Tuscany

Tuscany

Catherine Fabrizio
With this list and interactive digital map, you'll find places to stay in Tuscany, small towns to visit, landmarks, wineries & restaurants.
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Hotels

Borgo San Vincenzo
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4.7 stars 154 Google reviews 4-star hotel September prices: Non-refundable 380 - 440 Refundable 475 - 550
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Dimora Santa Margherita - Relais di Charme - Suite di Lusso
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4.7 stars 89 Google reviews September 6-12 - $400, $2405 (3 bookings left as 4.13.2024)
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VILLA POGGIANO Boutique Hotel
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4.7 stars 79 Google reviews September 6 - 12, 270 (nonrefundable) 300 refundable
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La Bagnaia Golf Resort
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4.3 stars 64 Google reviews 5-star hotel Sept 6 - 16: Refundable - 1784.00 EUR
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Borgo Iesolana
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4.7 stars 131 Google reviews Farmstay in Italy 4.740,00 € for 6 nights (it is a "cottage") and be split between the 4 of us Living room with island kitchen with 2 double and two single bedrooms, 2 bathrooms with shower and large fenced private garden, private gazebo in the pool.
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Villa le Calvane
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Villa di Piazzano
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VIESCA TOSCANA - Small Luxury Hotel
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Relais Sant'Elena | Relais di Charme, Vacanze Bibbona Toscana
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Locanda le Piazze
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Cerreto Guidi
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Salvadonica - Borgo del Chianti
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Castello di Spaltenna
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Relais Val d'Orcia
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Villa del Sole
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Villa Tolomei Hotel & Resort
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hu Norcenni Girasole village
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Castello di Fonterutoli
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Relais Borgo Scopeto
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Terme San Giovanni
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Agriturismo Podere Cunina
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Locanda in Tuscany
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Il Verreno Resort - Cucina Donnaluisa
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Villa San Paolo Resort & Spa Hotel San Gimignano
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Antica Fonte
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Palazzo Petrvs
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5.0 review 11 Google reviews (newer) Hotel (no pool) €364 - 469 Per Night
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Laqua Vineyard
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4.7 stars 148 Google reviews Resort hotel (no pool) 2214.00 EUR
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Wineries

Ornellaia s.r.l.
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Marchesi Antinori S.p.A.
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The Antinori family have been making wines since 1385, though their sleek, newly-opened winery—the Marchesi Antinori Chianti Classico Cellar—is nothing less than a contemporary architectural masterpiece. The winery offers excellent vineyard-to-bottle tours topped off by generous pours at the wine tasting. Antinori’s Tignanello, released in 1971, is still considered one of the world’s greatest wines, and they continue to be one of Tuscany’s most important wine producers today.
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Castello Banfi - Il Borgo
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You might want to set aside an entire weekend for Castello Banfi, a family-owned vineyard estate and winery in Brunello di Montalcino. Though it’s famous for its award-winning Brunellos, syrahs, merlots, cabernets, and blends, you’ll want to stay long after the wine tasting to soak in the spectacular surrounds (the estate boasts 7,000 acres of vineyards, olive groves, and cypress trees).
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Avignonesi Winery Fattoria Le Capezzine
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The stunning Avignonesi winery, located in the village of Valiano near Montepulciano, produces eight red wines (including an award-winning merlot), a chardonnay, and three grappas. The winery boasts one of Italy’s most ancient and beautiful wine cellars, allegedly built in the late 16th century. We recommend the general tour, which takes you through the vineyards, cellar and attic, followed by an excellent four-course meal with wine pairings.
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Castello di Brolio
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Barone Ricasoli
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Many say that you won’t get a better Chianti than one from Barone Ricasoli—a pretty lofty claim, but highly probable considering that Baron Bettino Ricasoli himself invented it in 1872. Ricasoli is Italy’s oldest winery, producing some of Tuscany’s finest wine since 1141. To this day, the family continues to produce more than three million bottles a year. The winery offers an excellent tour of its cellars and grounds, including the majestic Castello di Brolio, capped by a private wine tasting.
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Small Towns to Visit

San Gimignano
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Epitome of a hill town, spiked with 14 medieval towers offering superb views; popular with tourists who crowd the narrow alleys by day and an evocative delight by night.
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Pienza
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Pint-sized Renaissance-planned architectural gem of a town nestled in a scenic hilly landscape.
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Siena
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Red-brick hilltop city known for its medieval pageantry, Palio horse race, proud spirit, and a stunning traffic-free main square — great anytime but best after dark. Also a fine jumping-off point for exploring the Tuscan countryside with a driving tour of the Crete Senesi region.
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Montepulciano
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Rugged town crowning a ridge, with dreamy vistas of the countryside and wine-tasting in inviting cantinas; makes a good home base for drivers.
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Volterra
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Authentic, walled hill town just far enough off the beaten path, with a long Etruscan heritage that makes for unusually interesting sightseeing for such a small town.
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Val d'Orcia
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The Val d'Orcia was added to the UNESCO list of World Heritage Sites in 2004. Medieval castles, sinuous gills, ancient villages, gorgeous farmhouses, isolated homesteads, roads lined with cypress trees, fabulous vineyards and olive groves and golden fields of grain and sunflowers: these are just some of the elements that form the fantastic and harmonious landscapes of the Val d'Orcia.
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San Quirico d'Orcia
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One of the most beautiful and charming medieval towns of the Orcia Valley located to the south of Siena.
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Crete Senesi
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The Crete Senesi refers to an area of the Italian region of Tuscany immediately to the south of Siena. It consists of a range of hills and woods among villages and includes the comuni of Asciano, Buonconvento, Monteroni d'Arbia, Rapolano Terme and San Giovanni d'Asso, all within the province of Siena. They border to the north with the Chianti Senese area, to the east with Val di Chiana and to the south-west with Val d'Orcia.
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Montalcino
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Wine-lovers' paradise boasting a dramatic 14th-century castle, encircled by olive groves and famous vineyards (and a manageable home base for nondrivers).
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Cortona
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Hillside town basking under the Tuscan sun, with historic churches and museums featuring Etruscan and Renaissance artifacts and art; easy stop for drivers heading to or from neighboring Umbria.
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Restaurants

Il Borgo Machiavelli
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The oldest restaurant in Tuscany
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Saporium Firenze
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Landmarks

Piazza del Duomo
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Torre del Mangia
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ABOUT THE AUTHOR
Catherine Fabrizio
I'm Catherine, and I've spent all 33 years of my life in the vibrant city of Pittsburgh. I recently got married, tying the knot in beautiful Charleston, SC, during the summer of 2022. By day, I'm deeply immersed in the world of finance and accounting, but my heart truly belongs to exploring new places. My husband, an architect with a passion for design, had the opportunity to study abroad in Florence. This allowed him to travel to different destinations on weekends. He also has a unique childhood experience of living in Tokyo for 3 years, which has enriched our understanding of diverse cultures. Our passion lies in those precious 5 weeks of annual PTO, which we use to embark on adventures. We're avid foodies, always on the lookout for delectable treats wherever we go. What's our secret to traveling extensively? I'm a pro at finding the best flight and hotel deals, ensuring that we can allocate more of our budget to immersive experiences, Michelin-starred restaurants, the world's best 50 bars and restaurants, shopping, and collecting art from around the world. Join me on Thatch, and together, we can uncover the art of making the most of our travels. Let's embark on a journey to explore and savor the world one adventure at a time!
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