31 days in Italy Itinerary

31 days in Italy Itinerary

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Route & dates

31 days in Italy Itinerary

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, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Explore Siena's surroundings by going to Abbazia di San Galgano (in Chiusdino), San Gimignano (Torre Salvucci Maggiore, Historic Centre of San Gimignano, &more) and Castello di Monterinaldi (in Radda in Chianti). The adventure continues: make a trip to Piazza del Campo, head outdoors with 43parallelo, relax in the rural setting at Fattoria, and gain insight at Scuola di Cucina di Lella.

To find ratings, other places to visit, maps, and tourist information, you can read our Siena travel route planner.

Singapore, Singapore to Siena is an approximately 21-hour combination of flight and train. You'll gain 7 hours traveling from Singapore to Siena due to the time zone difference. Expect colder temperatures when traveling from Singapore in April; daily highs in Siena reach 23°C and lows reach 9°C. Finish up your sightseeing early on the 8th (Wed) so you can travel to Roccalbegna.

Things to do in Siena

Historic Sites Tours Museums

Side Trips

San Gimignano, Spas, Fattoria Pianporcino, Castello di Monterinaldi, Abbazia di San Galgano
Find places to stay Apr 1 — 8:
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

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. Explore Roccalbegna's surroundings by going to Montemerano (Chiesa di San Giorgio & Piazza del Castello di Montemerano), Cascate del Mulino (in Saturnia) and Abbadia San Salvatore (Abbazia San Salvatore & Mining Museum Park). There's much more to do: look for all kinds of wild species at Bosco Rocconi, Head underground at Via Cava, appreciate the extensive heritage of Sorano Centro Storico, and browse the collection at Polo Culturale Pietro Aldi.

To find ratings, reviews, traveler tips, and more tourist information, read our Roccalbegna journey builder website .

You can drive from Siena to Roccalbegna in 2 hours. In April, plan for daily highs up to 23°C, and evening lows to 9°C. Finish 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.
Change things up with these side-trips from Montepulciano: Orvieto (Palazzo Coelli, Duomo di Orvieto, &more), Cortona (Museo Diocesano & Eremo Le Celle) and Montalcino (Castello Romitorio, Mate Winery, &more). There's much more to do: contemplate the long history of Val d'Orcia, do a tasting at Az. Maria Caterina Dei, appreciate the extensive heritage of Civita di Bagnoregio, and awaken your taste buds at some of the top wineries in the area.

For where to stay, photos, traveler tips, and more tourist information, refer to the Montepulciano trip itinerary planning website .

Drive from Roccalbegna to Montepulciano in 2 hours. In April, plan for daily highs up to 23°C, and evening lows to 9°C. Finish your sightseeing early on the 19th (Sun) to allow enough time to drive 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
Val d'Orcia ©
Val d'Orcia
Podere Il Cocco ©
Podere Il Cocco
Mate Winery ©
Mate Winery

7
nights
Arezzo

Arezzo ©
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Get out of town with these interesting Arezzo side-trips: 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). There's much more to do: see the interesting displays at Museo del Pianoforte Storico e del Suono, take in the architecture and atmosphere at San Francesco, Arezzo, learn about winemaking at Villa La Ripa, and steep yourself in history at Museo Casa di Giorgio Vasari.

For reviews, maps, where to stay, and other tourist information, you can read our Arezzo tour itinerary planner.

Drive from Montepulciano to Arezzo in an hour. Alternatively, you can take a bus; or do a combination of bus and 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, Forte di San Leo
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: explore the world behind art at Academy Of Florence Art Gallery, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, get to know the fascinating history of Piazza del Duomo, and don't miss a visit to Piazzale Michelangelo.

To find where to stay, traveler tips, photos, and tourist information, read Florence trip itinerary planner.

You can drive from Arezzo to Florence in 1.5 hours. Other options are to take a train; or take a bus. In April, daily temperatures in Florence can reach 22°C, while at night they dip to 11°C. Cap off your sightseeing on the 30th (Thu) early enough 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
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Piazzale Michelangelo ©
Piazzale Michelangelo

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