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

1
Siena
— 7 nights
2
Roccalbegna
— 4 nights
3
Montepulciano
— 7 nights
4
Arezzo
— 7 nights
5
Florence
— 4 nights

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), Abbazia di San Galgano (in Chiusdino) and San Gimignano (Torre Salvucci Maggiore, Historic Centre of San Gimignano, &more). 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 · Museums

Side Trips

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

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. Get out of town with these interesting Roccalbegna side-trips: Abbadia San Salvatore (Abbazia San Salvatore & Mining Museum Park), Montemerano (Chiesa di San Giorgio & Piazza del Castello di Montemerano) and Cascate del Mulino (in Saturnia). There's much more to do: look for all kinds of wild species at Bosco Rocconi, contemplate the geological forces at Monte Amiata, get to know the fascinating history of Sorano Centro Storico, and take in the spiritual surroundings of Antico Ghetto e Sinagoga Pitigliano.

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, Montemerano, Saturnia
Find places to stay Apr 8 — 12:
Highlights from your plan
Pitigliano Centro Storico ©
Pitigliano Centro Storico
Cascate del Mulino ©
Cascate del Mulino
Abbazia San Salvatore ©
Abbazia San Salvatore

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: Orvieto (Palazzo Coelli, Duomo di Orvieto, &more), Cortona (Museo Diocesano & Eremo Le Celle) and Montalcino (Castello Romitorio, Mate Winery, &more). There's still lots to do: admire the verdant scenery at Val d'Orcia, learn about winemaking at Vinoteca Terra Toscana, enjoy breathtaking views from Castello e Torre Monaldeschi, and go for a walk through Civita di Bagnoregio.

For where to stay, traveler tips, other places to visit, and tourist information, refer to the Montepulciano trip itinerary planning app.

Drive from Roccalbegna to Montepulciano in 1.5 hours. Expect a daytime high around 23°C in April, and nighttime lows around 9°C. 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, Cortona, San Quirico d'Orcia
Find places to stay Apr 12 — 19:
Highlights from your plan
Mate Winery ©
Mate Winery
Eremo Le Celle ©
Eremo Le Celle
Val d'Orcia ©
Val d'Orcia

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: Urbino (Chiesa di San Domenico, Palazzo Ducale di Urbino, &more), Montevarchi (Il Cassero per la Scultura Italiana dell'Ottocento e del Novecento & Villa Masini) and Monastero di San Girolamo (in Frontino). The adventure continues: examine the collection at Museo del Pianoforte Storico e del Suono, learn about winemaking at Villa La Ripa, don't miss a visit to Piazza Grande, and contemplate in the serene atmosphere at San Francesco, Arezzo.

To see other places to visit, photos, and tourist information, go to the Arezzo trip planner.

Traveling by car from Montepulciano to Arezzo takes an hour. Alternatively, you can take a bus; or take a train. Finish your sightseeing early on the 26th (Sun) so you can drive to Florence.

Things to do in Arezzo

Museums · Historic Sites · Parks

Side Trips

Urbino, Gubbio, Montevarchi, Fabriano, Grotte di Frasassi
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 · Shopping
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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