26 days in Bologna & Tuscany Itinerary

26 days in Bologna & Tuscany Itinerary

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Route & dates

26 days in Bologna & Tuscany Itinerary

Start: Amman
+2
bus + foot + Fly:  8​h 15​min
1
Bologna
— 1 night
Drive:  1​h 45​min
2
Florence
— 6 nights
Drive:  1​h 15​min
3
San Gimignano
— 5 nights
Drive:  1​h 30​min
4
Montalcino
— 4 nights
Drive:  3​h
5
Portoferraio, Elba Island
— 4 nights
ferry + Drive:  2​h 30​min
6
Lucca
— 4 nights
Drive:  27​h
End: Amman

1
night
Bologna

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
On the 5th (Mon), take in the architecture and design of Academya Lingue, take in the spiritual surroundings of Basilica - Santuario di Santo Stefano, pause for some serene contemplation at Basilica di San Petronio, then get engrossed in the history at La Macchina del Tempo, then don't miss a visit to Piazza Maggiore, and finally contemplate the long history of Piazza Maggiore. On the 6th (Tue), you'll have a packed day of sightseeing: pause for some serene contemplation at Santuario di Madonna di San Luca, then examine the collection at Museo Ferrari, then indulge your taste buds at Acetaia Villa San Donnino, and finally contemplate the long history of Castello Estense.

For photos, other places to visit, where to stay, and tourist information, read our Bologna travel planner.

Amman, Jordan to Bologna is an approximately 8.5-hour combination of bus and flight. You can also do a combination of bus, flight, and train; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Amman to Bologna. Expect a daytime high around 36°C in August, and nighttime lows around 22°C. Wrap up your sightseeing on the 6th (Tue) early enough to take a train to Florence.

Things to do in Bologna

Historic Sites Museums Tours

Side Trips

Museo Ferrari, Piazza Maggiore, Acetaia Villa San Donnino, Castello Estense
Highlights from your plan
Academya Lingue ©
Academya Lingue
Le Due Torri Torre degli Asinell ©
Basilica - Santuario di Santo Stefano ©

6
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Take a break from Florence with a short trip to Castello del Trebbio in Santa Brigida, about 36 minutes away. Next up on the itinerary: explore the world behind art at Gallerie Degli Uffizi, take an in-depth tour of Basilica di Santa Croce, pause for some serene contemplation at Cathedral of Santa Maria del Fiore, and see the interesting displays at Academy Of Florence Art Gallery.

To find other places to visit, more things to do, ratings, and tourist information, use the Florence trip itinerary planner.

Take a train from Bologna to Florence in an hour. Alternatively, you can take a bus; or drive. Expect a daytime high around 35°C in August, and nighttime lows around 20°C. Wrap up your sightseeing on the 12th (Mon) to allow time to drive to San Gimignano.

Things to do in Florence

Tours Museums Historic Sites

Side Trip

Castello del Trebbio
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

5
nights
San Gimignano

San Gimignano ©
A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
You'll find plenty of places to visit near San Gimignano: Castello di Monteriggioni (in Monteriggioni), Siena (Duomo di Siena, Museo dell'Opera Metropolitana, & more) and CavallinoMatto (in Marina di Castagneto Carducci). And it doesn't end there: learn about winemaking at Guardastelle Vineyard, contemplate the long history of Torre e Casa Campatelli, awaken your taste buds at some of the top wineries in the area, and don't miss a visit to Historic Centre of San Gimignano.

For reviews, where to stay, ratings, and tourist information, read our San Gimignano online trip itinerary maker .

Traveling by car from Florence to San Gimignano takes 1.5 hours. Alternatively, you can take a bus; or take a train. In August in San Gimignano, expect temperatures between 35°C during the day and 20°C at night. Wrap up your sightseeing on the 17th (Sat) to allow time to drive to Montalcino.

Things to do in San Gimignano

Historic Sites Wineries Theme Parks

Side Trips

Siena, Cavallino Matto, Castello di Monteriggioni
Highlights from your plan
Fattoria Il Piano ©
Fattoria Il Piano
Duomo di Siena ©
Duomo di Siena
Museo dell'Opera Metropolitana ©
Museo dell'Opera Metropolitana

4
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Explore Montalcino's surroundings by going to Cortona (Museo Diocesano, MAEC - Museo dell'Accademia Etrusca, & more), Piazza Grande a Montepulciano (in Montepulciano) and Orvieto (Duomo di Orvieto & Pozzo di San Patrizio). There's lots more to do: learn about winemaking at Ciacci Piccolomini d'Aragona, steep yourself in history at Abbazia di Sant'Antimo, look for gifts at Franci Bio, and stroll through Val d'Orcia.

To see more things to do, other places to visit, and tourist information, refer to the Montalcino trip itinerary builder app .

You can drive from San Gimignano to Montalcino in 1.5 hours. Other options are to do a combination of train and bus; or take a bus. Expect a daytime high around 37°C in August, and nighttime lows around 22°C. Finish your sightseeing early on the 21st (Wed) so you can drive to Portoferraio.

Things to do in Montalcino

Wineries Historic Sites Spas

Side Trips

Cortona, Orvieto, Piazza Grande a Montepulciano, Spas, Val d'Orcia
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Mate Winery ©
Mate Winery
Podere Il Cocco ©
Podere Il Cocco

4
nights
Portoferraio, Elba Island

Portoferraio ©
Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Explore Portoferraio's surroundings by going to Spiaggia di Fetovaia (in Campo nell'Elba) and Spiaggia di Cavoli (in Seccheto). There's still lots to do: enjoy the sand and surf at Spiaggia Di Sansone, stroll through Spiaggia di Capo Bianco, get up close and personal with brilliant marine life at Acquario dell'Elba, and stop by Gelateria Zero Gradi.

To see maps, more things to do, and tourist information, refer to the Portoferraio online trip builder .

You can drive from Montalcino to Portoferraio in 3 hours. While traveling from Montalcino, expect little chillier days and about the same nights in Portoferraio, ranging from highs of 33°C to lows of 23°C. Wrap up your sightseeing on the 25th (Sun) early enough to travel to Lucca.

Things to do in Portoferraio

Parks Beaches Outdoors

Side Trips

Marina di Campo, Spiaggia di Cavoli, Spiaggia di Fetovaia
Highlights from your plan
Spiaggia Di Sansone ©
Spiaggia Di Sansone
Spiaggia di Cavoli ©
Spiaggia di Cavoli
Padulella Beach ©
Padulella Beach

4
nights
Lucca

Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
You'll find plenty of places to visit near Lucca: Footpath Monterosso - Vernazza (in Monterosso al Mare), Pisa (Piazza dei Miracoli, Leaning Tower of Pisa, & more) and Vernazza (in Vernazza). And it doesn't end there: learn about winemaking at Fattoria al Dotto, take in panoramic vistas at Torre Guinigi, admire the striking features of St Martin Cathedral, and pause for some serene contemplation at Chiesa di Sant'Anastasio.

To find ratings, where to stay, traveler tips, and tourist information, use the Lucca trip itinerary builder website .

Traveling by combination of ferry and car from Portoferraio to Lucca takes 2.5 hours. Alternatively, you can do a combination of ferry and train; or do a combination of ferry and bus. In August in Lucca, expect temperatures between 35°C during the day and 20°C at night. Finish your sightseeing early on the 29th (Thu) so you can travel back home.

Things to do in Lucca

Tours Historic Sites Parks

Side Trips

Pisa, Cinque Terre, Montecatini Alto
Highlights from your plan
Wine Tours & Tastings
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza

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