21 days in Tuscany Itinerary

21 days in Tuscany Itinerary

Created using Inspirock Tuscany itinerary planner

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Route & dates

21 days in Tuscany Itinerary

Start: Cape Town
Fly:  17​h 15​min
1
Florence
— 4 nights
bus:  45​min
2
Greve in Chianti
— 2 nights
Drive:  1​h 45​min
3
Montalcino
— 2 nights
Drive:  1​h 30​min
4
San Gimignano
— 4 nights
Drive:  1​h
5
Siena
— 3 nights
Drive:  1​h
6
Montepulciano
— 3 nights
Drive + Fly:  25​h
End: Cape Town

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Change things up with a short trip to Leaning Tower of Pisa in Pisa (about 1h 10 min away). Next up on the itinerary: admire the masterpieces at Gallerie Degli Uffizi, examine the collection at Academy Of Florence Art Gallery, get engrossed in the history at Basilica di Santa Croce, and awaken your taste buds at some of the top wineries in the area.

To find reviews, ratings, photos, and more tourist information, you can read our Florence online sightseeing planner .

Cape Town, South Africa to Florence is an approximately 17.5-hour flight. You can also do a combination of flight and train. The time zone difference moving from South Africa Standard Time to Central European Time is minus 1 hour. In May, daily temperatures in Florence can reach 25°C, while at night they dip to 13°C. Wrap up your sightseeing on the 10th (Sun) to allow time to take a bus to Greve in Chianti.

Things to do in Florence

Historic Sites Museums Tours

Side Trip

Leaning Tower of Pisa
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

2
nights
Greve in Chianti

Greve in Chianti ©
Kick off your visit on the 10th (Sun): relax in the rural setting at Castello di Verrazzano, then do a tasting at Enoteca Falorni, then do a tasting at Montefioralle Winery, and finally stop by Piccole Armonie Country. Here are some ideas for day two: learn about winemaking at Cantina Antinori, make a trip to Piazza Matteotti, do a tasting at Castello di Monterinaldi, then learn about winemaking at Accademia del Buon Gusto, and finally do a tasting at Fattoria Le Fonti.

For traveler tips, where to stay, reviews, and tourist information, read Greve in Chianti visit planner.

You can take a bus from Florence to Greve in Chianti in an hour. Another option is to drive. In May in Greve in Chianti, expect temperatures between 25°C during the day and 13°C at night. Wrap up your sightseeing on the 12th (Tue) early enough to drive to Montalcino.

Things to do in Greve in Chianti

Wineries Historic Sites Shopping

Side Trips

Cantina Antinori, Castello di Monterinaldi
Highlights from your plan
Castello di Verrazzano ©
Castello di Verrazzano
Enoteca Falorni ©
Enoteca Falorni
Fattoria Le Fonti ©
Fattoria Le Fonti

2
nights
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 12th (Tue): contemplate in the serene atmosphere at Abbazia di Monte Oliveto Maggiore, then learn about winemaking at Podere Il Cocco, then do a tasting at Ciacci Piccolomini d'Aragona, and finally pause for some serene contemplation at Abbazia di Sant'Antimo. Get ready for a full day of sightseeing on the next day: do a tasting at Mate Winery, steep yourself in history at San Quirico d'Orcia, and then make a trip to Terme Bagno Vignoni.

For other places to visit, ratings, photos, and more tourist information, go to the Montalcino planner .

Traveling by car from Greve in Chianti to Montalcino takes 2 hours. Alternatively, you can do a combination of taxi, train, and bus; or take a bus. In May in Montalcino, expect temperatures between 27°C during the day and 13°C at night. Finish your sightseeing early on the 14th (Thu) so you can drive to San Gimignano.

Things to do in Montalcino

Historic Sites Wineries Shopping

Side Trips

Abbazia di Monte Oliveto Maggiore, Terme Bagno Vignoni, San Quirico d'Orcia
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Mate Winery ©
Mate Winery
Podere Il Cocco ©
Podere Il Cocco

4
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.
You'll find plenty of places to visit near San Gimignano: Museo Leonardiano di Vinci (in Vinci), CavallinoMatto (in Marina di Castagneto Carducci) and Bolgheri - Borgo Medievale (in Bolgheri). There's still lots to do: learn about winemaking at Guardastelle Vineyard, contemplate the long history of Torre Grossa, pause for some serene contemplation at Church of Sant'Agostino, and make a trip to Historic Centre of San Gimignano.

For photos, traveler tips, other places to visit, and other tourist information, read San Gimignano online trip maker .

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. May in San Gimignano sees daily highs of 25°C and lows of 13°C at night. Wrap up your sightseeing on the 18th (Mon) early enough to drive to Siena.

Things to do in San Gimignano

Wineries Historic Sites Museums

Side Trips

Comune Di Certaldo, Museo Leonardiano di Vinci, Bolgheri - Borgo Medievale, Walls of Monteriggioni, Cavallino Matto
Highlights from your plan
Fattoria Il Piano ©
Fattoria Il Piano
Duomo di San Gimignano ©
Duomo di San Gimignano

3
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 19th (Tue): don't miss a visit to Piazza del Campo and then indulge your senses at some of the top wineries in the area. On your second day here, contemplate the long history of Centro Storico di Siena, then pause for some serene contemplation at Duomo di Siena, then browse the collection at Biblioteca Piccolomini, and finally enjoy breathtaking views from Torre del Mangia.

For ratings, where to stay, and tourist information, you can read our Siena travel route planning app .

Getting from San Gimignano to Siena by car takes about an hour. Other options: take a bus; or do a combination of bus and train. In May, plan for daily highs up to 27°C, and evening lows to 13°C. Wrap up your sightseeing by early afternoon on the 21st (Thu) to allow time for the car ride to Montepulciano.

Things to do in Siena

Historic Sites Tours

Side Trip

Abbazia di San Galgano
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

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.
Venture out of the city with trips to Civita di Bagnoregio (in Civita di Bagnoregio), Antico Ghetto e Sinagoga Pitigliano (in Pitigliano) and Cortona (MAEC - Museo dell'Accademia Etrusca & Eremo Le Celle). The adventure continues: contemplate the long history of Duomo di Orvieto, make a trip to Piazza Grande a Montepulciano, walk around Parco dei Mostri, and contemplate in the serene atmosphere at Tempio di San Biagio.

For photos, traveler tips, other places to visit, and tourist information, go to the Montepulciano trip itinerary planner .

Drive from Siena to Montepulciano in an hour. Alternatively, you can take a train; or take a bus. In May, daily temperatures in Montepulciano can reach 27°C, while at night they dip to 13°C. On the 24th (Sun), you'll travel back home.

Things to do in Montepulciano

Historic Sites Parks Neighborhoods

Side Trips

Cortona, Orvieto, Antico Ghetto e Sinagoga Pitigliano, Parco dei Mostri, Civita di Bagnoregio
Highlights from your plan
Civita di Bagnoregio ©
Civita di Bagnoregio
Eremo Le Celle ©
Eremo Le Celle
Duomo di Orvieto ©
Duomo di Orvieto

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