9 days in Tuscany Itinerary

9 days in Tuscany Itinerary

Created using Inspirock Tuscany trip itinerary planner

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Route & dates

9 days in Tuscany Itinerary

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

1
night
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 5th (Tue), view the masterpieces at Balducci Ceramics.

To see reviews, photos, where to stay, and other tourist information, read our San Gimignano online route planner .

Tel Aviv, Israel to San Gimignano is an approximately 7-hour combination of flight and bus. You can also do a combination of flight and train. Due to the time zone difference, you'll gain 1 hour traveling from Tel Aviv to San Gimignano. Plan for little chillier temperatures traveling from Tel Aviv in May, with highs in San Gimignano at 25°C and lows at 13°C. Finish your sightseeing early on the 6th (Wed) so you can drive to Montalcino.

Things to do in San Gimignano

Shopping Wineries Outdoors

Side Trip

Siena
Find places to stay May 5 — 6:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Centopercento Camicie ©
Centopercento Camicie
Balducci Ceramics ©
Balducci Ceramics

2
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
On the 7th (Thu), look for all kinds of wild species at Crete Senesi, then appreciate the views at Val d'Orcia, and then do a tasting at Ciacci Piccolomini d'Aragona. On your second day here, do a tasting at Castiglion del Bosco, do a tasting at Mate Winery, learn about winemaking at Podere Il Cocco, then learn about winemaking at Winery Solaria Patrizia Cencioni, then take in the exciting artwork at Artemisia Gallery, and finally look for gifts at La Taverna del Pecorino.

For reviews, ratings, and more tourist information, read our Montalcino route planning tool .

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. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Cap off your sightseeing on the 8th (Fri) early enough to go by car to Portoferraio.

Things to do in Montalcino

Wineries Parks Nature

Side Trips

Pienza, Crete Senesi, Val d'Orcia
Find places to stay May 6 — 8:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Podere Il Cocco ©
Podere Il Cocco
Castiglion del Bosco ©
Castiglion del Bosco

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 9th (Sat): kick back and relax at Spiaggia di Capo Bianco, enjoy the sand and surf at Spiaggia Di Sansone, and then stroll through Percorso dell'Enfola. Here are some ideas for day two: kick back and relax at Spiaggia di Marina di Campo, then kick back and relax at Spiaggia del Relitto, and then stroll through Spiaggia di Cavoli.

To find traveler tips, reviews, and more tourist information, you can read our Portoferraio tour website .

You can drive from Montalcino to Portoferraio in 3 hours. Traveling from Montalcino in May, expect nights in Portoferraio to be about the same, around 15°C, while days are slightly colder, around 23°C. Wrap up your sightseeing on the 10th (Sun) to allow time to travel to Florence.

Things to do in Portoferraio

Outdoors Beaches Parks

Side Trips

Spiaggia di Marina di Campo, Spiaggia del Relitto, Spiaggia di Cavoli
Find places to stay May 8 — 10:
Highlights from your plan
Spiaggia Di Sansone ©
Spiaggia Di Sansone
Spiaggia di Cavoli ©
Spiaggia di Cavoli

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
For shopping fun, head to Mercato Centrale or Art Gallery Studio Iguarnieri. Get out of town with these interesting Florence side-trips: Castello del Trebbio (in Santa Brigida) and Canyon Park (in Bagni di Lucca). There's much more to do: examine the collection at Academy Of Florence Art Gallery, take in the exciting artwork at M.G. Design, make a trip to Ratto della Sabina, and take in the views from Ponte Vecchio.

Plan a trip to Florence easily and quickly by telling Inspirock to suggest an itinerary.

You can do a combination of ferry and car from Portoferraio to Florence in 3 hours. Other options are to do a combination of ferry and train; or do a combination of ferry, train, and bus. May in Florence sees daily highs of 25°C and lows of 13°C at night. Finish your sightseeing early on the 13th (Wed) so you can travel back home.

Things to do in Florence

Shopping Museums Outdoors

Side Trips

Canyon Park, Castello del Trebbio
Find places to stay May 10 — 13:
Highlights from your plan
Castello del Trebbio ©
Castello del Trebbio
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore

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