10 days in Tuscany Itinerary

10 days in Tuscany Itinerary

Created using Inspirock Tuscany travel planner

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Route & dates

10 days in Tuscany Itinerary

Start: Argos
+2
Drive + Fly + Drive:  10​h 45​min
1
Cortona
— 1 night
Drive:  1​h 15​min
2
Montalcino
— 2 nights
Drive:  2​h 45​min
3
Portoferraio, Elba Island
— 2 nights
Drive:  3​h
4
San Gimignano
— 3 nights
+2
Drive + Fly + Drive:  11​h
End: Argos

1
night
Cortona

Cortona ©
The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
On the 18th (Sat), learn about winemaking at Azienda Agricola Leuta, stop by Giancarlo Rossi, take in the spiritual surroundings of Eremo Le Celle, Head underground at Belvedere di Cortona, then take in the exciting artwork at Clelia Tondini, and finally view the masterpieces at La Torena Arte. Here are some ideas for day two: examine the collection at Museo Civico, then see the interesting displays at Museo Archeologico Nazionale, then do a tasting at Villa Sant'Anna, and finally view the masterpieces at Daniela Piegai Art Gallery.

For other places to visit, where to stay, more things to do, and tourist information, you can read our Cortona travel route planner .

Argos, Greece to Cortona is an approximately 11-hour flight. You can also drive. The time zone difference moving from Eastern European Time (EET) to Central European Time (CET) is minus 1 hour. Finish your sightseeing early on the 19th (Sun) to allow enough time to drive to Montalcino.

Things to do in Cortona

Museums Wineries Historic Sites

Side Trips

Chiusi, Villa Sant'Anna
Find places to stay May 18 — 19:
Highlights from your plan
Museo Civico ©
Museo Civico
Museo Archeologico Nazionale ©
Museo Archeologico Nazionale
Eremo Le Celle ©
Eremo Le Celle

2
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Kick off your visit on the 20th (Mon): take in the spiritual surroundings of Abbazia di Monte Oliveto Maggiore, take in the exciting artwork at La Porta Gallery, take a stroll through Borgo di Lucignano d’Arbia, then view the masterpieces at Art Studio di Adelina Quadri, then stop by La Taverna del Pecorino, and finally get into the urban bustle at San Quirico d'Orcia. Get ready for a full day of sightseeing on the next day: take in the architecture and atmosphere at Cathedral, steep yourself in history at Palazzo Piccolomini, view the masterpieces at Artemisia Gallery, then learn about winemaking at Terralsole, then steep yourself in history at Abbazia di Sant'Antimo, and finally do a tasting at Poggio Rubino.

For reviews, more things to do, and tourist information, use the Montalcino planning tool .

Getting from Cortona 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 21st (Tue) so you can travel to Portoferraio.

Things to do in Montalcino

Historic Sites Shopping Wineries

Side Trips

Pienza, Borgo di Lucignano d’Arbia, San Quirico d'Orcia, Abbazia di Monte Oliveto Maggiore, La Porta Gallery
Find places to stay May 19 — 21:
Highlights from your plan
Abbazia di Monte Oliveto Maggiore ©
Abbazia di Monte Oliveto Maggiore
San Quirico d'Orcia ©
San Quirico d'Orcia
Poggio Rubino ©
Poggio Rubino

2
nights
Portoferraio, Elba Island

Portoferraio ©
Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. On the 22nd (Wed), look for gifts at Gelateria Zero Gradi, then enjoy the sand and surf at Spiaggia di Capo Bianco, and then kick back and relax at Spiaggia Di Sansone. On the next day, take an in-depth tour of Museo del Mare, take in the exciting artwork at Gulliver - Terre d'Autore, then steep yourself in history at Casetta Drouot, and finally enjoy the sand and surf at Spiaggia di Cavoli.

To find photos, reviews, ratings, and other tourist information, use the Portoferraio journey maker .

Getting from Montalcino to Portoferraio by combination of car and ferry takes about 3 hours. Other options: do a combination of bus, train, and ferry. When traveling from Montalcino in May, plan for little chillier days in Portoferraio, with highs around 23°C, while nights are about the same with lows around 15°C. Wrap up your sightseeing on the 23rd (Thu) early enough to travel to San Gimignano.

Things to do in Portoferraio

Parks Outdoors Beaches

Side Trips

Marciana Marina, Spiaggia di Cavoli, Museo del Mare
Find places to stay May 21 — 23:
Highlights from your plan
Spiaggia Di Sansone ©
Spiaggia Di Sansone
Spiaggia di Cavoli ©
Spiaggia di Cavoli
Museo del Mare ©
Museo del Mare

3
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.
Start off your visit on the 24th (Fri): take in the exciting artwork at Vitalita Cultural Association, take in the exciting artwork at Oibo Re-Design, don't miss a visit to San Gimignano Bell Tower, then contemplate the long history of Historic Centre of San Gimignano, and finally don't miss a visit to Piazza della Cisterna. Keep things going the next day: appreciate the extensive heritage of San Gimignano 1300, then take an in-depth tour of Torre e Casa Campatelli, then enjoy breathtaking views from Torre del Mangia, and finally contemplate the long history of Centro Storico di Siena.

For reviews, where to stay, maps, and other tourist information, read San Gimignano travel route planner .

Getting from Portoferraio to San Gimignano by combination of ferry and car takes about 3 hours. Other options: do a combination of ferry and train; or do a combination of ferry, train, and bus. In May, daytime highs in San Gimignano are 25°C, while nighttime lows are 13°C. You will have some time to spend on the 26th (Sun) before leaving for home.

Things to do in San Gimignano

Historic Sites Museums Shopping

Side Trip

Siena
Find places to stay May 23 — 26:
Highlights from your plan
San Gimignano 1300 ©
San Gimignano 1300
Torre e Casa Campatelli ©
Torre e Casa Campatelli
Torre Grossa ©
Torre Grossa

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