14 days in Tuscany Itinerary

14 days in Tuscany Itinerary

Created using Inspirock Tuscany route builder

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Route & dates

14 days in Tuscany Itinerary

Start: Portland
Fly:  16​h 45​min
1
Florence
— 2 nights
bus:  1​h
2
Lucca
— 1 night
train:  30​min
3
Viareggio
— 3 nights
Drive + ferry:  2​h 15​min
4
Portoferraio, Elba Island
— 2 nights
Drive:  2​h 30​min
5
Montalcino
— 2 nights
Drive:  1​h 15​min
6
Saturnia
— 1 night
Drive + Fly:  23​h 15​min
End: Portland

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll discover tucked-away gems like San Gimignano 1300 and Loggia dei Lanzi. Step out of Florence to go to San Gimignano and see Historic Centre of San Gimignano, which is approximately 1 hour away. There's much more to do: ponder the world of politics at Bargello National Museum, pause for some photo ops at Perseus Statue, let your taste buds guide you at a local gastronomic tour, and admire the striking features of Basilica of Santa Maria Novella.

To see more things to do, photos, reviews, and other tourist information, use the Florence planner .

Portland, USA to Florence is an approximately 17-hour flight. You can also do a combination of train, bus, and flight. You'll lose 9 hours traveling from Portland to Florence due to the time zone difference. Traveling from Portland in October, plan for a bit warmer nights in Florence, with lows around 55°F. Wrap up your sightseeing on the 12th (Fri) to allow time to drive to Lucca.

Things to do in Florence

Historic Sites Museums Tours

Side Trip

San Gimignano
Find places to stay Oct 10 — 12:
Highlights from your plan
Centro Storico ©
Centro Storico
San Gimignano 1300 ©
San Gimignano 1300
Food Tours

1
night
Lucca

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Start off your visit on the 13th (Sat): don't miss a visit to Montecatini Alto, take in panoramic vistas at Guinigi Tower, then make a trip to Piazza Anfiteatro, then steep yourself in history at Le mura di Lucca, and finally admire the striking features of St Martin Cathedral.

To see more things to do, other places to visit, and other tourist information, read Lucca travel route planner .

Getting from Florence to Lucca by car takes about an hour. Other options: take a bus; or take a train. In October, plan for daily highs up to 70°F, and evening lows to 54°F. Wrap up your sightseeing on the 13th (Sat) early enough to take a train to Viareggio.

Things to do in Lucca

Historic Sites

Side Trip

Montecatini Alto
Find places to stay Oct 12 — 13:
Highlights from your plan
St Martin Cathedral ©
St Martin Cathedral
Le mura di Lucca ©
Le mura di Lucca
Montecatini Alto ©
Montecatini Alto

3
nights
Viareggio

Viareggio ©
Viareggio is a city and comune in northern Tuscany, Italy, on the coast of the Tyrrhenian Sea. Start off your visit on the 14th (Sun): make a trip to Piazza dei Cavalieri, admire the landmark architecture of Palazzo della Carovana, pause for some serene contemplation at Chiesa di San Frediano, then explore the different monuments and memorials at Camposanto, then take in the spiritual surroundings of Battistero, and finally admire the landmark architecture of Duomo di Pisa. Here are some ideas for day two: don't miss a visit to Terrazza Mascagni, pause for some serene contemplation at Santuario di Montenero, and then tour the pleasant surroundings at Bagno Maurizio.

For traveler tips, where to stay, more things to do, and other tourist information, you can read our Viareggio trip tool .

Viareggio is just a stone's throw from Lucca. In October, daytime highs in Viareggio are 71°F, while nighttime lows are 54°F. Wrap up your sightseeing on the 16th (Tue) to allow time to travel to Portoferraio.

Things to do in Viareggio

Historic Sites Parks Beaches

Side Trips

Pisa, Livorno
Find places to stay Oct 13 — 16:
Highlights from your plan
Duomo di Pisa ©
Duomo di Pisa
Bagno Maurizio ©
Bagno Maurizio
Santuario di Montenero ©
Santuario di Montenero

2
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. Start off your visit on the 16th (Tue): enjoy the sand and surf at Spiaggia La Sorgente and then stroll through Spiaggia Di Sansone. Here are some ideas for day two: kick back and relax at Spiaggia di Cavoli, then look for gifts at Elba Nostrale, and then enjoy the sand and surf at Spiaggia della Biodola.

For traveler tips, more things to do, and other tourist information, you can read our Portoferraio journey maker app .

Traveling by combination of car and ferry from Viareggio to Portoferraio takes 2.5 hours. Alternatively, you can do a combination of train, bus, and ferry. Traveling from Viareggio in October, expect nights in Portoferraio to be about the same, around 58°F, while days are slightly colder, around 66°F. Wrap up your sightseeing on the 18th (Thu) early enough to travel to Montalcino.

Things to do in Portoferraio

Parks Beaches Outdoors

Side Trips

Elba Nostrale, Spiaggia di Cavoli
Find places to stay Oct 16 — 18:
Highlights from your plan
Spiaggia Di Sansone ©
Spiaggia Di Sansone
Spiaggia La Sorgente ©
Spiaggia La Sorgente
Spiaggia Della Biodola ©
Spiaggia Della Biodola

2
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
On the 18th (Thu), awaken your taste buds at some of the top wineries in the area. On the 19th (Fri), you'll have a packed day of sightseeing: contemplate the long history of Abbazia di Sant'Antimo, learn about winemaking at Podere Il Cocco, steep yourself in history at Centro Storico di Siena, then take in panoramic vistas at Tower of Mangia, and finally browse the collection at Biblioteca Piccolomini.

For traveler tips, more things to do, where to stay, and tourist information, refer to the Montalcino tour builder app .

Traveling by combination of ferry and car from Portoferraio to Montalcino takes 2.5 hours. Alternatively, you can do a combination of ferry, bus, and train; or do a combination of ferry, bus, and train. In October in Montalcino, expect temperatures between 64°F during the day and 55°F at night. Wrap up your sightseeing on the 20th (Sat) early enough to drive to Saturnia.

Things to do in Montalcino

Tours Historic Sites Wineries

Side Trip

Siena
Find places to stay Oct 18 — 20:
Highlights from your plan
Podere Il Cocco ©
Podere Il Cocco
Abbazia di Sant'Antimo ©
Abbazia di Sant'Antimo
Wine Tours & Tastings

1
night
Saturnia

Saturnia ©
Kick off your visit on the 20th (Sat): do a tasting at Azienda Agricola Celestina Fe', take in nature's colorful creations at Giardino dei Tarocchi, and then do a tasting at Vini Montauto. On the next day, get to know the fascinating history of Pitigliano Centro Storico, make a trip to Via CAVA ETRUSCA SAN GIUSEPPE, look for gifts at Macelleria LA IMPERIALE, then don't miss a visit to Piazza del Castello di Montemerano, and finally witness a stunning natural landmark at Cascate del Mulino.

To find traveler tips, other places to visit, and tourist information, read our Saturnia route builder .

Drive from Montalcino to Saturnia in 1.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In October, daytime highs in Saturnia are 64°F, while nighttime lows are 55°F. Finish your sightseeing early on the 21st (Sun) to allow enough time to travel back home.

Things to do in Saturnia

Parks Wineries Historic Sites

Side Trips

Manciano, Pitigliano, Azienda Agricola Celestina Fe', Giardino dei Tarocchi, Piazza del Castello di Montemerano
Find places to stay Oct 20 — 21:
Highlights from your plan
Cascate del Mulino ©
Cascate del Mulino
Via CAVA ETRUSCA SAN GIUSEPPE ©
Via CAVA ETRUSCA SAN GIUSEPPE
Pitigliano Centro Storico ©
Pitigliano Centro Storico

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