9 days in Tuscany Itinerary

9 days in Tuscany Itinerary

Created using Inspirock Tuscany route planner

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Route & dates

Start: Tel Aviv
Fly:  6 h 45 min
1
Florence
— 2 nights
Drive + Ferry:  3 h
2
Portoferraio, Elba Island
— 2 nights
Drive:  3 h
3
Montalcino
— 1 night
Drive:  1 h 30 min
4
San Gimignano
— 3 nights
+4
Bus + Train + Bus + Foot + Fly:  9 h 45 min
End: Tel Aviv

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 22nd (Wed): get to know the fascinating history of Piazza della Signoria, appreciate the extensive heritage of Piazza del Duomo, and then contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore. Here are some ideas for day two: explore the world behind art at Florence Academy of Fine Arts, then learn about winemaking at Castello del Trebbio, and then admire the landmark architecture of The Baptistery of St. John.

To find more things to do, where to stay, photos, and more tourist information, you can read our Florence trip itinerary website.

Tel Aviv, Israel to Florence is an approximately 7- hour flight. You can also do a combination of flight and train; or do a combination of flight and bus. The time zone changes from Israel Standard Time (IST) to Central European Standard Time (CET), which is usually a -1 hour difference. In May, Florence is a bit cooler than Tel Aviv - with highs of 25°C and lows of 13°C. Finish your sightseeing early on the 24th (Fri) to allow enough time to travel to Portoferraio.

Things to do in Florence

Wineries Historic Sites Museums

Side Trips

Greve in Chianti, Castello del Trebbio
Find places to stay May 22 — 24:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Piazza del Duomo ©
Piazza del Duomo
The Baptistery of St. John ©
The Baptistery of St. John

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. Kick off your visit on the 25th (Sat): stroll through Spiaggia Luisi d'Angelo and then tour the pleasant surroundings at Spiaggia Di Sansone. On the 26th (Sun), you'll have a packed day of sightseeing: identify plant and animal life at Wildlife Areas and then stroll through Spiaggia di Cavoli.

To find ratings, where to stay, other places to visit, and more tourist information, refer to the Portoferraio trip itinerary planning website.

Getting from Florence to Portoferraio by combination of car and ferry takes about 3 hours. Other options: do a combination of train and ferry; or do a combination of bus, train, and ferry. May in Portoferraio sees daily highs of 23°C and lows of 15°C at night. Wrap up your sightseeing on the 26th (Sun) to allow time to drive to Montalcino.

Things to do in Portoferraio

Outdoors Beaches Parks

Side Trips

Dolphin & Whale Watching, Spiaggia Luisi d'Angelo, Spiaggia di Cavoli
Find places to stay May 24 — 26:
Highlights from your plan
Spiaggia Di Sansone ©
Spiaggia Di Sansone
Spiaggia di Cavoli ©
Spiaggia di Cavoli

1
night
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 27th (Mon): do a tasting at Podere Il Cocco, then learn about winemaking at Ciacci Piccolomini d'Aragona, and then do a tasting at Poggio Rubino.

To see traveler tips, maps, other places to visit, and tourist information, go to the Montalcino trip maker app.

Traveling by car from Portoferraio to Montalcino takes 3 hours. While traveling from Portoferraio, expect a bit warmer days and about the same nights in Montalcino, ranging from highs of 27°C to lows of 13°C. Wrap up your sightseeing on the 27th (Mon) to allow time to drive to San Gimignano.

Things to do in Montalcino

Wineries
Find places to stay May 26 — 27:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Podere Il Cocco ©
Podere Il Cocco
Poggio Rubino ©
Poggio Rubino

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.
On the 28th (Tue), steep yourself in history at Torre Grossa, then learn about winemaking at Guardastelle Vineyard, and then learn about winemaking at Fattoria Il Piano. On the next day, explore the historical opulence of Castello di Monterinaldi and then take a memorable tour with Tours.

To see where to stay, ratings, traveler tips, and other tourist information, use the San Gimignano trip itinerary maker app.

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 May in San Gimignano, expect temperatures between 25°C during the day and 13°C at night. On the 30th (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in San Gimignano

Wineries Wildlife Tours

Side Trips

Nature & Wildlife Tours, Castello di Monterinaldi
Find places to stay May 27 — 30:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Castello di Monterinaldi ©
Castello di Monterinaldi
Torre Grossa ©
Torre Grossa

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