21 days in Tuscany Itinerary

21 days in Tuscany Itinerary

Created using Inspirock Tuscany holiday maker

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Route & dates

21 days in Tuscany Itinerary

Start: Windhoek
Fly:  22​h 15​min
1
Florence
— 2 nights
Bus:  1​h 15​min
2
Lucca
— 4 nights
Drive:  1​h 45​min
3
San Gimignano
— 3 nights
Drive:  1​h 45​min
4
Cortona
— 3 nights
Drive:  1​h 15​min
5
Montalcino
— 4 nights
Drive:  1​h 30​min
6
Pitigliano
— 2 nights
Drive + Fly:  24​h
End: Windhoek

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Popular historic sites such as Centro Storico and Basilica San Miniato al Monte are in your itinerary. Museo Nazionale del Bargello and Corridoio Vasariano will appeal to museum buffs. Venture out of the city with trips to Castello di Verrazzano (in Greve in Chianti) and Museo Mario Romoli (in Rufina). Next up on the itinerary: explore the world behind art at Museum of Opera of Saint Maria of Fiore, shop like a local with Clet's Studio, pause for some serene contemplation at Basilica of Santa Maria Novella, and admire the striking features of Loggia dei Lanzi.

To see other places to visit and more tourist information, use the Florence travel itinerary planner.

Windhoek, Namibia to Florence is an approximately 22.5-hour flight. You'll gain 1 hour traveling from Windhoek to Florence due to the time zone difference. Prepare for slightly colder weather when traveling from Windhoek in October: high temperatures in Florence hover around 25°C and lows are around 14°C. Finish up your sightseeing early on the 19th (Sat) so you can go by car to Lucca.

Things to do in Florence

Historic Sites Museums Wineries

Side Trips

Castello di Verrazzano, Museo Mario Romoli
Find places to stay Oct 17 — 19:
Highlights from your plan
Museo Nazionale del Bargello ©
Museo Nazionale del Bargello
Centro Storico ©
Centro Storico
Basilica San Miniato al Monte
Basilica San Miniato al Monte

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.
Get a sense of the local culture at Duomo di Pisa and Knights' Square. Do your shopping at La Cantina del Vino and Via del Fosso di Lucca. You'll find plenty of places to visit near Lucca: Museo del Castagno - Lavoro Vita Civiltà, Loc. Colognora (in Colognora), Botanical Garden Maria Ansaldi Pania di Corfino (in Villa Collemandina) and Museo Etnografico Don Luigi Pellegrini (in San Pellegrino In Alpe). Next up on the itinerary: take in the spiritual surroundings of Battistero, make a trip to Porta San Gervasio, contemplate the long history of Sillico, and admire the landmark architecture of St Martin Cathedral.

For where to stay, maps, ratings, and more tourist information, refer to the Lucca trip itinerary builder website .

Traveling by car from Florence to Lucca takes 1.5 hours. Alternatively, you can take a bus; or take a train. In October, daily temperatures in Lucca can reach 25°C, while at night they dip to 14°C. Wrap up your sightseeing on the 23rd (Wed) to allow time to drive to San Gimignano.

Things to do in Lucca

Museums Historic Sites Outdoors

Side Trips

Pisa, Lido Di Camaiore, Calci, La Cantina del Vino, Museo Etnografico Don Luigi Pellegrini
Find places to stay Oct 19 — 23:
Highlights from your plan
Duomo di Pisa ©
Duomo di Pisa
Baptistery of St. John ©
Baptistery of St. John
Knights’ Square ©
Knights’ Square

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.
Get some historical perspective at San Gimignano 1300 and Historic Centre of San Gimignano. Head to La Fornace Art Gallery and La Bottega del Sale di Duccio Nacci photographerfor some retail therapy. Change things up with these side-trips from San Gimignano: Siena (Centro Storico di Siena & Bianco e Nero di Sonia Staccioli ) and Abbazia di San Galgano (in Chiusdino). The adventure continues: view the masterpieces at Vitalita Cultural Association, get a taste of the local shopping with Art Gallery in Tuscany, and get into the urban bustle at Comune Di Certaldo.

To see ratings, more things to do, other places to visit, and tourist information, refer to the San Gimignano sightseeing planning app .

Getting from Lucca to San Gimignano by car takes about 2 hours. Other options: take a train; or take a bus. In October, plan for daily highs up to 25°C, and evening lows to 14°C. Wrap up your sightseeing on the 26th (Sat) early enough to drive to Cortona.

Things to do in San Gimignano

Historic Sites Shopping Museums

Side Trips

Siena, La Fornace Art Gallery, Comune Di Certaldo, Abbazia di San Galgano
Find places to stay Oct 23 — 26:
Highlights from your plan
San Gimignano 1300 ©
San Gimignano 1300
Abbazia di San Galgano ©
Abbazia di San Galgano
Comune Di Certaldo ©
Comune Di Certaldo

3
nights
Cortona

Cortona ©
The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
Your cultural itinerary includes sights like Eremo Le Celle and Museo Civico Archeologico. You'll explore and learn at Pinacoteca di Castiglion Fiorentino and Clelia Tondini. The adventure continues: shop like a local with La Torena Arte, take in the architecture and atmosphere at Basilica di Santa Margherita, view the masterpieces at Daniela Piegai Art Gallery, and examine the collection at Museo Diocesano.

For more things to do, ratings, other places to visit, and tourist information, read our Cortona trip planner .

Traveling by car from San Gimignano to Cortona takes 2 hours. Alternatively, you can take a train; or take a bus. Finish your sightseeing early on the 29th (Tue) to allow enough time to drive to Montalcino.

Things to do in Cortona

Museums Historic Sites Wineries

Side Trip

Castiglion Fiorentino
Find places to stay Oct 26 — 29:
Highlights from your plan
Eremo Le Celle ©
Eremo Le Celle
Azienda Agricola Leuta ©
Azienda Agricola Leuta
Famiglia Buccelletti Winery ©
Famiglia Buccelletti Winery

4
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Let the collections at Archeological Museum and Tomb of Hell's Quadriga and Artemisia Gallery capture your imagination. Do some cultural sightseeing at Abbazia di Sant'Antimo and Art Studio di Adelina Quadri. Change things up with these side-trips from Montalcino: Piazza della Cisterna (in Rocca d'Orcia), Quinteaquadri Lab Gallery (in Montepulciano) and Borgo di Lucignano d’Arbia (in Lucignano d'Arbia). There's still lots to do: contemplate the long history of San Quirico d'Orcia, do a tasting at Poggio Rubino, explore the world behind art at Presepi dal Mondo, and take in the exciting artwork at La Porta Gallery.

To find where to stay, photos, and tourist information, you can read our Montalcino road trip planner .

Drive from Cortona to Montalcino in 1.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Wrap up your sightseeing on the 2nd (Sat) to allow time to drive to Pitigliano.

Things to do in Montalcino

Wineries Museums Historic Sites

Side Trips

Sarteano, Pienza, Buonconvento, Piazza della Cisterna, Borgo di Lucignano d’Arbia
Find places to stay Oct 29 — Nov 2:
Highlights from your plan
San Quirico d'Orcia ©
San Quirico d'Orcia
Abbazia di Sant'Antimo ©
Abbazia di Sant'Antimo
Mate Winery ©
Mate Winery

2
nights
Pitigliano

Pitigliano ©
Pitigliano is a town in the province of Grosseto, located about 80km south-east of the city of Grosseto, in Italy. On the 3rd (Sun), appreciate the extensive heritage of Pitigliano Centro Storico, look for gifts at Macelleria LA IMPERIALE, contemplate in the serene atmosphere at Chiesa di San Giorgio, then explore the historical opulence of Piazza del Castello di Montemerano, and finally admire the sheer force of Cascate del Mulino. On the 4th (Mon), you'll have a packed day of sightseeing: pause for some serene contemplation at Chiesa di Santa Maria e San Rocco, contemplate in the serene atmosphere at Antico Ghetto e Sinagoga Pitigliano, then appreciate the extensive heritage of Sorano Centro Storico, and finally admire the striking features of Masso Leopoldino.

To see maps, reviews, more things to do, and other tourist information, refer to the Pitigliano road trip site .

Traveling by car from Montalcino to Pitigliano takes 1.5 hours. Alternatively, you can take a bus. In November, daily temperatures in Pitigliano can reach 17°C, while at night they dip to 8°C. Wrap up your sightseeing on the 4th (Mon) to allow time to travel back home.

Things to do in Pitigliano

Historic Sites Nature Parks

Side Trips

Sorano, Montemerano, Cascate del Mulino, Macelleria LA IMPERIALE
Find places to stay Nov 2 — 4:
Highlights from your plan
Pitigliano Centro Storico ©
Pitigliano Centro Storico
Cascate del Mulino ©
Cascate del Mulino
Piazza del Castello di Montemerano ©

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