22 days in Tuscany Itinerary

22 days in Tuscany Itinerary

Created using Inspirock Tuscany journey planner

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Route & dates

22 days in Tuscany Itinerary

Start: Sydney
Fly + Train:  27​h
1
Lucca
— 4 nights
Drive:  2​h
2
Montepulciano
— 4 nights
Drive:  1​h 30​min
3
San Gimignano
— 4 nights
Drive:  1​h 15​min
4
Florence
— 7 nights
Train + Fly:  25​h
End: Sydney

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.
Venture out of the city with trips to Pisa (Battistero, Leaning Tower of Pisa, & more), Fortezza delle Verrucole - Archeopark (in San Romano in Garfagnana) and Sillico (in Pieve Fosciana). And it doesn't end there: learn about winemaking at Fattoria al Dotto, take in the spiritual surroundings of Duomo di Pisa, enjoy the sand and surf at Bagno Maurizio, and get reinvigorated at Canyon Park.

To find other places to visit, where to stay, ratings, and tourist information, you can read our Lucca itinerary maker app .

Sydney, Australia to Lucca is an approximately 27-hour combination of flight and train. You can also do a combination of flight and bus; or fly. The time zone changes from Australian Eastern Standard Time (New South Wales) (AEST) to Central European Time (CET), which is usually a -9 hour difference. May in Lucca sees daily highs of 25°C and lows of 13°C at night. Wrap up your sightseeing on the 11th (Mon) to allow time to drive to Montepulciano.

Things to do in Lucca

Parks Outdoors Historic Sites

Side Trips

Pisa, Sillico, Fortezza delle Verrucole - Archeopark, Canyon Park, Bagno Maurizio
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

4
nights
Montepulciano

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Explore the numerous day-trip ideas around Montepulciano: Montalcino (Podere Il Cocco, Mate Winery, & more), Wine Tours & Tastings (in Siena) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). There's still lots to do: experience rural life at Fattoria, do a tasting at Famiglia Buccelletti Winery, see the interesting displays at Museo Diocesano, and appreciate the views at Val d'Orcia.

To see where to stay, maps, reviews, and tourist information, you can read our Montepulciano trip builder tool .

Drive from Lucca to Montepulciano in 2 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Finish up your sightseeing early on the 15th (Fri) so you can go by car to San Gimignano.

Things to do in Montepulciano

Wineries Tours Historic Sites

Side Trips

Cortona, Montalcino, Siena, Famiglia Buccelletti Winery, Val d'Orcia
Find places to stay May 11 — 15:
Highlights from your plan
Wine Tours & Tastings
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
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.
You'll find plenty of places to visit near San Gimignano: Siena (Basilica Cateriniana Di S. Domenico, Scuola di Cucina di Lella, & more) and Castello di Monterinaldi (in Radda in Chianti). It doesn't end there: learn about winemaking at Guardastelle Vineyard and steep yourself in history at Torre Grossa.

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

Drive from Montepulciano to San Gimignano in 1.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Cap off your sightseeing on the 19th (Tue) early enough to go by car to Florence.

Things to do in San Gimignano

Historic Sites Wineries Museums

Side Trips

Siena, Castello di Monterinaldi
Find places to stay May 15 — 19:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

7
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Go for a jaunt from Florence to Santa Brigida to see Castello del Trebbio about 36 minutes away. There's lots more to do: examine the collection at Academy Of Florence Art Gallery, take in panoramic vistas at Campanile di Giotto, admire the masterpieces at Pitti Palace, and get to know the fascinating history of Piazza del Duomo.

For reviews and other tourist information, read our Florence route planner.

You can drive from San Gimignano to Florence in 1.5 hours. Other options are to take a bus; or take a train. In May, plan for daily highs up to 25°C, and evening lows to 13°C. Wrap up your sightseeing by early afternoon on the 26th (Tue) to allow enough time to travel back home.

Things to do in Florence

Historic Sites Tours Museums

Side Trip

Castello del Trebbio
Find places to stay May 19 — 26:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo
Cathedral of Santa Maria del Fiore ©

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