30 days in Italy Itinerary

30 days in Italy Itinerary

Created using Inspirock Tuscany trip planner

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Route & dates

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. Get out of town with these interesting Roccalbegna side-trips: Romitori di Ischia di Castro (in Ischia di Castro), Riserva Naturale Regionale Selva del Lamone (in Farnese) and Villa Acquaviva - La Fattoria (in Montemerano). Next up on the itinerary: identify plant and animal life at Bosco Rocconi, don't miss a visit to Cana, experience rural life at Aia Della Colonna, and do a tasting at Maremma Vigna Mia.

To find maps, traveler tips, and tourist information, refer to the Roccalbegna vacation app.

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. Plan for cooler temperatures traveling from Singapore in April, with highs in Roccalbegna at 23°C and lows at 9°C. Wrap up your sightseeing on the 4th (Sat) early enough to travel to Siena.

Things to do in Roccalbegna

Wineries Historic Sites Outdoors

Side Trips

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

5
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Change things up with a short trip to Guardastelle Vineyard in San Gimignano (about 54 minutes away). The adventure continues: awaken your taste buds at some of the top wineries in the area, pause for some serene contemplation at Duomo di Siena, don't miss a visit to Porta Nova, and explore the world behind art at Pinacoteca Nazionale.

To see reviews, where to stay, more things to do, and tourist information, read our Siena itinerary planner.

You can drive from Roccalbegna to Siena in 2 hours. In April, daytime highs in Siena are 23°C, while nighttime lows are 9°C. Finish your sightseeing early on the 9th (Thu) so you can drive 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
Guardastelle Vineyard ©
Guardastelle Vineyard
ASD Paintball Siena ©
ASD Paintball 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.
Get out of town with these interesting Montepulciano side-trips: Duomo di Orvieto (in Orvieto), Winery Solaria Patrizia Cencioni (in Montalcino) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). There's much more to do: pause for some serene contemplation at Chiesa di San Pietro, do a tasting at Cantina Fattoria della Talosa, take in nature's colorful creations at La Serpara, and look for all kinds of wild species at Riserva Naturale Lago di Montepulciano.

To find ratings, other places to visit, where to stay, and other tourist information, read Montepulciano online tour planner.

Getting from Siena to Montepulciano by car takes about an hour. Other options: do a combination of train and bus; or take a bus. In April, plan for daily highs up to 23°C, and evening lows to 9°C. Finish your sightseeing early on the 13th (Mon) to allow enough time to drive to Arezzo.

Things to do in Montepulciano

Wineries Parks Historic Sites

Side Trips

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

6
nights
Arezzo

Arezzo ©
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Explore Arezzo's surroundings by going to Assisi (Rocca Maggiore, Museo della Memoria, &more), Frantoio Di Spello Uccd (in Spello) and Santa Maria degli Angeli (Fiori E Fantasia & Museo della Porziuncola). There's still lots to do: do a tasting at Villa La Ripa, cruise along Very Tuscany, see the interesting displays at Museo della Fauna Selvatica, and make a trip to Corso Italia.

To find ratings, other places to visit, and more tourist information, refer to the Arezzo day trip 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. Finish your sightseeing early on the 19th (Sun) to allow enough time to drive 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
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
San Damiano ©
San Damiano
Museo della Porziuncola ©
Museo della Porziuncola

10
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll find plenty of places to visit near Florence: Bologna (Piazza Maggiore, De Paz, &more), Museo Giorgio Kienerk (in Fauglia) and Leaning Tower of Pisa (in Pisa). The adventure continues: admire the masterpieces at Florence Academy of Fine Arts, awaken your taste buds at some of the top wineries in the area, take in panoramic vistas at Campanile di Giotto, and get the lay of the land with Walking tours.

To see maps, traveler tips, photos, and other tourist information, use the Florence trip itinerary builder app.

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 29th (Wed) to allow enough time to travel back home.

Things to do in Florence

Historic Sites Museums Tours

Side Trips

Bologna, Ravenna, Museo Giorgio Kienerk, Leaning Tower of Pisa, Castello del Trebbio
Find places to stay Apr 19 — 29:
Highlights from your plan
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
The Baptistery of St. John ©
The Baptistery of St. John

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