21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Italy route planner

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Route & dates

21 days in Italy Itinerary

Start: Eindhoven
Fly:  4​h 45​min
1
Pisa
— 1 night
train:  1​h
2
Florence
— 3 nights
bus:  45​min
3
Greve in Chianti
— 2 nights
Drive:  1​h
4
Monteriggioni
— 2 nights
train:  15​min
5
Siena
— 2 nights
Drive:  1​h
6
Montepulciano
— 2 nights
Drive:  1​h 30​min
7
San Gimignano
— 3 nights
Drive:  1​h 30​min
8
Vada
— 1 day
Drive:  2​h
9
La Spezia
— 2 nights
Drive:  1​h
10
Lucca
— 3 nights
Fly:  8​h 30​min
End: Eindhoven

1
night
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Start off your visit on the 18th (Sun): pause for some serene contemplation at Basilica romanica di San Piero a Grado, make a trip to Leaning Tower of Pisa, get a new perspective on nature at Museo di Storia Naturale e del Territorio, learn about winemaking at Podere La Chiesa, then take in the spiritual surroundings of Santuario Della Madonna del Ghisallo - Museo Del Ciclismo, and finally step into the grandiose world of Castello dei Vicari. Get ready for a full day of sightseeing on the next day: indulge your taste buds at Agrisole SSA, enjoy the sand and surf at Il Paguro, then stroll through Bagno Vittorio Emanuele, and finally admire the landmark architecture of Palazzina Marconi.

To find ratings, photos, more things to do, and more tourist information, use the Pisa holiday builder .

Eindhoven, Holland to Pisa is an approximately 5-hour flight. You can also do a combination of flight and train; or drive. Traveling from Eindhoven in August, expect Pisa to be a bit warmer, temps between 35°C and 20°C. Finish up your sightseeing early on the 19th (Mon) so you can catch the train to Florence.

Things to do in Pisa

Outdoors Beaches Parks

Side Trips

Museo di Storia Naturale - Universita di Pisa, Madonna del Ghisallo, Podere Pellicciano - Agrisole, Podere La Chiesa, Castello dei Vicari
Find places to stay Aug 18 — 19:
Highlights from your plan
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Podere La Chiesa ©
Podere La Chiesa

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll discover tucked-away gems like Food Tours and Basilica San Miniato al Monte. Get some cultural insight at Centro Storico and Academy Of Florence Art Gallery. Take a break from Florence with a short trip to Castello del Trebbio in Santa Brigida, about 36 minutes away. The adventure continues: take in the views from Ponte Vecchio, contemplate in the serene atmosphere at The Baptistery of St. John, admire the striking features of Loggia dei Lanzi, and explore the world behind art at Uffizi Galleries.

To find ratings, where to stay, reviews, and more tourist information, read Florence trip itinerary planner.

Traveling by train from Pisa to Florence takes an hour. Alternatively, you can take a bus; or drive. Expect a daytime high around 35°C in August, and nighttime lows around 20°C. Finish your sightseeing early on the 22nd (Thu) to allow enough time to take a bus to Greve in Chianti.

Things to do in Florence

Historic Sites Museums Tours

Side Trip

Castello del Trebbio
Find places to stay Aug 19 — 22:
Highlights from your plan
Piazzale Michelangelo ©
Piazzale Michelangelo
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

2
nights
Greve in Chianti

Greve in Chianti ©
Start off your visit on the 23rd (Fri): do a tasting at Fattoria Casa Sola, do a tasting at Fattoria di Montecchio, learn about winemaking at L'Orcio a Ca di Pesa srl, do a tasting at Azienda Agricola Altiero, then do a tasting at Montefioralle Winery, and finally explore the historical opulence of Castello di Montefioralle. Get ready for a full day of sightseeing on the 24th (Sat): do a tasting at Fattoria Vignavecchia, do a tasting at Castello di Radda, learn about winemaking at Azienda Agricola Colle Bereto, then do a tasting at Lamole Di Lamole, then learn about winemaking at Accademia del Buon Gusto, and finally do a tasting at Azienda Agricola Il Palagio di Panzano.

To see ratings, photos, maps, and tourist information, use the Greve in Chianti trip itinerary planning app .

You can take a bus from Florence to Greve in Chianti in an hour. Another option is to drive. August in Greve in Chianti sees daily highs of 35°C and lows of 20°C at night. Finish your sightseeing early on the 24th (Sat) to allow enough time to drive to Monteriggioni.

Things to do in Greve in Chianti

Wineries Historic Sites

Side Trips

Radda in Chianti, Fattoria Casa Sola, Fattoria di Montecchio
Find places to stay Aug 22 — 24:
Highlights from your plan
Fattoria Casa Sola ©
Fattoria Casa Sola
Fattoria di Montecchio ©
Fattoria di Montecchio
Azienda Agricola Altiero ©
Azienda Agricola Altiero

2
nights
Monteriggioni

Monteriggioni ©
Monteriggioni is a comune in the province of Siena in the Italian region Tuscany. Start off your visit on the 25th (Sun): learn about winemaking at Fattoria Lornano, learn about winemaking at Casa Brancaia, learn about winemaking at Enoteca Bottega del Vino, then do a tasting at Tenuta Casanova, then appreciate the extensive heritage of Centro storico di Monteriggioni, and finally learn about winemaking at Fattoria Castello di Monteriggioni. Get ready for a full day of sightseeing on the next day: admire the landmark architecture of Walls of Monteriggioni, then learn about winemaking at Azienda Agricola Montalpruno, then learn about winemaking at Castello della Paneretta, and finally experience rural life at Azienda Agricola Casamonti.

To see maps, traveler tips, and more tourist information, read Monteriggioni trip itinerary planning tool .

Getting from Greve in Chianti to Monteriggioni by car takes about an hour. Other options: take a bus; or do a combination of bus and train. In August, daytime highs in Monteriggioni are 37°C, while nighttime lows are 22°C. Wrap up your sightseeing on the 26th (Mon) early enough to take a train to Siena.

Things to do in Monteriggioni

Wineries Historic Sites Classes

Side Trips

Castellina In Chianti, Castello della Paneretta, Azienda Agricola Montalpruno
Find places to stay Aug 24 — 26:
Highlights from your plan
Castello della Paneretta ©
Castello della Paneretta
Walls of Monteriggioni ©
Walls of Monteriggioni
Castello di Monteriggioni ©
Castello di Monteriggioni

2
nights
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 26th (Mon): don't miss a visit to Piazza del Campo. On the 27th (Tue), you'll have a packed day of sightseeing: examine the collection at Museo Civico Archeologico Isidoro Falchi, delve into the distant past at Area archeologica di Roselle, then get lost in a book at Biblioteca Piccolomini, then pause for some serene contemplation at Siena Cathedral, and finally admire the masterpieces at Parco Sculture Del Chianti.

To find photos, where to stay, more things to do, and more tourist information, read Siena trip planner .

Siena is just a stone's throw from Monteriggioni. In August, plan for daily highs up to 37°C, and evening lows to 22°C. Finish up your sightseeing early on the 28th (Wed) so you can go by car to Montepulciano.

Things to do in Siena

Historic Sites Wineries Museums

Side Trips

Gaiole in Chianti, Montalcino, Area Archeologica di Roselle, Abazzia di Torri, Museo Civico Archeologico Isidoro Falchi
Find places to stay Aug 26 — 28:
Highlights from your plan
Biblioteca Piccolomini ©
Biblioteca Piccolomini
Castiglion del Bosco ©
Castiglion del Bosco
Piazza del Campo ©
Piazza del Campo

2
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.
On the 29th (Thu), do a tasting at Icario Winery, learn about winemaking at Tenuta Valdipiatta, learn about winemaking at Az. Agr. Poliziano, then learn about winemaking at Gattavecchi Winery, then make a trip to Piazza Grande a Montepulciano, and finally do a tasting at Cantina Fattoria della Talosa. On the 30th (Fri), you'll have a packed day of sightseeing: take in the spiritual surroundings of Tempio di San Biagio, pause for some serene contemplation at Cappella della Madonna di Vitaleta, do a tasting at Podere Le Ripi, do a tasting at Mate Winery, then do a tasting at Poggio Rubino, and finally learn about winemaking at Azienda Agricola Patrizia Cencioni Solaria.

To find reviews, traveler tips, photos, and tourist information, read Montepulciano sightseeing planner .

You can drive from Siena to Montepulciano in an hour. Alternatively, you can take a train; or take a bus. In August, plan for daily highs up to 37°C, and evening lows to 22°C. Finish up your sightseeing early on the 30th (Fri) so you can go by car to San Gimignano.

Things to do in Montepulciano

Wineries Historic Sites

Side Trips

Montalcino, Cappella della Madonna di Vitaleta
Find places to stay Aug 28 — 30:
Highlights from your plan
Mate Winery ©
Mate Winery
Tempio di San Biagio ©
Tempio di San Biagio
Poggio Rubino ©
Poggio Rubino

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.
Kick off your visit on the 31st (Sat): do a tasting at Agricola Tamburini Emanuela, learn about winemaking at Corbucci, then learn about winemaking at Guardastelle Vineyard, and finally do a tasting at Fattoria Il Piano - Vineyard. Get ready for a full day of sightseeing on the next day: examine the collection at Museo della Geotermia, make a trip to Piazza dei Priori, learn about winemaking at Podere Poggio Alloro, view the masterpieces at Galleria Gagliardi, then appreciate the extensive heritage of San Gimignano 1300, and finally take an in-depth tour of Torre e Casa Campatelli.

To find ratings, photos, where to stay, and other tourist information, refer to the San Gimignano itinerary planner.

Traveling by car from Montepulciano to San Gimignano takes 1.5 hours. Alternatively, you can take a train; or take a bus. In August, plan for daily highs up to 35°C, and evening lows to 20°C. Finish your sightseeing early on the 2nd (Mon) to allow enough time to drive to Vada.

Things to do in San Gimignano

Wineries Museums Historic Sites

Side Trips

Gambassi Terme, Museo della Geotermia, Piazza dei Priori
Find places to stay Aug 30 — Sep 2:
Highlights from your plan
San Gimignano 1300 ©
San Gimignano 1300
Fattoria Il Piano ©
Fattoria Il Piano
Torre e Casa Campatelli ©
Torre e Casa Campatelli

1
day
Vada

Vada ©
Kick off your visit on the 2nd (Mon): kick back and relax at Bagno La Lanterna, then enjoy the sand and surf at Campo dei Fiori, and then kick back and relax at Bagni Il Delfino.

To find maps, other places to visit, reviews, and more tourist information, you can read our Vada vacation planner.

Drive from San Gimignano to Vada in 1.5 hours. Expect a daytime high around 30°C in September, and nighttime lows around 17°C. Wrap up your sightseeing on the 2nd (Mon) early enough to travel to La Spezia.

Things to do in Vada

Outdoors Beaches Parks

Side Trip

Bagni Il Delfino
Find places to stay Sep 2 — 3:
Highlights from your plan
Campo dei Fiori ©
Campo dei Fiori

2
nights
La Spezia

La Spezia ©
La Spezia, at the head of the Gulf of La Spezia in the Liguria region of Northern Italy, is the capital city of the province of La Spezia.In terms of population, La Spezia is the second city in the Liguria region, preceded just by Genoa. Start off your visit on the 3rd (Tue): wander the streets of Portovenere, examine the collection at Museo Civico Etnografico, then explore the historical opulence of Castello Doria, then pause for some serene contemplation at Santa Margherita di Antiochia Church, and finally see the interesting displays at Museo Civico Amedeo Lia. On the 4th (Wed), you'll have a packed day of sightseeing: do a tasting at Cantine Lunae, get a new perspective on nature at Punta Corvo, get to know the fascinating history of Centro Storico del Paese di Tellaro, then examine the collection at Castle of Saint Giorgio, then cruise along Ponte Thaon di Revel, and finally brush up on your military savvy at Museo Tecnico Navale della Spezia.

For traveler tips, photos, more things to do, and more tourist information, use the La Spezia road trip planning tool .

Traveling by car from Vada to La Spezia takes 1.5 hours. In September, daytime highs in La Spezia are 30°C, while nighttime lows are 17°C. Finish your sightseeing early on the 4th (Wed) so you can drive to Lucca.

Things to do in La Spezia

Museums Neighborhoods Historic Sites

Side Trips

Cinque Terre, Cantine Lunae, Portovenere, Punta Corvo, Centro Storico del Paese di Tellaro
Find places to stay Sep 2 — 4:
Highlights from your plan
Portovenere ©
Portovenere
Centro Storico del Paese di Tellaro ©
Cantine Lunae ©
Cantine Lunae

3
nights
Lucca

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
On the 5th (Thu), tour the pleasant surroundings at Bagno Maurizio, contemplate the long history of Le mura di Lucca, then examine the collection at Chiesa e Battistero di San Giovanni e Santa Reparata, then admire the striking features of St Martin Cathedral, and finally enjoy breathtaking views from Guinigi Tower. Get ready for a full day of sightseeing on the 6th (Fri): kick back and relax at Bagno Grazia, then kick back and relax at Bagno Carlo, and then take in the architecture and atmosphere at Duomo di San Cristoforo.

To see traveler tips, reviews, more things to do, and more tourist information, refer to the Lucca travel website .

Traveling by car from La Spezia to Lucca takes an hour. Alternatively, you can take a bus; or take a train. September in Lucca sees daily highs of 30°C and lows of 17°C at night. Wrap up your sightseeing by early afternoon on the 7th (Sat) to allow enough time to travel back home.

Things to do in Lucca

Outdoors Beaches Parks

Side Trips

Marina di Pietrasanta, Bagno Maurizio, Duomo di San Cristoforo
Find places to stay Sep 4 — 7:
Highlights from your plan
Fattoria al Dotto ©
Fattoria al Dotto
Bagno Maurizio ©
Bagno Maurizio
St Martin Cathedral ©
St Martin Cathedral

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