14 days in Northwest Italy & San Jose Itinerary

14 days in Northwest Italy & San Jose Itinerary

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Route & dates

Start: San Francisco, United States
Fly:  16 h
1
Milan, Italy
— 1 day
Train:  1 h 45 min
2
Florence, Italy
— 3 nights
Drive:  2 h 15 min
3
Assisi, Italy
— 1 night
Drive:  2 h 15 min
4
Rome, Italy
— 3 nights
Fly:  3 h 15 min
5
Venice, Italy
— 3 nights
+2
Fly + Subway + Train:  16 h 30 min
6
San Jose, United States
— 2 nights
Drive:  1 h
End: San Francisco, United States

1
day
Milan, Italy

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.
Start off your visit on the 19th (Sat): admire the landmark architecture of Galleria Vittorio Emanuele II and then take in the spiritual surroundings of Duomo di Milano.

For where to stay, traveler tips, and tourist information, read our Milan journey planner.

San Francisco, USA to Milan is an approximately 16- hour flight. You can also do a combination of flight and bus; or do a combination of flight and train. The time zone difference when traveling from San Francisco to Milan is 9 hours. Traveling from San Francisco in October, you will find days in Milan are slightly colder (65°F), and nights are about the same (52°F). Wrap up your sightseeing on the 19th (Sat) to allow time to take a train to Florence.

Things to do in Milan

Historic Sites Shopping
Find places to stay Oct 19 — 20:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II

3
nights
Florence, Italy

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Go for a jaunt from Florence to Pisa to see Leaning Tower of Pisa about 1h 10 min away. There's much more to do: explore the world behind art at Gallerie Degli Uffizi, snap pictures at Ponte Vecchio, take in the architecture and atmosphere at Basilica of Santa Croce, and contemplate in the serene atmosphere at The Baptistery of St. John.

To see ratings, traveler tips, maps, and other tourist information, go to the Florence trip planner.

Take a train from Milan to Florence in 2 hours. Alternatively, you can drive; or fly. When traveling from Milan in October, plan for somewhat warmer days and about the same nights in Florence: temperatures range from 71°F by day to 54°F at night. Wrap up your sightseeing on the 22nd (Tue) to allow time to drive to Assisi.

Things to do in Florence

Historic Sites Museums

Side Trip

Leaning Tower of Pisa
Find places to stay Oct 19 — 22:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts

1
night
Assisi, Italy

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
On the 23rd (Wed), do a tasting at Tili Vini Societa Agricola, do a tasting at BIBENDA ASSISI WINE BAR-WINE VINO, CHOCOLATE, OLIVE OIL,TRUFFLE TASTING, contemplate in the serene atmosphere at Eremo delle Carceri, walk around Mount Subasio, then appreciate the extensive heritage of Piazza Superiore di San Francesco, and finally take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi.

For ratings, maps, reviews, and tourist information, read our Assisi day trip website.

You can drive from Florence to Assisi in 2.5 hours. Another option is to take a train. In October, daytime highs in Assisi are 70°F, while nighttime lows are 51°F. Finish your sightseeing early on the 23rd (Wed) to allow enough time to drive to Rome.

Things to do in Assisi

Wineries Historic Sites Parks
Find places to stay Oct 22 — 23:
Highlights from your plan

3
nights
Rome, Italy

Rome ©
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, nightlife, and museums. Your plan includes some of its best attractions: explore the ancient world of Colosseum, take in the architecture and atmosphere at Pantheon, steep yourself in history at Palatine Hill, and ponder the design of Trevi Fountain.

To see other places to visit, more things to do, and tourist information, go to the Rome online trip builder.

You can drive from Assisi to Rome in 2.5 hours. Alternatively, you can take a train; or take a bus. October in Rome sees daily highs of 73°F and lows of 55°F at night. Cap off your sightseeing on the 26th (Sat) early enough to travel to Venice.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Find places to stay Oct 23 — 26:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

3
nights
Venice, Italy

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.
Venice is known for historic sites, museums, and nature. Your plan includes some of its best attractions: contemplate the waterfront views at Canal Grande, snap pictures at Ponte di Rialto, admire the striking features of St Mark's Campanile, and steep yourself in history at Ponte dei Sospiri.

To see reviews, other places to visit, and more tourist information, you can read our Venice online itinerary planner.

Traveling by flight from Rome to Venice takes 3.5 hours. Alternatively, you can take a train; or drive. Traveling from Rome in October, expect nights in Venice to be about the same, around 51°F, while days are little chillier, around 66°F. Wrap up your sightseeing on the 29th (Tue) early enough to travel to San Jose.

Things to do in Venice

Historic Sites Museums Parks
Find places to stay Oct 26 — 29:
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

2
nights
San Jose, United States

San Jose ©
The metropolitan center of Silicon Valley, San Jose considers itself a global city.
On the 30th (Wed), walk around Martial Cottle Park, then walk around Guadalupe Oak Grove Park, and then stroll around Santa Teresa County Park. On the 31st (Thu), you'll have a packed day of sightseeing: learn about winemaking at J. Lohr Vineyards & Wines, then make a trip to Sikh Gurdwara, then stroll around Emma Prusch Farm Park, and finally pause for some serene contemplation at Trinity Episcopal Cathedral.

For other places to visit, ratings, and more tourist information, refer to the San Jose trip itinerary builder website.

Traveling by combination of flight and train from Venice to San Jose takes 17.5 hours. Alternatively, you can do a combination of train and flight; or do a combination of flight and bus. The time zone difference moving from Central European Standard Time to Pacific Standard Time is minus 9 hours. While traveling from Venice, expect a bit warmer days and about the same nights in San Jose, ranging from highs of 77°F to lows of 54°F. Finish up your sightseeing early on the 31st (Thu) so you can go by car back home.

Things to do in San Jose

Parks Wineries Nature
Find places to stay Oct 29 — 31:
Highlights from your plan
Martial Cottle Park ©
Martial Cottle Park
Guadalupe Oak Grove Park ©
Guadalupe Oak Grove Park
Sikh Gurdwara ©
Sikh Gurdwara

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