37 days in Italy Itinerary

37 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

Plan created by another user. Make it yours
Fly
1
Milan
— 3 nights
Drive
2
Venice
— 5 nights
Drive
3
Cinque Terre
— 1 night
Drive
4
Florence
— 7 nights
Train
5
Rome
— 7 nights
Train
6
Naples
— 6 nights
Drive
7
Positano
— 3 nights
+2
Ferry to Sorrento, Train to Rome, Fly to Sydney

S M T W T F S
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31
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3
nights
Milan

Fashion Capital of World

In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
Do some cultural sightseeing at Duomo di Milano and Monumental Cemetery. Get some historical perspective at Basilica di Sant'Ambrogio and Il Cenacolo. Venture out of the city with trips to Sacro Monte di Ossuccio (in Ossuccio) and Chiosco Villa Carlotta (in Tremezzina). There's still lots to do: browse the different shops at Galleria Vittorio Emanuele II, appreciate the extensive heritage of Piazza del Duomo, take in the architecture and atmosphere at Chiesa di San Maurizio al Monastero Maggiore, and admire the masterpieces at Pinacoteca di Brera.

To find ratings, other places to visit, traveler tips, and more tourist information, go to the Milan trip itinerary planner.

Sydney, Australia to Milan is an approximately 26-hour flight. The time zone difference when traveling from Sydney to Milan is minus 9 hours. Traveling from Sydney in January, things will get much colder in Milan: highs are around 9°C and lows about 0°C. Finish your sightseeing early on the 4th (Sat) to allow enough time to drive to Venice.

Things to do in Milan

Side Trips

Highlights from your trip
Duomo di Milano ©
Must see
Duomo di Milano
4.8

5
nights
Venice

City of Romance

Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
For shopping fun, head to Piazza delle Erbe or Fondazione Bisazza. Let the collections at Doge's Palace and Peggy Guggenheim Collection capture your imagination. Get out of town with these interesting Venice side-trips: Arena di Verona (in Verona) and Padua (Scrovegni Chapel & Basilica of St. Anthony). The adventure continues: contemplate the waterfront views at Canal Grande, shop like a local with Segni nel Tempo antiquarian bookshop, admire the striking features of Basilica di San Marco, and take in the exciting artwork at Barovier & Toso.

To see where to stay, ratings, and other tourist information, you can read our Venice travel site.

Traveling by car from Milan to Venice takes 3 hours. Alternatively, you can take a train; or fly. In January, daytime highs in Venice are 9°C, while nighttime lows are 0°C. Finish your sightseeing early on the 9th (Thu) to allow enough time to drive to Cinque Terre.

Things to do in Venice

Side Trips

Highlights from your trip
Canal Grande ©
Must see
Canal Grande
4.8
Doge's Palace ©
Specialty Museum
Doge's Palace
4.7
Piazza San Marco ©
Historic Walking Area
Piazza San Marco
4.4

1
night
Cinque Terre

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Start off your visit on the 10th (Fri): contemplate in the serene atmosphere at Chiesa di San Lorenzo, then hike along Cinque Terre Trails, then trek along Footpath Monterosso - Vernazza, and finally take a stroll around Vernazza. Here are some ideas for day two: contemplate in the serene atmosphere at Chiesa Di San Pietro, explore the wealth of natural beauty at Parco Nazionale Cinque Terre, and then stop by Fannys Bazar.

To see where to stay, other places to visit, more things to do, and other tourist information, go to the Cinque Terre route planning tool.

Drive from Venice to Cinque Terre in 4.5 hours. Alternatively, you can take a train; or do a combination of bus and train. When traveling from Venice in January, plan for somewhat warmer days in Cinque Terre, with highs around 13°C, while nights are about the same with lows around 3°C. Finish up your sightseeing early on the 11th (Sat) so you can go by car to Florence.

Things to do in Cinque Terre

Parks · Nature · Historic Sites · Trails
Highlights from your trip
Cinque Terre Trails ©
Hiking Trail
Cinque Terre Trails
4.0

7
nights
Florence

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your inner history buff will appreciate Cathedral of Santa Maria del Fiore and The Baptistery of St. John. Florence Academy of Fine Arts and Ponte Vecchio are good opportunities to explore the local culture. Change things up with these side-trips from Florence: Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna (in Pratovecchio), Nature & Wildlife Tours (in Siena) and Castello del Trebbio (in Santa Brigida). There's much more to do: explore the world behind art at Pitti Palace, learn about winemaking at Ciacci Piccolomini d'Aragona, appreciate the views at Val d'Orcia, and appreciate the extensive heritage of Piazza della Signoria.

To find ratings, other places to visit, traveler tips, and other tourist information, use the Florence vacation planner.

You can drive from Cinque Terre to Florence in 2.5 hours. Alternatively, you can take a train. In January, daily temperatures in Florence can reach 13°C, while at night they dip to 3°C. Cap off your sightseeing on the 18th (Sat) early enough to catch the train to Rome.

Things to do in Florence

Museums · Wineries · Shopping · Parks

Side Trips

Highlights from your trip
Florence Academy of Fine Arts ©
World heritage site
Florence Academy of Fine Arts
4.4
Pitti Palace ©
World heritage site
Pitti Palace
4.4

7
nights
Rome

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Get some historical perspective at Colosseum and Pantheon. Get a sense of the local culture at St. Peter's Basilica and Vatican Museums. Next up on the itinerary: take an unorthodox tour of Catacombs of Saint Callixtus, steep yourself in history at Palatine Hill, take an in-depth tour of Musei Capitolini, and explore the world behind art at Galleria Borghese.

To see other places to visit, photos, ratings, and other tourist information, refer to the Rome online tour itinerary maker.

Traveling by train from Florence to Rome takes 2.5 hours. Alternatively, you can drive; or fly. In January, daytime highs in Rome are 15°C, while nighttime lows are 4°C. Cap off your sightseeing on the 25th (Sat) early enough to catch the train to Naples.

Things to do in Rome

Side Trip

Highlights from your trip
Vatican Museums
Must see
Vatican Museums
4.2
Pantheon ©
Must see
Pantheon
4.8

6
nights
Naples

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Do some cultural sightseeing at Pompeii Archaeological Park and Sol’Art Ceramiche. Museo Cappella Sansevero and Museo Archeologico Nazionale di Napoli will appeal to museum buffs. Venture out of the city with trips to Spiaggia Lannio (in Cetara), Vesuvio National Park (in Ottaviano) and Pompeii (Forum & Bosco de Medici Winery). The adventure continues: kick back and relax at Marina Di Vietri, pause for some serene contemplation at Cloister of Santa Chiara, stroll through Spiaggia di Marina d'Albori, and cool off at Lido Eureka.

For more things to do, reviews, where to stay, and other tourist information, go to the Naples online visit planner.

Getting from Rome to Naples by train takes about 2 hours. Other options: drive; or fly. Expect a daytime high around 15°C in January, and nighttime lows around 6°C. Wrap up your sightseeing on the 1st (Sat) early enough to drive to Positano.

Things to do in Naples

Historic Sites · Parks · Beaches · Outdoors

Side Trips

Highlights from your trip
Galleria Borbonica ©
Military Museum
Galleria Borbonica
4.8
Pompeii Archaeological Park ©
World heritage site
Pompeii Archaeological Park
4.6
Parco Acheologico di Ercolano ©
World heritage site
Parco Acheologico di Ercolano
4.6

3
nights
Positano

Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Kick off your visit on the 2nd (Sun): kick back and relax at Spiaggia Grande, take in the exciting artwork at Miniaci Art Gallery, kick back and relax at Fornillo, then contemplate in the serene atmosphere at Duomo di Sant'Andrea, and finally stop by Ceramiche Cosmolena di Margherita di Palma. Here are some ideas for day two: get engrossed in the history at MAR - Museo Archeologico Romano, kick back and relax at Bagni d'Arienzo Beach Club, Positano, then contemplate the long history of Duomo di Ravello, then admire the striking features of Villa Rufolo, and finally contemplate the long history of Villa Cimbrone Gardens.

To see more things to do, where to stay, ratings, and tourist information, go to the Positano trip maker website.

You can drive from Naples to Positano in 1.5 hours. Alternatively, you can take a bus. Traveling from Naples in February, you can expect nighttime temperatures to be somewhat warmer in Positano, with lows of 11°C. On the 4th (Tue), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Positano

Parks · Beaches · Outdoors · Historic Sites

Side Trips

Highlights from your trip
Duomo di Ravello ©
Religious Site
Duomo di Ravello
4.2
Duomo di Sant'Andrea ©
Religious Site
Duomo di Sant'Andrea
4.7

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