15 days in Tuscany Itinerary

15 days in Tuscany Itinerary

Created using Inspirock Tuscany vacation planner

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Route & dates

15 days in Tuscany Itinerary

Start: Calgary
Fly:  15 h 45 min
1
Florence
— 6 nights
Drive:  2 h
2
Montalcino
— 3 nights
Drive:  1 h 30 min
3
San Gimignano
— 4 nights
+4
Bus + Train + Bus + Foot + Fly:  18 h
End: Calgary

6
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Museum-lovers will appreciate Academy Of Florence Art Gallery and M.G. Design. Get a sense of the local culture at Cathedral of Santa Maria del Fiore and Art Gallery Studio Iguarnieri. You'll find plenty of places to visit near Florence: Castello del Trebbio (in Santa Brigida) and Fratelli Taccini - Studio del' Arte (in Vinci). There's much more to do: explore the world behind art at Pitti Palace, get to know the fascinating history of Piazza della Signoria, shop like a local with Limbo Art Gallery, and don't miss a visit to Piazzale Michelangelo.

For other places to visit, more things to do, traveler tips, and tourist information, use the Florence online trip builder.

Calgary, Canada to Florence is an approximately 16- hour flight. You can also do a combination of flight and train; or do a combination of bus and flight. The time zone difference moving from Mountain Standard Time to Central European Time is 8 hours. In May, Florence is a bit warmer than Calgary - with highs of 25°C and lows of 13°C. Finish your sightseeing early on the 8th (Sat) to allow enough time to drive to Montalcino.

Things to do in Florence

Museums Historic Sites Shopping

Side Trips

Castello del Trebbio, Fratelli Taccini - Studio del' Arte
Find places to stay May 2 — 8:
Highlights from your plan
Castello del Trebbio ©
Castello del Trebbio
Cathedral of Santa Maria del Fiore ©
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

3
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Get some cultural insight at Ciacci Piccolomini d'Aragona and Podere Il Cocco. You'll find plenty of places to visit near Montalcino: Azienda Agricola Leuta (in Pietraia), Hominis (in Cortona) and Famiglia Buccelletti Winery (in Castiglion Fiorentino). There's more to do: do a tasting at Mate Winery and wander the streets of Borgo di Lucignano d’Arbia.

To see more things to do, maps, ratings, and more tourist information, read our Montalcino journey planning website.

You can drive from Florence to Montalcino in 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. In May, daytime highs in Montalcino are 27°C, while nighttime lows are 13°C. Finish your sightseeing early on the 11th (Tue) to allow enough time to drive to San Gimignano.

Things to do in Montalcino

Wineries Shopping Museums

Side Trips

Cortona, Montepulciano, Borgo di Lucignano d’Arbia, Famiglia Buccelletti Winery
Find places to stay May 8 — 11:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Azienda Agricola Leuta ©
Azienda Agricola Leuta
Podere Il Cocco ©
Podere Il Cocco

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.
Do some cultural sightseeing at Guardastelle Vineyard and Castello di Monterinaldi. Shop till you drop at Siena Tartufi (truffle hunting) and Silvia Tanganelli. You'll find plenty of places to visit near San Gimignano: Fattoria di Montemaggio (in Radda in Chianti), Sant'Agnese Farm (in Castellina In Chianti) and Siena (Chiesa di S.Agostino, Duomo di Siena, &more). Next up on the itinerary: learn about winemaking at Fattoria Il Piano and contemplate the long history of Torre Grossa.

For ratings, maps, other places to visit, and more tourist information, read San Gimignano online trip planner.

You can drive from Montalcino to San Gimignano in 1.5 hours. Other options are to do a combination of bus and train; or take a bus. In May, daily temperatures in San Gimignano can reach 25°C, while at night they dip to 13°C. Wrap up your sightseeing by early afternoon on the 15th (Sat) to allow time for travel back home.

Things to do in San Gimignano

Wineries Historic Sites Shopping

Side Trips

Siena, Radda in Chianti, Accademia del Buon Gusto, Poggio al Bosco, Sant'Agnese Farm
Find places to stay May 11 — 15:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Duomo di Siena ©
Duomo di Siena
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico

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