15 days in Tuscany Itinerary

15 days in Tuscany Itinerary

Created using Inspirock Tuscany itinerary builder

Make it your trip
Fly
1
Pisa
— 3 nights
Drive
2
Siena
— 6 nights
Drive
3
Florence
— 5 nights
Fly

S M T W T F S
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Pisa

— 3 nights
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Explore Pisa's surroundings by going to Azienda Agricola Villanoviana (in Bolgheri), Italy Shore Drivers (in Cecina) and Lucca (San Michele in Foro, Torre Guinigi, &more). There's lots more to do: enjoy breathtaking views from Leaning Tower of Pisa, admire the landmark architecture of Palazzo Tori - Massoni, make a trip to Piazza dei Miracoli, and explore the different monuments and memorials at Camposanto.

To see more things to do, maps, where to stay, and other tourist information, use the Pisa road trip tool.

Toronto, Canada to Pisa is an approximately 13.5-hour flight. Due to the time zone difference, you'll lose 6 hours traveling from Toronto to Pisa. September in Pisa sees daily highs of 30°C and lows of 17°C at night. Finish up your sightseeing early on the 13th (Tue) so you can go by car to Siena.

Things to do in Pisa

Wineries · Tours · Historic Sites · Parks

Side Trips

Siena

— 6 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Explore Siena's surroundings by going to Poggio Amorelli (in Castellina In Chianti), La Grotta del Cristallo (in Colle di Val d'Elsa) and Montalcino (Mate Winery, Winery Solaria Patrizia Cencioni, &more). And it doesn't end there: learn about winemaking at Guardastelle Vineyard, take in the architecture and atmosphere at Duomo di Siena, gain insight at Scuola di Cucina di Lella, and don't miss a visit to Piazza del Campo.

To find ratings, reviews, maps, and tourist information, go to the Siena day trip planning site.

Traveling by car from Pisa to Siena takes 2 hours. Alternatively, you can take a train; or take a bus. In September, daytime highs in Siena are 32°C, while nighttime lows are 19°C. Wrap up your sightseeing on the 19th (Mon) to allow time to drive to Florence.

Things to do in Siena

Wineries · Tours · Museums · Historic Sites

Side Trips

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.
Florence is known for museums, historic sites, and shopping. Your plan includes some of its best attractions: explore the world behind art at Florence Academy of Fine Arts, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, indulge your senses at Scenic wine tours in Tuscany, and contemplate the long history of Basilica of Santa Croce.

To see traveler tips, where to stay, more things to do, and tourist information, read our Florence trip planning app.

Traveling by car from Siena to Florence takes 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 30°C in September, and nighttime lows around 17°C. Finish up your sightseeing early on the 24th (Sat) so you can catch the flight back home.

Things to do in Florence

Historic Sites · Tours · Museums · Wineries

Side Trip

Tuscany travel guide

4.4
Landmarks · Art Museums · Historic Walking Areas
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.