55 days in Italy Itinerary

Created using Inspirock Italy trip planner
Make it your trip
Fly
1
Milan
Train
2
Genoa
— 3 nights
Drive
3
Florence
— 1 night
Drive
4
Pisa
— 2 nights
Drive
5
Lucca
— 1 day
Drive
6
Pisa
— 1 night
Drive
7
Volterra
Drive
8
San Gimignano
— 1 day
Drive
9
Castellina In Chianti
— 1 night
Drive
10
Greve in Chianti
— 1 night
Drive
11
Radda in Chianti
— 1 night
Drive
12
Gaiole in Chianti
— 1 night
Drive
13
Siena
— 27 nights
Train
14
Rome
— 12 nights
Fly

S M T W T F S
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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.
Kick off your visit on the 18th (Sun): browse the exhibits of Basilica di Sant'Ambrogio.

For ratings, where to stay, and other tourist information, you can read our Milan day trip planner.

Singapore, Singapore to Milan is an approximately 15-hour flight. The time zone difference when traveling from Singapore to Milan is minus 7 hours. Prepare for colder weather when traveling from Singapore in December: high temperatures in Milan hover around 9°C and lows are around 1°C. Wrap up your sightseeing by early afternoon on the 18th (Sun) to allow time for the car ride to Genoa.
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Historic Sites · Museums
Highlights from your trip

Genoa — 3 nights

Once the most important harbor in the Mediterranean Sea, Genoa has a long history as a rich and powerful trade center in northern Italy.
Genoa is known for zoos & aquariums, historic sites, and sightseeing. Your trip includes some of its best attractions: contemplate in the serene atmosphere at Cattedrale di San Lorenzo - Duomo di Genova, take in the waterfront at Old Port, make a trip to Piazza De Ferrari, and examine the collection at Galata Museo del Mare.

For traveler tips, more things to do, where to stay, and tourist information, read our Genoa trip planner.

Traveling by car from Milan to Genoa takes 2 hours. Alternatively, you can take a train. In December, Genoa is somewhat warmer than Milan - with highs of 16°C and lows of 10°C. On the 21st (Wed), you'll travel to Florence.
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Museums · Historic Sites

Florence — 1 night

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 22nd (Thu), admire the masterpieces at Florence Academy of Fine Arts, don't miss a visit to Piazzale Michelangelo, take in the views from Ponte Vecchio, appreciate the extensive heritage of Piazza del Duomo, then take in the architecture and atmosphere at Cathedral of Santa Maria del Fiore, and finally enjoy breathtaking views from Campanile di Giotto.

To find ratings, where to stay, and more tourist information, you can read our Florence driving holiday planner.

Getting from Genoa to Florence by car takes about 2.5 hours. Other options: take a train; or take a bus. Plan for a bit cooler nights when traveling from Genoa in December since evenings lows in Florence dip to 4°C. Finish up your sightseeing early on the 22nd (Thu) so you can go by car to Pisa.
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Historic Sites · Museums

Pisa — 2 nights

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Kick off your visit on the 23rd (Fri): examine the collection at Museo Aviotruppe Esercito Italiano, then don't miss a visit to Murale Tuttomondo di Keith Haring, then see the interesting displays at Palazzo Blu, and finally contemplate in the serene atmosphere at Chiesa di Santa Maria della Spina. Here are some ideas for day two: take in the architecture and atmosphere at San Piero a Grado, take in the architecture and atmosphere at Santuario di Montenero, then get up close and personal with brilliant marine life at Acquario di Livorno, and finally don't miss a visit to Terrazza Mascagni.

For where to stay, reviews, traveler tips, and more tourist information, read Pisa travel route builder app.

You can drive from Florence to Pisa in 1.5 hours. Alternatively, you can take a bus; or take a train. In December, plan for daily highs up to 15°C, and evening lows to 4°C. Cap off your sightseeing on the 24th (Sat) early enough to go by car to Lucca.
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Historic Sites · Museums · Zoos & Aquariums · Parks
Side Trip

Lucca — 1 day

City of a Hundred Churches

Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Kick off your visit on the 25th (Sun): contemplate in the serene atmosphere at San Michele in Foro, admire the landmark architecture of St Martin Cathedral, enjoy breathtaking views from Torre Guinigi, then take in nature's colorful creations at Palazzo Pfanner, then don't miss a visit to Via Fillungo, and finally contemplate the long history of Le mura di Lucca.

To see traveler tips, ratings, reviews, and tourist information, read Lucca holiday planner.

Lucca is very close to Pisa. In December in Lucca, expect temperatures between 15°C during the day and 4°C at night. Finish your sightseeing early on the 25th (Sun) so you can drive to Pisa.
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Historic Sites · Parks

Pisa — 1 night

Start off your visit on the 26th (Mon): take in the spiritual surroundings of Battistero di San Giovanni, steep yourself in history at Camposanto, take in the spiritual surroundings of Duomo di Pisa, make a trip to Piazza dei Miracoli, then make a trip to Leaning Tower of Pisa, and finally steep yourself in history at Palazzo dell'Orologio.

To see traveler tips, where to stay, reviews, and tourist information, go to the Pisa tour itinerary builder.

Pisa is very close to Lucca. Wrap up your sightseeing on the 26th (Mon) early enough to drive to Volterra.
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Historic Sites

Volterra

Volterra is a walled mountaintop town in the Tuscany region of Italy of which its history dates to before the 7th century BC and has substantial structures from the Etruscan, Roman, and Medieval periods.HistoryVolterra, known to the ancient Etruscans as Velathri or Vlathri and to the Romans as Volaterrae, is a town and comune in the Tuscany region of Italy. To plan Volterra vacation without wasting time, ask Inspirock to design an itinerary.

You can drive from Pisa to Volterra in 1.5 hours. Another option is to take a bus. In December, daily temperatures in Volterra can reach 15°C, while at night they dip to 4°C. You will leave for San Gimignano on the 26th (Mon).
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Outdoors · Historic Sites · Parks · Tours

San Gimignano — 1 day

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
To find photos, maps, more things to do, and tourist information, use the San Gimignano trip planner.

Traveling by car from Volterra to San Gimignano takes an hour. December in San Gimignano sees daily highs of 15°C and lows of 4°C at night. You will leave for Castellina In Chianti on the 27th (Tue).
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Historic Sites · Wineries · Tours · Outdoors

Castellina In Chianti — 1 night

Castellina in Chianti is a comune (municipality) of c. Start off your visit on the 27th (Tue): look for gifts at Enoteca le Volte, explore the ancient world of Tombe Etrusche a Montecalvario, learn about winemaking at Poggio Amorelli, then don't miss a visit to Via delle Volte, and finally appreciate the extensive heritage of Centro Storico.

For ratings, traveler tips, other places to visit, and tourist information, go to the Castellina In Chianti trip planner.

Traveling by car from San Gimignano to Castellina In Chianti takes an hour. Alternatively, you can do a combination of train and bus; or take a bus. In December, daytime highs in Castellina In Chianti are 15°C, while nighttime lows are 4°C. Wrap up your sightseeing on the 28th (Wed) early enough to drive to Greve in Chianti.
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Historic Sites · Wineries · Shopping

Greve in Chianti — 1 night

Kick off your visit on the 28th (Wed): learn about winemaking at Cantina Antinori, then indulge your senses at Azienda Agricola Brogioni Maurizio, then step into the grandiose world of Castello di Verrazzano, and finally learn about winemaking at Enoteca Falorni.

For where to stay, ratings, and other tourist information, refer to the Greve in Chianti day trip planner.

Greve in Chianti is just a short distance from Castellina In Chianti. In December, daily temperatures in Greve in Chianti can reach 15°C, while at night they dip to 4°C. Finish your sightseeing early on the 29th (Thu) to allow enough time to drive to Radda in Chianti.
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Wineries · Historic Sites · Tours
Side Trip

Radda in Chianti — 1 night

Start off your visit on the 29th (Thu): do a tasting at Fattoria di Montemaggio, then do a tasting at Castello Monterinaldi, then learn about winemaking at La Cantina di Casalvento, and finally get great views at Volpaia.

To find traveler tips, photos, ratings, and other tourist information, go to the Radda in Chianti vacation tool.

Radda in Chianti is just a stone's throw from Greve in Chianti. In December, daily temperatures in Radda in Chianti can reach 14°C, while at night they dip to 2°C. Finish up your sightseeing early on the 30th (Fri) so you can go by car to Gaiole in Chianti.
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Wineries · Historic Sites

Gaiole in Chianti — 1 night

Gaiole in Chianti is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 40km southeast of Florence and about 15km northeast of Siena. On the 30th (Fri), do a tasting at Cantalici Winery, then do a tasting at Barone Ricasoli, then indulge your taste buds at Castello di Brolio, and finally do a tasting at I Sodi.

To see traveler tips, other places to visit, reviews, and other tourist information, read our Gaiole in Chianti itinerary planner.

Gaiole in Chianti is just a stone's throw from Radda in Chianti. Finish your sightseeing early on the 31st (Sat) so you can drive to Siena.
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Wineries · Historic Sites · Parks

Siena — 27 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Get out of town with these interesting Siena side-trips: Assisi (Palazzo Bonacquisti, Santa Maria sopra Minerva, &more), Gubbio (Palazzo dei Consoli and Museo Civico & Piazza Grande) and Spello (Torre di San Severino & Arco Romano). There's still lots to do: see the interesting displays at Museo della Porziuncola, steep yourself in history at Eremo Le Celle, admire the masterpieces at Studio Moretti Caselli, and do a tasting at Mate Winery.

To see reviews, other places to visit, traveler tips, and other tourist information, you can read our Siena online trip builder.

Traveling by car from Gaiole in Chianti to Siena takes an hour. Alternatively, you can take a bus. In December in Siena, expect temperatures between 16°C during the day and 5°C at night. Finish your sightseeing early on the 27th (Fri) so you can drive to Rome.
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Historic Sites · Museums · Wineries · Tours
Side Trips

Rome — 12 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Explore Rome's surroundings by going to Tivoli (Villa Adriana, Villa d'Este, &more). There's still lots to do: pause for some serene contemplation at St. Peter's Basilica, take a stroll through Trastevere, admire the local landmark of Trevi Fountain, and delve into the distant past at Colosseum.

For ratings, traveler tips, where to stay, and other tourist information, go to the Rome road trip planning tool.

Traveling by car from Siena to Rome takes 2.5 hours. Alternatively, you can take a bus; or take a train. In January, plan for daily highs up to 15°C, and evening lows to 4°C. Finish up your sightseeing early on the 8th (Wed) so you can catch the flight back home.
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Historic Sites · Museums · Neighborhoods · Tours
Side Trips

Italy travel guide

4.6
Landmarks · Ruins · Beaches
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.
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