55 days in Italy & San Marino Itinerary

55 days in Italy & San Marino Itinerary

Created using Inspirock Europe holiday planner
Make it your trip
Fly
1
Milan, Italy
— 5 nights
Drive
2
Verona, Italy
— 5 nights
Drive
3
Venice, Italy
— 7 nights
Drive
4
Bologna, Italy
— 5 nights
Drive
5
City of San Marino, San Marino
— 6 nights
Drive
6
Florence, Italy
— 6 nights
Train
7
Rome, Italy
— 8 nights
Train
8
Naples, Italy
— 6 nights
Fly
9
Turin, Italy
— 6 nights
Fly

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Milan, Italy — 5 nights

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.
Venture out of the city with trips to Santuary of Our Lady of Miracles (in Saronno), Como (Life Electric & Cathedral of Como (Duomo)) and Vincenzo casillo atelier (in Fino Mornasco). The adventure continues: take in the spiritual surroundings of Duomo di Milano, step into the grandiose world of Castello Sforzesco, explore the different monuments and memorials at Monumental Cemetery, and make a trip to Dialogo nel Buio.

To find traveler tips, more things to do, photos, and more tourist information, use the Milan trip planner.

Toronto, Canada to Milan is an approximately 11.5-hour flight. You'll lose 6 hours traveling from Toronto to Milan due to the time zone difference. Expect somewhat warmer temperatures when traveling from Toronto in January; daily highs in Milan reach 9°C and lows reach 0°C. Finish your sightseeing early on the 10th (Tue) so you can drive to Verona.
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Historic Sites · Museums · Shopping · Spas
Side Trips
Find places to stay Jan 5 — 10:

Verona, Italy — 5 nights

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.
Get out of town with these interesting Verona side-trips: Andalo (Scuola Italiana di Sci & Snowboard Kristal & Paganella), A&A Alpaca (in Monteviale) and Martist di Maurizio Boscheri (in Rovereto). Next up on the itinerary: listen to music at Arena di Verona, stop by Federica Casanova, make a trip to Piazza Bra, and take in the spiritual surroundings of Basilica di San Zeno Maggiore.

For photos, where to stay, more things to do, and tourist information, refer to the Verona vacation app.

You can drive from Milan to Verona in 2 hours. Another option is to take a train. Cap off your sightseeing on the 15th (Sun) early enough to go by car to Venice.
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Side Trips
Find places to stay Jan 10 — 15:

Venice, Italy — 7 nights

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.
Explore Venice's surroundings by going to Padua (Musei Civici Agli Eremitani, Room Escape Games, &more) and HaloWellness (in Vigonza). There's still lots to do: contemplate the waterfront views at Canal Grande, admire the masterpieces at Gallerie dell'Accademia, explore the galleries of Doge's Palace, and contemplate the long history of Peggy Guggenheim Collection.

To see reviews, other places to visit, maps, and other tourist information, use the Venice trip itinerary planner.

You can drive from Verona to Venice in 1.5 hours. Other options are to take a shuttle; or take a train. In January, daytime highs in Venice are 9°C, while nighttime lows are 0°C. Finish up your sightseeing early on the 22nd (Sun) so you can go by car to Bologna.
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Historic Sites · Museums · Childrens Museums · Tours
Side Trips
Find places to stay Jan 15 — 22:

Bologna, Italy — 5 nights

Heart of Italian Cuisine

A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Get out of town with these interesting Bologna side-trips: Ferrara (Ferrara Cathedral, Palazzo Schifanoia (Palazzo della Gioia) - World Heritage Site, &more), Ravenna (Battistero Neoniano (Battistero degli Ortodossi), Basilica di San Vitale, &more) and Modena (Acetaia Villa San Donnino & Acetaia Giuseppe Giusti). And it doesn't end there: make a trip to Le Due Torri Torre degli Asinell, admire the masterpieces at La Quadreria - Palazzo Rossi Poggi Marsili, take in the architecture and atmosphere at Basilica di San Petronio, and stop by Consorzio Vacche Rosse.

To see reviews, ratings, more things to do, and more tourist information, use the Bologna day trip site.

You can drive from Venice to Bologna in 2 hours. Alternatively, you can take a train. In January, daytime highs in Bologna are 9°C, while nighttime lows are 0°C. Cap off your sightseeing on the 27th (Fri) early enough to go by car to City of San Marino.
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Historic Sites · Museums · Breweries & Distilleries · Spas
Side Trips
Find places to stay Jan 22 — 27:

City of San Marino, San Marino — 6 nights

The capital of one of the world's smallest and oldest republics, the hillside city of San Marino boasts a World Heritage-listed old town that's known for its winding cobblestone streets and sweeping views of the surrounding countryside.
Pack the 31st (Tue) with family-friendly diversions at San Marino Adventures. There's still lots to do: make a trip to Montale Tower, take in the architecture and atmosphere at Basilica del Santo Marino, get a sense of history and politics at Palazzo Pubblico, and have fun and explore at Titanus Museum.

For reviews, other places to visit, more things to do, and more tourist information, you can read our City of San Marino sightseeing planning site.

Drive from Bologna to City of San Marino in 1.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. Expect a daytime high around 8°C in January, and nighttime lows around 3°C. Wrap up your sightseeing on the 2nd (Thu) to allow time to drive to Florence.
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Museums · Theme Parks · Historic Sites · Shopping
Side Trips
Find places to stay Jan 27 — Feb 2:

Florence, Italy — 6 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Venture out of the city with trips to Siena (Pinacoteca Nazionale, Piazza del Campo, &more). And it doesn't end there: admire the masterpieces at Florence Academy of Fine Arts, contemplate the long history of Basilica of Santa Croce, pause for some serene contemplation at Cathedral of Santa Maria del Fiore, and pause for some photo ops at Campanile di Giotto.

For photos, where to stay, maps, and tourist information, read Florence route builder site.

Traveling by car from City of San Marino to Florence takes 2.5 hours. Alternatively, you can do a combination of bus and train; or do a combination of bus and shuttle. Traveling from City of San Marino in February, expect nights in Florence to be about the same, around 5°C, while days are a bit warmer, around 14°C. Wrap up your sightseeing on the 8th (Wed) to allow time to take a train to Rome.
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Side Trip
Find places to stay Feb 2 — 8:

Rome, Italy — 8 nights

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: take in the architecture and atmosphere at St. Peter's Basilica, admire the local landmark of Trevi Fountain, take in the spiritual surroundings of Cupola di San Pietro, and explore the world behind art at Galleria Borghese.

To find traveler tips and more tourist information, refer to the Rome day trip planning site.

Traveling by train from Florence to Rome takes 2.5 hours. Alternatively, you can fly; or drive. February in Rome sees daily highs of 16°C and lows of 5°C at night. Wrap up your sightseeing on the 16th (Thu) early enough to take a train to Naples.
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Historic Sites · Museums · Neighborhoods · Nature
Side Trip
Find places to stay Feb 8 — 16:

Naples, Italy — 6 nights

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. You'll find plenty of places to visit near Naples: Salerno (Centro Storico Salerno, Porticciolo di Pastena, &more). Next up on the itinerary: take in the architecture and atmosphere at La Chiesa Di San Giovanni A Carbonara, explore the ancient world of Teatro Grande, get engrossed in the history at Museo e Real Bosco di Capodimonte, and make a trip to Piazza del Plebiscito.

To find reviews, where to stay, photos, and other tourist information, use the Naples road trip planning app.

Traveling by train from Rome to Naples takes 2 hours. Alternatively, you can drive; or fly. February in Naples sees daily highs of 17°C and lows of 7°C at night. Wrap up your sightseeing on the 22nd (Wed) early enough to fly to Turin.
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Historic Sites · Museums · Parks
Side Trips
Find places to stay Feb 16 — 22:

Turin, Italy — 6 nights

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.
Explore Turin's surroundings by going to Boroli - Cantina "La Brunella" (in Castiglione Falletto), Alba (Centro Storico & Fondazione Ferrero) and Abbazia di Santa Maria di Vezzolano (in Albugnano). There's lots more to do: admire the masterpieces at Museo Egizio, pause for some serene contemplation at Basilica di Superga, steep yourself in history at Duomo di Torino e Cappella della Sacra Sindone, and glide through natural beauty at Pista di Fondo Marmotta Rosa.

To see reviews, more things to do, other places to visit, and tourist information, read our Turin trip planner.

You can fly from Naples to Turin in 3 hours. Other options are to take a train; or drive. Prepare for little chillier weather when traveling from Naples in February: high temperatures in Turin hover around 5°C and lows are around 0°C. Finish your sightseeing early on the 28th (Tue) to allow enough time to fly back home.
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Museums · Historic Sites · Shopping · Outdoors
Side Trips
Find places to stay Feb 22 — 28:

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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San Marino travel guide

3.3
Historic Sites · Specialty Museums · Castles
San Marino is a country characterized by its architecture--namely, the three towers that adorn the country's flag and coat of arms. As a result, most of the tourist attractions here center around the structures protruding from the hill of the country. The third-smallest nation in Europe, it is surprising that San Marino managed to gain independence from robust Italy. This status has created great pride among the Sanmarinese, although Italian culture is still quite influential as the country is completely surrounded by Italy. And while its size has obvious disadvantages, the advantages for tourism strongly outweigh them. Visitors don't need to travel to get a sense of the country (there isn't far to go!), and this generates an intimacy and friendliness among locals that is lost in most larger countries.
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