9 days in New York City & Italy Itinerary

9 days in New York City & Italy Itinerary

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Route & dates

9 days in New York City & Italy Itinerary

Start: George Town, Cayman Islands
Fly + foot:  5​h
1
New York City, United States
— 2 nights
Fly:  17​h
2
Florence, Italy
— 1 night
Drive:  1​h 30​min
3
San Gimignano, Italy
— Few hours
Drive:  1​h 15​min
4
Florence, Italy
— 1 night
Drive:  1​h 30​min
5
Pisa, Italy
— Few hours
Drive:  1​h 30​min
6
Florence, Italy
— 1 night
7
Venice, Italy
— 2 nights
Fly:  16​h
End: George Town, Cayman Islands


Learn more about your trip

2
nights
New York City, United States

New York City
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
For other places to visit, traveler tips, more things to do, and other tourist information, read our New York City itinerary planning tool .

George Town, Cayman Islands to New York City is an approximately 5-hour combination of flight and bus. You can also fly; or do a combination of flight and train. While traveling from George Town, expect slightly colder days and colder nights in New York City, ranging from highs of 24°C to lows of 16°C. You'll set off for Florence on the 15th (Tue).

Things to do in New York City

Nightlife Parks Tours
Find places to stay Oct 13 — 15:

1
night
Florence, Italy

Florence
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
To find other places to visit, ratings, more things to do, and tourist information, you can read our Florence online tour builder .

Getting from New York City to Florence by flight takes about 14.5 hours. Other options: do a combination of bus and flight; or do a combination of bus, flight, and train. Traveling from New York City to Florence, you'll lose 6 hours due to the time zone difference. In October in Florence, expect temperatures between 25°C during the day and 14°C at night. You'll set off for San Gimignano on the 17th (Thu).

Things to do in Florence

Tours Outdoors Historic Sites
Find places to stay Oct 16 — 17:

few
hours
San Gimignano, Italy

San Gimignano
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 other places to visit, maps, photos, and more tourist information, read San Gimignano road trip planning site .

Traveling by car from Florence to San Gimignano takes 1.5 hours. Alternatively, you can take a bus; or take a train. In October, plan for daily highs up to 25°C, and evening lows to 14°C. You will leave for Florence on the 17th (Thu).

Things to do in San Gimignano

Outdoors Tours Historic Sites
Find places to stay Oct 17 — 18:

1
night
Florence, Italy

Florence
To find where to stay, other places to visit, traveler tips, and other tourist information, refer to the Florence road trip app .

Traveling by car from San Gimignano to Florence takes 1.5 hours. Alternatively, you can take a bus; or take a train. You will leave for Pisa on the 18th (Fri).

Things to do in Florence

Tours Outdoors Historic Sites
Find places to stay Oct 17 — 18:

few
hours
Pisa, Italy

Pisa
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
To find maps, reviews, other places to visit, and more tourist information, go to the Pisa online attractions planner .

You can take a train from Florence to Pisa in an hour. Alternatively, you can take a bus; or drive. In October, daily temperatures in Pisa can reach 25°C, while at night they dip to 14°C. On the 18th (Fri), you're off toFlorence.

Things to do in Pisa

Outdoors Parks Tours
Find places to stay Oct 18 — 19:

1
night
Florence, Italy

Florence
To find reviews, photos, ratings, and other tourist information, go to the Florence trip maker site .

Traveling by train from Pisa to Florence takes an hour. Alternatively, you can take a bus; or drive. On the 19th (Sat), you'll travel to Venice.

Things to do in Florence

Tours Outdoors Historic Sites
Find places to stay Oct 18 — 19:

2
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.
To find where to stay, maps, ratings, and more tourist information, go to the Venice planning site .

Getting from Florence to Venice by train takes about 2.5 hours. Other options: drive; or take a bus. Expect little chillier weather when traveling from Florence in October: highs in Venice hover around 22°C, while lows dip to 12°C. You'll set off for home on the 21st (Mon).

Things to do in Venice

Nightlife Outdoors Historic Sites
Find places to stay Oct 19 — 21:

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