14 days in Tuscany Itinerary

14 days in Tuscany Itinerary

Created using Inspirock Tuscany route builder

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Route & dates

Start: Portland
Bus + 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.
Explore the numerous day-trip ideas around Florence: San Gimignano (San Gimignano 1300 & Historic Centre of San Gimignano). And it doesn't end there: indulge your taste buds at Food & Drink, take in the spiritual surroundings of The Baptistery of St. John, pause for some photo ops at Perseus Statue, and admire the masterpieces at Pitti Palace.

To see maps, more things to do, photos, and other tourist information, use the Florence trip itinerary maker website.

Portland, USA to Florence is an approximately 17.5- hour combination of bus and flight. You can also do a combination of bus and flight; or do a combination of bus, flight, and train. The time zone difference moving from Pacific Standard Time (PST) to Central European Standard Time (CET) is 9 hours. In October in Florence, expect temperatures between 71°F during the day and 54°F at night. Wrap up your sightseeing on the 12th (Fri) to allow time to take a bus 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.
On the 13th (Sat), get to know the fascinating history of Montecatini Alto, enjoy breathtaking views from Torre Guinigi, make a trip to Piazza Anfiteatro, then make a trip to Le mura di Lucca, and finally admire the landmark architecture of St Martin Cathedral.

To see maps, ratings, where to stay, and more tourist information, read our Lucca road trip planner.

Take a bus from Florence to Lucca in 1.5 hours. Alternatively, you can drive; or take a train. October in Lucca sees daily highs of 71°F and lows of 54°F at night. Finish your sightseeing early on the 13th (Sat) to allow enough time 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
Montecatini Alto ©
Montecatini Alto
Le mura di Lucca ©
Le mura di Lucca
Piazza Anfiteatro ©
Piazza Anfiteatro

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): get to know the fascinating history of Knights’ Square, admire the landmark architecture of Palazzo della Carovana, pause for some serene contemplation at Chiesa di San Frediano, stroll the grounds of Camposanto, then contemplate in the serene atmosphere at Baptistery of St. John, and finally take in the spiritual surroundings of Duomo di Pisa. Get ready for a full day of sightseeing on the next day: make a trip to Terrazza Mascagni, pause for some serene contemplation at Santuario di Montenero, and then kick back and relax at Bagno Maurizio.

To see photos, other places to visit, reviews, and more tourist information, read Viareggio attractions planner.

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) early enough to travel to Portoferraio.

Things to do in Viareggio

Historic Sites Parks Outdoors

Side Trips

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

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 kick back and relax at Spiaggia Di Sansone. On your second day here, stroll through Spiaggia di Cavoli, then look for gifts at Elba Nostrale, and then enjoy the sand and surf at Spiaggia Della Biodola.

To see reviews, ratings, traveler tips, and tourist information, read our Portoferraio trip itinerary builder app.

You can do a combination of car and ferry from Viareggio to Portoferraio in 2.5 hours. Alternatively, you can do a combination of train, bus, and ferry; or do a combination of train and ferry. October in Portoferraio sees daily highs of 67°F and lows of 58°F at night. Finish your sightseeing early on the 18th (Thu) to allow enough time to drive to Montalcino.

Things to do in Portoferraio

Parks Outdoors Beaches

Side Trips

Spiaggia di Cavoli, Elba Nostrale
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.
Kick off your visit on the 18th (Thu): indulge your senses 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, do a tasting at Podere Il Cocco, steep yourself in history at Centro Storico di Siena, then enjoy breathtaking views from Torre del Mangia, and finally get lost in a book at Biblioteca Piccolomini.

For traveler tips, maps, more things to do, and more tourist information, read our Montalcino online route builder.

Getting from Portoferraio to Montalcino by car takes about 3 hours. Traveling from Portoferraio in October, expect nights in Montalcino to be about the same, around 56°F, while days are a bit warmer, around 73°F. Wrap up your sightseeing on the 20th (Sat) to allow time 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 ©
Start off your visit on the 20th (Sat): learn about winemaking at Azienda Agricola Celestina Fe', then admire the natural beauty at Giardino dei Tarocchi, and then learn about winemaking at Tenuta Montauto. Get ready for a full day of sightseeing on the 21st (Sun): 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 see where to stay and other tourist information, refer to the Saturnia trip itinerary planning tool.

Traveling by car from Montalcino to Saturnia takes 1.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In October, daily temperatures in Saturnia can reach 73°F, while at night they dip to 56°F. Finish up your sightseeing early on the 21st (Sun) so you can travel back home.

Things to do in Saturnia

Parks Wineries Historic Sites

Side Trips

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

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