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
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14:00 - Arrival and hotel transfer
From Fiumicino, take the Leonardo Express to Termini (32 min, €14). Drop bags and head out to explore.
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16:00 - Trevi Fountain
The most spectacular baroque fountain in the world. Toss a coin with your right hand over your left shoulder.
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17:30 - Spanish Steps and Via Condotti
Rome's most photographed staircase. Via Condotti is the luxury shopping street.
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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
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08:30 - Colosseum
The largest amphitheater ever built. 50,000 spectators watched gladiator battles here.
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11:00 - Roman Forum and Palatine Hill
The center of ancient Rome. Walk where Julius Caesar was assassinated and emperors ruled.
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13:30 - Lunch: Roscioli
One of Rome's best carbonaras. They also have a spectacular bakery and deli.
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15:30 - Pantheon
2,000 years of architectural perfection. The world's largest unreinforced concrete dome. Free entry.
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17:00 - Piazza Navona
Rome's most beautiful baroque square. Three Bernini fountains and street artist atmosphere.
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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
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08:00 - Vatican Museums and Sistine Chapel
One of the world's most important art collections. Michelangelo's ceiling is superhuman.
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11:30 - St. Peter's Basilica
The world's largest church. Michelangelo's Pietà and the dome with views of all Rome.
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13:30 - Lunch: Pizzarium (Bonci)
Rome's best pizza al taglio. Crispy dough, creative toppings. Always a queue but worth it.
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15:00 - Castel Sant'Angelo
Hadrian's mausoleum turned papal fortress. Terrace with views of the Tiber and St. Peter's.
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17:00 - Trastevere neighborhood
Stroll through ivy-covered cobblestone streets. Rome's most photogenic and bohemian quarter.
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19:30 - Dinner: Supplizio
Rome's best supplì (stuffed rice croquettes). The classic supplì al telefono is perfection.
Day 4: Rome → Florence: Renaissance Capital
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08:30 - Frecciarossa to Florence
High-speed train Rome-Florence in just 1h30. Book on Trenitalia or Italo in advance for best prices.
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11:00 - Florence Duomo
Brunelleschi's dome is an engineering masterpiece. The pink, green and white marble facade is mesmerizing.
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13:00 - Lunch: Trattoria Mario
Family-run trattoria since 1953. Shared tables, daily menu on chalkboard. Legendary ribollita and bistecca.
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14:30 - Ponte Vecchio
The world's most famous medieval bridge. Jewelry shops have lined both sides since the 16th century.
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16:00 - Piazzale Michelangelo
The best panoramic view of Florence. The entire city, the Arno and the Tuscan hills at your feet.
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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
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08:15 - Uffizi Gallery
The world's most important painting gallery. Botticelli, Leonardo, Raphael, Caravaggio. 2-3 hours minimum.
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11:30 - Mercato Centrale
Two-floor food market. Downstairs: fresh produce since 1874. Upstairs: gourmet food court.
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13:30 - Basilica of Santa Croce
Florence's 'Pantheon': tombs of Michelangelo, Galileo and Machiavelli.
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15:00 - Galleria dell'Accademia (David)
Michelangelo's David. 5.17 meters of perfection in Carrara marble. Far more impressive in person.
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17:00 - Gelato at Vivoli or La Sorbettiera
Florence is the birthplace of gelato. Vivoli (1930) is historic; La Sorbettiera has creative flavors.
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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)
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08:30 - Train/bus to San Gimignano
The 'Medieval Manhattan': 14 stone towers dominate the skyline. Tuscan landscape of cypress and vineyards.
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10:30 - San Gimignano
Stroll medieval streets, climb Torre Grossa and try gelato at Gelateria Dondoli (world champion).
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13:30 - Tuscan lunch
Pici with wild boar ragù, bruschetta with fresh olive oil and local Vernaccia wine.
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15:30 - Siena
Piazza del Campo is Europe's most beautiful medieval square. The Duomo has a unique marble floor.
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19:00 - Return to Florence
Head back by bus or car. Light dinner in Florence with whatever energy remains.
Day 7: Florence → Cinque Terre
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08:00 - Train to Cinque Terre
Train Florence-La Spezia (2h30) then local trains between villages. Buy the Cinque Terre Card.
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11:30 - Riomaggiore
The southernmost village. Colorful houses stacked on the cliff. Tiny, photogenic harbor.
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13:30 - Lunch in Manarola
Focaccia di Recco with stracchino cheese and fresh Genoese pesto. Eat by the harbor with sea views.
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15:00 - Trail: Manarola → Corniglia
1-hour coastal hike with spectacular Mediterranean views. Bring water and sun protection.
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17:00 - Vernazza
Perhaps the prettiest village. Natural harbor, medieval tower and the most accessible beach.
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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
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09:00 - Monterosso al Mare
The largest village with the best beach. Medieval old town and new seaside zone.
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11:30 - Trail: Monterosso → Vernazza
The most spectacular trail (1h30). Views of all the villages. Moderately challenging.
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14:00 - Lunch in Corniglia
The clifftop village. 382 steps to reach it. Focaccia, Monterosso anchovies and limoncello.
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16:00 - Mediterranean swim
Pick your favorite beach. Monterosso has sand; the others have rocks and crystal-clear water.
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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
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08:00 - Train to Venice
La Spezia → Venice Santa Lucia (4-5h with transfer in Milan or direct). Book in advance.
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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'.
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16:00 - St. Mark's Square
Napoleon's 'drawing room of Europe'. Byzantine basilica, Campanile and Doge's Palace.
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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
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09:00 - Doge's Palace and Bridge of Sighs
The power of the Serenissima. Tintoretto, council halls and the prisons with their famous bridge.
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11:30 - San Polo Sestiere and Rialto
The Rialto market has sold fresh fish since the 11th century. Side streets hide secret bacari.
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13:30 - Lunch: Trattoria alla Madonna
Classic Venetian trattoria by the Rialto. Risotto al nero di seppia and fritto misto are spectacular.
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15:30 - Dorsoduro: Gallerie dell'Accademia
The finest collection of Venetian painting: Bellini, Tintoretto, Veronese and Titian.
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17:30 - Punta della Dogana at sunset
The tip of the island with views of San Giorgio and the San Marco basin. Spectacular sunset.
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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)
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09:00 - Vaporetto to Murano
The glass-blowing island. Visit a working factory and watch master artisans in action.
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11:30 - Burano
Italy's most photogenic island. Houses painted in vibrant colors, handmade lace and traditional fishing.
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14:30 - Lunch in Burano
Risotto de gò (lagoon fish) or bussolà (traditional cookie). Trattoria al Gatto Nero is the star.
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16:30 - Torcello
The lagoon's oldest island. 7th-century Byzantine cathedral with extraordinary golden mosaics.
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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
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08:30 - Train to Verona
1h10 on regional train. Leave bags in station luggage storage and explore Romeo and Juliet's city.
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10:30 - Verona Arena
1st-century Roman amphitheater, nearly intact. Still used for open-air opera in summer.
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12:00 - Piazza delle Erbe and Juliet's Balcony
The market square with medieval frescoes. Juliet's balcony is small but iconic.
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13:30 - Veronese lunch
Risotto all'Amarone and pastissada de caval (horse stew). Osteria al Duca is authentic.
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15:30 - Train to Milan
1h20 on Frecciarossa. Arrive at Milano Centrale, one of Europe's most impressive stations.
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17:30 - The Last Supper (if tickets available)
Leonardo da Vinci's masterpiece at Santa Maria delle Grazie. Only viewable with a reservation.
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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
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09:00 - Milan Cathedral (Duomo)
Italy's largest Gothic cathedral. 135 spires, 3,400 statues. The rooftop terraces are spectacular.
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11:30 - Galleria Vittorio Emanuele II
Milan's 'living room'. The world's most elegant shopping arcade with Prada, Versace and historic cafés.
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13:00 - Lunch: Luini Panzerotti
Since 1888: fried panzerotti stuffed with mozzarella and tomato. Eternal queue but just €3. Unmissable.
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14:00 - Fashion Quadrilateral
Via Montenapoleone, Via della Spiga, Corso Venezia. The world's most important fashion district.
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16:00 - Pinacoteca di Brera
Milan's great art gallery. Mantegna, Caravaggio and Hayez's The Kiss.
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18:00 - Brera neighborhood
Bohemian streets, art galleries, pavement cafés and Milan's most charming quarter.
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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
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09:00 - Sforza Castle and Sempione Park
The Renaissance fortress houses Michelangelo's Rondanini Pietà (his last, unfinished work).
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11:00 - Last Italian coffee
An espresso at the counter of a historic bar. Marchesi 1824 or Cova are Milanese institutions.
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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.