17 days in Tuscany Itinerary

17 days in Tuscany Itinerary

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Route & dates

17 days in Tuscany Itinerary

Start: New York City
Fly:  14​h 15​min
1
Florence
— 4 nights
bus:  1​h 15​min
2
Lucca
— 2 nights
Drive:  2​h
3
Cortona
— 2 nights
Drive:  1​h 15​min
4
Montalcino
— 2 nights
Drive:  1​h 30​min
5
San Gimignano
— 5 nights
+2
bus + Fly + foot:  15​h
End: New York City

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence is known for museums, historic sites, shopping, nightlife, and classes. Your plan includes some of its best attractions: admire the masterpieces at Gallerie Degli Uffizi, get to know the fascinating history of Piazza del Duomo, examine the collection at Academy Of Florence Art Gallery, and take in the views from Ponte Vecchio.

To see maps, ratings, photos, and more tourist information, read our Florence itinerary planning website .

New York City, USA to Florence is an approximately 14.5-hour flight. You can also do a combination of bus and flight; or do a combination of bus, flight, and train. You'll lose 6 hours traveling from New York City to Florence due to the time zone difference. In May, plan for daily highs up to 71°F, and evening lows to 52°F. Cap off your sightseeing on the 1st (Mon) early enough to catcht the bus to Lucca.

Things to do in Florence

Tours Historic Sites Museums
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Piazzale Michelangelo ©
Piazzale Michelangelo

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.
Kick off your visit on the 2nd (Tue): make a trip to Piazza dei Miracoli, admire the striking features of Leaning Tower of Pisa, and then enjoy breathtaking views from Torre Guinigi. Get ready for a full day of sightseeing on the next day: contemplate in the serene atmosphere at Duomo di Pisa, steep yourself in history at Camposanto, learn about winemaking at Fattoria al Dotto, then steep yourself in history at Le mura di Lucca, then take in the spiritual surroundings of San Michele in Foro, and finally admire the landmark architecture of St Martin Cathedral.

To see reviews, maps, other places to visit, and other tourist information, read Lucca road trip planner.

Traveling by bus from Florence to Lucca takes 1.5 hours. Alternatively, you can drive; or take a train. Traveling from Florence in June, expect little chillier with lows of 60°F in Lucca. Wrap up your sightseeing on the 3rd (Wed) to allow time to drive to Cortona.

Things to do in Lucca

Historic Sites Wineries

Side Trip

Pisa
Highlights from your plan
Fattoria al Dotto ©
Fattoria al Dotto
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Piazza dei Miracoli ©
Piazza dei Miracoli

2
nights
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.
Start off your visit on the 4th (Thu): examine the collection at Museo Diocesano and then indulge your senses at some of the top wineries in the area. Keep things going the next day: look for gifts at DelBrenna Jewelry, get engrossed in the history at MAEC - Museo dell'Accademia Etrusca, contemplate in the serene atmosphere at Eremo Le Celle, then do a tasting at Famiglia Buccelletti Winery, then don't miss a visit to Palazzone di Cortona, and finally do a tasting at Azienda Agricola Leuta.

For photos, traveler tips, and tourist information, refer to the Cortona driving holiday planner.

You can drive from Lucca to Cortona in 2 hours. Alternatively, you can take a train. Finish your sightseeing early on the 5th (Fri) so you can drive to Montalcino.

Things to do in Cortona

Tours Wineries Historic Sites

Side Trips

Famiglia Buccelletti Winery, Wine Tours & Tastings
Highlights from your plan
Wine Tours & Tastings
Azienda Agricola Leuta ©
Azienda Agricola Leuta
Famiglia Buccelletti Winery ©
Famiglia Buccelletti Winery

2
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Start off your visit on the 6th (Sat): appreciate the extensive heritage of Borgo Medioevale di Monticchiello, admire the verdant scenery at Val d'Orcia, then learn about winemaking at Podere Il Cocco, and finally do a tasting at Ciacci Piccolomini d'Aragona. Keep things going the next day: appreciate the extensive heritage of Borgo Medievale Cinto da Mura, identify plant and animal life at Crete Senesi, then learn about winemaking at Castiglion del Bosco, then learn about winemaking at Poggio Rubino, and finally do a tasting at Winery Solaria Patrizia Cencioni.

For maps, where to stay, traveler tips, and tourist information, use the Montalcino day trip tool .

Getting from Cortona to Montalcino by car takes about 1.5 hours. Other options: take a bus; or do a combination of train and bus. In June in Montalcino, expect temperatures between 84°F during the day and 61°F at night. Wrap up your sightseeing on the 7th (Sun) to allow time to drive to San Gimignano.

Things to do in Montalcino

Wineries Parks Historic Sites

Side Trips

Borgo Medioevale di Monticchiello, Val d'Orcia, Crete Senesi, Borgo Medievale Cinto da Mura
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Podere Il Cocco ©
Podere Il Cocco
Val d'Orcia ©
Val d'Orcia

5
nights
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.
Explore the numerous day-trip ideas around San Gimignano: Siena (Basilica Cateriniana Di S. Domenico, Scuola di Cucina di Lella, & more). The adventure continues: learn about winemaking at Guardastelle Vineyard, pause for some serene contemplation at Duomo di San Gimignano, take an in-depth tour of Torre e Casa Campatelli, and steep yourself in history at Torre Grossa.

To find where to stay, more things to do, maps, and tourist information, read San Gimignano trip itinerary planner .

Traveling by car from Montalcino to San Gimignano takes 1.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In June, daily temperatures in San Gimignano can reach 81°F, while at night they dip to 60°F. On the 12th (Fri), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in San Gimignano

Historic Sites Wineries Museums

Side Trip

Siena
Highlights from your plan
Food Tours
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

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