15 days in Tuscany Itinerary

15 days in Tuscany Itinerary

Created using Inspirock Tuscany travel planner

Make it your trip
Fly
1
Florence
— 4 nights
Drive
2
Cortona
— 1 night
Drive
3
Siena
— 4 nights
+2
Drive to Piombino, Ferry to Portoferraio, Drive to Capoliveri
4
Capoliveri, Elba Island
— 4 nights
+2
Drive to Portoferraio, Ferry to Piombino, Drive to Pisa
5
Pisa
— 1 night
Fly

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Florence

— 4 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: pause for some serene contemplation at Cathedral of Santa Maria del Fiore, explore the world behind art at Pitti Palace, take in nature's colorful creations at The Boboli Gardens, and make a trip to Piazzale Michelangelo.

To see traveler tips, photos, reviews, and more tourist information, use the Florence road trip planning site.

New York City, USA to Florence is an approximately 15-hour flight. You'll lose 6 hours traveling from New York City to Florence due to the time zone difference. Plan for a bit cooler nights when traveling from New York City in August since evenings lows in Florence dip to 64°F. Cap off your sightseeing on the 5th (Thu) early enough to go by car to Cortona.

Things to do in Florence

Historic Sites · Museums · Tours · Parks
Find places to stay Aug 1 — 5:

Cortona

— 1 night

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.
Start off your visit on the 6th (Fri): do a tasting at Buccelletti - Cantina, learn about winemaking at winery Agriturismo Santo Stefano, then take in the spiritual surroundings of Eremo Le Celle, then see the interesting displays at Museo Diocesano, and finally get engrossed in the history at MAEC - Museo dell'Accademia Etrusca.

To find other places to visit, where to stay, ratings, and more tourist information, you can read our Cortona trip maker.

Drive from Florence to Cortona in 2 hours. Alternatively, you can take a train. Finish your sightseeing early on the 6th (Fri) to allow enough time to drive to Siena.

Things to do in Cortona

Wineries · Historic Sites · Museums

Side Trip

Find places to stay Aug 5 — 6:

Siena

— 4 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 San Gimignano (Torre Grossa, Guardastelle Vineyard, &more), Poggio al Bosco (in Tavarnelle Val di Pesa) and A Solatio Organic Farm (in Certaldo). Next up on the itinerary: make a trip to Piazza del Campo, gain insight at Scuola di Cucina di Lella, explore the world behind art at Museo dell'Opera Metropolitana, and take in the architecture and atmosphere at Basilica Cateriniana San Domenico.

To find more things to do, ratings, traveler tips, and tourist information, read our Siena online day trip planner.

Getting from Cortona to Siena by car takes about 1.5 hours. Other options: take a train; or do a combination of train and bus. In August, plan for daily highs up to 89°F, and evening lows to 67°F. Cap off your sightseeing on the 10th (Tue) early enough to travel to Capoliveri.

Things to do in Siena

Wineries · Historic Sites · Tours · Museums

Side Trips

Find places to stay Aug 6 — 10:

Capoliveri, Elba Island

— 4 nights
Capoliveri is a comune (municipality) on the island of Elba in Italy. Venture out of the city with trips to Spiaggia di Forno (in Scaglieri) and Walking trail to Spiaggia della Biodola (in Procchio). And it doesn't end there: get outside with Centro Subacqueo Il Corsaro, hike along Capo Stella, tour the pleasant surroundings at Spiaggia Luisi d'Angelo, and get up close to creatures of the deep with Aviosail Charter.

To see reviews, photos, more things to do, and other tourist information, go to the Capoliveri trip builder tool.

Do a combination of car and ferry from Siena to Capoliveri in 4 hours. Alternatively, you can do a combination of train, ferry, and bus; or do a combination of bus and ferry. When traveling from Siena in August, plan for a bit cooler days and about the same nights in Capoliveri: temperatures range from 83°F by day to 68°F at night. Finish up your sightseeing early on the 14th (Sat) so you can travel to Pisa.

Things to do in Capoliveri

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Aug 10 — 14:

Pisa

— 1 night
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Start off your visit on the 15th (Sun): don't miss a visit to Piazza dei Miracoli and then take in panoramic vistas at Leaning Tower of Pisa.

To find photos, maps, traveler tips, and other tourist information, read Pisa trip planner.

Traveling by combination of car and ferry from Capoliveri to Pisa takes 3.5 hours. Alternatively, you can do a combination of bus, ferry, and train. In August, daily temperatures in Pisa can reach 86°F, while at night they dip to 64°F. On the 15th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.
Find places to stay Aug 14 — 15:

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.