30 days in Italy Itinerary

30 days in Italy Itinerary

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Route & dates

30 days in Italy Itinerary

Start: Singapore
Fly + Drive:  19​h 30​min
1
Roccalbegna
— 3 nights
Drive:  1​h 45​min
2
Siena
— 5 nights
Drive:  1​h
3
Montepulciano
— 4 nights
Drive:  1​h
4
Arezzo
— 6 nights
Drive:  1​h 30​min
5
Florence
— 10 nights
Fly:  18​h
End: Singapore

3
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. Change things up with these side-trips from Roccalbegna: Riserva Naturale Regionale Selva del Lamone (in Farnese), Romitori di Ischia di Castro (in Ischia di Castro) and Villa Acquaviva - La Fattoria (in Montemerano). And it doesn't end there: look for all kinds of wild species at Bosco Rocconi, experience rural life at Aia Della Colonna, learn about winemaking at Maremma Vigna Mia, and don't miss a visit to Cana.

To find photos, ratings, reviews, and tourist information, use the Roccalbegna holiday planning tool .

Singapore, Singapore to Roccalbegna is an approximately 19.5-hour combination of flight and car. You'll gain 7 hours traveling from Singapore to Roccalbegna due to the time zone difference. Expect cooler temperatures when traveling from Singapore in April; daily highs in Roccalbegna reach 23°C and lows reach 9°C. Finish your sightseeing early on the 4th (Sat) to allow enough time to travel to Siena.

Things to do in Roccalbegna

Wineries Historic Sites Outdoors

Side Trips

Villa Acquaviva - La Fattoria, Riserva Naturale Regionale Selva del Lamone, Chiesa della Nativita di Maria, Romitori di Ischia di Castro, Basile Azienda Agricola Biologica
Find places to stay Apr 1 — 4:
Highlights from your plan
Basile Azienda Agricola Biologica ©
Romitori di Ischia di Castro ©
Romitori di Ischia di Castro

5
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Step out of Siena to go to San Gimignano and see Guardastelle Vineyard, which is approximately 52 minutes away. Next up on the itinerary: make a trip to Piazza del Campo, get to know the fascinating history of Contrada della Torre, explore the world behind art at Palazzo Pubblico and Museo Civico, and awaken your taste buds at some of the top wineries in the area.

To see ratings, where to stay, and more tourist information, refer to the Siena online road trip planner .

You can drive from Roccalbegna to Siena in 2 hours. In April, plan for daily highs up to 23°C, and evening lows to 9°C. Finish up your sightseeing early on the 9th (Thu) so you can go by car to Montepulciano.

Things to do in Siena

Historic Sites Tours Wineries

Side Trip

Guardastelle Vineyard
Find places to stay Apr 4 — 9:
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

4
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.
Explore Montepulciano's surroundings by going to Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate), Winery Solaria Patrizia Cencioni (in Montalcino) and Duomo di Orvieto (in Orvieto). The adventure continues: take in the architecture and atmosphere at Chiesa di San Pietro, stroll around La Serpara, contemplate in the serene atmosphere at Eremo Le Celle, and appreciate the extensive heritage of Centro storico.

To see traveler tips, photos, maps, and tourist information, read our Montepulciano route planning website .

Traveling by car from Siena to Montepulciano takes an hour. Alternatively, you can take a train; or take a bus. Expect a daytime high around 23°C in April, and nighttime lows around 9°C. Finish your sightseeing early on the 13th (Mon) so you can drive to Arezzo.

Things to do in Montepulciano

Wineries Parks Historic Sites

Side Trips

Montalcino, Cortona, Chiesa di San Pietro, La Serpara, Duomo di Orvieto
Find places to stay Apr 9 — 13:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Chiesa di San Pietro ©
Chiesa di San Pietro
Eremo Le Celle ©
Eremo Le Celle

6
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: Frantoio Di Spello Uccd (in Spello), Assisi (Rocca Maggiore, Museo della Memoria, & more) and Santa Maria degli Angeli (Fiori E Fantasia & Museo della Porziuncola). And it doesn't end there: do a tasting at Villa La Ripa, examine the collection at Museo della Fauna Selvatica, cruise along Very Tuscany, and admire the landmark architecture of Badia delle Sante Flora e Lucilla.

For ratings, photos, traveler tips, and tourist information, read our Arezzo attractions app .

Getting from Montepulciano to Arezzo by car takes about an hour. Other options: take a bus; or do a combination of bus and train. Cap off your sightseeing on the 19th (Sun) early enough to go by car to Florence.

Things to do in Arezzo

Historic Sites Wineries Scenic Drive

Side Trips

Assisi, Frantoio Di Spello Uccd
Find places to stay Apr 13 — 19:
Highlights from your plan
Museo della Porziuncola ©
Museo della Porziuncola
Eremo delle Carceri ©
Eremo delle Carceri

10
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Change things up with these side-trips from Florence: Museo Giorgio Kienerk (in Fauglia), Leaning Tower of Pisa (in Pisa) and Bologna (Piazza Maggiore, De Paz, & more). The adventure continues: admire the masterpieces at Gallerie Degli Uffizi, get to know the fascinating history of Piazza del Duomo, see the interesting displays at Academy Of Florence Art Gallery, and pause for some photo ops at Campanile di Giotto.

To see other places to visit, reviews, maps, and tourist information, use the Florence road trip planning site .

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. Finish up your sightseeing early on the 29th (Wed) so you can travel back home.

Things to do in Florence

Historic Sites Museums Tours

Side Trips

Bologna, Ravenna, Castello del Trebbio, Museo Giorgio Kienerk, Leaning Tower of Pisa
Find places to stay Apr 19 — 29:
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

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