17 days in Tuscany Itinerary

17 days in Tuscany Itinerary

Created using Inspirock Tuscany vacation planner
Make it your trip
Fly
1
Pisa
— 4 nights
Drive
2
Florence
— 5 nights
Drive
3
Cortona
— 2 nights
Drive
4
Siena
— 5 nights
Fly

S M T W T F S
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Pisa — 4 nights

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
You'll find plenty of places to visit near Pisa: Lucca (San Michele in Foro, Torre Guinigi, &more), Bagno Maurizio (in Viareggio) and Podere Pellicciano - Agrisole (in San Miniato). Next up on the itinerary: take in panoramic vistas at Leaning Tower of Pisa, steep yourself in history at Camposanto, do a tasting at Terre del Marchesato, and examine the collection at Museo Aviotruppe Esercito Italiano.

To see photos, reviews, where to stay, and tourist information, read Pisa trip planner.

New York City, USA to Pisa is an approximately 14.5-hour flight. The time zone changes from Eastern Standard Time (EST) to Central European Standard Time (CET), which is usually a 6 hour difference. Traveling from New York City in September, expect slightly colder with lows of 59°F in Pisa. Finish your sightseeing early on the 4th (Tue) to allow enough time to drive to Florence.
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Parks · Outdoors · Beaches · Wineries
Side Trips
Find places to stay Sep 30 — Oct 4:

Florence — 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Dedicate the 8th (Sat) to wine at some of the top wineries in the area. Next up on the itinerary: admire the masterpieces at Florence Academy of Fine Arts, get to know the fascinating history of Piazza del Duomo, take in the views from Ponte Vecchio, and examine the collection at Pitti Palace.

Quickly create a custom-made itinerary for Florence using our trip planner.

Traveling by car from Pisa to Florence takes 1.5 hours. Alternatively, you can take a bus; or take a train. In October, daily temperatures in Florence can reach 71°F, while at night they dip to 54°F. Wrap up your sightseeing on the 9th (Sun) to allow time to drive to Cortona.
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Tours · Historic Sites · Wineries · Museums
Find places to stay Oct 4 — 9:

Cortona — 2 nights

City of Art

The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
On the 10th (Mon), learn about winemaking at Tenuta Valdipiatta, learn about winemaking at Icario Winery, learn about winemaking at Az. Agr. Poliziano, then learn about winemaking at Buccelletti - Cantina, and finally look for gifts at Silvia Taccola Vanni - Laboratorio Stilistico. Get ready for a full day of sightseeing on the 11th (Tue): indulge your senses at some of the top wineries in the area, examine the collection at Museo Diocesano, then take an in-depth tour of MAEC - Museo dell'Accademia Etrusca, and finally get a taste of the local shopping with La Torena Arte.

For reviews, maps, other places to visit, and other tourist information, go to the Cortona travel route planner.

You can drive from Florence to Cortona in 2 hours. Another option is to take a train. Finish your sightseeing early on the 11th (Tue) to allow enough time to drive to Siena.
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Wineries · Tours · Museums · Shopping
Side Trips
Find places to stay Oct 9 — 11:

Siena — 5 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Get out of town with these interesting Siena side-trips: Fattoria Casa Sola (in Barberino Val d'Elsa) and Guardastelle Vineyard (in San Gimignano). The adventure continues: take in the architecture and atmosphere at Duomo di Siena, indulge your taste buds at Food & Drink, browse the exhibits of Palazzo Pubblico and Museo Civico, and make a trip to Piazza del Campo.

To find ratings, traveler tips, maps, and tourist information, read our Siena online tour itinerary planner.

Traveling by car from Cortona to Siena takes 1.5 hours. Alternatively, you can take a train; or do a combination of train and bus. Expect a daytime high around 73°F in October, and nighttime lows around 56°F. On the 16th (Sun), wrap the sightseeing up by early afternoon so you can fly back home.
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Tours · Wineries · Historic Sites · Museums
Side Trips
Find places to stay Oct 11 — 16:

Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.
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