21 days in Italy Itinerary

21 days in Italy Itinerary

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Route & dates

21 days in Italy Itinerary

Start: Amsterdam
Fly:  5 h
1
Florence
— 1 night
Bus:  1 h 15 min
2
Siena
— 1 night
Bus:  1 h 15 min
3
San Gimignano
— Few hours
Bus + Train:  1 h 30 min
4
Siena
— 1 night
Train:  2 h 45 min
5
Arezzo
— 2 nights
Train:  30 min
6
Cortona
— 1 night
Drive:  1 h
7
Pienza
— 5 nights
Drive:  1 h 30 min
8
Fiesole
— 1 night
Drive:  30 min
9
Florence
— 3 nights
Bus:  1 h 15 min
10
Lucca
— 5 nights
Fly:  5 h 30 min
End: Amsterdam

1
night
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 15th (Fri): appreciate the extensive heritage of Piazza del Duomo and then take in the spiritual surroundings of Cathedral of Santa Maria del Fiore.

Take the guesswork out of planning a Florence vacation by using our trip itinerary maker.

Amsterdam, The Netherlands to Florence is an approximately 5-hour flight. You can also do a combination of flight and train; or drive. Expect a bit warmer weather when traveling from Amsterdam in May: highs in Florence hover around 25°C, while lows dip to 13°C. Finish your sightseeing early on the 16th (Sat) so you can take a bus to Siena.

Things to do in Florence

Historic Sites
Find places to stay May 15 — 16:
Highlights from your plan
Piazza del Duomo ©
Piazza del Duomo
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore

1
night
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 16th (Sat): contemplate in the serene atmosphere at San Francesco, then examine the collection at Archivio di Stato, then contemplate in the serene atmosphere at Sinagoga di Siena, and finally take in the spiritual surroundings of Cappella di Piazza.

To find reviews, where to stay, topicsMoreInfo.option.ratings, and more tourist information, use the Siena holiday planner.

Take a bus from Florence to Siena in 1.5 hours. Alternatively, you can drive; or take a train. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Cap off your sightseeing on the 17th (Sun) early enough to go by car to San Gimignano.

Things to do in Siena

Historic Sites Museums
Find places to stay May 16 — 17:
Highlights from your plan
San Francesco ©
San Francesco
Cappella di Piazza ©
Cappella di Piazza
Sinagoga di Siena ©
Sinagoga di Siena

few
hours
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.
Kick off your visit on the 17th (Sun): take in panoramic vistas at Rocca of Montestaffoli, then take an in-depth tour of Torre e Casa Campatelli, and then admire the landmark architecture of Mura di San Gimignano.

To see photos, traveler tips, other places to visit, and tourist information, use the San Gimignano online journey planner .

Traveling by car from Siena to San Gimignano takes an hour. Alternatively, you can take a bus; or do a combination of train and bus. In May, daytime highs in San Gimignano are 25°C, while nighttime lows are 13°C. On the 17th (Sun), wrap the sightseeing up by early afternoon so you can drive to Siena.

Things to do in San Gimignano

Historic Sites Museums
Find places to stay May 17 — 18:
Highlights from your plan
Rocca of Montestaffoli ©
Rocca of Montestaffoli
Torre e Casa Campatelli ©
Torre e Casa Campatelli
Mura di San Gimignano ©
Mura di San Gimignano

1
night
Siena

Siena ©
Start off your visit on the 17th (Sun): steep yourself in history at Loggia della Mercanzia and then take in the architecture and atmosphere at Basilica di San Clemente in Santa Maria dei Servi.

For traveler tips, reviews, photos, and tourist information, read our Siena trip planner.

Traveling by car from San Gimignano to Siena takes an hour. Alternatively, you can take a bus; or do a combination of bus and train. You'll have a few hours on the 18th (Mon) to wrap things up before traveling to Arezzo.

Things to do in Siena

Historic Sites
Find places to stay May 17 — 18:
Highlights from your plan
Loggia della Mercanzia ©
Loggia della Mercanzia

2
nights
Arezzo

Arezzo ©
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
On the 18th (Mon), learn about winemaking at Villa La Ripa and then contemplate the long history of Museo Casa di Giorgio Vasari. Get ready for a full day of sightseeing on the next day: examine the collection at Ivan Bruschi House & Museum, contemplate in the serene atmosphere at Santa Maria della Pieve, then take in the architecture and atmosphere at Cattedrale di san Giovanni Evangelista, then examine the collection at Aboca Museum, and finally examine the collection at Museo Madonna del Parto.

To see more things to do, traveler tips, other places to visit, and tourist information, read Arezzo trip maker site .

You can drive from Siena to Arezzo in 1.5 hours. Alternatively, you can take a bus; or take a train. You'll have a few hours on the 20th (Wed) to wrap things up before traveling to Cortona.

Things to do in Arezzo

Museums Historic Sites Wineries

Side Trips

Sansepolcro, Museo Madonna del Parto
Find places to stay May 18 — 20:
Highlights from your plan
Villa La Ripa ©
Villa La Ripa
San Francesco, Arezzo ©
San Francesco, Arezzo
Museo Madonna del Parto ©
Museo Madonna del Parto

1
night
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.
Kick off your visit on the 20th (Wed): stop by DelBrenna Jewelry, contemplate in the serene atmosphere at Chiesa San Francesco, contemplate in the serene atmosphere at Chiesa di San Domenico, then take in the spiritual surroundings of Santa Maria del Calcinaio, and finally contemplate the long history of Abbazia Farneta.

Take the guesswork out of planning a Cortona vacation by using our trip itinerary maker.

Cortona is just a stone's throw from Arezzo. Finish your sightseeing early on the 21st (Thu) to allow enough time to drive to Pienza.

Things to do in Cortona

Historic Sites Shopping
Find places to stay May 20 — 21:
Highlights from your plan
Chiesa San Francesco ©
Chiesa San Francesco
Abbazia Farneta ©
Abbazia Farneta
Santa Maria del Calcinaio ©
Santa Maria del Calcinaio

5
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. Appreciate the collections at Museo Civico and Art Studio di Adelina Quadri. Explore hidden gems such as Tempio di San Biagio and Borgo Medioevale di Monticchiello. Explore the numerous day-trip ideas around Pienza: Sarteano (Archeological Museum and Tomb of Hell's Quadriga & Castello di Sarteano), Chiesa di San Giorgio (in Montemerano) and Museo Archeologico Nazionale (in Chiusi). There's still lots to do: don't miss a visit to Piazza Pio II, get to know the fascinating history of Sorano Centro Storico, contemplate the long history of Palazzo Piccolomini, and wander the streets of Monticchiello.

To see where to stay, photos, other places to visit, and tourist information, go to the Pienza trip builder tool .

You can drive from Cortona to Pienza in an hour. Other options are to take a bus; or do a combination of train and bus. May in Pienza sees daily highs of 27°C and lows of 13°C at night. Wrap up your sightseeing by early afternoon on the 26th (Tue) to allow time for the car ride to Fiesole.

Things to do in Pienza

Historic Sites Museums Wineries

Side Trips

Chiusi, Montalcino, Acquapendente, Sarteano, San Quirico d'Orcia
Find places to stay May 21 — 26:
Highlights from your plan
Mate Winery ©
Mate Winery
Tempio di San Biagio ©
Tempio di San Biagio
Podere Il Cocco ©
Podere Il Cocco

1
night
Fiesole

Fiesole ©
Fiesole is a town and comune of the Metropolitan City of Florence in the Italian region of Tuscany, on a scenic height above Florence, 8km northeast of that city. Start off your visit on the 26th (Tue): browse the exhibits of Convento di San Francesco.

To see where to stay, other places to visit, topicsMoreInfo.option.ratings, and more tourist information, read Fiesole trip planning app .

Traveling by car from Pienza to Fiesole takes 1.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Finish up your sightseeing early on the 27th (Wed) so you can go by car to Florence.

Things to do in Fiesole

Historic Sites Parks Museums
Find places to stay May 26 — 27:
Highlights from your plan
Convento di San Francesco ©
Convento di San Francesco
San Domenico Fiesole ©
San Domenico Fiesole
Convent of San Domenico ©
Convent of San Domenico

3
nights
Florence

Florence ©
Start off your visit on the 28th (Thu): explore the historical opulence of Castello di Verrazzano, then explore the world behind art at Pitti Palace, and then admire the striking features of The Baptistery of St. John. Here are some ideas for day two: don't miss a visit to Piazzale Michelangelo, admire the landmark architecture of Basilica San Miniato al Monte, then explore the world behind art at Academy Of Florence Art Gallery, and finally get to know the fascinating history of Centro Storico.

For photos, traveler tips, topicsMoreInfo.option.ratings, and tourist information, refer to the Florence trip itinerary planning site .

Florence is just a stone's throw from Fiesole. Finish up your sightseeing early on the 30th (Sat) so you can catch the bus to Lucca.

Things to do in Florence

Historic Sites Wineries Museums

Side Trip

Castello di Verrazzano
Find places to stay May 27 — 30:
Highlights from your plan
Pitti Palace ©
Pitti Palace
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Centro Storico ©
Centro Storico

5
nights
Lucca

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Museum-lovers will appreciate Piaggio Museum and Museo di Storia Naturale - Universita di Pisa. Step off the beaten path and head to Duomo di Pisa and San Pietro Church. Explore the numerous day-trip ideas around Lucca: Tellaro (Chiesa di San Giorgio & Centro Storico del Paese di Tellaro), Castello di Lerici (in Lerici) and Chiesa di Santa Maria della Spina (in Pisa). And it doesn't end there: take in the spiritual surroundings of Basilica of San Frediano, admire the striking features of St Martin Cathedral, see the interesting displays at Puccini Museum - Casa Natale, and make a trip to Via Fillungo.

For other places to visit, traveler tips, photos, and other tourist information, read our Lucca trip app .

Traveling by bus from Florence to Lucca takes 1.5 hours. Alternatively, you can drive; or take a train. In May, daytime highs in Lucca are 25°C, while nighttime lows are 13°C. Wrap up your sightseeing by early afternoon on the 4th (Thu) to allow time for travel back home.

Things to do in Lucca

Historic Sites Museums Parks

Side Trips

Pisa, Calci, Tellaro, Park of Villa Reale, Castello di Lerici
Find places to stay May 30 — Jun 4:
Highlights from your plan
Duomo di Pisa ©
Duomo di Pisa
Centro Storico del Paese di Tellaro ©
Piaggio Museum ©
Piaggio Museum

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