33 days in Italy Itinerary
Created using Inspirock Europe travel route maker
Start: Singapore
Fly
1
Milan
Drive
2
Como
— 2 nights
Fly
3
Naples
— 3 nights
Train
4
Florence
— 2 nights
Drive
5
Castellina In Chianti
— 2 nights
6
Castellina In Chianti
— 2 nights
Drive
7
Gaiole in Chianti
— 2 nights
Drive
8
Radda in Chianti
— 2 nights
Drive
9
Greve in Chianti
— 2 nights
Drive
10
Venice
— 2 nights
Fly
11
Ravello
— 2 nights
Taxi to Salerno, Train to Verona
12
Verona
— 1 night
Train
13
Turin
— 1 night
Fly
14
Salerno
— 4 nights
Drive
15
Rome
— 4 nights
Fly
End: Singapore
Sat, Dec 17 - Wed, Jan 18
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View full calendar
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.To see photos, traveler tips, where to stay, and tourist information, go to the Milan tour itinerary planner.
Singapore, Singapore to Milan is an approximately 15-hour flight. You'll gain 7 hours traveling from Singapore to Milan due to the time zone difference. Plan for cooler temperatures traveling from Singapore in December, with highs in Milan at 9°C and lows at 1°C. You'll set off for Como on the 18th (Sun).
Find places to stay Dec 17 — 18:
Como — 2 nights
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City of Silk
Known for its idyllic location on the shores of Lake Como and at the foot of the Alps, Como is one of northern Italy's most popular tourist destinations.On the 18th (Sun), take in the pleasant sights at Centro Storico, pause for some serene contemplation at Cathedral of Como (Duomo), then take a stroll around Broletto, and finally appreciate the history behind Life Electric. Here are some ideas for day two: explore the activities along Lago di Como, then take in the spiritual surroundings of Chiesa di S. Carlo, and then make a trip to Faro voltiano.
To see other places to visit, photos, more things to do, and other tourist information, go to the Como driving holiday planner.
Getting from Milan to Como by car takes about an hour. Other options: take a train; or take a bus. December in Como sees daily highs of 8°C and lows of -1°C at night. Finish your sightseeing early on the 20th (Tue) so you can fly to Naples.
Side Trips
Find places to stay Dec 18 — 20:
Highlights from your trip
Naples — 3 nights
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Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Naples is known for museums, historic sites, and sightseeing. Your trip includes some of its best attractions: steep yourself in history at Pompeii Archaeological Park, take in the architecture and atmosphere at Cloister of Santa Chiara, examine the collection at Museo Archeologico Nazionale di Napoli, and explore the galleries of Chiesa Museo di Santa Luciella ai Librai.
To see other places to visit, maps, where to stay, and other tourist information, you can read our Naples visit planner.
You can fly from Como to Naples in 3 hours. Other options are to take a train; or drive. Traveling from Como in December, expect Naples to be somewhat warmer, temps between 17°C and 6°C. Finish your sightseeing early on the 23rd (Fri) so you can take a train to Florence.
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To see other places to visit, maps, where to stay, and other tourist information, you can read our Naples visit planner.
You can fly from Como to Naples in 3 hours. Other options are to take a train; or drive. Traveling from Como in December, expect Naples to be somewhat warmer, temps between 17°C and 6°C. Finish your sightseeing early on the 23rd (Fri) so you can take a train to Florence.
Side Trips
Find places to stay Dec 20 — 23:
Florence — 2 nights
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Birthplace of the Italian Renaissance
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.On the 23rd (Fri), don't miss a visit to Mercato Centrale, pick up some local products at La Bottega del Produttore, explore the world behind art at Florence Academy of Fine Arts, then admire the masterpieces at Pitti Palace, then make a trip to Piazzale Michelangelo, and finally snap pictures at Ponte Vecchio. Here are some ideas for day two: pause for some photo ops at Loggia dei Lanzi, take in the architecture and atmosphere at Basilica of Santa Croce, enjoy breathtaking views from Campanile di Giotto, steep yourself in history at Cathedral of Santa Maria del Fiore, then appreciate the extensive heritage of Piazza del Duomo, and finally ponder the world of politics at Palazzo Vecchio.
To see maps, photos, and more tourist information, you can read our Florence sightseeing tool.
You can take a train from Naples to Florence in 3 hours. Alternatively, you can do a combination of train and flight; or drive. In December, plan for daily highs up to 15°C, and evening lows to 4°C. Cap off your sightseeing on the 25th (Sun) early enough to go by car to Castellina In Chianti.
Find places to stay Dec 23 — 25:
Highlights from your trip
Castellina In Chianti — 2 nights
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Castellina in Chianti is a comune (municipality) of c. Kick off your visit on the 25th (Sun): learn about winemaking at La Castellina, look for gifts at Emporio Chianti, learn about winemaking at Marchesi Mazzei, then appreciate the extensive heritage of Centro storico di Monteriggioni, and finally explore the historical opulence of La Rocca di Staggia. Get ready for a full day of sightseeing on the next day: learn about winemaking at Azienda Agricola Casa Emma, then learn about winemaking at Corbucci, then take an in-depth tour of Casa di Boccaccio, and finally take in the architecture and atmosphere at Chiesa dei Santissimi Jacopo e Filippo.
For more things to do, ratings, and other tourist information, go to the Castellina In Chianti trip planner.
You can drive from Florence to Castellina In Chianti in an hour. Other options are to drive; or do a combination of train and taxi. December in Castellina In Chianti sees daily highs of 15°C and lows of 4°C at night. Finish your sightseeing early on the 27th (Tue) to allow enough time to travel to Castellina In Chianti.
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For more things to do, ratings, and other tourist information, go to the Castellina In Chianti trip planner.
You can drive from Florence to Castellina In Chianti in an hour. Other options are to drive; or do a combination of train and taxi. December in Castellina In Chianti sees daily highs of 15°C and lows of 4°C at night. Finish your sightseeing early on the 27th (Tue) to allow enough time to travel to Castellina In Chianti.
Side Trips
Certaldo, Corbucci, Centro storico di Monteriggioni, La Rocca di Staggia, Azienda Agricola Casa Emma
Find places to stay Dec 25 — 27:
Highlights from your trip
Castellina In Chianti — 2 nights
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Start off your visit on the 27th (Tue): do a tasting at Sant'Agnese Farm, look for gifts at Enoteca le Volte, then make a trip to Via delle Volte, then do a tasting at Poggio Amorelli, and finally delve into the distant past at Tombe Etrusche a Montecalvario. Get ready for a full day of sightseeing on the next day: see the interesting displays at Palazzo Pretorio - Comune di Certaldo, enjoy unforgettable views with a balloon tour, and then do a tasting at Poggio al Bosco.
For maps, reviews, more things to do, and other tourist information, read Castellina In Chianti travel planning app.
Finish your sightseeing early on the 29th (Thu) to allow enough time to drive to Gaiole in Chianti.
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For maps, reviews, more things to do, and other tourist information, read Castellina In Chianti travel planning app.
Finish your sightseeing early on the 29th (Thu) to allow enough time to drive to Gaiole in Chianti.
Side Trips
Find places to stay Dec 27 — 29:
Highlights from your trip
Gaiole in Chianti — 2 nights
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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. Start off your visit on the 29th (Thu): pause for some serene contemplation at Pieve di Sant'Andreino alle Cave, relax and rejuvenate at some of the best spas, appreciate the extensive heritage of Borgo di San Gusme, then take in nature's colorful creations at Castello di Brolio, and finally do a tasting at Barone Ricasoli. Get ready for a full day of sightseeing on the 30th (Fri): learn about winemaking at Cantalici Winery, learn about winemaking at I Sodi, then contemplate in the serene atmosphere at Abbazia di Monte Oliveto Maggiore, and finally take in the architecture and atmosphere at Cappella dei Santi Fabiano e Sebastiano.
To see photos, ratings, traveler tips, and tourist information, read Gaiole in Chianti trip itinerary planner.
Traveling by car from Castellina In Chianti to Gaiole in Chianti takes an hour. Wrap up your sightseeing on the 31st (Sat) early enough to drive to Radda in Chianti.
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To see photos, ratings, traveler tips, and tourist information, read Gaiole in Chianti trip itinerary planner.
Traveling by car from Castellina In Chianti to Gaiole in Chianti takes an hour. Wrap up your sightseeing on the 31st (Sat) early enough to drive to Radda in Chianti.
Side Trips
Find places to stay Dec 29 — 31:
Highlights from your trip
Radda in Chianti — 2 nights
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On the 31st (Sat), do a tasting at Fattoria di Montemaggio, do a tasting at La Cantina di Casalvento, then experience rural life at Pornanino, and finally do a tasting at Brancaia. Get ready for a full day of sightseeing on the next day: get to know the fascinating history of Centro Storico, do a tasting at Castello San Donato in Perano, then indulge in some personalized pampering at Spa Vignavecchia, and finally sample the tasty concoctions at Chianti Brew Fighters.
To see maps, other places to visit, ratings, and other tourist information, go to the Radda in Chianti online trip itinerary builder.
Radda in Chianti is very close to Gaiole in Chianti. Expect a daytime high around 14°C in December, and nighttime lows around 2°C. Wrap up your sightseeing on the 2nd (Mon) early enough to drive to Greve in Chianti.
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To see maps, other places to visit, ratings, and other tourist information, go to the Radda in Chianti online trip itinerary builder.
Radda in Chianti is very close to Gaiole in Chianti. Expect a daytime high around 14°C in December, and nighttime lows around 2°C. Wrap up your sightseeing on the 2nd (Mon) early enough to drive to Greve in Chianti.
Find places to stay Dec 31 — Jan 2:
Highlights from your trip
Greve in Chianti — 2 nights
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Start off your visit on the 2nd (Mon): explore the historical opulence of Castello di Verrazzano, buy something for everyone on your list at The Mall, and then do a tasting at Enoteca Falorni. Keep things going the next day: learn about winemaking at Cantina Antinori, do a tasting at Montefioralle Winery, then do a tasting at Accademia del Buon Gusto, then don't miss a visit to Piazza Matteotti, and finally look for gifts at Piccole Armonie Country.
For where to stay, reviews, photos, and more tourist information, use the Greve in Chianti trip planner.
Greve in Chianti is just a short distance from Radda in Chianti. In January in Greve in Chianti, expect temperatures between 13°C during the day and 3°C at night. Finish your sightseeing early on the 4th (Wed) so you can drive to Venice.
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For where to stay, reviews, photos, and more tourist information, use the Greve in Chianti trip planner.
Greve in Chianti is just a short distance from Radda in Chianti. In January in Greve in Chianti, expect temperatures between 13°C during the day and 3°C at night. Finish your sightseeing early on the 4th (Wed) so you can drive to Venice.
Side Trips
Find places to stay Jan 2 — 4:
Highlights from your trip
Venice — 2 nights
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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.Kick off your visit on the 4th (Wed): admire the masterpieces at Peggy Guggenheim Collection, admire the landmark architecture of Doge's Palace, then contemplate the waterfront views at Canal Grande, and finally steep yourself in history at Squero di San Trovaso. Get ready for a full day of sightseeing on the next day: admire the masterpieces at Ca' d'Oro, make a trip to Piazza San Marco, contemplate the long history of Ponte dei Sospiri, then admire the striking features of Basilica di San Marco, then take in the views from Ponte di Rialto, and finally don't miss a visit to Basilica dei Santi Giovanni e Paolo (San Zanipolo).
To see reviews, ratings, and other tourist information, use the Venice online trip itinerary maker.
You can drive from Greve in Chianti to Venice in 3 hours. Another option is to do a combination of bus and train. In January, Venice is slightly colder than Greve in Chianti - with highs of 9°C and lows of 0°C. Finish your sightseeing early on the 6th (Fri) to allow enough time to fly to Ravello.
Find places to stay Jan 4 — 6:
Highlights from your trip
Ravello — 2 nights
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Best known for its celebrated terraced gardens, Ravello is a hidden gem of Italy's Amalfi Coast.Start off your visit on the 6th (Fri): take in the exciting artwork at Ceramiche Cosmolena di Margherita di Palma, see the interesting displays at Museo della Carta, pause for some serene contemplation at Duomo di Sant'Andrea, then take in the spiritual surroundings of Cloister del Paradiso, then admire the natural beauty at Villa Cimbrone Gardens, and finally steep yourself in history at Duomo di Ravello. Get ready for a full day of sightseeing on the 7th (Sat): take in the architecture and atmosphere at Convento Frati Minori Conventuali S.Francesco, don't miss a visit to Villa Rufolo, pause for some serene contemplation at Cappella Sant'Angelo all'Ospedale, then get great views at Chiesa Dell'Annunziata, then take in the dramatic scenery at Valle delle Ferriere, and finally contemplate in the serene atmosphere at Parrocchia San Giovanni.
To find other places to visit, ratings, traveler tips, and tourist information, use the Ravello trip itinerary site.
Fly from Venice to Ravello in 3 hours. Alternatively, you can do a combination of train and taxi; or drive. Traveling from Venice in January, things will get a bit warmer in Ravello: highs are around 15°C and lows about 10°C. Finish up your sightseeing early on the 8th (Sun) so you can travel to Verona.
Side Trips
Find places to stay Jan 6 — 8:
Highlights from your trip
Verona — 1 night
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City of Romeo and Juliet
The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.Start off your visit on the 8th (Sun): wander the streets of Piazza delle Erbe, make a trip to Torre dei Lamberti, see the interesting displays at Casa di Giulietta, look for gifts at GIULIETTAVERONA, then steep yourself in history at Museo di Castelvecchio, and finally contemplate in the serene atmosphere at Basilica di San Zeno Maggiore.
To find more things to do, photos, traveler tips, and more tourist information, go to the Verona trip tool.
Traveling by combination of taxi and train from Ravello to Verona takes 6 hours. Alternatively, you can drive; or do a combination of bus, train, and flight. Wrap up your sightseeing on the 9th (Mon) to allow time to take a train to Turin.
Find places to stay Jan 8 — 9:
Highlights from your trip
Turin — 1 night
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City of Magic
A city of technology and industry, Turin is in northwestern Italy, a one-hour drive from the French border and slightly more than that from the Mediterranean Sea.On the 9th (Mon), take in the architecture and atmosphere at Basilica di Superga, then examine the collection at Museo Nazionale del Cinema, then make a trip to Piazza Castello, and finally make a trip to Piazza San Carlo. On the next day, test your problem-solving skills at popular escape rooms, stroll around Parco del Valentino, and then explore the world behind art at Museo Egizio.
For where to stay, traveler tips, more things to do, and other tourist information, use the Turin trip planning app.
Take a train from Verona to Turin in 3 hours. Alternatively, you can drive; or take a bus. In January, daily temperatures in Turin can reach 6°C, while at night they dip to 1°C. Finish up your sightseeing early on the 10th (Tue) so you can catch the flight to Salerno.
Find places to stay Jan 9 — 10:
Highlights from your trip
Salerno — 4 nights
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Unspoilt Gem of the Amalfi Coast
While often overshadowed by the Amalfi Coast's array of quaint villages, Salerno has become one of the region's main areas for culture and entertainment, while remaining relatively unmarked by tourism.Salerno is known for sightseeing, historic sites, and parks. Your trip includes some of its best attractions: take in nature's colorful creations at Villa Comunale, ponder the world of politics at Palazzo d'Avossa, make a trip to Chiesa di San Giorgio, and pause for some serene contemplation at Duomo di Salerno.
To find photos, where to stay, other places to visit, and more tourist information, read Salerno attractions planner.
You can fly from Turin to Salerno in 3 hours. Alternatively, you can take a train; or drive. Plan for somewhat warmer temperatures traveling from Turin in January, with highs in Salerno at 15°C and lows at 10°C. Finish your sightseeing early on the 14th (Sat) so you can drive to Rome.
Side Trip
Find places to stay Jan 10 — 14:
Highlights from your trip
Rome — 4 nights
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Eternal City
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.Rome is known for historic sites, sightseeing, and nightlife. Your trip includes some of its best attractions: steep yourself in history at St. Peter's Basilica, don't miss a visit to Spanish Steps, take in the architecture and atmosphere at Church of St. Louis of the French, and admire the masterpieces at Vatican Museums.
For maps, more things to do, where to stay, and tourist information, read Rome road trip tool.
You can drive from Salerno to Rome in 3 hours. Alternatively, you can take a train; or take a bus. Traveling from Salerno in January, expect a bit cooler with lows of 4°C in Rome. Cap off your sightseeing on the 18th (Wed) early enough to catch the flight back home.
Side Trip
Find places to stay Jan 14 — 18:
Highlights from your trip
Italy travel guide
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.
Amalfi Coast travel guide
Renowned for its beautiful landscape and medieval fishing villages that cling precariously to the Mediterranean cliffs, the Amalfi Coast is one of Italy's top vacation destinations. This World Heritage Site stretches for about 50 km (30 mi) on the southern side of the Sorrentine peninsula and offers numerous places to visit, from terraced lemon gardens and whitewashed villas to cliff-top views of the sea. Explore the coastline's towns, bays, and resorts. During the peak tourist season, the Amalfi Coast's single seaside road is often jammed with dozens of buses. For that reason, the ubiquitous scooter may be the best way to get around and sightsee. You can also access quite a bit by bicycle.
