13 days in Tuscany Itinerary

13 days in Tuscany Itinerary

Created using Inspirock Tuscany vacation maker

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Route & dates

13 days in Tuscany Itinerary

Start: Milan
Drive:  3​h
1
Florence
— 3 nights
Drive:  1​h 15​min
2
Arezzo
— 4 nights
Drive:  1​h 45​min
3
San Gimignano
— 5 nights
Drive:  3​h 30​min
End: Milan

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Dedicate the 10th (Thu) to wine at some of the top wineries in the area. There's much more to do: admire the masterpieces at Uffizi Galleries, appreciate the extensive heritage of Piazza del Duomo, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, and step into the grandiose world of Palazzo Vecchio.

To find ratings, traveler tips, photos, and tourist information, read our Florence visit planner .

Milan to Florence is an approximately 2-hour train ride. You can also drive; or fly. When traveling from Milan in October, plan for somewhat warmer days in Florence, with highs around 25°C, while nights are about the same with lows around 14°C. Finish your sightseeing early on the 11th (Fri) so you can drive to Arezzo.

Things to do in Florence

Historic Sites Tours Museums
Find places to stay Oct 8 — 11:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo
Cathedral of Santa Maria del Fiore ©

4
nights
Arezzo

Arezzo ©
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Change things up with these side-trips from Arezzo: Assisi (Eremo delle Carceri, Basilica inferiore di San Francesco d'Assisi, & more), Rocca Paolina (in Perugia) and Museo della Porziuncola (in Santa Maria degli Angeli). There's still lots to do: do a tasting at Ciacci Piccolomini d'Aragona, take in the spiritual surroundings of Duomo San Donato, make a trip to Piazza Grande, and contemplate the long history of Duomo di Orvieto.

To find more things to do, other places to visit, maps, and more tourist information, read Arezzo trip itinerary maker site .

Traveling by car from Florence to Arezzo takes 1.5 hours. Alternatively, you can take a train; or take a bus. Finish your sightseeing early on the 15th (Tue) to allow enough time to drive to San Gimignano.

Things to do in Arezzo

Historic Sites Wineries Museums

Side Trips

Assisi, Montalcino, Rocca Paolina, Duomo di Orvieto
Find places to stay Oct 11 — 15:
Highlights from your plan

5
nights
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.
Get out of town with these interesting San Gimignano side-trips: Siena (Wine Tours & Tastings, Piazza del Campo, & more) and Leaning Tower of Pisa (in Pisa). The adventure continues: learn about winemaking at Guardastelle Vineyard, view the masterpieces at La Bottega del Sale di Duccio Nacci photographer, contemplate the long history of Torre Grossa, and make a trip to Historic Centre of San Gimignano.

To find where to stay, photos, reviews, and other tourist information, read our San Gimignano trip itinerary builder tool .

Getting from Arezzo to San Gimignano by car takes about 2 hours. Other options: take a bus; or take a train. Expect a daytime high around 25°C in October, and nighttime lows around 14°C. Cap off your sightseeing on the 20th (Sun) early enough to go by car back home.

Things to do in San Gimignano

Historic Sites Tours Wineries

Side Trips

Siena, Leaning Tower of Pisa
Find places to stay Oct 15 — 20:
Highlights from your plan
Wine Tours & Tastings
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Piazza del Campo ©
Piazza del Campo

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