22 days in Tuscany Itinerary

22 days in Tuscany Itinerary

Steve Dickey

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Route & dates

22 days in Tuscany Itinerary

Start: Los Angeles
Austrian Airlines OS 82 + Austrian Airlines OS 531
14 h 30 min See details
1
Florence
— 4 nights
Bus:  1 h 30 min
2
Siena
— 3 nights
Drive:  1 h
3
Montepulciano
— 1 night
Drive:  30 min
4
Pienza
— 7 nights
Drive:  2 h
5
Volterra
— 3 nights
Drive:  1 h 45 min
6
Lucca
— 2 nights
Swiss International Air Lines LX 1679 + Swiss International Air Lines LX 40
18 h 15 min See details
End: Los Angeles

4
nights
Florence

Florence
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Basilica di San Lorenzo and Basilica San Miniato al Monte will appeal to history buffs. There's more to do: visit Oltrarno and appreciate the history behind Ercole e Caco.

To find photos, topicsMoreInfo.option.ratings, and other tourist information, go to the Florence online trip itinerary maker .

Los Angeles, USA to Florence is an approximately 16.5-hour flight. You can also do a combination of flight and train. The time zone difference when traveling from Los Angeles to Florence is 9 hours. Expect a bit cooler evenings in Florence when traveling from Los Angeles in May, with lows around 52°F. You'll set off for Siena on the 3rd (Wed).

Things to do in Florence

Historic Sites Neighborhoods Museums
Highlights from your plan
Basilica San Miniato al Monte
Basilica San Miniato al Monte
Basilica di San Lorenzo ©
Basilica di San Lorenzo
Ercole e Caco ©
Ercole e Caco

3
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Popular historic sites such as Duomo di Siena and Castello di Monterinaldi are in your itinerary. Get a sense of the local culture at Piazza del Campo and Palazzo Pubblico and Museo Civico. Venture out of the city with trips to Fattoria di Montemaggio (in Radda in Chianti), Abbazia di San Galgano (in Chiusdino) and Spas (in Rapolano Terme). The adventure continues: contemplate the long history of Centro Storico di Siena, learn about winemaking at Sant'Agnese Farm, contemplate in the serene atmosphere at San Francesco, and take in panoramic vistas at Torre del Mangia.

To see where to stay, other places to visit, reviews, and more tourist information, use the Siena itinerary planning website .

You can take a bus from Florence to Siena in 1.5 hours. Other options are to drive; or take a train. In June, daytime highs in Siena are 84°F, while nighttime lows are 61°F. Finish your sightseeing early on the 5th (Fri) to allow enough time to drive to Montepulciano.

Things to do in Siena

Historic Sites Wineries Spas

Side Trips

Greve in Chianti, Radda in Chianti, Fattoria Casa Sola, Sant'Agnese Farm, Castello di Monteriggioni
Highlights from your plan
Castello di Monterinaldi ©
Castello di Monterinaldi
Duomo di Siena ©
Duomo di Siena
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico

1
night
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.
Start off your visit on the 6th (Sat): do a tasting at Azienda Agricola Ercolani, make a trip to Piazza Grande a Montepulciano, learn about winemaking at Cantina Fattoria della Talosa, then indulge in some personalized pampering at some of the best spas, then learn about winemaking at Avignonesi, and finally do a tasting at Azienda Agricola Leuta.

To see ratings, maps, reviews, and tourist information, use the Montepulciano road trip app .

Getting from Siena to Montepulciano by car takes about an hour. Other options: take a train; or take a bus. In June, daytime highs in Montepulciano are 84°F, while nighttime lows are 61°F. Wrap up your sightseeing on the 6th (Sat) to allow time to drive to Pienza.

Things to do in Montepulciano

Wineries Spas

Side Trips

Spas, Azienda Agricola Leuta
Highlights from your plan
Azienda Agricola Leuta ©
Azienda Agricola Leuta
Cantina Fattoria della Talosa ©
Cantina Fattoria della Talosa
Azienda Agricola Ercolani ©
Azienda Agricola Ercolani

7
nights
Pienza

Pienza ©
Pienza, a town and comune in the province of Siena, in the Val d'Orcia in Tuscany (central Italy), between the towns of Montepulciano and Montalcino, is the "touchstone of Renaissance urbanism."In 1996, UNESCO declared the town a World Heritage Site, and in 2004 the entire valley, the Val d'Orcia, was included on the list of UNESCO's World Cultural Landscapes.HistoryBefore the village was renamed to Pienza its name was Corsignano. Do some cultural sightseeing at Ciacci Piccolomini d'Aragona and Winery Solaria Patrizia Cencioni. Get some historical perspective at Val d'Orcia and Abbazia di Sant'Antimo. Get out of town with these interesting Pienza side-trips: Sorano Centro Storico (in Sorano), Montalcino (San Polino Winery, Mate Winery, &more) and Castello di Montorio (in Montorio). There's much more to do: do a tasting at Poggio Rubino, take a stroll through Monticchiello, take in the spiritual surroundings of Chiesa di San Giorgio, and take in the architecture and atmosphere at Cappella della Madonna di Vitaleta.

To find more things to do, traveler tips, maps, and other tourist information, refer to the Pienza vacation planner.

Pienza is just a short distance from Montepulciano. Expect a daytime high around 84°F in June, and nighttime lows around 61°F. Wrap up your sightseeing on the 13th (Sat) to allow time to drive to Volterra.

Things to do in Pienza

Historic Sites Wineries Parks

Side Trips

Montalcino, Sorano, Tuscany, Montemerano, San Quirico d'Orcia
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Podere Il Cocco ©
Podere Il Cocco
Mate Winery ©
Mate Winery

3
nights
Volterra

Volterra ©
Volterra is a walled mountaintop town in the Tuscany region of Italy of which its history dates to before the 7th century BC and has substantial structures from the Etruscan, Roman, and Medieval periods.HistoryVolterra, known to the ancient Etruscans as Velathri or Vlathri and to the Romans as Volaterrae, is a town and comune in the Tuscany region of Italy. Teatro Persio Flacco has been added to your itinerary. On the 13th (Sat), catch a live performance at Teatro Persio Flacco, take in the spiritual surroundings of Cathedral of Santa Maria Assunta, steep yourself in history at Roman Theatre, contemplate the long history of Piazza dei Priori, then explore the historical opulence of Palazzo dei Priori, and finally take an in-depth tour of Museo della Tortura. Keep things going the next day: explore the ancient world of Porta all'Arco, take an in-depth tour of Palazzo Viti, then contemplate in the serene atmosphere at Chiesa di San Michele Arcangelo, and finally examine the collection at Museo Etrusco Guarnacci.

To see photos, where to stay, traveler tips, and tourist information, you can read our Volterra travel route planning website .

You can drive from Pienza to Volterra in 2 hours. Other options are to take a bus; or do a combination of bus and train. Expect a daytime high around 81°F in June, and nighttime lows around 60°F. Finish your sightseeing early on the 14th (Sun) so you can drive to Lucca.

Things to do in Volterra

Historic Sites Museums Nightlife
Highlights from your plan
Roman Theatre ©
Roman Theatre
Porta all'Arco ©
Porta all'Arco
Palazzo dei Priori ©
Palazzo dei Priori

2
nights
Lucca

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Start off your visit on the 16th (Tue): make a trip to Piazza Anfiteatro and then contemplate the long history of Le mura di Lucca. Get ready for a full day of sightseeing on the next day: admire the landmark architecture of St Martin Cathedral, contemplate in the serene atmosphere at San Michele in Foro, enjoy breathtaking views from Torre Guinigi, then stroll the grounds of Camposanto, then contemplate in the serene atmosphere at Duomo di Pisa, and finally contemplate in the serene atmosphere at Baptistery of St. John.

For more things to do, traveler tips, and more tourist information, go to the Lucca road trip planning app .

You can drive from Volterra to Lucca in 2 hours. Other options are to take a bus; or do a combination of bus and train. In June, daytime highs in Lucca are 81°F, while nighttime lows are 60°F. Cap off your sightseeing on the 18th (Thu) early enough to travel back home.

Things to do in Lucca

Historic Sites

Side Trip

Pisa
Highlights from your plan
Le mura di Lucca ©
Le mura di Lucca
Leaning Tower of Pisa ©
Leaning Tower of Pisa
San Michele in Foro ©
San Michele in Foro

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