18 days in Tuscany Itinerary

18 days in Tuscany Itinerary

Created using Inspirock Tuscany tour itinerary maker
Make it your trip
— 4 nights
— 5 nights
— 6 nights
— 2 nights


Siena — 4 nights

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: Podere L'Aja (in Radda in Chianti) and San Gimignano (Fattoria Il Piano & Guardastelle Vineyard). There's lots more to do: make a trip to Piazza del Campo, pause for some serene contemplation at Duomo di Siena, gain insight at Scuola di Cucina di Lella, and explore the world behind art at Museo dell'Opera Metropolitana.

To find traveler tips, other places to visit, maps, and more tourist information, you can read our Siena driving holiday planner.

Brussels, Belgium to Siena is an approximately 5-hour flight. You can also drive; or take a train. Plan for a bit warmer temperatures traveling from Brussels in June, with highs in Siena at 34°C and lows at 19°C. Finish your sightseeing early on the 5th (Sun) so you can drive to Pienza.
Wineries · Historic Sites · Tours · Museums
Side Trips
Find places to stay Jun 1 — 5:

Pienza — 5 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. Venture out of the city with trips to Castelnuovo dell'Abate (Ciacci Piccolomini d'Aragona & Abbazia di Sant'Antimo), Montalcino (Podere Le Ripi, Mate Winery, &more) and Crete Senesi (in Asciano). And it doesn't end there: tour the pleasant surroundings at Val d'Orcia, don't miss a visit to Parco Archeologico Pava, contemplate in the serene atmosphere at Tempio di San Biagio, and do a tasting at De' Ricci.

To find other places to visit, reviews, ratings, and more tourist information, refer to the Pienza trip planner.

You can drive from Siena to Pienza in 1.5 hours. Other options are to take a bus; or do a combination of train and bus. In June, daytime highs in Pienza are 34°C, while nighttime lows are 19°C. Finish up your sightseeing early on the 10th (Fri) so you can go by car to Florence.
Wineries · Historic Sites · Parks · Nature
Side Trips
Find places to stay Jun 5 — 10:

Florence — 6 nights

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence is known for sightseeing, museums, and historic sites. Your trip includes some of its best attractions: explore the world behind art at Florence Academy of Fine Arts, admire the landmark architecture of The Baptistery of St. John, take in the views from Ponte Vecchio, and take in panoramic vistas at Campanile di Giotto.

To see maps, other places to visit, ratings, and other tourist information, read our Florence tour builder website.

Drive from Pienza to Florence in 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. In June, daytime highs in Florence are 33°C, while nighttime lows are 21°C. Finish your sightseeing early on the 16th (Thu) so you can drive to Pisa.
Historic Sites · Museums · Tours · Parks
Find places to stay Jun 10 — 16:

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.
Start off your visit on the 17th (Fri): enjoy breathtaking views from Leaning Tower of Pisa, don't miss a visit to Piazza dei Miracoli, and then examine the collection at Museo Aviotruppe Esercito Italiano. Get ready for a full day of sightseeing on the 18th (Sat): don't miss a visit to Le mura di Lucca, do a tasting at Fattoria al Dotto, and then look for gifts at Zazzi.

Inspirock's itinerary builder makes planning a Pisa trip simple and quick.

You can drive from Florence to Pisa in 1.5 hours. Other options are to take a bus; or take a train. Plan for little chillier nights when traveling from Florence in June since evenings lows in Pisa dip to 18°C. Finish up your sightseeing early on the 18th (Sat) so you can catch the flight back home.
Wineries · Shopping · Museums · Historic Sites
Side Trip
Find places to stay Jun 16 — 18:

Tuscany travel guide

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.