21 days in Tuscany Itinerary

21 days in Tuscany Itinerary

Created using Inspirock Tuscany route planner

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Route & dates

21 days in Tuscany Itinerary

Start: Geneva
Fly + bus:  5​h 30​min
1
Siena
— 2 nights
Drive:  1​h
2
San Gimignano
— 3 nights
Drive:  1​h
3
Greve in Chianti
— 2 nights
Drive:  1​h 30​min
4
Lucca
— 4 nights
Drive:  2​h
5
Montepulciano
— 3 nights
Drive:  2​h 30​min
6
Marina di Pietrasanta
— 3 nights
Drive:  2​h 15​min
7
Radda in Chianti
— 3 nights
Drive + Fly:  6​h
End: Geneva

2
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Start off your visit on the 24th (Tue): don't miss a visit to Piazza del Campo and then awaken your taste buds at some of the top wineries in the area. Keep things going the next day: take in the architecture and atmosphere at Duomo di Siena, steep yourself in history at Centro Storico di Siena, and then get lost in a book at Biblioteca Piccolomini.

For traveler tips, reviews, ratings, and tourist information, read our Siena online travel route planner .

Geneva, Switzerland to Siena is an approximately 5.5-hour combination of flight and bus. You can also do a combination of flight and train; or drive. Traveling from Geneva in September, expect Siena to be somewhat warmer, temps between 32°C and 19°C. Wrap up your sightseeing on the 25th (Wed) early enough to drive to San Gimignano.

Things to do in Siena

Historic Sites Tours
Highlights from your plan
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena
Wine Tours & Tastings

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 26th (Thu): learn about winemaking at Guardastelle Vineyard, make a trip to Historic Centre of San Gimignano, and then make a trip to San Gimignano Bell Tower. Keep things going the next day: learn about winemaking at Tenuta Torciano Vineyards, contemplate the long history of Walls of Monteriggioni, take in the spiritual surroundings of Church of Sant'Agostino, make a trip to Piazza della Cisterna, then get a taste of the local shopping with La Bottega del Sale di Duccio Nacci photographer, and finally steep yourself in history at Torre Grossa.

To see where to stay, maps, more things to do, and other tourist information, you can read our San Gimignano planner .

Getting from Siena to San Gimignano by car takes about an hour. Other options: take a bus; or do a combination of train and bus. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Wrap up your sightseeing by early afternoon on the 28th (Sat) to allow enough time to drive to Greve in Chianti.

Things to do in San Gimignano

Historic Sites Wineries Museums

Side Trip

Walls of Monteriggioni
Highlights from your plan
Podere La Marronaia- Sosta Alle Colonne ©
Historic Centre of San Gimignano ©
Historic Centre of San Gimignano
Duomo di San Gimignano ©
Duomo di San Gimignano

2
nights
Greve in Chianti

Greve in Chianti ©
On the 28th (Sat), stop by Piccole Armonie Country and then do a tasting at Cantina Antinori. Get ready for a full day of sightseeing on the 29th (Sun): learn about winemaking at Castello di Verrazzano, do a tasting at Accademia del Buon Gusto, and then do a tasting at Montefioralle Winery.

To find photos, reviews, ratings, and other tourist information, use the Greve in Chianti trip itinerary planner .

Traveling by car from San Gimignano to Greve in Chianti takes an hour. Alternatively, you can take a bus; or do a combination of train and bus. In September, daytime highs in Greve in Chianti are 30°C, while nighttime lows are 17°C. Wrap up your sightseeing by early afternoon on the 30th (Mon) to allow enough time to drive to Lucca.

Things to do in Greve in Chianti

Wineries Historic Sites Shopping

Side Trip

Cantina Antinori
Highlights from your plan
Castello di Verrazzano ©
Castello di Verrazzano
Enoteca Falorni ©
Enoteca Falorni

4
nights
Lucca

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Venture out of the city with trips to Pisa (Leaning Tower of Pisa, Piazza dei Miracoli, & more), Terrazza Mascagni (in Livorno) and Santuario Della Madonna del Ghisallo - Museo Del Ciclismo (in Magreglio). There's much more to do: contemplate the long history of Le mura di Lucca, enjoy breathtaking views from Torre Guinigi, don't miss a visit to Montecatini Alto, and admire the landmark architecture of St Martin Cathedral.

To see reviews, photos, ratings, and other tourist information, refer to the Lucca trip planner.

You can drive from Greve in Chianti to Lucca in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Cap off your sightseeing on the 4th (Fri) early enough to go by car to Montepulciano.

Things to do in Lucca

Historic Sites Nature Adventure

Side Trips

Pisa, Canyon Park, Acetaia Giuseppe Giusti, Palazzo dei Capitani della Montagna, Montecatini Alto
Highlights from your plan
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Le mura di Lucca ©
Le mura di Lucca
Piazza dei Miracoli ©
Piazza dei Miracoli

3
nights
Montepulciano

Montepulciano ©
Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Kick off your visit on the 5th (Sat): take in the natural beauty of Cascate del Mulino, then learn about winemaking at Ciacci Piccolomini d'Aragona, and then don't miss a visit to Piazza Grande a Montepulciano. Here are some ideas for day two: contemplate in the serene atmosphere at Tempio di San Biagio, take in nature's colorful creations at Parco dei Mostri, and then wander the streets of Civita di Bagnoregio.

To see photos, reviews, maps, and tourist information, go to the Montepulciano trip maker .

You can drive from Lucca to Montepulciano in 2 hours. Alternatively, you can take a train; or take a bus. In October, daytime highs in Montepulciano are 26°C, while nighttime lows are 15°C. Wrap up your sightseeing by early afternoon on the 7th (Mon) to allow time for travel to Marina di Pietrasanta.

Things to do in Montepulciano

Historic Sites Parks Wineries

Side Trips

Duomo di Orvieto, Ciacci Piccolomini d'Aragona, Civita di Bagnoregio, Parco dei Mostri, Cascate del Mulino
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Cascate del Mulino ©
Cascate del Mulino
Duomo di Orvieto ©
Duomo di Orvieto

3
nights
Marina di Pietrasanta

Marina di Pietrasanta ©
Venture out of the city with trips to Centro Storico del Paese di Tellaro (in Tellaro) and Acquario di Livorno (in Livorno).

To see traveler tips, where to stay, other places to visit, and other tourist information, use the Marina di Pietrasanta online sightseeing planner .

Drive from Montepulciano to Marina di Pietrasanta in 2.5 hours. In October, daytime highs in Marina di Pietrasanta are 24°C, while nighttime lows are 16°C. Cap off your sightseeing on the 10th (Thu) early enough to travel to Radda in Chianti.

Things to do in Marina di Pietrasanta

Parks Beaches Outdoors

Side Trips

Viareggio, Piazza Duomo, Grotta Turistica Antro del Corchia, Centro Storico del Paese di Tellaro, Pontile Bellavista Vittoria
Highlights from your plan
Grotta Turistica Antro del Corchia ©
Bagno Maurizio ©
Bagno Maurizio
Centro Storico del Paese di Tellaro ©

3
nights
Radda in Chianti

Radda in Chianti ©
On the 11th (Fri), learn about winemaking at Fattoria di Montemaggio, do a tasting at Castello San Donato in Perano, then contemplate the long history of Volpaia, then learn about winemaking at Castello di Monterinaldi, and finally do a tasting at La Cantina di Casalvento. On your second day here, do a tasting at Le Miccine, step into the grandiose world of Castello di Meleto, then take in nature's colorful creations at Castello di Brolio, then relax in the rural setting at Pornanino, and finally do a tasting at Castello di Albola.

For ratings, photos, traveler tips, and tourist information, read Radda in Chianti route maker app .

Getting from Marina di Pietrasanta to Radda in Chianti by car takes about 2 hours. In October, plan for daily highs up to 26°C, and evening lows to 13°C. Wrap up your sightseeing by early afternoon on the 13th (Sun) to allow enough time to travel back home.

Things to do in Radda in Chianti

Wineries Historic Sites Parks

Side Trips

Gaiole in Chianti, Castellina In Chianti
Highlights from your plan
Fattoria di Montemaggio ©
Fattoria di Montemaggio
Poggio Amorelli ©
Poggio Amorelli
Volpaia ©
Volpaia

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