22 days in Tuscany Itinerary

22 days in Tuscany Itinerary

Created using Inspirock Tuscany trip planner

Make it your trip
Fly
1
Pisa
— 3 nights
Drive
2
Lucca
— 2 nights
Drive
3
Arezzo
— 3 nights
Drive
4
Capalbio
— 1 night
Drive
5
Siena
— 3 nights
Drive
6
San Casciano in Val di Pesa
— 1 night
Drive
7
Florence
— 7 nights
Fly

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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.
Eschew the tourist crowds and head to Duomo di Pisa and Knights’ Square. Palazzo Blu and Museo di Palazzo Reale will appeal to museum buffs. Explore the numerous day-trip ideas around Pisa: Museo Diocesano Della Spezia (in La Spezia), San Pietro Church (in Porto Venere) and Tellaro (Chiesa di San Giorgio & Centro Storico del Paese di Tellaro). Next up on the itinerary: appreciate the extensive heritage of Via Giuseppe Garibaldi, admire the masterpieces at Palazzo Ducale, admire the striking features of Logge di Banchi, and take in the spiritual surroundings of Chiesa di Santa Maria della Spina.

Start your trip to Pisa by creating a personalized itinerary on Inspirock.

Fort Lauderdale, USA to Pisa is an approximately 15.5-hour flight. Traveling from Fort Lauderdale to Pisa, you'll lose 6 hours due to the time zone difference. Traveling from Fort Lauderdale in May, you will find days in Pisa are little chillier (71°F), and nights are cooler (52°F). Finish your sightseeing early on the 6th (Wed) to allow enough time to drive to Lucca.

Things to do in Pisa

Historic Sites · Museums · Childrens Museums

Side Trips

Find places to stay May 3 — 6:

Lucca

— 2 nights

City of a Hundred Churches

Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Start off your visit on the 7th (Thu): take in the spiritual surroundings of San Michele in Foro, stroll through Palazzo Pfanner, take in the architecture and atmosphere at Chiesa di Sant'Agostino, don't miss a visit to Piazza Anfiteatro, then admire the masterpieces at Museo Nazionale di Palazzo Mansi, and finally examine the collection at Puccini Museum - Casa Natale. On the 8th (Fri), you'll have a packed day of sightseeing: make a trip to Torre delle Ore, enjoy breathtaking views from Torre Guinigi, take in the architecture and atmosphere at Chiesa di Sant'Anastasio, contemplate the long history of St Martin Cathedral, then take in the spiritual surroundings of Basilica of San Frediano, and finally don't miss a visit to Via Fillungo.

For photos, traveler tips, where to stay, and tourist information, you can read our Lucca trip maker site.

Lucca is just a short distance from Pisa. Expect a daytime high around 71°F in May, and nighttime lows around 52°F. Wrap up your sightseeing on the 8th (Fri) to allow time to drive to Arezzo.

Things to do in Lucca

Historic Sites · Museums · Parks
Find places to stay May 6 — 8:

Arezzo

— 3 nights

Ancient City

Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Discover out-of-the-way places like Anghiari and City Centre. Museum-lovers will get to explore Studio Moretti Caselli and Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti. Venture out of the city with trips to Civita di Bagnoregio (in Bagnoregio), Museo Diocesano (in Cortona) and Civita di Bagnoregio (Cappella Della Madonna Del Carcere & Museo Geologico e delle Frane). There's much more to do: explore the world behind art at Galleria Nazionale dell'Umbria, don't miss a visit to Fontana Maggiore, step into the grandiose world of Rocca Paolina, and examine the collection at Museo Tela Umbra.

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

Drive from Lucca to Arezzo in 1.5 hours. Alternatively, you can take a train. Finish your sightseeing early on the 11th (Mon) to allow enough time to drive to Capalbio.

Things to do in Arezzo

Museums · Historic Sites · Neighborhoods · Childrens Museums

Side Trips

Find places to stay May 8 — 11:

Capalbio

— 1 night
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 12th (Tue), admire the natural beauty at Giardino dei Tarocchi.

To see reviews, maps, photos, and other tourist information, read Capalbio road trip planner.

You can drive from Arezzo to Capalbio in 3 hours. Other options are to take a train; or take a bus. In May, plan for daily highs up to 69°F, and evening lows to 55°F. Wrap up your sightseeing on the 12th (Tue) early enough to drive to Siena.

Things to do in Capalbio

Parks · Museums
Find places to stay May 11 — 12:
Highlights from your trip

Siena

— 3 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Museum-lovers will get to explore Palazzo Pubblico and Museo Civico and Museo dell'Opera Metropolitana. Step off the beaten path and head to Centro Storico di Siena and Castello di Monteriggioni. Explore the numerous day-trip ideas around Siena: Chiusdino (Abbazia di San Galgano & Eremo di Montesiepi) and Guardastelle Vineyard (in San Gimignano). There's still lots to do: enjoy breathtaking views from Torre del Mangia, don't miss a visit to Piazza del Campo, take in the architecture and atmosphere at Duomo di Siena, and get engrossed in the history at MOnd - Museo della Contrada Capitana dell'Onda.

To find maps, ratings, where to stay, and tourist information, use the Siena tour itinerary app.

You can drive from Capalbio to Siena in 2 hours. Other options are to take a train; or take a bus. May in Siena sees daily highs of 74°F and lows of 53°F at night. Wrap up your sightseeing on the 15th (Fri) to allow time to drive to San Casciano in Val di Pesa.

Things to do in Siena

Historic Sites · Wineries · Museums

Side Trips

Find places to stay May 12 — 15:

San Casciano in Val di Pesa

— 1 night
San Casciano in Val di Pesa is a comune (municipality) in the Province of Florence in the Italian region Tuscany, located about 15km southwest of Florence.San Casciano in Val di Pesa borders the following municipalities; Greve in Chianti, Impruneta, Montespertoli, Scandicci and Tavarnelle Val di Pesa.HistorySan Casciano’s territory was inhabited since Etruscan times, as evidenced by archaeological findings in Montefiridolfi (The Bowman’s Grave) and Valigondoli (Poggio La Croce’s excavations). On the 16th (Sat), take in the architecture and atmosphere at Pieve di San Pancrazio, learn about winemaking at Poggio al Bosco, do a tasting at Solatione, step into the grandiose world of Castello di Bibbione, then get to know the fascinating history of Mura di San Casciano, and finally explore the galleries of Casa Museo Machiavelli.

To see other places to visit, where to stay, maps, and tourist information, you can read our San Casciano in Val di Pesa online attractions planner.

Traveling by car from Siena to San Casciano in Val di Pesa takes an hour. Alternatively, you can take a bus; or do a combination of train and bus. May in San Casciano in Val di Pesa sees daily highs of 71°F and lows of 52°F at night. Wrap up your sightseeing on the 16th (Sat) to allow time to drive to Florence.

Things to do in San Casciano in Val di Pesa

Wineries · Historic Sites · Museums

Side Trip

Find places to stay May 15 — 16:

Florence

— 7 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get some cultural insight at Cathedral of Santa Maria del Fiore and Pitti Palace. Discover out-of-the-way places like Centro Storico and Palazzo Strozzi. Venture out of the city with trips to Chiesa di San Procolo (in Bologna), Modena (Duomo di Modena, MEF-Museo Enzo Ferrari, &more) and Ravenna (Parrochia Santa Maria del Suffragio, Basilica San Vitale, &more). There's lots more to do: engage your brain at Museo Galileo - Institute and Museum of the History of Science, get engrossed in the history at Museum of Opera of Saint Maria of Fiore, admire the striking features of Loggia dei Lanzi, and explore the galleries of Museo Nazionale del Bargello.

For where to stay, other places to visit, maps, and other tourist information, go to the Florence road trip site.

You can drive from San Casciano in Val di Pesa to Florence in an hour. Another option is to take a bus. In May, daytime highs in Florence are 71°F, while nighttime lows are 52°F. Wrap up your sightseeing by early afternoon on the 23rd (Sat) to allow enough time to fly back home.

Things to do in Florence

Museums · Historic Sites · Childrens Museums

Side Trips

Find places to stay May 16 — 23:

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.