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Immerse yourself in the splendor of one of the most beautiful cities in Italy. The hilltop town of Siena, located in the heart of the Tuscan countryside, provides a fascinating trip back in time to the Middle Ages, when it was one of the great city-states of the Tuscany area. Set on three hills, the city is drawn together by winding alleyways and steep steps, whilst the Piazza del Campo stands at its heart, and the Duomo and St Maria della Scala serve as additional cultural landmarks. In addition to the bustling daily life of the streets and squares of the city, Siena offers many cultural events, concerts, cinema, theatre and a wide range of sporting activities.

Luxuriate in your sumptuous accommodations in a palace that dates from the 1600’s and offers privileged views onto architectural wonders such as the Piazza dei Salembini, the Duomo of Siena, and the Monti dei Peschi, the oldest bank in the world. The palazzo houses up to 6 people, with 3 bedrooms and 4 bathrooms, antique furniture, and beautiful murals. For your comfort, the accommodation has AC, WIFI, a jacuzzi and a sauna. In the winding medieval streets around the house you will find high fashion shopping, lots of restaurants, wineries, bars and supermarkets with typical Tuscan products.

Taste Tuscan wine and explore the charming streets of San Gimignano with this 5-hour tour from Siena. The first stop is historic San Gimignano, a UNESCO-recognized town where you will explore at your leisure and see landmarks such as the Collegiata and Piazza del Duomo. Afterward, venture into the hills of Tuscany for a behind the scenes winery tour that will take you to the bottling rooms and aging cellars of a Tuscan estate. You will taste Chianti blends and classic Tuscan snacks while learning about the winemaking process. The tour finishes with transportation back to Siena. During the winery tour, you will stroll through the vineyards and visit the bottling rooms and aging cellars of a Tuscan estate. The tour ends with transportation back to Siena.

Your 2-hour sightseeing tour, led by an expert guide, gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo, the superlative square that is home to the Palio, a wild horse race that takes place every summer. Stroll the streets with your guide learning about the history of the town. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket.

  • 7-night stay in palazzo for up to 6 people in Siena, Tuscany

  • Day trip from Siena: Chianti wine tasting and tour of San Gimignano

  • Private walking tour of Siena with skip-the-line Duomo ticket

  • Pre-trip planning and booking assistance


A stay can be reserved, based on availability, anytime during the year with a minimum of 60 days advance notice. Winner has 24 months to use. May be subject to refundable damage deposit to be paid by package winner; all purchases are non-refundable; packages cannot be resold; air and ground transportation are not included.

Charity Cost: $
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