44 days in Tuscany Itinerary

44 days in Tuscany Itinerary

Created using Inspirock Tuscany trip itinerary maker
Make it your trip
Fly
1
Florence
— 7 nights
Drive
2
Cortona
— 6 nights
Drive
3
Montalcino
— 5 nights
Drive to Porto S.Stefano, Ferry to Isola Del Giglio
4
Isola Del Giglio
— 5 nights
Ferry to Porto S.Stefano, Drive to San Gimignano
5
San Gimignano
— 7 nights
+2
Drive to Piombino, Ferry to Portoferraio, Drive to Capoliveri
6
Capoliveri, Elba Island
— 7 nights
Drive
7
Marina di Pietrasanta
— 6 nights
Drive to Pisa International Airport, Fly to Washington

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Florence — 7 nights

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get some historical perspective at Cathedral of Santa Maria del Fiore and Piazza del Duomo. Head to M.G. Design and Museo Mario Romolifor plenty of shopping. Change things up with these side-trips from Florence: Greve in Chianti (Castello di Verrazzano & Azienda Agricola Altiero (Winery)) and Castello del Trebbio (in Santa Brigida). There's much more to do: admire the masterpieces at Florence Academy of Fine Arts, take in panoramic vistas at Campanile di Giotto, browse the eclectic array of goods at Mercato Centrale, and view the masterpieces at Limbo Art Gallery.

For other places to visit, reviews, photos, and more tourist information, go to the Florence trip website.

Washington, USA to Florence is an approximately 16.5-hour flight. Due to the time zone difference, you'll lose 6 hours traveling from Washington to Florence. In June in Florence, expect temperatures between 83°F during the day and 65°F at night. Finish up your sightseeing early on the 25th (Sat) so you can go by car to Cortona.
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Museums · Historic Sites · Shopping · Wineries
Side Trips
Find places to stay Jun 18 — 25:

Cortona — 6 nights

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.
Get a sense of the local culture at Hominis and Cortona Wine Tours. Visit Belvedere di Cortona and Eremo Le Celle for their historical value. Explore the numerous day-trip ideas around Cortona: Montepulciano (Tenuta Valdipiatta, Az. Agr. Poliziano, &more), Villa Sant'Anna (in Abbadia di Montepulciano) and Ravagni since 1421 (in Anghiari). There's lots more to do: view the masterpieces at La Torena Arte, do a tasting at Cantina Gabriele Mazzeschi, examine the collection at Museo Diocesano, and take an in-depth tour of MAEC - Museo dell'Accademia Etrusca.

To find where to stay, maps, more things to do, and more tourist information, you can read our Cortona road trip site.

You can drive from Florence to Cortona in 2 hours. Alternatively, you can take a train. Finish your sightseeing early on the 1st (Fri) to allow enough time to drive to Montalcino.
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Wineries · Shopping · Museums · Tours
Side Trips
Find places to stay Jun 25 — Jul 1:

Montalcino — 5 nights

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Shop till you drop at Caseificio Val d'Orcia and Art Studio di Adelina Quadri. Popular historic sites such as Val d'Orcia and Abbazia di Sant'Antimo are in your itinerary. Next up on the itinerary: learn about winemaking at Ciacci Piccolomini d'Aragona, get into the urban bustle at San Quirico d'Orcia, and view the masterpieces at Artemisia Gallery.

To see ratings, where to stay, and more tourist information, you can read our Montalcino road trip site.

You can drive from Cortona to Montalcino in 1.5 hours. Other options are to take a bus; or do a combination of train and bus. In July, daytime highs in Montalcino are 89°F, while nighttime lows are 67°F. Wrap up your sightseeing on the 6th (Wed) early enough to travel to Isola Del Giglio.
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Wineries · Shopping · Historic Sites · Museums
Side Trips
Find places to stay Jul 1 — 6:

Isola Del Giglio — 5 nights

Take a break from the city and head to La Playa del Carma and Bagno Giglio Blu.

To find more things to do, photos, ratings, and tourist information, you can read our Isola Del Giglio sightseeing planning website.

Getting from Montalcino to Isola Del Giglio by combination of car and ferry takes about 3 hours. Other options: do a combination of bus and ferry; or do a combination of bus, train, and ferry. July in Isola Del Giglio sees daily highs of 89°F and lows of 67°F at night. Finish your sightseeing early on the 11th (Mon) so you can travel to San Gimignano.
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Parks · Outdoors · Beaches · Nature
Find places to stay Jul 6 — 11:

San Gimignano — 7 nights

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.
Get some historical perspective at Duomo di Siena and Duomo di San Gimignano. Get some cultural insight at Poggio al Bosco and Sant'Agnese Farm. Explore San Gimignano's surroundings by going to Siena (Piazza del Mercato, Centro Storico di Siena, &more), Panzano in Chianti (Wine Gourmet La Ripa & Accademia del Buon Gusto) and Volterra (Piazza dei Priori, Kalpa Art Living, &more). There's still lots to do: view the masterpieces at Vitalita Cultural Association, do a tasting at Fattoria di Montemaggio, shop like a local with Galleria Gagliardi, and stop by (MR) Marri e Rossi.

To find more things to do, other places to visit, photos, and more tourist information, you can read our San Gimignano planning site.

You can do a combination of ferry and car from Isola Del Giglio to San Gimignano in 4 hours. Other options are to do a combination of ferry and bus; or do a combination of ferry, bus, and train. Expect a daytime high around 86°F in July, and nighttime lows around 65°F. Finish your sightseeing early on the 18th (Mon) so you can travel to Capoliveri.
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Wineries · Shopping · Museums · Historic Sites
Side Trips
Find places to stay Jul 11 — 18:

Capoliveri, Elba Island — 7 nights

Capoliveri is a comune (municipality) on the island of Elba in Italy. Escape the urban bustle at Aviosail Charter and Spiaggia Peducelli. Get out of town with these interesting Capoliveri side-trips: Spiaggia di Cotoncello (in Marciana), Marciana Marina (La Crocetta & Borgo del Cotone - Il Cotone) and Cavo Beach (in Cavo). There's lots more to do: explore the landscape on two wheels at Capoliveri Bike Park, stroll through Capo Stella, enjoy the sand and surf at Spiaggia di Barabarca, and take your sightseeing to a higher altitude at Monte Calamita.

For where to stay, traveler tips, and tourist information, read Capoliveri trip builder website.

Do a combination of car and ferry from San Gimignano to Capoliveri in 4 hours. Alternatively, you can do a combination of train, ferry, and bus. In July, daily temperatures in Capoliveri can reach 83°F, while at night they dip to 69°F. Wrap up your sightseeing on the 25th (Mon) to allow time to drive to Marina di Pietrasanta.
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Outdoors · Parks · Beaches · Trails
Side Trips
Find places to stay Jul 18 — 25:

Marina di Pietrasanta — 6 nights

Get in touch with nature at Bagno Stella Focette and Bagno Carlo. Change things up with these side-trips from Marina di Pietrasanta: Pania della Croce (in Molazzana), Centro Ippico Pegaso (in Marina di Carrara) and Asciutti Carlo (in Carrara).

For photos, reviews, more things to do, and more tourist information, read Marina di Pietrasanta trip itinerary builder website.

You can drive from Capoliveri to Marina di Pietrasanta in 3 hours. Alternatively, you can drive. In July, daytime highs in Marina di Pietrasanta are 82°F, while nighttime lows are 68°F. Wrap up your sightseeing by early afternoon on the 31st (Sun) to allow enough time to travel back home.
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Outdoors · Parks · Beaches · Nature
Side Trips
Find places to stay Jul 25 — 31:

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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