31 days in Tuscany Itinerary

31 days in Tuscany Itinerary

Created using Inspirock Tuscany sightseeing planner

Plan created by another user. Make it yours

Route & dates

1
Siena
— 8 nights
2
Portoferraio, Elba Island
— 8 nights
3
Viareggio
— 7 nights
4
Fiesole
— 7 nights

8
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Explore Siena's surroundings by going to Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate), San Gimignano (Guardastelle Vineyard, Historic Centre of San Gimignano, &more) and Montalcino (Poggio Rubino & Podere Il Cocco). There's much more to do: indulge your taste buds at Food & Drink, contemplate the long history of Centro Storico di Siena, learn the tricks of the trade with Take Me Out in Tuscany, and pause for some serene contemplation at Duomo di Siena.

To see reviews, photos, traveler tips, and other tourist information, you can read our Siena trip planner.

Florence to Siena is an approximately 1.5-hour car ride. You can also take a bus; or take a train. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Finish your sightseeing early on the 9th (Tue) to allow enough time to travel to Portoferraio.

Things to do in Siena

Wineries · Tours · Historic Sites

Side Trips

San Gimignano, Montalcino, Famiglia Buccelletti Winery, Fattoria di Montemaggio, Poggio al Bosco
Find places to stay Oct 1 — 9:
Highlights from your plan
Wine Tours & Tastings
Scuola di Cucina di Lella ©
Scuola di Cucina di Lella
Duomo di Siena ©
Duomo di Siena

8
nights
Portoferraio, Elba Island

Portoferraio ©
Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Change things up with these side-trips from Portoferraio: Spiaggia del Relitto (in Pomonte), Monte Capanne (in Marciana) and Spiaggia di Cavoli (in Seccheto). There's still lots to do: kick back and relax at Spiaggia Di Sansone, don't miss a visit to Bastioni Medicei, and tour the pleasant surroundings at Spiaggia di Capo Bianco.

To see where to stay, photos, maps, and tourist information, read Portoferraio holiday planner.

You can do a combination of car and ferry from Siena to Portoferraio in 3.5 hours. Alternatively, you can do a combination of train and ferry; or do a combination of bus, train, and ferry. Expect slightly colder weather when traveling from Siena in October: highs in Portoferraio hover around 22°C, while lows dip to 17°C. Cap off your sightseeing on the 17th (Wed) early enough to travel to Viareggio.

Things to do in Portoferraio

Parks · Outdoors · Beaches

Side Trips

Campo nell'Elba, Marina di Campo, Marciana, Spiaggia Canata, Spiaggia di Cavoli
Find places to stay Oct 9 — 17:
Highlights from your plan
Spiaggia di Seccione ©
Spiaggia di Seccione
Spiaggia Di Sansone ©
Spiaggia Di Sansone
Spiaggia La Sorgente ©
Spiaggia La Sorgente

7
nights
Viareggio

Viareggio ©
Viareggio is a city and comune in northern Tuscany, Italy, on the coast of the Tyrrhenian Sea. Change things up with these side-trips from Viareggio: Lucca (St Martin Cathedral, Torre Guinigi, &more). There's much more to do: take in panoramic vistas at Leaning Tower of Pisa, tour the pleasant surroundings at Bagno Eva, kick back and relax at Bagno Maurizio, and look for all kinds of wild species at La Lecciona.

For traveler tips, reviews, and tourist information, read Viareggio road trip website.

Do a combination of ferry and car from Portoferraio to Viareggio in 3.5 hours. Alternatively, you can do a combination of ferry and train. In October, plan for daily highs up to 25°C, and evening lows to 14°C. On the 24th (Wed), you'll travel to Fiesole.

Things to do in Viareggio

Outdoors · Beaches · Parks

Side Trips

Lucca, Pisa, La Vela BeachClub, Bagno Eva
Find places to stay Oct 17 — 24:
Highlights from your plan
Bagno Maurizio ©
Bagno Maurizio
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Le mura di Lucca ©
Le mura di Lucca

7
nights
Fiesole

Fiesole ©
Fiesole is a town and comune of the Metropolitan City of Florence in the Italian region of Tuscany, on a scenic height above Florence, 8km northeast of that city. Explore the numerous day-trip ideas around Fiesole: Florence (Pitti Palace, Piazza della Signoria, &more). The adventure continues: admire the masterpieces at Florence Academy of Fine Arts, see the interesting displays at Museo di San Marco, don't miss a visit to Piazzale Michelangelo, and let your taste buds guide you at a local gastronomic tour.

For photos, traveler tips, maps, and tourist information, refer to the Fiesole trip planner.

Traveling by car from Viareggio to Fiesole takes 1.5 hours. Alternatively, you can take a bus; or take a train. In October, daily temperatures in Fiesole can reach 25°C, while at night they dip to 14°C. Finish up your sightseeing early on the 31st (Wed) so you can go by car back home.

Things to do in Fiesole

Historic Sites · Tours · Museums

Side Trip

Florence
Find places to stay Oct 24 — 31:
Highlights from your plan
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts
Piazzale Michelangelo ©
Piazzale Michelangelo
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi

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