43 days in Tuscany Itinerary

43 days in Tuscany Itinerary

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

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San Gimignano — 6 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.
Explore the numerous day-trip ideas around San Gimignano: Siena (Basilica Cateriniana San Domenico, Battistero di San Giovanni, &more), A Solatio Organic Farm (in Certaldo) and Fattoria Casa Sola (in Barberino Val d'Elsa). There's lots more to do: do a tasting at Fattoria Il Piano, pause for some serene contemplation at Church of Sant'Agostino, relax in the rural setting at Corbucci, and contemplate the long history of Torre Grossa.

For ratings, maps, traveler tips, and other tourist information, you can read our San Gimignano driving holiday planner.

Vancouver, Canada to San Gimignano is an approximately 15.5-hour flight. Due to the time zone difference, you'll lose 9 hours traveling from Vancouver to San Gimignano. Traveling from Vancouver in July, expect San Gimignano to be somewhat warmer, temps between 35°C and 21°C. Finish up your sightseeing early on the 10th (Mon) so you can go by car to Florence.
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Wineries · Tours · Historic Sites · Museums
Side Trips
Find places to stay Jul 3 — 10:

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.
Step out of Florence to go to Santa Brigida and see Castello del Trebbio, which is approximately 36 minutes away. Dedicate the 16th (Sun) to wine at some of the top wineries in the area. Next up on the itinerary: admire the masterpieces at Florence Academy of Fine Arts, ponder the world of politics at Palazzo Vecchio, steep yourself in history at Basilica of Santa Croce, and appreciate the extensive heritage of Piazza del Duomo.

To find where to stay, other places to visit, photos, and tourist information, go to the Florence road trip app.

Getting from San Gimignano to Florence by car takes about 1.5 hours. Other options: take a train; or take a bus. In July, daytime highs in Florence are 35°C, while nighttime lows are 21°C. Cap off your sightseeing on the 16th (Sun) early enough to go by car to Arezzo.
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Historic Sites · Wineries · Tours · Museums
Side Trips
Find places to stay Jul 10 — 16:

Arezzo — 6 nights

Ancient City

Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Explore the numerous day-trip ideas around Arezzo: Cortona (Daniela Piegai Art Gallery, Hominis, &more), Castiglion Fiorentino (Buccelletti - Cantina, winery Agriturismo Santo Stefano, &more) and Ravagni since 1421 (in Anghiari). There's lots more to do: learn about winemaking at Villa La Ripa, take a memorable drive along Very Tuscany, explore the striking landscape at Le Balze, and take an in-depth tour of Munacs.

To see where to stay, photos, ratings, and tourist information, go to the Arezzo trip builder.

You can drive from Florence to Arezzo in 1.5 hours. Alternatively, you can take a train. Wrap up your sightseeing on the 22nd (Sat) early enough to travel to Isola Del Giglio.
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Wineries · Tours · Scenic Drive · Outdoors
Side Trips
Find places to stay Jul 16 — 22:

Isola Del Giglio — 4 nights

Isola Del Giglio is known for beaches, nature, and wildlife. Your trip includes some of its best attractions: kick back and relax at La Playa del Carma, head off the coast to Giglio Island, take advantage of the amenities at Bagno Giglio Blu, and tour the water at your own pace with Spiaggia delle Caldane.

For reviews, where to stay, maps, and more tourist information, go to the Isola Del Giglio online road trip planner.

You can do a combination of car and ferry from Arezzo to Isola Del Giglio in 4 hours. Alternatively, you can do a combination of train, bus, and ferry; or do a combination of bus and ferry. In July, daytime highs in Isola Del Giglio are 37°C, while nighttime lows are 22°C. Finish your sightseeing early on the 26th (Wed) to allow enough time to travel to Montalcino.
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Outdoors · Parks · Beaches · Tours
Find places to stay Jul 22 — 26:

Montalcino — 6 nights

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Get out of town with these interesting Montalcino side-trips: Il villaggio dei bambini (in Chianciano Terme), Agriturismo il Molinello (in Asciano) and Montepulciano (Quinteaquadri Lab Gallery, Tenuta Valdipiatta, &more). It doesn't end there: learn about winemaking at Ciacci Piccolomini d'Aragona and appreciate the views at Val d'Orcia.

For other places to visit, more things to do, reviews, and more tourist information, go to the Montalcino route app.

You can do a combination of ferry and car from Isola Del Giglio to Montalcino in 3 hours. Other options are to do a combination of ferry and bus; or do a combination of ferry, bus, and train. In July, plan for daily highs up to 37°C, and evening lows to 22°C. Wrap up your sightseeing on the 1st (Tue) to allow time to travel to Capoliveri.
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Wineries · Historic Sites · Shopping · Museums
Side Trips
Find places to stay Jul 26 — Aug 1:

Capoliveri, Elba Island — 7 nights

Capoliveri is a comune (municipality) on the island of Elba in Italy. Explore the numerous day-trip ideas around Capoliveri: Spiaggia di Cavoli (in Seccheto) and Spiaggia La Sorgente (in Portoferraio). There's much more to do: get outside with Rio Diving Center, enjoy the sand and surf at Acqua marina, see some colorful creatures with Centro Subacqueo Il Corsaro, and tour the pleasant surroundings at Spiaggia Di Buzzancone o Cera.

For traveler tips, photos, maps, and more tourist information, read Capoliveri planner.

You can do a combination of car and ferry from Montalcino to Capoliveri in 3.5 hours. Alternatively, you can do a combination of bus, train, and ferry. Expect little chillier weather when traveling from Montalcino in August: highs in Capoliveri hover around 33°C, while lows dip to 23°C. Finish your sightseeing early on the 8th (Tue) so you can travel to Pisa.
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Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Aug 1 — 8:

Pisa — 6 nights

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Explore Pisa's surroundings by going to Pieve di San Martino (in Palaia), Temple of Minerva Medica in Montefoscoli (in Montefoscoli) and San Miniato (Podere Pellicciano - Agrisole, Chiesa di Sant'Jacopo e Lucia, &more). There's much more to do: make a trip to Leaning Tower of Pisa, kick back and relax at Bagno Carlo, tour the pleasant surroundings at Cala San Quirico, and learn about winemaking at Terre del Marchesato.

For traveler tips, ratings, other places to visit, and tourist information, read our Pisa online vacation builder.

Do a combination of car and ferry from Capoliveri to Pisa in 3.5 hours. Alternatively, you can do a combination of bus, ferry, and train. In August, plan for daily highs up to 35°C, and evening lows to 20°C. Wrap up your sightseeing on the 14th (Mon) early enough to fly back home.
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Parks · Outdoors · Beaches · Wineries
Side Trips
Find places to stay Aug 8 — 14:

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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