Italy in 14 Days: From Rome to Milan

The ultimate route through the land of art, pasta and la dolce vita: Roman ruins, Renaissance, coastline and the Alps

14-day Italy itinerary. Rome, Florence, Cinque Terre, Venice and Milan. Complete guide with real restaurants, trains and expert tips.

Day 1: Rome: Arrival and Historic Center

  • 14:00 - Arrival and hotel transfer

    From Fiumicino, take the Leonardo Express to Termini (32 min, €14). Drop bags and head out to explore.

  • 16:00 - Trevi Fountain

    The most spectacular baroque fountain in the world. Toss a coin with your right hand over your left shoulder.

  • 17:30 - Spanish Steps and Via Condotti

    Rome's most photographed staircase. Via Condotti is the luxury shopping street.

  • 19:00 - Dinner in Trastevere

    Rome's most authentic neighborhood for dining. Try Da Enzo al 29 (legendary cacio e pepe) or Tonnarello.

Day 2: Rome: Colosseum and Roman Forum

  • 08:30 - Colosseum

    The largest amphitheater ever built. 50,000 spectators watched gladiator battles here.

  • 11:00 - Roman Forum and Palatine Hill

    The center of ancient Rome. Walk where Julius Caesar was assassinated and emperors ruled.

  • 13:30 - Lunch: Roscioli

    One of Rome's best carbonaras. They also have a spectacular bakery and deli.

  • 15:30 - Pantheon

    2,000 years of architectural perfection. The world's largest unreinforced concrete dome. Free entry.

  • 17:00 - Piazza Navona

    Rome's most beautiful baroque square. Three Bernini fountains and street artist atmosphere.

  • 19:00 - Aperitivo at Campo de' Fiori

    The daytime market square transforms into a bar area. Aperol Spritz and bruschette at sunset.

Day 3: Rome: Vatican and Museums

  • 08:00 - Vatican Museums and Sistine Chapel

    One of the world's most important art collections. Michelangelo's ceiling is superhuman.

  • 11:30 - St. Peter's Basilica

    The world's largest church. Michelangelo's Pietà and the dome with views of all Rome.

  • 13:30 - Lunch: Pizzarium (Bonci)

    Rome's best pizza al taglio. Crispy dough, creative toppings. Always a queue but worth it.

  • 15:00 - Castel Sant'Angelo

    Hadrian's mausoleum turned papal fortress. Terrace with views of the Tiber and St. Peter's.

  • 17:00 - Trastevere neighborhood

    Stroll through ivy-covered cobblestone streets. Rome's most photogenic and bohemian quarter.

  • 19:30 - Dinner: Supplizio

    Rome's best supplì (stuffed rice croquettes). The classic supplì al telefono is perfection.

Day 4: Rome → Florence: Renaissance Capital

  • 08:30 - Frecciarossa to Florence

    High-speed train Rome-Florence in just 1h30. Book on Trenitalia or Italo in advance for best prices.

  • 11:00 - Florence Duomo

    Brunelleschi's dome is an engineering masterpiece. The pink, green and white marble facade is mesmerizing.

  • 13:00 - Lunch: Trattoria Mario

    Family-run trattoria since 1953. Shared tables, daily menu on chalkboard. Legendary ribollita and bistecca.

  • 14:30 - Ponte Vecchio

    The world's most famous medieval bridge. Jewelry shops have lined both sides since the 16th century.

  • 16:00 - Piazzale Michelangelo

    The best panoramic view of Florence. The entire city, the Arno and the Tuscan hills at your feet.

  • 19:00 - Dinner in Santo Spirito quarter

    Florence's Trastevere. Try Il Latini (shared bistecca) or Trattoria Sostanza (butter al piatto).

Day 5: Florence: Art and Gastronomy

  • 08:15 - Uffizi Gallery

    The world's most important painting gallery. Botticelli, Leonardo, Raphael, Caravaggio. 2-3 hours minimum.

  • 11:30 - Mercato Centrale

    Two-floor food market. Downstairs: fresh produce since 1874. Upstairs: gourmet food court.

  • 13:30 - Basilica of Santa Croce

    Florence's 'Pantheon': tombs of Michelangelo, Galileo and Machiavelli.

  • 15:00 - Galleria dell'Accademia (David)

    Michelangelo's David. 5.17 meters of perfection in Carrara marble. Far more impressive in person.

  • 17:00 - Gelato at Vivoli or La Sorbettiera

    Florence is the birthplace of gelato. Vivoli (1930) is historic; La Sorbettiera has creative flavors.

  • 18:00 - Stroll through the Oltrarno

    The 'other' bank of the Arno: artisan workshops, galleries and Florence's most authentic, local side.

Day 6: Day Trip: Tuscany (San Gimignano and Siena)

  • 08:30 - Train/bus to San Gimignano

    The 'Medieval Manhattan': 14 stone towers dominate the skyline. Tuscan landscape of cypress and vineyards.

  • 10:30 - San Gimignano

    Stroll medieval streets, climb Torre Grossa and try gelato at Gelateria Dondoli (world champion).

  • 13:30 - Tuscan lunch

    Pici with wild boar ragù, bruschetta with fresh olive oil and local Vernaccia wine.

  • 15:30 - Siena

    Piazza del Campo is Europe's most beautiful medieval square. The Duomo has a unique marble floor.

  • 19:00 - Return to Florence

    Head back by bus or car. Light dinner in Florence with whatever energy remains.

Day 7: Florence → Cinque Terre

  • 08:00 - Train to Cinque Terre

    Train Florence-La Spezia (2h30) then local trains between villages. Buy the Cinque Terre Card.

  • 11:30 - Riomaggiore

    The southernmost village. Colorful houses stacked on the cliff. Tiny, photogenic harbor.

  • 13:30 - Lunch in Manarola

    Focaccia di Recco with stracchino cheese and fresh Genoese pesto. Eat by the harbor with sea views.

  • 15:00 - Trail: Manarola → Corniglia

    1-hour coastal hike with spectacular Mediterranean views. Bring water and sun protection.

  • 17:00 - Vernazza

    Perhaps the prettiest village. Natural harbor, medieval tower and the most accessible beach.

  • 19:30 - Seafood dinner in Vernazza

    Trofie al pesto, mixed fried seafood and local white wine. Gambero Rosso or Ristorante Belforte.

Day 8: Cinque Terre: Day Two

  • 09:00 - Monterosso al Mare

    The largest village with the best beach. Medieval old town and new seaside zone.

  • 11:30 - Trail: Monterosso → Vernazza

    The most spectacular trail (1h30). Views of all the villages. Moderately challenging.

  • 14:00 - Lunch in Corniglia

    The clifftop village. 382 steps to reach it. Focaccia, Monterosso anchovies and limoncello.

  • 16:00 - Mediterranean swim

    Pick your favorite beach. Monterosso has sand; the others have rocks and crystal-clear water.

  • 19:00 - Final dinner in Cinque Terre

    Fresh seafood with Sciacchetrà wine (local sweet wine made from sun-dried grapes).

Day 9: Cinque Terre → Venice

  • 08:00 - Train to Venice

    La Spezia → Venice Santa Lucia (4-5h with transfer in Milan or direct). Book in advance.

  • 14:00 - Arrival in Venice and vaporetto

    From Santa Lucia, take vaporetto line 1 down the Grand Canal. The world's most beautiful 'bus ride'.

  • 16:00 - St. Mark's Square

    Napoleon's 'drawing room of Europe'. Byzantine basilica, Campanile and Doge's Palace.

  • 18:30 - Cicchetti at Rialto

    Venetian 'tapas'. Bacari (bars) with baccalà mantecato, sarde in saor and spritz. Try All'Arco or Cantina Do Mori.

Day 10: Venice: Canals and Treasures

  • 09:00 - Doge's Palace and Bridge of Sighs

    The power of the Serenissima. Tintoretto, council halls and the prisons with their famous bridge.

  • 11:30 - San Polo Sestiere and Rialto

    The Rialto market has sold fresh fish since the 11th century. Side streets hide secret bacari.

  • 13:30 - Lunch: Trattoria alla Madonna

    Classic Venetian trattoria by the Rialto. Risotto al nero di seppia and fritto misto are spectacular.

  • 15:30 - Dorsoduro: Gallerie dell'Accademia

    The finest collection of Venetian painting: Bellini, Tintoretto, Veronese and Titian.

  • 17:30 - Punta della Dogana at sunset

    The tip of the island with views of San Giorgio and the San Marco basin. Spectacular sunset.

  • 19:30 - Dinner in Cannaregio

    The most local quarter. Avoid San Marco for dining. Osteria Boccadoro or Anice Stellato for seafood.

Day 11: Venice: Islands (Murano, Burano, Torcello)

  • 09:00 - Vaporetto to Murano

    The glass-blowing island. Visit a working factory and watch master artisans in action.

  • 11:30 - Burano

    Italy's most photogenic island. Houses painted in vibrant colors, handmade lace and traditional fishing.

  • 14:30 - Lunch in Burano

    Risotto de gò (lagoon fish) or bussolà (traditional cookie). Trattoria al Gatto Nero is the star.

  • 16:30 - Torcello

    The lagoon's oldest island. 7th-century Byzantine cathedral with extraordinary golden mosaics.

  • 18:30 - Return to Venice and evening stroll

    Walk without a map through Venice's sestieri at night. Without tourists, the city is magical.

Day 12: Venice → Verona → Milan

  • 08:30 - Train to Verona

    1h10 on regional train. Leave bags in station luggage storage and explore Romeo and Juliet's city.

  • 10:30 - Verona Arena

    1st-century Roman amphitheater, nearly intact. Still used for open-air opera in summer.

  • 12:00 - Piazza delle Erbe and Juliet's Balcony

    The market square with medieval frescoes. Juliet's balcony is small but iconic.

  • 13:30 - Veronese lunch

    Risotto all'Amarone and pastissada de caval (horse stew). Osteria al Duca is authentic.

  • 15:30 - Train to Milan

    1h20 on Frecciarossa. Arrive at Milano Centrale, one of Europe's most impressive stations.

  • 17:30 - The Last Supper (if tickets available)

    Leonardo da Vinci's masterpiece at Santa Maria delle Grazie. Only viewable with a reservation.

  • 19:30 - Milanese aperitivo in Navigli

    Milan's canals come alive at sunset. Spritz with buffet included (€10-15). Naviglio Grande is the epicenter.

Day 13: Milan: Fashion, Art and Design

  • 09:00 - Milan Cathedral (Duomo)

    Italy's largest Gothic cathedral. 135 spires, 3,400 statues. The rooftop terraces are spectacular.

  • 11:30 - Galleria Vittorio Emanuele II

    Milan's 'living room'. The world's most elegant shopping arcade with Prada, Versace and historic cafés.

  • 13:00 - Lunch: Luini Panzerotti

    Since 1888: fried panzerotti stuffed with mozzarella and tomato. Eternal queue but just €3. Unmissable.

  • 14:00 - Fashion Quadrilateral

    Via Montenapoleone, Via della Spiga, Corso Venezia. The world's most important fashion district.

  • 16:00 - Pinacoteca di Brera

    Milan's great art gallery. Mantegna, Caravaggio and Hayez's The Kiss.

  • 18:00 - Brera neighborhood

    Bohemian streets, art galleries, pavement cafés and Milan's most charming quarter.

  • 20:00 - Dinner: Risotto alla milanese

    Saffron risotto is THE Milan dish. Trattoria Milanese (since 1933) or Ratanà are excellent.

Day 14: Milan: Farewell and Flight

  • 09:00 - Sforza Castle and Sempione Park

    The Renaissance fortress houses Michelangelo's Rondanini Pietà (his last, unfinished work).

  • 11:00 - Last Italian coffee

    An espresso at the counter of a historic bar. Marchesi 1824 or Cova are Milanese institutions.

  • 12:00 - Airport transfer

    Malpensa Express (50 min to Malpensa, €13) or bus to Linate/Bergamo. Arrive 2-3h before your flight.

FAQ

Is it easy to travel around Italy by train?
Yes, the Frecciarossa high-speed network links Rome, Florence, Venice and Milan quickly and comfortably. Book tickets in advance on Trenitalia or Italo to get the best prices.
Do you tip in Italian restaurants?
Tipping is not mandatory or expected the way it is in the US: Italians round up or leave loose change for great service. A coperto (cover charge, €1-3) is already included at most traditional restaurants.
How does the cuisine differ between Rome, Florence and Venice?
Rome shines with carbonara, cacio e pepe and supplì; Florence is synonymous with bistecca alla fiorentina and ribollita; Venice offers cicchetti (Venetian bar snacks), risotto al nero di seppia and bacalà mantecato.
Is there a tourist tax in Italy?
Yes, the tassa di soggiorno ranges from €1-7 per person per night depending on the city and hotel category. It is rarely included in the booking price, so be prepared to pay it directly at the property.
Is renting a car a good idea in Italy?
In major cities (Rome, Florence, Venice) a car is more hindrance than help: ZTL restricted traffic zones generate unexpected fines. For rural Tuscany or the Amalfi Coast, however, a car is the best way to explore.