37 days in Italy Itinerary

37 days in Italy Itinerary

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Route & dates

37 days in Italy Itinerary

Start: Sydney
Fly:  25​h
1
Milan
— 3 nights
train:  2​h 30​min
2
Venice
— 5 nights
Drive:  4​h 15​min
3
Cinque Terre
— 1 night
Drive:  2​h 30​min
4
Florence
— 7 nights
train:  1​h 45​min
5
Rome
— 7 nights
train:  1​h 15​min
6
Naples
— 6 nights
bus:  1​h 30​min
7
Positano
— 3 nights
+3
ferry + foot + train + Fly:  28​h
End: Sydney

3
nights
Milan

Milan ©
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.
Duomo di Milano and Il Cenacolo will appeal to history buffs. Let the collections at Chiosco Villa Carlotta and Basilica di Sant'Ambrogio capture your imagination. Step out of Milan with an excursion to Sacro Monte di Ossuccio in Ossuccio--about 1h 25 min away. There's much more to do: admire the landmark architecture of Galleria Vittorio Emanuele II, admire the masterpieces at Pinacoteca Ambrosiana, appreciate the extensive heritage of Piazza del Duomo, and steep yourself in history at Chiesa di San Maurizio al Monastero Maggiore.

To see reviews, more things to do, where to stay, and more tourist information, read our Milan online sightseeing planner .

Sydney, Australia to Milan is an approximately 25-hour flight. You can also do a combination of flight and train; or do a combination of train and flight. You'll gain 9 hours traveling from Sydney to Milan due to the time zone difference. Plan for much colder temperatures traveling from Sydney in January, with highs in Milan at 9°C and lows at 0°C. Cap off your sightseeing on the 4th (Sat) early enough to catch the train to Venice.

Things to do in Milan

Historic Sites Museums Shopping

Side Trips

Sacro Monte di Ossuccio, Chiosco Villa Carlotta
Find places to stay Jan 1 — 4:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana
Sacro Monte di Ossuccio ©
Sacro Monte di Ossuccio

5
nights
Venice

Venice ©
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.
Piazza San Marco and Piazza delle Erbe are good opportunities to explore the local culture. Appreciate the collections at Doge's Palace and Gallerie dell'Accademia. Explore Venice's surroundings by going to Padua (Scrovegni Chapel & Basilica di Sant’Antonio), Fondazione Bisazza (in Montecchio Maggiore) and Arena di Verona (in Verona). There's lots more to do: take in the architecture and atmosphere at Basilica di San Marco, explore the activities along Canal Grande, shop like a local with Barovier & Toso, and view the masterpieces at Codex Art Gallery.

To find traveler tips, ratings, other places to visit, and other tourist information, read Venice tour website .

Getting from Milan to Venice by train takes about 2.5 hours. Other options: drive; or do a combination of flight and train. Expect a daytime high around 9°C in January, and nighttime lows around 0°C. Finish up your sightseeing early on the 9th (Thu) so you can go by car to Cinque Terre.

Things to do in Venice

Museums Historic Sites Shopping

Side Trips

Verona, Padua, Fondazione Bisazza
Find places to stay Jan 4 — 9:
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Piazza San Marco ©
Piazza San Marco

1
night
Cinque Terre

Cinque Terre ©
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): take in the spiritual surroundings of Chiesa di San Lorenzo, trek along Cinque Terre Trails, then trek along Footpath Monterosso - Vernazza, and finally get into the urban bustle at Vernazza. Here are some ideas for day two: take in the spiritual surroundings of Chiesa Di San Pietro, explore the wealth of natural beauty at Parco Nazionale Cinque Terre, and then stop by Fannys Bazar.

For other places to visit and tourist information, refer to the Cinque Terre online itinerary planner .

Getting from Venice to Cinque Terre by car takes about 4.5 hours. Other options: take a train; or take a bus. Traveling from Venice in January, you will find days in Cinque Terre are somewhat warmer (13°C), and nights are about the same (3°C). Cap off your sightseeing on the 11th (Sat) early enough to go by car to Florence.

Things to do in Cinque Terre

Parks Nature Historic Sites
Find places to stay Jan 9 — 11:
Highlights from your plan
Cinque Terre Trails ©
Cinque Terre Trails
Parco Nazionale Cinque Terre ©
Parco Nazionale Cinque Terre
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza

7
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get some cultural insight at Cathedral of Santa Maria del Fiore and Academy Of Florence Art Gallery. Appreciate the collections at Pitti Palace and Limbo Art Gallery. Change things up with these side-trips from Florence: Nature & Wildlife Tours (in Siena), Castello del Trebbio (in Santa Brigida) and Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna (in Pratovecchio). The adventure continues: view the masterpieces at M.G. Design, don't miss a visit to Piazzale Michelangelo, appreciate the extensive heritage of Piazza del Duomo, and contemplate in the serene atmosphere at The Baptistery of St. John.

To see reviews, other places to visit, where to stay, and more tourist information, you can read our Florence day trip planner .

You can drive from Cinque Terre to Florence in 2.5 hours. Another option is to take a train. January in Florence sees daily highs of 13°C and lows of 3°C at night. Cap off your sightseeing on the 18th (Sat) early enough to catch the train to Rome.

Things to do in Florence

Museums Wineries Shopping

Side Trips

Nature & Wildlife Tours, Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna, Ciacci Piccolomini d'Aragona, Guardastelle Vineyard, Val d'Orcia
Find places to stay Jan 11 — 18:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Cathedral of Santa Maria del Fiore ©
Pitti Palace ©
Pitti Palace

7
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Museum-lovers will get to explore Vatican Museums and Soqquadro APS. Escape the urban bustle at Catacombe di San Callisto and Colle del Gianicolo. And it doesn't end there: get to know the fascinating history of Piazza Navona, wander the streets of Trastevere, contemplate the long history of St. Peter's Basilica, and take in the architecture and atmosphere at Church of St. Louis of the French.

Plan trip to Rome with our itinerary maker to find out where to go and what to do.

Traveling by train from Florence to Rome takes 2 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

Museums Shopping Historic Sites

Side Trip

Vatican City
Find places to stay Jan 18 — 25:
Highlights from your plan
Piazza Navona ©
Piazza Navona
St. Peter's Basilica ©
St. Peter's Basilica
Vatican Museums
Vatican Museums

6
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Let the collections at Sol’Art Ceramiche and Ospedale delle Bambole capture your imagination. Pompeii Archaeological Park and Galleria Borbonica are good opportunities to explore the local culture. Change things up with these side-trips from Naples: Vesuvio National Park (in Ottaviano), Pompeii (Forum & Bosco de Medici Winery) and Spiaggia di Marina d'Albori (in Vietri sul Mare). The adventure continues: explore the world behind art at Museo Cappella Sansevero, take in the exciting artwork at Museodivino, take in the architecture and atmosphere at Duomo di Salerno, and get engrossed in the history at Museo e Real Bosco di Capodimonte.

To see ratings, maps, photos, and tourist information, you can read our Naples holiday planner .

Getting from Rome to Naples by train takes about 1.5 hours. Other options: drive; or take a bus. In January, daily temperatures in Naples can reach 15°C, while at night they dip to 6°C. Cap off your sightseeing on the 1st (Sat) early enough to catcht the bus to Positano.

Things to do in Naples

Historic Sites Parks Beaches

Side Trips

Salerno, Pompeii, Vietri sul Mare, Spiaggia Lannio, Marina Grande Public Beach
Find places to stay Jan 25 — Feb 1:
Highlights from your plan
Sol’Art Ceramiche ©
Sol’Art Ceramiche
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Museo Cappella Sansevero ©
Museo Cappella Sansevero

3
nights
Positano

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.
On the 2nd (Sun), kick back and relax at Spiaggia Grande, get a taste of the local shopping with Miniaci Art Gallery, then kick back and relax at Fornillo, then take in the spiritual surroundings of Duomo di Sant'Andrea, and finally get a taste of the local shopping with Ceramiche Cosmolena di Margherita di Palma. Here are some ideas for day two: take an in-depth tour of MAR - Museo Archeologico Romano, stroll through Bagni d'Arienzo Beach Club, Positano, steep yourself in history at Duomo di Ravello, then admire the landmark architecture of Villa Rufolo, and finally steep yourself in history at Villa Cimbrone Gardens.

For maps, where to stay, and more tourist information, refer to the Positano online vacation builder .

Traveling by bus from Naples to Positano takes 1.5 hours. Alternatively, you can drive; or do a combination of subway and bus. Traveling from Naples in February, Positano is a bit warmer at night with lows of 11°C. Wrap up your sightseeing by early afternoon on the 4th (Tue) to allow enough time to travel back home.

Things to do in Positano

Parks Beaches Outdoors

Side Trips

Ravello, Amalfi
Find places to stay Feb 1 — 4:
Highlights from your plan
Fornillo ©
Fornillo
Duomo di Ravello ©
Duomo di Ravello
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea

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