31 days in Tuscany Itinerary

31 days in Tuscany Itinerary

Created using Inspirock Tuscany tour planner
Make it your trip
Fly
1
Saturnia
— 3 nights
Drive
2
Montalcino
— 6 nights
Drive
3
Gaiole in Chianti
— 2 nights
Drive
4
San Gimignano
— 5 nights
Drive to Piombino, Ferry to Portoferraio
5
Portoferraio, Elba Island
— 3 nights
Ferry to Piombino, Drive to Pisa
6
Pisa
— 4 nights
Drive
7
Florence
— 7 nights
Fly

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Saturnia — 3 nights

Get a sense of the local culture at Pitigliano Centro Storico and Sorano Centro Storico. You'll discover tucked-away gems like Cascate del Mulino and Santuario della Madonna delle Grazie. Explore Saturnia's surroundings by going to Giardino dei Tarocchi (in Pescia Fiorentina) and Chiesa di San Giovanni Battista (in Magliano in Toscana).

To find traveler tips, maps, other places to visit, and tourist information, refer to the Saturnia travel itinerary planner.

Toronto, Canada to Saturnia is an approximately 11.5-hour flight. The time zone difference moving from Eastern Standard Time (EST) to Central European Standard Time (CET) is 6 hours. Expect much hotter weather when traveling from Toronto in March: highs in Saturnia hover around 19°C, while lows dip to 6°C. Wrap up your sightseeing on the 3rd (Mon) early enough to drive to Montalcino.
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Historic Sites · Wineries · Parks · Nature
Side Trips
Find places to stay Mar 31 — Apr 3:

Montalcino — 6 nights

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Eremo Le Celle and Terme Bagno Vignoni will appeal to history buffs. Eschew the tourist crowds and head to Azienda Agricola Ercolani and Abbazia di Sant'Antimo. Venture out of the city with trips to Montepulciano (Vinoteca Terra Toscana, Avignonesi, &more), Buccelletti - Cantina (in Castiglion Fiorentino) and Cortona (Wine Tours & Tastings, Daniela Piegai Art Gallery, &more). And it doesn't end there: do a tasting at Ciacci Piccolomini d'Aragona, contemplate the long history of Historic Centre of the City of Pienza, make a trip to Palazzo Piccolomini, and explore the historical opulence of Castello Romitorio.

For ratings, maps, reviews, and tourist information, use the Montalcino trip planner.

You can drive from Saturnia to Montalcino in 1.5 hours. Alternatively, you can do a combination of bus and train. Expect a daytime high around 23°C in April, and nighttime lows around 9°C. Wrap up your sightseeing on the 9th (Sun) early enough to drive to Gaiole in Chianti.
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Side Trips
Find places to stay Apr 3 — 9:

Gaiole in Chianti — 2 nights

Gaiole in Chianti is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 40km southeast of Florence and about 15km northeast of Siena. Start off your visit on the 10th (Mon): admire the natural beauty at Castello di Brolio, then learn about winemaking at Fattoria della Aiola, then do a tasting at La Cantina di Casalvento, and finally do a tasting at Poggio Amorelli. Keep things going the next day: do a tasting at Fattoria di Montemaggio, then do a tasting at Montefioralle Winery, then do a tasting at Azienda Agricola Altiero (Winery), and finally learn about winemaking at Castello Monterinaldi.

To find traveler tips, more things to do, where to stay, and tourist information, you can read our Gaiole in Chianti travel route planner.

Drive from Montalcino to Gaiole in Chianti in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Wrap up your sightseeing on the 11th (Tue) to allow time to drive to San Gimignano.
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Find places to stay Apr 9 — 11:

San Gimignano — 5 nights

Town of Fine Towers

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.
Abbazia di San Galgano and Centro Storico di Siena will appeal to history buffs. Satisfy your inner culture vulture at Wine Tours & Tastings and Palazzo Pubblico and Museo Civico. Get out of town with these interesting San Gimignano side-trips: Eremo di Montesiepi (in Chiusdino), Castello di Monteriggioni (in Monteriggioni) and Siena (Societa Agricola Madonna Bella, GioieSelli s.n.c, &more). There's lots more to do: learn about winemaking at Guardastelle Vineyard, don't miss a visit to Piazza della Cisterna, take in the architecture and atmosphere at Duomo di San Gimignano, and contemplate the long history of Torre Grossa.

To find ratings, reviews, more things to do, and tourist information, you can read our San Gimignano online trip itinerary planner.

You can drive from Gaiole in Chianti to San Gimignano in 1.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In April, plan for daily highs up to 22°C, and evening lows to 9°C. Finish your sightseeing early on the 16th (Sun) so you can travel to Portoferraio.
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Side Trips
Find places to stay Apr 11 — 16:

Portoferraio, Elba Island — 3 nights

Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Forte Focardo and Centro Storico are good opportunities to explore the local culture. You'll discover tucked-away gems like Spiaggia di Cavoli and Spiaggia delle Ghiaie. Get out of town with these interesting Portoferraio side-trips: Scogliera delle Piscine (in Marina di Campo) and Monte Capanne (in Marciana). And it doesn't end there: kick back and relax at Spiaggia di Capo Bianco, get to know the fascinating history of Borgo del Cotone - Il Cotone, tour the pleasant surroundings at Spiaggia Di Sansone, and look for gifts at Elba Nostrale.

To see maps, traveler tips, more things to do, and other tourist information, read our Portoferraio trip planner.

Getting from San Gimignano to Portoferraio by combination of car and ferry takes about 3.5 hours. Other options: do a combination of train and ferry; or do a combination of bus, train, and ferry. In April, plan for daily highs up to 19°C, and evening lows to 11°C. Cap off your sightseeing on the 19th (Wed) early enough to travel to Pisa.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips
Find places to stay Apr 16 — 19:

Pisa — 4 nights

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Get a sense of the local culture at Duomo di Pisa and Knights’ Square. Visit Battistero di San Giovanni and Basilica of San Frediano for their historical value. Change things up with these side-trips from Pisa: Montecatini Alto (in Montecatini Alto), Terrazza Mascagni (in Livorno) and Lucca (Piazza Anfiteatro, Torre Guinigi, &more). And it doesn't end there: take in the spiritual surroundings of Chiesa di Santa Maria della Spina, enjoy breathtaking views from Leaning Tower of Pisa, admire the landmark architecture of St Martin Cathedral, and don't miss a visit to Murale Tuttomondo di Keith Haring.

To find reviews, more things to do, photos, and more tourist information, read Pisa trip builder tool.

You can do a combination of ferry and car from Portoferraio to Pisa in 3 hours. Another option is to do a combination of ferry and train. Expect a daytime high around 22°C in April, and nighttime lows around 9°C. Finish your sightseeing early on the 23rd (Sun) to allow enough time to drive to Florence.
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Historic Sites · Parks
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Find places to stay Apr 19 — 23:

Florence — 7 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your inner history buff will appreciate Cathedral of Santa Maria del Fiore and Museo Nazionale del Bargello. Satisfy your inner culture vulture at Piazzale Michelangelo and Florence Academy of Fine Arts. When in Florence, make a side trip to see Castello del Trebbio in Santa Brigida, approximately Santa Brigida away. There's much more to do: appreciate the extensive heritage of Centro Storico, admire the masterpieces at Church and Museum of Orsanmichele, snap pictures at Ponte Vecchio, and pause for some serene contemplation at Basilica of Santa Maria Novella.

To see more things to do, where to stay, ratings, and tourist information, use the Florence online road trip planner.

You can drive from Pisa to Florence in 1.5 hours. Alternatively, you can take a bus; or take a train. In April, plan for daily highs up to 22°C, and evening lows to 11°C. Finish your sightseeing early on the 30th (Sun) to allow enough time to fly back home.
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Historic Sites · Museums · Wineries · Shopping
Side Trip
Find places to stay Apr 23 — 30:

Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.
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