9 days in Tuscany Itinerary

9 days in Tuscany Itinerary

Created using Inspirock Tuscany route planner

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Route & dates

9 days in Tuscany Itinerary

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
bus + 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.
Kick off your visit on the 22nd (Wed): don't miss a visit to Piazza della Signoria, then get to know the fascinating history of Piazza del Duomo, and then steep yourself in history at Cathedral of Santa Maria del Fiore. On the next day, examine the collection at Academy Of Florence Art Gallery, then do a tasting at Castello del Trebbio, and then take in the spiritual surroundings of The Baptistery of St. John.

For other places to visit, more things to do, maps, and more tourist information, use the Florence road trip planning site .

Tel Aviv, Israel to Florence is an approximately 7-hour flight. You can also do a combination of flight and train. The time zone changes from Israel Standard Time (IST) to Central European Time (CET), which is usually a -1 hour difference. Expect a bit cooler temperatures when traveling from Tel Aviv in May; daily highs in Florence reach 25°C and lows reach 13°C. Finish your sightseeing early on the 24th (Fri) so you can 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 ©
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. Start off your visit on the 25th (Sat): stroll through Spiaggia Luisi d'Angelo and then enjoy the sand and surf at Spiaggia Di Sansone. On the 26th (Sun), you'll have a packed day of sightseeing: get up close to creatures of the deep with a dolphin and whale watching tour and then stroll through Spiaggia di Cavoli.

For other places to visit, where to stay, reviews, and tourist information, read our Portoferraio trip builder .

Traveling by combination of car and ferry from Florence to Portoferraio takes 3 hours. Alternatively, you can do a combination of train and ferry; or do a combination of bus, train, and ferry. In May, daytime highs in Portoferraio are 23°C, while nighttime lows are 15°C. Wrap up your sightseeing on the 26th (Sun) early enough to drive to Montalcino.

Things to do in Portoferraio

Outdoors Beaches Parks

Side Trips

Spiaggia Luisi d'Angelo, Dolphin & Whale Watching, 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.
On the 27th (Mon), learn about winemaking at Podere Il Cocco, then do a tasting at Ciacci Piccolomini d'Aragona, and then learn about winemaking at Poggio Rubino.

To see other places to visit, maps, photos, and tourist information, use the Montalcino trip itinerary builder .

Drive from Portoferraio to Montalcino in 3 hours. Traveling from Portoferraio in May, you will find days in Montalcino are somewhat warmer (27°C), and nights are about the same (13°C). Wrap up your sightseeing on the 27th (Mon) early enough 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), contemplate the long history of Torre Grossa, then do a tasting at Guardastelle Vineyard, and then do a tasting at Fattoria Il Piano - Vineyard. On the 29th (Wed), you'll have a packed day of sightseeing: do a tasting at Castello di Monterinaldi and then get a dose of the wild on a nature and wildlife tour.

For reviews, where to stay, ratings, and more tourist information, read San Gimignano road trip planning 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, daytime highs in San Gimignano are 25°C, while nighttime lows are 13°C. Wrap up your sightseeing by early afternoon on the 30th (Thu) to allow enough time to travel back home.

Things to do in San Gimignano

Wineries Outdoors Wildlife

Side Trips

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

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