18 days in Tuscany Itinerary

18 days in Tuscany Itinerary

Created using Inspirock Tuscany itinerary maker

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Route & dates

Start: Florence
Drive:  2 h
1
Montalcino
— 3 nights
Drive:  1 h 30 min
2
San Gimignano
— 4 nights
Drive:  1 h 45 min
3
Lucca
— 4 nights
Bus:  1 h 15 min
4
Florence
— 6 nights
End: Florence

3
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Explore Montalcino's surroundings by going to Borgo di Lucignano d’Arbia (in Lucignano d'Arbia), Cortona (Eremo Le Celle, MAEC - Museo dell'Accademia Etrusca, &more) and Crete Senesi (in Asciano). There's much more to do: learn about winemaking at Ciacci Piccolomini d'Aragona, get outside with Il Destriero, and appreciate the views at Val d'Orcia.

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

Florence to Montalcino is an approximately 2- hour car ride. You can also take a bus; or do a combination of train and bus. In April, daytime highs in Montalcino are 23°C, while nighttime lows are 9°C. Finish your sightseeing early on the 3rd (Sun) to allow enough time to drive to San Gimignano.

Things to do in Montalcino

Wineries Historic Sites Parks

Side Trips

Cortona, Buonconvento, Zazzeri Pienza, Val d'Orcia, Borgo di Lucignano d’Arbia
Find places to stay Apr 30 — May 3:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Podere Il Cocco ©
Podere Il Cocco
Mate Winery ©
Mate Winery

4
nights
San Gimignano

San Gimignano ©
A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Explore San Gimignano's surroundings by going to Siena (Basilica Cateriniana San Domenico, Scuola di Cucina di Lella, &more). Next up on the itinerary: learn about winemaking at Guardastelle Vineyard.

To find photos, more things to do, where to stay, and other tourist information, read our San Gimignano planning tool.

Getting from Montalcino to San Gimignano by car takes about 1.5 hours. Other options: do a combination of bus and train; or take a bus. In May, plan for daily highs up to 25°C, and evening lows to 13°C. Finish your sightseeing early on the 7th (Thu) to allow enough time to drive to Lucca.

Things to do in San Gimignano

Historic Sites Tours Wineries

Side Trip

Siena
Find places to stay May 3 — 7:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

4
nights
Lucca

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
You'll find plenty of places to visit near Lucca: Pisa (Piazza dei Miracoli, Leaning Tower of Pisa, &more), Pieve dei Santi Giovanni ed Ermolao (in Calci) and Le Fortificazioni e Le Mura di Pistoia (in Pistoia). There's much more to do: learn about winemaking at Fattoria al Dotto, get to know the fascinating history of Sillico, take in panoramic vistas at Torre Guinigi, and contemplate the long history of St Martin Cathedral.

To find ratings, where to stay, other places to visit, and more tourist information, you can read our Lucca day trip planning website.

You can drive from San Gimignano to Lucca in 2 hours. Other options are to do a combination of bus and train; or take a bus. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Finish up your sightseeing early on the 11th (Mon) so you can catch the bus to Florence.

Things to do in Lucca

Historic Sites Parks Wineries

Side Trips

Pisa, Svizzera Pesciatina, Palazzo al Borgo di Corliano, Giardino Botanico Maria Ansaldi Pania di Corfino, Sillico
Find places to stay May 7 — 11:
Highlights from your plan
Fattoria al Dotto ©
Fattoria al Dotto
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Piazza dei Miracoli ©
Piazza dei Miracoli

6
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence is known for museums, historic sites, and shopping. Your plan includes some of its best attractions: take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, don't miss a visit to Piazzale Michelangelo, admire the natural beauty at The Boboli Gardens, and snap pictures at Ponte Vecchio.

For reviews, photos, maps, and other tourist information, go to the Florence travel tool.

Take a bus from Lucca to Florence in 1.5 hours. Alternatively, you can drive; or take a train. In May, plan for daily highs up to 25°C, and evening lows to 13°C. Wrap up your sightseeing on the 17th (Sun) early enough to travel back home.

Things to do in Florence

Museums Historic Sites Tours

Side Trip

Fiesole Cathedral Cattedrale di San Romolo - Fiesole
Find places to stay May 11 — 17:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts
Piazzale Michelangelo ©
Piazzale Michelangelo

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