Golf & Wine Experience at Castiglion del Bosco
A refined golf and wine experience at Castiglion del Bosco, pairing Tom Weiskopf’s signature course with iconic wines, gourmet bites and sweeping Tuscan views.
Area
Tuscany
Type
Active
Food & Drink
Grade
Luxurious
Who
Adults
Difficulty
Leisurely
Duration
Half Day
Discover the essence of Castiglion del Bosco through a refined pairing of golf and wine in the heart of Brunello country. Set within one of Tuscany’s most celebrated estates, this experience combines signature holes on Tom Weiskopf’s course with a leisurely tasting of the property’s most iconic wines, including Millecento Brunello di Montalcino Riserva.
Surrounded by vineyards and the UNESCO-protected Val d’Orcia landscape, guests can enjoy a memorable journey that brings together exceptional golf, outstanding wines and the flavours of Tuscan tradition.
Recommended Hotels Nearby
A selection of luxury hotel options in the area, handpicked and recommended by our travel specialists.
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View AccommodationCOMO Castello del Nero
The beautifully converted 12th century COMO Castello del Nero is nestled in the undulating hills of the Chianti region of Tuscany. Siena, Florence and Pisa are just a stone's throw away and you can take your pick from superb local Chianti wineries.
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View AccommodationBorgo Santo Pietro
This stunning boutique hotel located in the heart of the Tuscan countryside exudes charm and history. The lovingly converted 13th century villa, the centre of Borgo Santo Pietro, offers guests a luxurious haven in which to relax and unwind.
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View AccommodationRosewood Castiglion del Bosco
Rosewood Castiglion del Bosco in Tuscany is an exclusive country estate offering luxurious suites and villas with private heated pools, exceptional cuisine and great outdoor activities, set against the magnificent backdrop of the Val d'Orcia.
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View AccommodationBorgo San Felice
Sink into an oasis of rural luxury in the heart of Tuscany, immersed in vineyards, with an abundance of facilities this is paradise found. This former hamlet has been transformed into a luxury hotel estate, nestled in the beautiful Chianti region.
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View Accommodation
Hotel Il Pellicano
Il Pellicano offers timeless Italian elegance on the Argentario coast with stunning sea views, Michelin-star dining, a private beach, wellness spa, and individually styled rooms and suites for a serene luxury escape.
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View AccommodationBorgo Pignano
Cocooned in 750 acres of organic farmlands, landscaped gardens and rolling Tuscan countryside, Borgo Pignano is housed in an 18th century villa, cottages and farmhouses with exceptional views and one of the most picturesque pools imaginable.
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View AccommodationBelmond Castello di Casole
Belmond Castello di Casole commands a prominent hilltop position, offering magical views of the Tuscan countryside, combining Old World Tuscan charm with modern boutique luxury, elegance and sophistication.
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View AccommodationMonteverdi Tuscany
An exclusive boutique retreat in a restored medieval village above the Val d’Orcia. Monteverdi blends 31 bespoke rooms, three private villas, a world-class spa, fine-dining, culinary academy, art, music and immersive Tuscan experiences.
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View AccommodationLa Bandita Townhouse
Escape to Pienza, an idyllic medieval city that is small in size but grand in character. Tucked away amongst its golden-stoned buildings, La Bandita Townhouse is a hip oasis of modern design with exceptional cuisine and a laid back vibe.
More Experiences in This Area
Discover more things to do in the area and chat to our specialists about crafting these experiences into your tailor-made holiday.
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View Experience
Wine Tours of Tuscany
Discover first hand the reason Italian wines have become some of the most well known and best loved wines in the world.
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View ExperienceWine Tasting at Borgo Pignano
Enjoy a wine tasting session in Borgo Pignano's medieval wine cellar, where you'll have the opportunity to taste a selection of local organic wines, as well as those produced on the estate.
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View ExperienceTuscan cooking class
Discover the art of Tuscan cuisine with a private cooking class at a local farm. Under the guidance of a local cook, you'll learn how to prepare traditional recipes and then enjoy your dishes for lunch.
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View ExperienceWine tasting in Montalcino and Montepulciano
Spend a day discovering the delights of Tuscan wine as you explore the charming towns of Montalcino and Montepulciano, both renowned worldwide for their wine production.
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View ExperienceExplore Pienza and the Val d'Orcia
Located in the Val d'Orcia, Pienza is a charming town boasting a wealth of beautiful Renaissance architecture. Explore the town with your private guide and enjoy incredible views across the Tuscan countryside.
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View ExperienceWine tasting and lunch in Chianti
Journey through Chianti’s rolling hills to two renowned wineries. Enjoy guided tastings, a private cellar visit, and a relaxed wine-paired lunch—all set against the breathtaking backdrop of Tuscany’s vineyards and olive groves.
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View ExperienceTruffle hunting at Borgo Pignano
Explore the forests of Borgo Pignano's estate with your experienced truffle hunter and their dog, searching for renowned Tuscan truffles, and discover the unique skills required to find these famous treasures.
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View ExperienceCycling in the Val d'Orcia
Visit the charming town of Pienza and explore its picturesque streets before cycling through the spectacular Val d'Orcia on an e-bike with your private guide.
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View ExperienceCooking class at Borgo Pignano
Learn the art of Tuscan cooking with a class at Borgo Pignano, where ingredients from the farm and vegetable garden are used to create the freshest dishes with a real farm-to-table ethos.
Call us on 212 372 7009 to start planning