36 days in Tuscany Itinerary

Created using Inspirock Tuscany planner
Make it your trip
Fly
1
Pisa
— 5 nights
+2
Drive to Piombino, Ferry to Portoferraio, Drive to Capoliveri
2
Capoliveri, Elba Island
— 6 nights
+2
Drive to Portoferraio, Ferry to Piombino, Drive to Montalcino
3
Montalcino
— 6 nights
Drive
4
Arezzo
— 5 nights
Drive
5
San Gimignano
— 6 nights
Drive
6
Florence
— 6 nights
Fly

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Pisa — 5 nights

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Venture out of the city with trips to Italy Shore Drivers (in Cecina), Lucca (San Michele in Foro, Torre Guinigi, &more) and Terre del Marchesato (in Bolgheri). There's still lots to do: take in panoramic vistas at Leaning Tower of Pisa, admire the landmark architecture of Duomo di Pisa, don't miss a visit to Piazza dei Miracoli, and contemplate the long history of St Martin Cathedral.

For reviews, maps, ratings, and tourist information, read our Pisa trip itinerary tool.

Perth, Australia to Pisa is an approximately 23-hour flight. The time zone difference moving from Australian Western Standard Time (AWST) to Central European Standard Time (CET) is minus 7 hours. Plan for somewhat warmer temperatures traveling from Perth in September, with highs in Pisa at 30°C and lows at 17°C. Finish your sightseeing early on the 23rd (Thu) to allow enough time to travel to Capoliveri.
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Capoliveri, Elba Island — 6 nights

Capoliveri is a comune (municipality) on the island of Elba in Italy. You'll find plenty of places to visit near Capoliveri: Spiaggia La Sorgente (in Portoferraio), Spiaggia di Cavoli (in Seccheto) and Spiaggia del Relitto (in Pomonte). Next up on the itinerary: get outside with Aloha Center, tour the pleasant surroundings at Spiaggia Canata, enjoy the sand and surf at Spiaggia di Capo Bianco, and look for all kinds of wild species at Rio Diving Center.

For photos, ratings, maps, and tourist information, read our Capoliveri trip planning app.

Traveling by combination of car and ferry from Pisa to Capoliveri takes 3.5 hours. Alternatively, you can do a combination of train, ferry, and bus. September in Capoliveri sees daily highs of 28°C and lows of 19°C at night. Finish your sightseeing early on the 29th (Wed) to allow enough time to travel to Montalcino.
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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.
Explore Montalcino's surroundings by going to Crete Senesi (in Asciano), Montepulciano (Piazza Grande a Montepulciano, Tempio di San Biagio, &more) and Chiesa della Nativita di Maria (in Castel Del Piano). There's much more to do: learn about winemaking at Winery Solaria Patrizia Cencioni, contemplate the long history of Abbazia di Sant'Antimo, indulge your taste buds at Food & Drink, and appreciate the views at Val d'Orcia.

To see more things to do, photos, reviews, and other tourist information, read our Montalcino trip planner.

You can do a combination of car and ferry from Capoliveri to Montalcino in 3.5 hours. Alternatively, you can do a combination of bus, ferry, and train. While traveling from Capoliveri, expect a bit warmer days and about the same nights in Montalcino, ranging from highs of 32°C to lows of 19°C. Wrap up your sightseeing on the 5th (Tue) early enough to drive to Arezzo.
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Arezzo — 5 nights

Ancient City

Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Get out of town with these interesting Arezzo side-trips: Villa Sant'Anna (in Abbadia di Montepulciano), Azienda Agricola Leuta (in Pietraia) and Buccelletti - Cantina (in Castiglion Fiorentino). There's much more to do: learn about winemaking at Villa La Ripa, take in the spiritual surroundings of Eremo Le Celle, see the interesting displays at Museo Nazionale d'Arte Medievale e Moderna, and awaken your taste buds at some of the top wineries in the area.

To find photos, where to stay, more things to do, and other tourist information, use the Arezzo online tour planner.

Traveling by car from Montalcino to Arezzo takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Finish your sightseeing early on the 10th (Sun) so you can drive to San Gimignano.
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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: Fattoria di Montemaggio (in Radda in Chianti), Fattoria Casa Sola (in Barberino Val d'Elsa) and Siena (Basilica Cateriniana San Domenico, Wine Tours & Tastings, &more). The adventure continues: do a tasting at Guardastelle Vineyard, contemplate the long history of Torre Grossa, make a trip to Historic Centre of San Gimignano, and take in the spiritual surroundings of Church of Sant'Agostino.

To find out how to plan a trip to San Gimignano, use our trip itinerary maker.

Traveling by car from Arezzo to San Gimignano takes 2 hours. Alternatively, you can take a bus; or take a train. In October, daily temperatures in San Gimignano can reach 25°C, while at night they dip to 14°C. Finish up your sightseeing early on the 16th (Sat) so you can go by car to Florence.
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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.
Change things up with a short trip to Castello del Trebbio in Santa Brigida (about 36 minutes away). Dedicate the 22nd (Fri) to wine at some of the top wineries in the area. There's lots more to do: explore the world behind art at Florence Academy of Fine Arts, admire the landmark architecture of The Baptistery of St. John, examine the collection at Pitti Palace, and enjoy breathtaking views from Campanile di Giotto.

To find reviews, maps, more things to do, and more tourist information, read our Florence online route planner.

Drive from San Gimignano to Florence in 1.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 25°C in October, and nighttime lows around 14°C. Cap off your sightseeing on the 22nd (Fri) early enough to catch the flight back home.
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Tuscany travel guide

4.4
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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