5 days in Tuscany Itinerary

5 days in Tuscany Itinerary

Created using Inspirock Tuscany trip itinerary planner

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Route & dates

5 days in Tuscany Itinerary

Start: San Francisco
Fly:  17​h 15​min
1
Pisa
— Few hours
Drive:  2​h 30​min
2
San Quirico d'Orcia
— 1 night
Drive:  1​h 30​min
3
San Gimignano
— 2 nights
train + Fly:  18​h 45​min
End: San Francisco

few
hours
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Kick off your visit on the 22nd (Wed): get to know the fascinating history of Knights' Square, look for gifts at L'Orsa Minore, Libri & Mappe, take in the spiritual surroundings of Battistero, then contemplate the long history of Camposanto, and finally take in the spiritual surroundings of Duomo di Pisa.

For maps, ratings, photos, and other tourist information, go to the Pisa trip itinerary builder tool .

San Francisco, USA to Pisa is an approximately 17.5-hour flight. You can also do a combination of flight and train; or do a combination of train and flight. Traveling from San Francisco to Pisa, you'll lose 9 hours due to the time zone difference. In May, daytime highs in Pisa are 71°F, while nighttime lows are 52°F. Finish your sightseeing early on the 22nd (Wed) to allow enough time to drive to San Quirico d'Orcia.

Things to do in Pisa

Historic Sites Shopping
Find places to stay May 22 — 23:
Highlights from your plan
Duomo di Pisa ©
Duomo di Pisa
Battistero ©
Battistero
Camposanto ©
Camposanto

1
night
San Quirico d'Orcia

San Quirico d'Orcia ©
San Quirico d'Orcia is a comune (municipality) of about 2,500 inhabitants in the Province of Siena in the Italian region Tuscany, located about 80km southeast of Florence and about 35km southeast of Siena inside the Valdorcia landscape. On the 23rd (Thu), look for gifts at Dedalo Tuscan Atmosphere, then take a stroll around San Quirico d'Orcia, then admire the verdant scenery at Val d'Orcia, and finally identify plant and animal life at Fosso Bianco - Bagni San Filippo.

To see other places to visit, where to stay, reviews, and other tourist information, you can read our San Quirico d'Orcia travel route planner.

You can drive from Pisa to San Quirico d'Orcia in 2.5 hours. Other options are to take a bus; or do a combination of train and bus. Expect a daytime high around 74°F in May, and nighttime lows around 53°F. Finish your sightseeing early on the 23rd (Thu) so you can drive to San Gimignano.

Things to do in San Quirico d'Orcia

Parks Historic Sites Wildlife

Side Trips

Val d'Orcia, Fosso Bianco - Bagni San Filippo
Find places to stay May 22 — 23:
Highlights from your plan
San Quirico d'Orcia ©
San Quirico d'Orcia
Val d'Orcia ©
Val d'Orcia
Fosso Bianco - Bagni San Filippo ©
Fosso Bianco - Bagni San Filippo

2
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.
Kick off your visit on the 24th (Fri): get into the urban bustle at Comune Di Certaldo, stop by Artesia Ceramica, then don't miss a visit to San Gimignano Bell Tower, and finally steep yourself in history at Historic Centre of San Gimignano.

To find photos, maps, and more tourist information, refer to the San Gimignano travel planner .

Getting from San Quirico d'Orcia to San Gimignano by car takes about 1.5 hours. Other options: do a combination of bus and train; or take a bus. Expect a daytime high around 71°F in May, and nighttime lows around 52°F. On the 25th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in San Gimignano

Shopping Historic Sites Museums

Side Trip

Certaldo
Find places to stay May 23 — 25:
Highlights from your plan
Comune Di Certaldo ©
Comune Di Certaldo
San Gimignano Bell Tower ©
San Gimignano Bell Tower
Historic Centre of San Gimignano ©
Historic Centre of San Gimignano

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