliffs, and the absence of any road or car visible from the sea makes the Cinque Terre comprehensible in a way that the train access or the hiking trail does not. The afternoon boat tour from La Spezia, returning to Riomaggiore by train at sunset, is the finest single Cinque Terre experience.
  7. The Langhe Hills of Piedmont in October (Truffle Season) — The fog of October in the Langhe: the mist filling the valleys between the Barolo and Barbaresco vineyards, the truffle hunters at dawn in the oak woods, and the white truffle market of Alba (the finest food event in Piedmont, October–November). The combination of the vintage, the truffles, and the fog over the Piedmontese hills is the most seasonally specific experience in Northern Italy.
  8. Cividale del Friuli & the Lombard Heritage (UNESCO) — The town in Friuli-Venezia Giulia where the Lombards established their first duchy after the fall of Rome: the Tempietto Longobardo (a 8th-century stucco relief sanctuary of extraordinary quality, the finest surviving example of Lombard decorative art in Italy), the Museo Archeologico Nazionale, and the Ponte del Diavolo (the Devil’s Bridge across the Natisone gorge). UNESCO-listed for its Lombard heritage; entirely unvisited by international tourists.
  9. The Dolomite Road (Grande Strada delle Dolomiti) — The 110-kilometre road from Bolzano to Cortina d’Ampezzo, through the Rosengarten, the Sella massif, and the Falzarego Pass: the finest mountain driving route in Italy, with the Tre Cime di Lavaredo accessible at the northern end. The road at dawn in September, with the summer visitors gone and the larch forests turning gold, is the finest seasonal driving experience in the Alps.
  10. The Via Francigena — Walking to Rome — The ancient pilgrim road from Canterbury to Rome, entering Italy at the Great St Bernard Pass in the Alps and descending through Aosta, Vercelli, Fidenza, Lucca, Siena, and Viterbo: 1,000 kilometres of walking that covers the finest combination of landscapes and historic towns in Italy. The final stage into Rome, over the Monte Mario and down to the Vatican, is the most emotionally charged ending of any long-distance walk in Europe.
  11. The Sacro Monte di Varallo (UNESCO) — The first of the Italian sacred mountains: a 15th-century devotional complex of 45 chapels on a hillside above the Sesia Valley in Piedmont, each containing life-size terracotta figure groups (4,000 in total) depicting scenes from the life of Christ, with frescoed backgrounds integrating the figures into architectural settings of extraordinary illusionistic ambition. UNESCO World Heritage Site; entirely off the tourism circuit.
  12. Otranto & the Adriatic Coast of Puglia — The easternmost city of Italy: the Cathedral of Otranto (with the 12th-century mosaic floor — the largest medieval floor mosaic in Europe, 54 metres long, depicting the Tree of Life and a cosmological programme of extraordinary complexity), the castle where the Turkish siege of 1480 produced 813 martyrs (their skulls are displayed in a chapel behind the cathedral), and the sea visible from the Puglia-Albania coast on clear days. The most specifically southeastern Italian experience available.
  13. The Piano Grande of the Sibillini Mountains, Umbria — The high plateau above the Sibillini National Park: a flat-bottomed glacial valley at 1,300 metres, surrounded by the bare limestone peaks of the Apennines, which in May fills with wild lentil flowers in a carpet of purple, white, and yellow that is one of the finest wildflower landscapes in Europe. The town of Castelluccio (formerly the highest village in Umbria, destroyed by earthquake in 2016 and under reconstruction) overlooks the plain from the ridge above.

Practical Italy

  1. The Frecciarossa High-Speed Train — The Roma–Firenze–Venezia–Milano axis is connected by Italy’s finest railway: the Frecciarossa travels at 300 km/h, connecting Rome to Florence in 1.5 hours and Florence to Venice in 2 hours. Book in advance at Trenitalia.com for the cheapest fares; the Prima class is comparable to business class air travel at a fraction of the price. The most efficient and the most civilised way to traverse northern and central Italy.
  2. Renting a Car in Tuscany or Puglia — The countryside experience: the Val d’Orcia, the Chianti, and the Trulli Valley are accessible only by car. A Fiat Punto on the SS2 Cassia south from Florence to Siena and Montalcino, with no fixed itinerary, is the finest self-directed travel experience in Italy — the landscape reveals itself through the windscreen rather than from a coach window, and the cellar door of an estate that appears on the right is a decision that changes the afternoon.
  3. Staying in an Agriturismo — The farm stay network of Italy: farmhouses that offer accommodation and meals using their own produce, with the breakfast table including homemade jam, local honey, and the estate’s olive oil. The standard of Italian agriturismo — particularly in Tuscany, Umbria, and Puglia — is the finest rural hotel culture in Europe, at prices that make the Florence hotels look expensive.
  4. The Passeggiata (Evening Promenade) — The most specific Italian social institution: every Italian town between 6pm and 8pm fills with its residents walking the main street or piazza, greeting each other, meeting for aperitivo, and demonstrating the collective social fabric of a city that still lives outdoors. Walking the Corso Vannucci in Perugia, the Piazza del Campo in Siena, or the Lungomare of Bari at passeggiata hour is the finest single observation of Italian daily life.
  5. Swimming at a Lido on the Amalfi Coast or in Sardinia — The Italian beach lido: a private beach club with loungers, an umbrella, a bar, and the specific social culture of the Italian summer — the espresso at 10am, the Campari Soda at noon, the lunch of grilled fish, the afternoon swim in the crystalline water. The lidos of the Amalfi Coast (the most beautiful setting) and the beach clubs of Sardinia’s Emerald Coast (the clearest water) are the finest versions.

The Most Italian Experiences

  1. Driving the Amalfi Coast Road — The SS163, the Strada Statale Amalfitana: 46 kilometres of serpentine coastal road with a lane-and-a-half of carriageway shared between coaches, delivery trucks, Vespas, and the occasional tourist in a rented Alfa Romeo. Terrifying, beautiful, and entirely Italian. Drive eastward (Sorrento to Salerno) so the passenger window faces the sea; drive in April or October to avoid the July gridlock.
  2. An Italian Opera in a Small Theatre — Not La Scala or the Verona Arena — but the opera in the municipal theatre of Lucca (Puccini’s birthplace, where his early operas are performed in the theatre named for him), Ferrara, Modena, or Pesaro (Rossini’s birthplace, where the Rossini Opera Festival produces all 39 of his operas in rotation): the most specifically Italian cultural experience at the most human scale.
  3. A Sunday Lunch at a Family-Run Trattoria — The Sunday lunch of Italy: the three-course menu fisso of antipasto, primo (pasta), secondo (meat or fish), contorno (vegetable), dolce, and the house wine in a carafe, at a family trattoria that has been run by the same family for 30 years, in a town with no other restaurant. This meal — in Umbria, or Calabria, or the Marche — costs under €25 per person and is the finest single value experience Italy offers.
  4. The Night Train from Rome to Palermo — The overnight train that crosses the Strait of Messina: the last train ferry in Western Europe, where the locomotive and carriages are loaded onto a ferry at Villa San Giovanni in Calabria and cross the Strait of Messina to Villa San Giovanni in Sicily, arriving in Palermo at dawn. The most cinematically specific rail experience in Italy.
  5. The Aperitivo Hour at a Venetian Bacaro — The Venetian bar culture of cicchetti (small plates of crostino, baccalà mantecato, and marinated sardines) with a glass of Prosecco or a Spritz at a bacaro (a traditional Venetian wine bar) in the Cannaregio or Dorsoduro districts in the hour before dinner: the oldest and the most specifically Venetian version of the Italian aperitivo tradition, at prices that make the tourist restaurants look dishonest.
  6. Watch the Dawn from the Pincian Hill, Rome — On your last morning in Italy, take the long walk through the Borghese gardens to the Pincian Terrace above the Piazza del Popolo before sunrise. The city emerges from the dark in stages: first the dome of St Peter’s, then the Vittoriano, then the domes of the baroque churches, then the Palatine, then the Colosseum, and finally — when the sun clears the Alban Hills to the east and the first direct light crosses the Tiber and illuminates the stone of the Eternal City — Rome in its full extent, seen from the same vantage point that every painter and poet who arrived from the north first saw it. Italy does not reveal itself in a single visit. It never finishes. The stone is older than any civilisation you know how to compare it with, and the morning light on it is the same morning light that has been happening here since the first Latin farmers came down from those hills and decided, with extraordinary and enduring confidence, that this was the place.

Quick Facts for Visitors

Best time to visitApril–June (spring, wildflowers, before the peak heat) · September–October (harvest, fewer crowds, golden light)
SummerJuly–August — very hot (35–40°C in the south); extremely busy at major sites
WinterNovember–March — off-season; many agriturismo close; museums quiet; ski season in the Alps and Dolomites
CurrencyEuro (€)
LanguageItalian; English in tourist areas; French widely understood in the northwest
Getting aroundFrecciarossa (high-speed train) between cities · Car hire essential for countryside and the south · Local buses for smaller towns
Pre-booking essentialSistine Chapel · Last Supper (8 months) · Borghese Gallery · Uffizi · Colosseum in summer
Coffee noteStanding at the bar costs less than sitting at a table. This is not a trick; it is how Italians drink coffee
Ideal trip length10 days for the Classic Route · 2 weeks adds Puglia, Sicily, or the Italian Lakes · 3 weeks for the full country

Italy does not ask for your enthusiasm. It simply provides the conditions under which enthusiasm becomes unavoidable: the light on the stone, the pasta on the plate, the Baroque facade in a side street you walked past by mistake, and the specific quality of an Italian afternoon in which nothing needs to happen for everything to be entirely satisfactory. Go slowly. Eat well. Come back.

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