8 days in Tuscany Itinerary

8 days in Tuscany Itinerary

Created using Inspirock Tuscany trip itinerary planner

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Route & dates

8 days in Tuscany Itinerary

Start: New York City
Fly + Train:  14 h 15 min
1
Florence
— 2 nights
Drive:  1 h 15 min
2
San Gimignano
— 4 nights
+2
Bus + Fly + Foot:  15 h
End: New York City

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence with an excursion to Castello del Trebbio in Santa Brigida--about 36 minutes away. There's lots more to do: examine the collection at Academy Of Florence Art Gallery, explore the world behind art at Pitti Palace, take in the views from Ponte Vecchio, and admire the natural beauty at The Boboli Gardens.

Use Inspirock's suggestions to plan your Florence trip and find the best activities and attractions for your vacation.

New York City, USA to Florence is an approximately 14.5-hour flight. You can also 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. Expect a daytime high around 71°F in October, and nighttime lows around 54°F. Wrap up your sightseeing on the 15th (Thu) early enough to drive to San Gimignano.

Things to do in Florence

Historic Sites Museums Wineries

Side Trip

Castello del Trebbio
Find places to stay Oct 12 — 15:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Piazzale Michelangelo ©
Piazzale Michelangelo

4
nights
San Gimignano

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.
Change things up with these side-trips from San Gimignano: Duomo di Siena (in Siena), Montalcino (Mate Winery, Castiglion del Bosco, & more) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). There's still lots to do: learn about winemaking at Guardastelle Vineyard, steep yourself in history at Torre Grossa, and explore the galleries of Torre e Casa Campatelli.

For traveler tips, where to stay, photos, and tourist information, refer to the San Gimignano holiday planning app .

Traveling by car from Florence to San Gimignano takes 1.5 hours. Alternatively, you can take a bus; or take a train. In October in San Gimignano, expect temperatures between 71°F during the day and 54°F at night. Wrap up your sightseeing by early afternoon on the 19th (Mon) to allow time for travel back home.

Things to do in San Gimignano

Wineries Historic Sites Museums

Side Trips

Montalcino, Accademia del Buon Gusto, Fattoria Casa Sola, Duomo di Siena, A Solatio Organic Farm
Find places to stay Oct 15 — 19:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Duomo di Siena ©
Duomo di Siena

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