Start: San Juan
Fly
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Bologna
— 2 nights
Drive
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Venice
— 2 nights
Drive
3
Vigo di Fassa
— 3 nights
Drive
4
Garda
— 1 night
Drive
5
Como
— 2 nights
Drive
6
Milan
— 2 nights
Fly
End: San Juan
Mon, Sep 7 - Sat, Sep 19
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Heart of Italian Cuisine
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.Kick off your visit on the 8th (Tue): take in the architecture and atmosphere at Ferrara Cathedral, step into the grandiose world of Castello Estense, don't miss a visit to Mausoleo di Galla Placidia, then contemplate in the serene atmosphere at Basilica San Vitale, and finally contemplate the long history of Loggetta Lombardesca. Get ready for a full day of sightseeing on the next day: contemplate the long history of Basilica di San Petronio, pause for some serene contemplation at Basilica - Santuario di Santo Stefano, then admire the landmark architecture of Palazzo Sampieri Talon, then steep yourself in history at Piazza Maggiore, and finally take in panoramic vistas at Le Due Torri Torre degli Asinell.
To find where to stay, reviews, maps, and tourist information, you can read our Bologna tour itinerary planner.
San Juan, Puerto Rico to Bologna is an approximately 15.5-hour flight. The time zone difference when traveling from San Juan to Bologna is 5 hours. Traveling from San Juan in September, expect Bologna to be slightly colder, temps between 30°C and 17°C. Wrap up your sightseeing on the 9th (Wed) to allow time to drive to Venice.
Things to do in Bologna
Side Trips
Find places to stay Sep 7 — 9:
Highlights from your trip
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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 10th (Thu): steep yourself in history at St Mark's Campanile, then admire the striking features of Basilica di San Marco, then contemplate the long history of Doge's Palace, and finally contemplate the waterfront views at Canal Grande. Keep things going the next day: contemplate the long history of Basilica dei Santi Giovanni e Paolo (San Zanipolo), snap pictures at Ponte di Rialto, appreciate the extensive heritage of Piazza San Marco, steep yourself in history at Ponte dei Sospiri, then pause for some photo ops at Punta della Dogana, and finally contemplate the long history of Peggy Guggenheim Collection.
To see traveler tips, maps, ratings, and more tourist information, read Venice route maker tool.
Drive from Bologna to Venice in 2 hours. Alternatively, you can take a train; or take a bus. In September, daily temperatures in Venice can reach 29°C, while at night they dip to 17°C. Wrap up your sightseeing on the 11th (Fri) early enough to travel to Vigo di Fassa.
Things to do in Venice
Find places to stay Sep 9 — 11:
Highlights from your trip
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Vigo di Fassa is a comune (municipality) in Trentino in the northern Italian region Trentino-Alto Adige/Südtirol, located about 60km northeast of Trento. Explore the numerous day-trip ideas around Vigo di Fassa: Tre Cime di Lavaredo (in Auronzo di Cadore) and Canazei (Funivia Pass Pordoi, Sass Pordoi, &more). And it doesn't end there: stroll through Da Ciampedie a Gardeccia, examine the collection at Museo Ladino di Fassa, pause for some serene contemplation at Parrocchia dei Santi Filippo e Giacomo, and make a trip to Passo San Pellegrino.
For photos, reviews, other places to visit, and more tourist information, read our Vigo di Fassa trip planner.
Traveling by car from Venice to Vigo di Fassa takes 3 hours. Expect a daytime high around 29°C in September, and nighttime lows around 15°C. Finish your sightseeing early on the 14th (Mon) to allow enough time to travel to Garda.
For photos, reviews, other places to visit, and more tourist information, read our Vigo di Fassa trip planner.
Traveling by car from Venice to Vigo di Fassa takes 3 hours. Expect a daytime high around 29°C in September, and nighttime lows around 15°C. Finish your sightseeing early on the 14th (Mon) to allow enough time to travel to Garda.
Things to do in Vigo di Fassa
Side Trips
Canazei, Passo San Pellegrino, Tre Cime di Lavaredo, Parrocchia dei Santi Filippo e Giacomo, Lago di Carezza
Find places to stay Sep 11 — 14:
Highlights from your trip
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Kick off your visit on the 15th (Tue): stroll through Punta di San Vigilio, explore the activities along Lago di Garda, then steep yourself in history at Villa degli Albertini, and finally head outdoors with La Rocca.
For more things to do, traveler tips, photos, and more tourist information, refer to the Garda driving holiday planner.
You can drive from Vigo di Fassa to Garda in 2.5 hours. Expect a daytime high around 29°C in September, and nighttime lows around 17°C. Wrap up your sightseeing on the 15th (Tue) to allow time to drive to Como.
For more things to do, traveler tips, photos, and more tourist information, refer to the Garda driving holiday planner.
You can drive from Vigo di Fassa to Garda in 2.5 hours. Expect a daytime high around 29°C in September, and nighttime lows around 17°C. Wrap up your sightseeing on the 15th (Tue) to allow time to drive to Como.
Things to do in Garda
Find places to stay Sep 14 — 15:
Highlights from your trip
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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.Kick off your visit on the 16th (Wed): look for gifts at Tea World, pause for some serene contemplation at Cathedral of Como (Duomo), then take in the spiritual surroundings of Basilica di San Fedele, then contemplate in the serene atmosphere at Basilica di Sant'Abbondio, and finally take a tour by water with My Lake Como Concierge. Get ready for a full day of sightseeing on the next day: see the sights as you ascend with Lake Como Adventures, admire the landmark architecture of Villa del Balbianello, and then admire the natural beauty at Villa Carlotta.
For ratings, maps, and more tourist information, use the Como attractions planner.
Traveling by car from Garda to Como takes 2.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In September, plan for daily highs up to 28°C, and evening lows to 16°C. Finish your sightseeing early on the 17th (Thu) to allow enough time to drive to Milan.
Things to do in Como
Side Trip
Find places to stay Sep 15 — 17:
Highlights from your trip
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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 (Fri): get to know the fascinating history of Piazza del Duomo, contemplate in the serene atmosphere at Duomo di Milano, then step into the grandiose world of Castello Sforzesco, and finally stroll the grounds of Monumental Cemetery.
To find maps, where to stay, other places to visit, and tourist information, refer to the Milan road trip tool.
You can drive from Como to Milan in an hour. Alternatively, you can drive; or take a train. In September, daytime highs in Milan are 28°C, while nighttime lows are 16°C. On the 19th (Sat), you'll have the morning to explore before heading back home.
Things to do in Milan
Find places to stay Sep 17 — 19:
Highlights from your trip
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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.
Veneto travel guide
An independent republic until Napoleon's invasion in 1797, Veneto is among the wealthiest and most developed regions in the country. The region has a bustling tourism industry, drawing nearly 70 million visitors annually to its historical, natural, artistic, cultural, musical, and culinary treasures. Though most tourists begin and end their Veneto holiday in Venice, the area has plenty more to offer. A range of attractions await beyond the capital city, including World Heritage-listed Palladian villas, seaside resorts, vineyards, lakes, beaches, thermal baths, lush parks, and imposing mountain ranges. Veneto's clubs, bars, and restaurants make for a lively nightlife in the region's thriving cities.
Lake Como travel guide
A favorite vacation spot for more than a century, Lake Como was once an exclusive retreat for local aristocrats and wealthy people. It is not only one of Europe's most beautiful lakes, but also one of the deepest at more than 400 m (1,300 ft). Surrounded by elegant villas, the lake has become a popular holiday destination for tourists because of its range of attractions, from landscapes, wildlife, and spas, to activities like sailing, windsurfing, and kite-surfing. The area has been an inspiration for artists since Roman times. English poet Percy Bysshe Shelley wrote, "This lake exceeds anything I ever beheld in beauty…It is long and narrow and has the appearance of a mighty river winding among the mountains and the forests."
