15 days in Tuscany Itinerary

15 days in Tuscany Itinerary

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Route & dates

15 days in Tuscany Itinerary

Start: Calgary
Fly:  15 h 45 min
1
Florence
— 4 nights
Drive:  2 h
2
Montalcino
— 3 nights
Drive:  1 h 30 min
3
San Gimignano
— 4 nights
Drive:  1 h 45 min
4
Lucca
— 2 nights
Fly:  16 h
End: Calgary

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
For shopping fun, head to Art Gallery Studio Iguarnieri or Scarpelli Mosaici. Your inner history buff will appreciate Cathedral of Santa Maria del Fiore and The Baptistery of St. John. Change things up with a short trip to Castello del Trebbio in Santa Brigida (about 36 minutes away). There's much more to do: explore the world behind art at Academy Of Florence Art Gallery, enjoy breathtaking views from Campanile di Giotto, appreciate the extensive heritage of Piazza della Signoria, and examine the collection at Pitti Palace.

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

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 changes from Mountain Standard Time to Central European Time, which is usually an 8 hour difference. Expect somewhat warmer temperatures when traveling from Calgary in May; daily highs in Florence reach 25°C and lows reach 13°C. Cap off your sightseeing on the 6th (Thu) early enough to go by car to Montalcino.

Things to do in Florence

Museums Shopping Historic Sites

Side Trips

Castello del Trebbio, Convent of San Domenico
Find places to stay May 2 — 6:
Highlights from your plan
Art Gallery Studio Iguarnieri ©
Art Gallery Studio Iguarnieri
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.
Museum-lovers will get to explore Daniela Piegai Art Gallery and Clelia Tondini. Your cultural itinerary includes sights like Ciacci Piccolomini d'Aragona and Azienda Agricola Leuta. Venture out of the city with trips to Borgo di Lucignano d’Arbia (in Lucignano d'Arbia), Piazza del Tribunale (in Lucignano) and La Braccesca (in Montepulciano). And it doesn't end there: do a tasting at Mate Winery, stop by Librorcia Bagno Vignoni, and take in the spiritual surroundings of Abbazia di Monte Oliveto Maggiore.

For where to stay, maps, reviews, and tourist information, read Montalcino trip itinerary planner.

You can drive from Florence to Montalcino in 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Finish up your sightseeing early on the 9th (Sun) so you can go by car to San Gimignano.

Things to do in Montalcino

Wineries Historic Sites Shopping

Side Trips

Cortona, Abbazia di Monte Oliveto Maggiore, Borgo di Lucignano d’Arbia, Piazza del Tribunale, Librorcia Bagno Vignoni
Find places to stay May 6 — 9:
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.
Shop till you drop at Silvia Tanganelli and AC Laboratorio Artistico. Appreciate the collections at Palazzo Pubblico and Museo Civico and Pinacoteca Nazionale. Get out of town with these interesting San Gimignano side-trips: Siena (Duomo di Siena, Battistero di San Giovanni, &more), Panzano in Chianti (Monte Bernardi & Accademia del Buon Gusto) and Castello di Monterinaldi (in Radda in Chianti). There's lots more to do: do a tasting at Guardastelle Vineyard, get engrossed in the history at Torre e Casa Campatelli, and shop like a local with Galleria Gagliardi.

To find where to stay, photos, traveler tips, and tourist information, refer to the San Gimignano road trip app.

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. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Wrap up your sightseeing on the 13th (Thu) early enough to drive to Lucca.

Things to do in San Gimignano

Wineries Museums Historic Sites

Side Trips

Siena, Greve in Chianti, Castello di Monterinaldi, Sant'Agnese Farm
Find places to stay May 9 — 13:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Duomo di Siena ©
Duomo di Siena
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico

2
nights
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 14th (Fri), take in the spiritual surroundings of Basilica of San Frediano, enjoy breathtaking views from Leaning Tower of Pisa, then get a taste of the local shopping with PALP Palazzo Pretorio, and finally admire the striking features of Castello dei Vicari. Keep things going the next day: contemplate the long history of Le mura di Lucca and then learn about winemaking at Fattoria al Dotto.

For reviews, photos, ratings, and other tourist information, go to the Lucca day trip planning app.

You can drive from San Gimignano to Lucca in 2 hours. Alternatively, you can take a train; or take a bus. In May, daytime highs in Lucca are 25°C, while nighttime lows are 13°C. Wrap up your sightseeing on the 15th (Sat) early enough to travel back home.

Things to do in Lucca

Historic Sites Wineries Shopping

Side Trips

Leaning Tower of Pisa, PALP Palazzo Pretorio, Castello dei Vicari
Find places to stay May 13 — 15:
Highlights from your plan
Fattoria al Dotto ©
Fattoria al Dotto
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Le mura di Lucca ©
Le mura di Lucca

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