29 days in Tuscany Itinerary

29 days in Tuscany Itinerary

Created using Inspirock Tuscany trip maker

Make it your trip
Fly
1
Florence
— 5 nights
Drive
2
Pratovecchio
— 7 nights
Drive
3
Cortona
— 3 nights
Drive
4
Siena
— 5 nights
Taxi to Piombino, Ferry to Portoferraio
5
Portoferraio, Elba Island
— 4 nights
Ferry to Piombino, Drive to Pisa
6
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.
Step out of Florence with an excursion to Castello del Trebbio in Santa Brigida--about 36 minutes away. Dedicate the 22nd (Wed) to wine at some of the top wineries in the area. There's still lots to do: explore the world behind art at Florence Academy of Fine Arts, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, snap pictures at Ponte Vecchio, and appreciate the extensive heritage of Piazza del Duomo.

For traveler tips, where to stay, ratings, and tourist information, read Florence online tour builder.

Gothenburg, Sweden to Florence is an approximately 7-hour flight. You can also drive; or do a combination of car and train. In September, Florence is somewhat warmer than Gothenburg - with highs of 30°C and lows of 17°C. Finish your sightseeing early on the 24th (Fri) so you can drive to Pratovecchio.

Things to do in Florence

Tours · Wineries · Historic Sites · Museums

Side Trips

Pratovecchio

— 7 nights
Your day by day itinerary now includes Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna. Explore Pratovecchio's surroundings by going to Sasso Simone (in Sestino), Spazio Culturale "La Guerra e La Memoria" (in Firenzuola) and Carpegna (Parco del Sasso Simone e Simoncello & Palazzo dei Principi).

For more things to do, reviews, traveler tips, and more tourist information, you can read our Pratovecchio journey planner.

You can drive from Florence to Pratovecchio in 1.5 hours. Expect a daytime high around 29°C in September, and nighttime lows around 19°C. Finish up your sightseeing early on the 1st (Fri) so you can travel to Cortona.

Things to do in Pratovecchio

Parks · Nature · Wildlife · Historic Sites

Side Trips

Cortona

— 3 nights

City of Art

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.
Change things up with these side-trips from Cortona: Art Studio di Adelina Quadri (in Monticchiello), Montepulciano (Vinoteca Terra Toscana, Az. Agr. Poliziano, &more) and Wine Tours & Tastings (in Monte San Savino). There's lots more to do: appreciate the views at Val d'Orcia, get engrossed in the history at MAEC - Museo dell'Accademia Etrusca, make a trip to Palazzone di Cortona, and contemplate in the serene atmosphere at Eremo Le Celle.

To find other places to visit, ratings, where to stay, and more tourist information, read our Cortona itinerary planner.

You can drive from Pratovecchio to Cortona in 1.5 hours. Finish your sightseeing early on the 4th (Mon) to allow enough time to drive to Siena.

Things to do in Cortona

Wineries · Historic Sites · Museums · Nature

Side Trips

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.
Change things up with these side-trips from Siena: San Gimignano (Podere La Marronaia- Sosta Alle Colonne & Guardastelle Vineyard), Barberino Val d'Elsa (La Ripa & Fattoria Casa Sola) and A Solatio Organic Farm (in Certaldo). There's much more to do: indulge your senses at some of the top wineries in the area, steep yourself in history at Battistero di San Giovanni, gain insight at Scuola di Cucina di Lella, and get a sense of history and politics at Palazzo Pubblico and Museo Civico.

To find other places to visit, ratings, maps, and more tourist information, read our Siena vacation builder site.

You can drive from Cortona to Siena in 1.5 hours. Other options are to take a train; or do a combination of train and bus. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Wrap up your sightseeing on the 9th (Sat) to allow time to travel to Portoferraio.

Things to do in Siena

Wineries · Historic Sites · Tours · Museums

Side Trips

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: Capoliveri (Centro Subacqueo Il Corsaro & Spiaggia Di Buzzancone o Cera), Spiaggia di Chiessi (in Chiessi) and Monte Capanne (in Marciana). There's lots more to do: take a tour by water with Boat Tours & Water Sports, enjoy the sand and surf at Spiaggia Canata, tour the pleasant surroundings at Spiaggia di Barabarca, and get outside with Aloha Center.

For maps, photos, other places to visit, and other tourist information, you can read our Portoferraio trip planning site.

You can do a combination of taxi and ferry from Siena to Portoferraio in 3.5 hours. Other options are to do a combination of train and ferry; or do a combination of bus, train, and ferry. When traveling from Siena in October, plan for slightly colder days in Portoferraio, with highs around 22°C, while nights are about the same with lows around 17°C. Cap off your sightseeing on the 13th (Wed) early enough to travel to Pisa.

Things to do in Portoferraio

Outdoors · Parks · Beaches · Wildlife

Side Trips

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.
Change things up with these side-trips from Pisa: Podere Pellicciano - Agrisole (in San Miniato), Italy Shore Drivers (in Cecina) and Lucca (Torre Guinigi, Fattoria al Dotto, &more). There's much more to do: admire the landmark architecture of Leaning Tower of Pisa, examine the collection at Museo Aviotruppe Esercito Italiano, steep yourself in history at St Martin Cathedral, and don't miss a visit to Piazza dei Miracoli.

To find where to stay, traveler tips, ratings, and more tourist information, go to the Pisa day trip site.

Getting from Portoferraio to Pisa by combination of ferry and car takes about 3 hours. Other options: do a combination of ferry and train. In October, plan for daily highs up to 25°C, and evening lows to 14°C. Finish your sightseeing early on the 17th (Sun) to allow enough time to fly back home.

Things to do in Pisa

Wineries · Tours · Historic Sites · Museums

Side Trips

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.