15 days in Tuscany Itinerary

15 days in Tuscany Itinerary

Created using Inspirock Tuscany travel planner

Make it your trip
Fly
1
Pisa
— 2 nights
Drive
2
Siena
— 4 nights
Drive
3
Pienza
— 4 nights
Drive
4
Florence
— 4 nights
Fly

S M T W T F S
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Pisa

— 2 nights
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
On the 3rd (Mon), enjoy breathtaking views from Leaning Tower of Pisa, don't miss a visit to Piazza dei Miracoli, then examine the collection at Chiesa e Battistero di San Giovanni e Santa Reparata, and finally don't miss a visit to Le mura di Lucca. On the 4th (Tue), you'll have a packed day of sightseeing: examine the collection at Museo Aviotruppe Esercito Italiano, contemplate in the serene atmosphere at Battistero di San Giovanni, take in panoramic vistas at Torre Guinigi, then steep yourself in history at St Martin Cathedral, and finally do a tasting at Podere Pellicciano - Agrisole.

To see where to stay, reviews, traveler tips, and tourist information, you can read our Pisa travel planner.

Boston, USA to Pisa is an approximately 13.5-hour flight. Traveling from Boston to Pisa, you'll lose 6 hours due to the time zone difference. May in Pisa sees daily highs of 71°F and lows of 52°F at night. Cap off your sightseeing on the 4th (Tue) early enough to go by car to Siena.

Things to do in Pisa

Museums · Historic Sites · Wineries

Side Trips

Find places to stay May 2 — 4:

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 La Grotta del Cristallo (in Colle di Val d'Elsa) and San Gimignano (Guardastelle Vineyard & Fattoria Il Piano). There's lots more to do: make a trip to Piazza del Campo, get a sense of history and politics at Palazzo Pubblico and Museo Civico, awaken your taste buds at some of the top wineries in the area, and identify plant and animal life at Wildlife Areas.

For more things to do, maps, ratings, and other tourist information, read our Siena online trip maker.

You can drive from Pisa to Siena in 2 hours. Alternatively, you can take a train; or take a bus. In May, daily temperatures in Siena can reach 74°F, while at night they dip to 53°F. Cap off your sightseeing on the 8th (Sat) early enough to go by car to Pienza.

Things to do in Siena

Wineries · Historic Sites · Tours · Outdoors

Side Trips

Find places to stay May 4 — 8:

Pienza

— 4 nights
Pienza, a town and comune in the province of Siena, in the Val d'Orcia in Tuscany (central Italy), between the towns of Montepulciano and Montalcino, is the "touchstone of Renaissance urbanism."In 1996, UNESCO declared the town a World Heritage Site, and in 2004 the entire valley, the Val d'Orcia, was included on the list of UNESCO's World Cultural Landscapes.HistoryBefore the village was renamed to Pienza its name was Corsignano. Get out of town with these interesting Pienza side-trips: Montalcino (Castiglion del Bosco Winery, Mate Winery, &more), Crete Senesi (in Asciano) and Pianigiani Bags (in Buonconvento). Next up on the itinerary: do a tasting at Ciacci Piccolomini d'Aragona, contemplate in the serene atmosphere at Eremo Le Celle, contemplate the long history of Val d'Orcia, and pause for some serene contemplation at Chiesa di Santa Maria Assunta.

For traveler tips, maps, other places to visit, and more tourist information, you can read our Pienza trip planner.

Traveling by car from Siena to Pienza takes 1.5 hours. Alternatively, you can 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. Cap off your sightseeing on the 12th (Wed) early enough to go by car to Florence.

Things to do in Pienza

Wineries · Historic Sites · Parks · Wildlife

Side Trips

Find places to stay May 8 — 12:

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: admire the masterpieces at Florence Academy of Fine Arts, don't miss a visit to The Baptistery of St. John, take in panoramic vistas at Campanile di Giotto, and steep yourself in history at Basilica of Santa Croce.

To find other places to visit, where to stay, more things to do, and tourist information, refer to the Florence trip site.

Traveling by car from Pienza to Florence takes 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, daytime highs in Florence are 71°F, while nighttime lows are 52°F. Finish up your sightseeing early on the 16th (Sun) so you can travel back home.

Things to do in Florence

Historic Sites · Museums · Tours · Parks
Find places to stay May 12 — 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.