Fall Escape to the Tuscan CountrysideGo wine tasting, wander between fields of beautiful olive trees, and admire the colors of Tuscan trees turning yellow and orange on a fall trip to Tuscany. On your visit, treat yourself to the most delicious gelatos and homemade pasta. Authorskatherinebeard
DestinationsTuscanyItinerary

Florence

The Place Firenze
A true, modern Italian stay, this hotel is beautiful from the rooms to the property itself. Every detail is well thought out and executed.
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Florence Private WALKING TOUR
This walking tour will take you to all of the sights in the city while you are able to learn about its history from a knowledgeable, local guide!
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Piazzale Michelangelo
Visit this famous plaza in the heart of Florence with views of the iconic statue and great people watching.
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Ponte Vecchio
Come here at sunset for beautiful views of boats passing under the bridge and the golden hue enveloping the buildings.
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Leccio Outlet
Designer outlets? Yes please! Shop at spots like Alexander McQueen, Gucci, Prada, and more allll at heavy discounts.
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Giotto's Bell Tower
Climb up a narrow staircase to enjoy views of all of downtown Florence and the Duomo. Absolutely worth it!
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Piazza del Duomo
This iconic church is a must-visit when you are in Florence. Admire the architecure from the outside and head inside for wondrous ceilings, paintings, and sculptures.
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Exclusive Brunello di Montalcino tour from Florence
This wine tour sounds IDEAL. No worries about driving and indulging in 3 different boutique vineyard visits, sign me up!
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Lucca

Duomo di San Martino
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Madonna dello Stellario
Look up! There is the Madonna dello Stellario statue near the Walled City.
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Buccellato Taddeucci
A great spot for an afternoon sandwich or sweet treat, like cake! Totally local.
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Trattoria da Nonna Clara
A quaint restaurant serving handmade pastas with quick service.
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Piazza San Michele
Wander this quaint square in Lucca to admire the Italian architecture and do some people watching.
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Chiesa di San Michele in Foro
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Pisa

Casale Podernovo
This is an increbile stay just outside downtown Pisa in the Tuscan countryisde. Admire the rolling hills or take a stroll on the property as the cool breeze hits your face here.
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Piazza dei Miracoli
Part of the leaning tower of Pisa's grounds, this piazza boasts views of the leaning tower, sculptures and statues, and other famed buildings in the area. Take a stroll through in the early morning to avoid the crowds.
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Tower of Pisa
Visit the iconic leaning tower! Historians say that the uneven settling of the building's foundations in the soft ground are what make it lean now. Make sure to snap a photo of you propping it up!
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Siena

Castello di Monteriggioni
Just north of Siena, stay in a revamped Italian castle at this spot. Hosts are very kind and you will feel like royalty here!
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Siena Cathedral
The facade of this cathedral is amazing! So prominent in the square. Its striped rock on the sides makes it so distinguishable and unique.
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Cripta del Duomo di Siena
Explore the underground of the Siena Cathedral in the crypt. The walls are filled with vibrant fresco paintings!
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Piazza del Campo
A great spot to stop into a café and people watch in this grand plaza. It is super open and filled with fresh air.
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Vestri Palace
A charming palace that hosts the Chigiana Music Academy. Wander around here admiring the architecture or maybe even the music.
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Truffle Hunting Experience Siena Tartufi
An authentic Tuscan experience where you hunt for truffles and then try them back at the shop at the end.
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Montepulciano & Surrounding

Valdorcia Belvedere b&b
A bed and breakfast fit for royalty, nestled right at the entrance to the Castello di Spedaletto.
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Agriturismo Castello di Spedaletto da Laura
A castle, cultural site, and a hotel to stay in! Fit for royalty for sure. Quieter and more secluded option with lovely courtyards and green spaces.
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Trattoria da Fiorella
A homey-feeling restaurant with delicious pasta dishes in the Tuscan countryside. Give the gnocchi a try, it's outstanding!
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Chapel Vitaleta
A scenic chapel amidst the rolling Tuscan hills and framed by beautiful trees.
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Nicchia Via della Piaggia
Wander the streets of Montepulciano and head to this lookout over the adorable town and its rolling Tuscan hills in the distance.
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Osteria del Borgo
A delightful family-run stay/restaurant with the most divine pasta I have ever eaten. Try their locally sourced specials when you are here.
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Acqua Di Bagno Vignoni
Come here for adorable souvenirs and beautiful hand painted pottery pieces.
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Osteria Porcellum
Stop here for a midday charcuterie board with a cocktail. The setting is so lovely out on the patio when it is sunny.
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A wine tour and tasting that will delight your tastebuds! Don't worry about driving, and sit back sipping to your hearts content on this tour.
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Olive Oil Tours and Tasting at Frantoio di Montalcino
Known for olive oil and trees, take this tour and tasting while you are in the heart of olive oil production country.
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