22 days in Tuscany Itinerary

22 days in Tuscany Itinerary

Created using Inspirock Tuscany journey builder
Make it your trip
Fly
1
Florence
— 5 nights
Drive
2
Arezzo
— 3 nights
Bus
3
Siena
— 5 nights
Taxi to Piombino, Ferry to Portoferraio
4
Portoferraio, Elba Island
— 4 nights
Ferry to Piombino, Drive to Pisa
5
Pisa
— 4 nights
Fly

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Florence — 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get out of town with these interesting Florence side-trips: Ponte Mediceo (in Pontassieve) and Castello del Trebbio (in Santa Brigida). Dedicate the 11th (Mon) 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, take in the architecture and atmosphere at Basilica of Santa Croce, steep yourself in history at Cathedral of Santa Maria del Fiore, and make a trip to Piazzale Michelangelo.

Plan a trip to Florence easily and quickly by telling Inspirock to suggest an itinerary.

Toronto, Canada to Florence is an approximately 13-hour flight. The time zone difference when traveling from Toronto to Florence is 6 hours. In September, daytime highs in Florence are 30°C, while nighttime lows are 17°C. Finish your sightseeing early on the 12th (Tue) so you can drive to Arezzo.
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Wineries · Tours · Historic Sites · Museums
Side Trips
Find places to stay Sep 7 — 12:

Arezzo — 3 nights

Ancient City

Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Explore Arezzo's surroundings by going to Cortona (Wine Tours & Tastings, Palazzo Comunale, &more), Montepulciano (Az. Agr. Poliziano & Tenuta Valdipiatta) and Buccelletti - Cantina (in Castiglion Fiorentino). Next up on the itinerary: learn about winemaking at Villa La Ripa, take in the spiritual surroundings of Santa Maria della Pieve, pause for some serene contemplation at Chiesa di Santa Maria delle Grazie, and explore the world behind art at Galleria Ivan Bruschi.

To see reviews, maps, and other tourist information, use the Arezzo online tour planner.

You can drive from Florence to Arezzo in 1.5 hours. Alternatively, you can take a train. Cap off your sightseeing on the 15th (Fri) early enough to catch the bus to Siena.
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Wineries · Tours · Museums · Historic Sites
Side Trips
Find places to stay Sep 12 — 15:

Siena — 5 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Venture out of the city with trips to Fattoria Casa Sola (in Barberino Val d'Elsa), Guardastelle Vineyard (in San Gimignano) and Montalcino (Winery Solaria Patrizia Cencioni & Mate Winery). There's much more to do: take in the architecture and atmosphere at Duomo di Siena, explore the world behind art at Museo dell'Opera Metropolitana, get a sense of history and politics at Palazzo Pubblico and Museo Civico, and don't miss a visit to Piazza del Campo.

Quickly create a custom-made itinerary for Siena using our trip planner.

You can take a bus from Arezzo to Siena in 1.5 hours. Alternatively, you can drive; or take a train. In September, daily temperatures in Siena can reach 32°C, while at night they dip to 19°C. Cap off your sightseeing on the 20th (Wed) early enough to travel to Portoferraio.
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Tours · Wineries · Historic Sites · Museums
Side Trips
Find places to stay Sep 15 — 20:

Portoferraio, Elba Island — 4 nights

Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. You'll find plenty of places to visit near Portoferraio: Marciana (Unzipo & Monte Capanne), Scogliera delle Piscine (in Marina di Campo) and Spiaggia Peducelli (in Capoliveri). There's much more to do: get outside with Aloha Center, kick back and relax at Spiaggia di Capo Bianco, stroll through Spiaggia di Chiessi, and discover the deep blue sea with Rio Diving Center.

To find maps, ratings, other places to visit, and more tourist information, go to the Portoferraio trip itinerary tool.

Traveling by combination of taxi and ferry from Siena to Portoferraio takes 3.5 hours. Alternatively, you can do a combination of train and ferry; or do a combination of bus, train, and ferry. Traveling from Siena in September, expect nights in Portoferraio to be about the same, around 19°C, while days are little chillier, around 28°C. Finish your sightseeing early on the 24th (Sun) so you can travel to Pisa.
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Outdoors · Parks · Beaches · Wildlife
Side Trips
Find places to stay Sep 20 — 24:

Pisa — 4 nights

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
You'll find plenty of places to visit near Pisa: La Terrazza Luminosa (in Massa), Lucca (Torre Guinigi, San Michele in Foro, &more) and Bagno Maurizio (in Viareggio). There's lots more to do: enjoy breathtaking views from Leaning Tower of Pisa, do a tasting at Podere Pellicciano - Agrisole, look for gifts at Salumeria Cordoni, and take in the spiritual surroundings of Pieve di San Martino.

To see traveler tips, more things to do, other places to visit, and more tourist information, read our Pisa trip planner.

Do a combination of ferry and car from Portoferraio to Pisa in 3 hours. Alternatively, you can do a combination of ferry and train. In September, daily temperatures in Pisa can reach 30°C, while at night they dip to 17°C. Cap off your sightseeing on the 28th (Thu) early enough to catch the flight back home.
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Wineries · Parks · Beaches · Outdoors
Side Trips
Find places to stay Sep 24 — 28:

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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