16 days in Tuscany Itinerary

Created using Inspirock Tuscany itinerary maker
Make it your trip
Fly
1
Montalcino
— 3 nights
Drive
2
Capalbio
— 2 nights
Drive
3
San Gimignano
— 3 nights
Drive
4
Pisa
— 1 night
Drive
5
Florence
— 6 nights
Fly

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Montalcino — 3 nights

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Deepen your sense of the past at sights like Abbazia di Sant'Antimo and Palazzo Comunale di Pienza. Do some cultural sightseeing at il Cocco and Corso il Rossellino. Explore Montalcino's surroundings by going to Museo di Lucignano (in Lucignano), Via di Gracciano nel Corso (in Montepulciano) and Monticchiello (in Pienza). It doesn't end there: do a tasting at Winery Solaria Patrizia Cencioni.

To see other places to visit, maps, more things to do, and more tourist information, go to the Montalcino road trip website.

Sao Paulo, Brazil to Montalcino is an approximately 17-hour flight. Traveling from Sao Paulo to Montalcino, you'll lose 4 hours due to the time zone difference. Plan for little chillier temperatures traveling from Sao Paulo in April, with highs in Montalcino at 23°C and lows at 9°C. Wrap up your sightseeing on the 1st (Mon) to allow time to drive to Capalbio.
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Wineries · Historic Sites · Neighborhoods · Museums
Side Trips
Find places to stay Apr 28 — May 1:

Capalbio — 2 nights

Capalbio is a comune (municipality) in the Province of Grosseto in the Italian region Tuscany, located about 150km south of Florence and about 45km southeast of Grosseto.Capalbio borders the following municipalities: Manciano, Montalto di Castro, Orbetello.HistoryThe name derives probably from the Latin Caput Album or Campus Albus (White Cape or Field, respectively), due to the white alabaster stone dug in the area.Capalbio is known for the first time in 805 CE, when it was donated to the Abbey of the Tre Fontane, near Rome, by Charlemagne. On the 2nd (Tue), contemplate the long history of Piazza Carlo Giordano, do a tasting at Jacobelli Liquori, look for gifts at IL BUTTERO,negozio tipico di abbigliamento maremmano,pelletteria., then make a trip to Centro Storico di Capalbio, and finally take in the architecture and atmosphere at Pieve di San Nicola. Here are some ideas for day two: don't miss a visit to Piccola Gerusalemme di Maremma, then pause for some serene contemplation at Chiesa di Santa Maria e San Rocco, and then get to know the fascinating history of Pitigliano Centro Storico.

Plan my day in Capalbio using traveler tips and tourist information provided by Inspirock.

Getting from Montalcino to Capalbio by car takes about 1.5 hours. Other options: do a combination of bus and train; or take a bus. Traveling from Montalcino in May, you will find days in Capalbio are a bit cooler (24°C), and nights are about the same (15°C). Finish up your sightseeing early on the 3rd (Wed) so you can go by car to San Gimignano.
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Historic Sites · Neighborhoods · Wineries · Shopping
Side Trip
Find places to stay May 1 — 3:

San Gimignano — 3 nights

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Duomo di San Gimignano and Porta San Giovanni are good opportunities to explore the local culture. Your inner history buff will appreciate Torre e Casa Campatelli and Historic Centre of San Gimignano. And it doesn't end there: enjoy breathtaking views from Rocca of Montestaffoli, take in the architecture and atmosphere at Pieve di Cellole, get a taste of the local shopping with La Bottega del Sale di Duccio Nacci photographer, and see the interesting displays at Vernaccia di San Gimignano Wine Experience - La Rocca.

To find traveler tips, reviews, ratings, and other tourist information, read our San Gimignano travel route site.

Drive from Capalbio to San Gimignano in 2.5 hours. Alternatively, you can take a train; or do a combination of train and bus. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Finish up your sightseeing early on the 6th (Sat) so you can go by car to Pisa.
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Historic Sites · Museums · Wineries · Shopping
Find places to stay May 3 — 6:

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 7th (Sun): enjoy breathtaking views from Leaning Tower of Pisa, contemplate in the serene atmosphere at Chiesa di Santa Caterina d'Alessandria, explore the different monuments and memorials at Camposanto, then take in the spiritual surroundings of Duomo di Pisa, and finally appreciate the extensive heritage of Knights’ Square.

To see maps, reviews, more things to do, and tourist information, use the Pisa online journey planner.

You can drive from San Gimignano to Pisa in 1.5 hours. Other options are to take a train; or take a bus. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Wrap up your sightseeing on the 7th (Sun) to allow time to drive to Florence.
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Historic Sites
Find places to stay May 6 — 7:

Florence — 6 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence Academy of Fine Arts and Corridoio Vasariano will appeal to museum buffs. Your inner history buff will appreciate Cathedral of Santa Maria del Fiore and Basilica of Santa Maria Novella. And it doesn't end there: contemplate in the serene atmosphere at The Baptistery of St. John, see the interesting displays at Synagogue and Jewish Museum of Florence, explore the galleries of Palazzo Strozzi, and admire the masterpieces at Pitti Palace.

For reviews, other places to visit, ratings, and tourist information, read our Florence trip planner.

You can drive from Pisa to Florence in 1.5 hours. Alternatively, you can take a bus; or take a train. In May, daily temperatures in Florence can reach 25°C, while at night they dip to 13°C. You will have some time to spend on the 13th (Sat) before leaving for home.
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Museums · Historic Sites · Childrens Museums
Find places to stay May 7 — 13:

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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