31 days in Italy Itinerary

31 days in Italy Itinerary

Created using Inspirock Tuscany itinerary planner

Plan created by another user.Make it yours

Route & dates

Start: Singapore
Fly + Train:  20 h 45 min
1
Siena
— 7 nights
Drive:  1 h 45 min
2
Roccalbegna
— 4 nights
Drive:  1 h 45 min
3
Montepulciano
— 7 nights
Drive:  1 h
4
Arezzo
— 7 nights
Drive:  1 h 30 min
5
Florence
— 4 nights
Fly:  18 h
End: Singapore

7
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Change things up with these side-trips from Siena: Castello di Monterinaldi (in Radda in Chianti), San Gimignano (Torre Salvucci Maggiore, Historic Centre of San Gimignano, &more) and Abbazia di San Galgano (in Chiusdino). The adventure continues: don't miss a visit to Piazza del Campo, ponder the world of politics at Palazzo Pubblico and Museo Civico, enjoy breathtaking views from Torre del Mangia, and deepen your understanding at Scuola di Cucina di Lella.

To see traveler tips, reviews, photos, and tourist information, read Siena road trip planner.

Singapore, Singapore to Siena is an approximately 21-hour combination of flight and train. The time zone difference when traveling from Singapore to Siena is minus 7 hours. Plan for cooler temperatures traveling from Singapore in April, with highs in Siena at 23°C and lows at 9°C. Wrap up your sightseeing on the 8th (Wed) to allow time to travel to Roccalbegna.

Things to do in Siena

Historic Sites Wineries Tours

Side Trips

San Gimignano, Castello di Monterinaldi, Fattoria Pianporcino, Spas, Abbazia di San Galgano
Find places to stay Apr 1 — 8:
Highlights from your plan
Scuola di Cucina di Lella ©
Scuola di Cucina di Lella
Piazza del Campo ©
Piazza del Campo
Guardastelle Vineyard ©
Guardastelle Vineyard

4
nights
Roccalbegna

Roccalbegna ©
Roccalbegna is a comune (municipality) in the Province of Grosseto in the Italian region Tuscany, located about 110km south of Florence and about 35km east of Grosseto.HistoryRoccalbegna was a fief of the Aldobrandeschi in the Middle Ages; later it was part of the Republic of Siena, until the latter's fall in the hands of the Medici, who sold the town to the County of Santa Fiora. You'll find plenty of places to visit near Roccalbegna: Abbadia San Salvatore (Abbazia San Salvatore & Mining Museum Park), Cascate del Mulino (in Saturnia) and Montemerano (Chiesa di San Giorgio & Piazza del Castello di Montemerano). There's much more to do: look for all kinds of wild species at Bosco Rocconi, explore the fascinating underground world of Via Cava, contemplate in the serene atmosphere at Chiesa della Nativita di Maria, and appreciate the extensive heritage of Pitigliano Centro Storico.

For other places to visit, more things to do, traveler tips, and tourist information, use the Roccalbegna trip tool.

Getting from Siena to Roccalbegna by car takes about 2 hours. In April in Roccalbegna, expect temperatures between 23°C during the day and 9°C at night. Finish up your sightseeing early on the 12th (Sun) so you can travel to Montepulciano.

Things to do in Roccalbegna

Historic Sites Parks Nature

Side Trips

Sorano, Pitigliano, Abbadia San Salvatore, Saturnia, Montemerano
Find places to stay Apr 8 — 12:
Highlights from your plan
Pitigliano Centro Storico ©
Pitigliano Centro Storico
Cascate del Mulino ©
Cascate del Mulino
Chiesa dei santi Pietro e Paolo ©
Chiesa dei santi Pietro e Paolo

7
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.
You'll find plenty of places to visit near Montepulciano: Montalcino (Castello Romitorio, Mate Winery, &more), Cortona (Museo Diocesano & Eremo Le Celle) and Orvieto (Palazzo Coelli, Duomo di Orvieto, &more). There's much more to do: do a tasting at Tenuta Valdipiatta, take in panoramic vistas at Castello e Torre Monaldeschi, go for a walk through Civita di Bagnoregio, and admire the verdant scenery at Val d'Orcia.

To find maps, more things to do, and tourist information, read our Montepulciano online itinerary planner.

Getting from Roccalbegna to Montepulciano by car takes about 1.5 hours. In April in Montepulciano, expect temperatures between 23°C during the day and 9°C at night. Finish up your sightseeing early on the 19th (Sun) so you can go by car to Arezzo.

Things to do in Montepulciano

Historic Sites Wineries Parks

Side Trips

Orvieto, Pienza, Montalcino, San Quirico d'Orcia, Cortona
Find places to stay Apr 12 — 19:
Highlights from your plan
Mate Winery ©
Mate Winery
Tenuta Valdipiatta ©
Tenuta Valdipiatta
Eremo Le Celle ©
Eremo Le Celle

7
nights
Arezzo

Arezzo ©
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Change things up with these side-trips from Arezzo: Monastero di San Girolamo (in Frontino), Montevarchi (Il Cassero per la Scultura Italiana dell'Ottocento e del Novecento & Villa Masini) and Urbino (Chiesa di San Domenico, Palazzo Ducale di Urbino, &more). The adventure continues: see the interesting displays at Museo del Pianoforte Storico e del Suono, take in the architecture and atmosphere at Arezzo Cathedral, make a trip to Piazza Grande, and take in the spiritual surroundings of San Francesco, Arezzo.

For where to stay, traveler tips, more things to do, and tourist information, go to the Arezzo trip planner.

You can drive from Montepulciano to Arezzo in an hour. Alternatively, you can take a bus; or take a train. Wrap up your sightseeing on the 26th (Sun) to allow time to drive to Florence.

Things to do in Arezzo

Museums Historic Sites Parks

Side Trips

Urbino, Gubbio, Fabriano, Montevarchi, Museo Il Mondo Di Tonino Guerra
Find places to stay Apr 19 — 26:
Highlights from your plan
Villa La Ripa ©
Villa La Ripa
Santa Maria della Pieve ©
Santa Maria della Pieve
San Francesco, Arezzo ©
San Francesco, Arezzo

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence is known for museums, historic sites, and shopping. Your plan includes some of its best attractions: admire the masterpieces at Florence Academy of Fine Arts, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, pause for some serene contemplation at Basilica of Santa Croce, and admire the striking features of The Baptistery of St. John.

To see traveler tips, ratings, more things to do, and other tourist information, read Florence vacation planner.

Traveling by car from Arezzo to Florence takes 1.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 22°C in April, and nighttime lows around 11°C. Finish your sightseeing early on the 30th (Thu) to allow enough time to travel back home.

Things to do in Florence

Historic Sites Museums Fun & Games
Find places to stay Apr 26 — 30:
Highlights from your plan
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Piazzale Michelangelo ©
Piazzale Michelangelo

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