13 days in Province of Siena Itinerary

Created using Inspirock Province of Siena visit planner
Make it your trip
Fly to Peretola Airport, Drive to San Gimignano
San Gimignano
— 6 nights
— 5 nights
— 1 night
Drive to Peretola Airport, Fly to Toronto


San Gimignano — 6 nights

Town of Fine Towers

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.
Venture out of the city with trips to Castello di Monteriggioni (in Monteriggioni), Siena (San Francesco, Palazzo Pubblico and Museo Civico, &more) and Bindi Sergardi Estates & Vineyards (in Vagliagli). And it doesn't end there: steep yourself in history at Historic Centre of San Gimignano, do a tasting at Podere La Marronaia- Le Colonne Biodynamic Winery & Farm, take in panoramic vistas at Torre Salvucci Maggiore, and explore the galleries of Torre e Casa Campatelli.

To see more things to do, traveler tips, and other tourist information, refer to the San Gimignano road trip planning app.

Toronto, Canada to San Gimignano is an approximately 15-hour combination of flight and car. The time zone difference when traveling from Toronto to San Gimignano is 6 hours. May in San Gimignano sees daily highs of 25°C and lows of 13°C at night. Finish your sightseeing early on the 8th (Mon) so you can drive to Montalcino.
Historic Sites · Wineries · Museums · Tours
Side Trips
Find places to stay May 2 — 8:

Montalcino — 5 nights

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Change things up with these side-trips from Montalcino: Spas (in Rapolano Terme), Montepulciano (Vinoteca Terra Toscana, Az. Agr. Poliziano, &more) and Terme Bagno Vignoni (in Bagno Vignoni). There's lots more to do: learn about winemaking at Ciacci Piccolomini d'Aragona, identify plant and animal life at Crete Senesi, and steep yourself in history at Abbazia di Sant'Antimo.

To find photos, traveler tips, maps, and tourist information, refer to the Montalcino road trip planner.

Getting from San Gimignano to Montalcino by car takes about 1.5 hours. Other options: do a combination of train and bus; or take a bus. May in Montalcino sees daily highs of 27°C and lows of 13°C at night. Finish your sightseeing early on the 13th (Sat) to allow enough time to drive to Chiusdino.
Wineries · Historic Sites · Shopping · Spas
Side Trips
Find places to stay May 8 — 13:

Chiusdino — 1 night

Chiusdino is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 70km south of Florence and about 30km southwest of Siena. On the 14th (Sun), step into the grandiose world of Castello del Poggiarello di Stigliano and then take in the architecture and atmosphere at Abbazia di San Galgano.

To see ratings, maps, other places to visit, and other tourist information, read Chiusdino visit planner.

Getting from Montalcino to Chiusdino by car takes about 1.5 hours. Other options: take a bus; or do a combination of bus and train. In May, daytime highs in Chiusdino are 27°C, while nighttime lows are 13°C. Wrap up your sightseeing by early afternoon on the 14th (Sun) to allow time for travel back home.
Historic Sites
Side Trip
Find places to stay May 13 — 14:

Province of Siena travel guide

Landmarks · Wineries & Vineyards · Churches
Siena is a city in Tuscany, Italy. It is the capital of the province of Siena.The historic centre of Siena has been declared by UNESCO a World Heritage Site. It is one of the nation's most visited tourist attractions, with over 163,000 international arrivals in 2008. Siena is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year.HistorySiena, like other Tuscan hill towns, was first settled in the time of the Etruscans (c. 900–400 BC) when it was inhabited by a tribe called the Saina. The Etruscans were a tribe of advanced people who changed the face of central Italy through their use of irrigation to reclaim previously unfarmable land, and their custom of building their settlements in well-defended hill forts. A Roman town called Saena Julia was founded at the site in the time of the Emperor Augustus. Some archaeologists assert that Siena was controlled for a period by a Gaulish tribe called the Senones.According to local legend, Siena was founded by Senius and Aschius, two sons of Remus and thus nephews of Romulus, after whom Rome was named. Supposedly after their father's murder by Romulus, they fled Rome, taking with them the statue of the she-wolf suckling the infants (Capitoline Wolf), thus appropriating that symbol for the town. Additionally they rode white and black horses, giving rise to the Balzana, or coat of arms of Siena with a white band atop a dark band. Some claim the name Siena derives from Senius. Other etymologies derive the name from the Etruscan family name Saina, the Roman family name Saenii, or the Latin word senex "old" or its derived form seneo "to be old".