60 days in Tuscany Itinerary

60 days in Tuscany Itinerary

Created using Inspirock Tuscany trip planner

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Route & dates

60 days in Tuscany Itinerary

Start: Florence
Drive:  2 h 15 min
1
Fivizzano
— 6 nights
Drive:  1 h 30 min
2
Lucca
— 9 nights
Drive:  1 h 30 min
3
Arezzo
— 9 nights
Train + Taxi:  2 h
4
Pitigliano
— 6 nights
Drive:  2 h
5
Siena
— 11 nights
Drive:  1 h
6
Greve in Chianti
— 6 nights
Bus:  45 min
7
Florence
— 12 nights
End: Florence

6
nights
Fivizzano

Fivizzano ©
Fivizzano, a walled city in the province of Massa and Carrara, Tuscany (Italy), became part of the Republic of Florence in the 15th century thus gaining the Tuscan republic an important foothold in Lunigiana, a key region which Genoa, Lucca, Pisa, Milan and Florence had sought to dominate since the early Middle Ages. Visit Borgo Medievale di Ponticello and Chiesa Vecchia di Gorfigliano for their historical value. Venture out of the city with trips to Castiglione di Garfagnana (Rocca Medievale, Borgo Medievale di Castiglione di Garfagnana, & more), Museo Delle Mummie Roccapelago (in Pievepelago) and Castello di Castiglione del Terziere (in Castiglione). There's lots more to do: make a trip to Fortezza delle Verrucole - Archeopark, hike along Ostello dei Balocchi, take in the spiritual surroundings of Pieve di San Paolo a Vendaso, and explore the historical opulence of Castle dell'Aquila.

For maps, reviews, ratings, and tourist information, use the Fivizzano tour itinerary tool .

Florence to Fivizzano is an approximately 2.5-hour car ride. In May, daily temperatures in Fivizzano can reach 25°C, while at night they dip to 13°C. Cap off your sightseeing on the 19th (Sun) early enough to go by car to Lucca.

Things to do in Fivizzano

Historic Sites Outdoors Parks

Side Trips

Fosdinovo, Castiglione di Garfagnana, Minucciano, Vagli Sotto, Filattiera
Highlights from your plan
Chiesa Vecchia di Gorfigliano ©
Chiesa Vecchia di Gorfigliano
Castello di Castiglione del Terziere ©

9
nights
Lucca

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Le mura di Lucca and St Martin Cathedral will appeal to history buffs. You'll find plenty of places to visit near Lucca: Duomo di San Cristoforo (in Barga), Pieve Fosciana (Pieve di San Giovanni Battista & Sillico) and Centro Storico Castelvecchio Di Rocca Barbena (in Castelvecchio Pascoli). The adventure continues: enjoy breathtaking views from Leaning Tower of Pisa, don't miss a visit to Denzano, appreciate the extensive heritage of Svizzera Pesciatina, and appreciate the history behind Monumento a Camillo Cavour.

To find maps, reviews, more things to do, and other tourist information, go to the Lucca journey maker .

Traveling by car from Fivizzano to Lucca takes 1.5 hours. May in Lucca sees daily highs of 25°C and lows of 13°C at night. Finish your sightseeing early on the 28th (Tue) to allow enough time to drive to Arezzo.

Things to do in Lucca

Historic Sites Parks Outdoors

Side Trips

Pisa, Pieve Fosciana, Marano sul Panaro, Capannori, Centro Storico di Buggiano
Highlights from your plan
Le mura di Lucca ©
Le mura di Lucca
San Michele in Foro ©
San Michele in Foro
Madonna del Ghisallo ©
Madonna del Ghisallo

9
nights
Arezzo

Arezzo ©
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Get some historical perspective at Basilica of Saint Peter and Basilica di San Francesco. Get out of town with these interesting Arezzo side-trips: Chiesa di Santa Maria della Reggia (in Umbertide), Vineria del Carmine (in La Bruna) and Tomba del Faggeto (in Perugia). And it doesn't end there: contemplate in the serene atmosphere at Eremo Le Celle, get to know the fascinating history of Rio Vitoschio, do a tasting at Villa La Ripa, and take in the architecture and atmosphere at Cappella delle Stimmate.

For photos, where to stay, reviews, and more tourist information, refer to the Arezzo trip planner .

Drive from Lucca to Arezzo in 1.5 hours. Alternatively, you can take a train. Wrap up your sightseeing on the 6th (Thu) early enough to travel to Pitigliano.

Things to do in Arezzo

Historic Sites Wineries Parks

Side Trips

Cortona, Cesena, Camaldoli, Bibbiena, Perugia
Highlights from your plan
Basilica of Saint Peter ©
Basilica of Saint Peter
Eremo Le Celle ©
Eremo Le Celle
San Francesco, Arezzo ©
San Francesco, Arezzo

6
nights
Pitigliano

Pitigliano ©
Pitigliano is a town in the province of Grosseto, located about 80km south-east of the city of Grosseto, in Italy. Chiesa dei SS. Apostoli Pietro e Paolo and Piazza del Castello di Montemerano will appeal to history buffs. Explore Pitigliano's surroundings by going to Montemerano (Chiesa di San Giorgio & Villa Acquaviva - La Fattoria), Il ghetto degli ebrei (in Santa Fiora) and Abbazia di San Salvatore (in Roccastrada). And it doesn't end there: get to know the fascinating history of Pitigliano Centro Storico, take in the spiritual surroundings of Chiesa della Nativita di Maria, pause for some serene contemplation at Chiesa dei santi Pietro e Paolo, and look for all kinds of wild species at Bosco Rocconi.

Planning Pitigliano trip won't be overwheling when you use's Insprock itinerary maker.

Do a combination of train and taxi from Arezzo to Pitigliano in 2 hours. Alternatively, you can drive. Expect a daytime high around 32°C in June, and nighttime lows around 17°C. Finish your sightseeing early on the 12th (Wed) to allow enough time to drive to Siena.

Things to do in Pitigliano

Historic Sites Wineries Parks

Side Trips

Sorano, Montemerano, Roccalbegna, Chiesa di San Michele Arcangelo, Chiesa di San Giovanni Battista
Highlights from your plan
Chiesa dei SS. Apostoli Pietro e Paolo ©
Piazza del Castello di Montemerano ©
Pitigliano Centro Storico ©
Pitigliano Centro Storico

11
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Deepen your sense of the past at sights like Siena Cathedral and Basilica di San Domenico. Get out of town with these interesting Siena side-trips: Cappella della Madonna di Vitaleta (in San Quirico d'Orcia), Fattoria Il Piano - Vineyard (in San Gimignano) and Abbazia di San Galgano (in Chiusdino). Dedicate the 15th (Sat) to wine at some of the top wineries in the area. There's much more to do: make a trip to Centro Storico di Siena, take in the spiritual surroundings of San Francesco, pause for some serene contemplation at Cappella di Piazza, and contemplate the long history of Santa Maria del Carmine (San Niccolo al Carmine).

To see where to stay, other places to visit, maps, and tourist information, you can read our Siena route planner .

You can drive from Pitigliano to Siena in 2 hours. Another option is to do a combination of taxi and train. In June, daytime highs in Siena are 34°C, while nighttime lows are 19°C. Finish your sightseeing early on the 23rd (Sun) to allow enough time to drive to Greve in Chianti.

Things to do in Siena

Historic Sites Tours Museums

Side Trips

Abbazia di San Galgano, Fattoria Il Piano, Cappella della Madonna di Vitaleta, Val d'Orcia
Highlights from your plan
Val d'Orcia ©
Val d'Orcia
Duomo di Siena ©
Duomo di Siena
Battistero di San Giovanni ©
Battistero di San Giovanni

6
nights
Greve in Chianti

Greve in Chianti ©
Popular historic sites such as Castello di Monterinaldi and Castello di Verrazzano are in your itinerary. Change things up with these side-trips from Greve in Chianti: Santuario Maria SS. Madre della Divina Provvidenza (in Pancole), San Gimignano (Piazza del Duomo, Torre Grossa, & more) and Barberino Val d'Elsa (Barberino Val d'Elsa & Pieve di Sant'Appiano).

For maps, other places to visit, ratings, and more tourist information, use the Greve in Chianti itinerary planner .

You can drive from Siena to Greve in Chianti in an hour. Other options are to take a bus; or do a combination of train and bus. In June, plan for daily highs up to 32°C, and evening lows to 18°C. Finish your sightseeing early on the 29th (Sat) to allow enough time to take a bus to Florence.

Things to do in Greve in Chianti

Wineries Historic Sites Classes

Side Trips

San Gimignano, Radda in Chianti, Castellina In Chianti, Barberino Val d'Elsa, Poggio al Bosco
Highlights from your plan
Castello di Monterinaldi ©
Castello di Monterinaldi
Castello di Verrazzano ©
Castello di Verrazzano
Duomo di San Gimignano ©
Duomo di San Gimignano

12
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Visit Cathedral of Santa Maria del Fiore and Campanile di Giotto for their historical value. Venture out of the city with trips to Leaning Tower of Pisa (in Pisa), Siena (San Francesco, Contrada della Torre, & more) and Guardastelle Vineyard (in San Gimignano). Next up on the itinerary: explore the world behind art at Uffizi Galleries, examine the collection at Pitti Palace, don't miss a visit to Palazzo Vecchio, and appreciate the extensive heritage of Piazza della Signoria.

To see other places to visit, where to stay, and tourist information, you can read our Florence trip website .

You can take a bus from Greve in Chianti to Florence in an hour. Another option is to drive. In June, daytime highs in Florence are 33°C, while nighttime lows are 21°C. Wrap up your sightseeing on the 11th (Thu) early enough to travel back home.

Things to do in Florence

Historic Sites Museums Tours

Side Trips

Siena, Bologna, Guardastelle Vineyard, Leaning Tower of Pisa
Highlights from your plan
Tuscan Wine Tour by Italy and Wine ©
Tuscan Wine Tour by Italy and Wine
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Basilica of Santa Croce ©
Basilica of Santa Croce

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