21 days in Tuscany Itinerary

21 days in Tuscany Itinerary

Created using Inspirock Tuscany holiday maker

Plan created by another user. Make it yours
Fly
1
Florence
— 2 nights
Drive
2
Lucca
— 4 nights
Drive
3
San Gimignano
— 3 nights
Drive
4
Cortona
— 3 nights
Drive
5
Montalcino
— 4 nights
Drive
6
Pitigliano
— 2 nights
Drive to Leonardo da Vinci–Fiumicino Airport, Fly to Hosea Kutako International Airport

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2
nights
Florence

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Head to Officina Profumo-Farmaceutica di Santa Maria Novella and Museo Mario Romolifor plenty of shopping. Satisfy your inner culture vulture at Centro Storico and Museum of Opera of Saint Maria of Fiore. Take a break from Florence with a short trip to Castello di Verrazzano in Greve in Chianti, about 46 minutes away. The adventure continues: admire the masterpieces at Museo Nazionale del Bargello, admire the landmark architecture of Basilica of Santa Maria Novella, take some stellar pictures from Basilica San Miniato al Monte, and view the masterpieces at Clet's Studio.

Inspirock's itinerary builder makes planning a Florence trip simple and quick.

Windhoek, Namibia to Florence is an approximately 18-hour flight. Traveling from Windhoek in October, expect Florence to be a bit cooler, temps between 25°C and 14°C. Cap off your sightseeing on the 19th (Sat) early enough to go by car to Lucca.

Things to do in Florence

Historic Sites · Museums · Wineries · Shopping

Side Trips

Find places to stay Oct 17 — 19:

4
nights
Lucca

City of a Hundred Churches

Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Duomo di Pisa and Knights’ Square will appeal to history buffs. Head to Fondazione Centro Studi sull Arte Licia e Carlo Ludovico Ragghianti and La Cantina del Vinofor plenty of shopping. Get out of town with these interesting Lucca side-trips: Museo del Castagno - Lavoro Vita Civiltà, Loc. Colognora (in Colognora), Giardino Botanico Maria Ansaldi Pania di Corfino (in Villa Collemandina) and Pisa (Baptistery of St. John & Camposanto). And it doesn't end there: admire the striking features of St Martin Cathedral, get to know the fascinating history of Sillico, make a trip to Porta San Gervasio, and learn more about the world around you at Museo Nazionale della Certosa Monumentale di Calci.

To see more things to do, photos, where to stay, and other tourist information, read Lucca trip itinerary website.

You can drive from Florence to Lucca in 1.5 hours. Other options are to 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 · Shopping

Side Trips

Find places to stay Oct 19 — 23:

3
nights
San Gimignano

Town of Fine Towers

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.
Appreciate the collections at San Gimignano 1300 and La Fornace Art Gallery. Deepen your sense of the past at sights like Abbazia di San Galgano and Historic Centre of San Gimignano. Explore the numerous day-trip ideas around San Gimignano: Siena (Centro Storico di Siena & Bianco e Nero di Sonia Staccioli ). The adventure continues: take a stroll around Comune Di Certaldo, take in the exciting artwork at Vitalita Cultural Association, and get a taste of the local shopping with La Bottega del Sale di Duccio Nacci photographer.

Plan my day in San Gimignano using traveler tips and tourist information provided by Inspirock.

You can drive from Lucca to San Gimignano in 2 hours. Other options are to take a train; or take a bus. In October, daytime highs in San Gimignano are 25°C, while nighttime lows are 14°C. Cap off your sightseeing on the 26th (Sat) early enough to go by car to Cortona.

Things to do in San Gimignano

Historic Sites · Shopping · Museums

Side Trips

Find places to stay Oct 23 — 26:

3
nights
Cortona

City of Art

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.
Satisfy your inner culture vulture at Eremo Le Celle and Duomo di Cortona. You'll discover tucked-away gems like Azienda Agricola Leuta and Azienda Agricola Baldetti Alfonso. And it doesn't end there: learn about winemaking at Buccelletti - Cantina, examine the collection at Pinacoteca di Castiglion Fiorentino, get engrossed in the history at Museo Civico Archeologico, and steep yourself in history at Abbazia Farneta.

To see maps, ratings, photos, and tourist information, read our Cortona travel 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 · Wineries · Historic Sites · Shopping

Side Trip

Find places to stay Oct 26 — 29:

4
nights
Montalcino

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Do your shopping at San Quirico d'Orcia and Artemisia Gallery. You'll discover tucked-away gems like Abbazia di Sant'Antimo and Podere Le Ripi. You'll find plenty of places to visit near Montalcino: Quinteaquadri Lab Gallery (in Montepulciano), Borgo di Lucignano d’Arbia (in Lucignano d'Arbia) and Art Studio di Adelina Quadri (in Monticchiello). And it doesn't end there: do a tasting at Mate Winery, appreciate the extensive heritage of Piazza della Cisterna, take in the exciting artwork at La Porta Gallery, and examine the collection at Archeological Museum and Tomb of Hell's Quadriga.

To see photos, other places to visit, traveler tips, and more tourist information, use the Montalcino online trip itinerary planner.

You can drive from Cortona to Montalcino in 1.5 hours. Other options are to do a combination of train and bus; or take a bus. In October, plan for daily highs up to 26°C, and evening lows to 15°C. Finish up your sightseeing early on the 2nd (Sat) so you can go by car to Pitigliano.

Things to do in Montalcino

Wineries · Museums · Historic Sites · Shopping

Side Trips

Find places to stay Oct 29 — Nov 2:

2
nights
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), get to know the fascinating history of Pitigliano Centro Storico, look for gifts at Macelleria LA IMPERIALE, take in the spiritual surroundings of Chiesa di San Giorgio, then step into the grandiose world of Piazza del Castello di Montemerano, and finally take in the dramatic scenery at 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, then take in the spiritual surroundings of Antico Ghetto e Sinagoga Pitigliano, then appreciate the extensive heritage of Sorano Centro Storico, and finally admire the landmark architecture of Masso Leopoldino.

To find other places to visit, traveler tips, more things to do, and tourist information, use the Pitigliano trip builder site.

Drive from Montalcino to Pitigliano in 1.5 hours. In November, daily temperatures in Pitigliano can reach 17°C, while at night they dip to 8°C. Finish up your sightseeing early on the 4th (Mon) so you can travel back home.

Things to do in Pitigliano

Historic Sites · Parks · Nature · Shopping

Side Trips

Find places to stay Nov 2 — 4:

Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.