A Taste of Tuscany

The perfect mix of Italian culture, history and active adventure

During this retreat, we’ll embark on a journey through the lush rolling hill towns of Tuscany, immersing ourselves in the timeless beauty of the region. Our exploration will lead us to the medieval city of Siena and Tuscany’s vibrant capital, Florence. Throughout our stay, we’ll reside in a charming mid-15th-century farmhouse nestled within its own vineyard, just outside the picturesque medieval village of San Gimignano. The enchanting setting of this farmhouse, surrounded by vineyards and overlooking the Tuscan countryside, promises to be an experience you’ll forever cherish.

We begin our journey in the picturesque, tuscan, medieval village of San Gimignano

The origins of Guardastelle date back to the middle of the fifteenth century. The Villa has been enlarged over the centuries in order to house the children of the peasants, the last part of the house was built in the 1950s. The estate was originally a farmstead for all intents and purposes, surrounded by immaculately kept olive groves, gardens and vineyards. Also on the property there is a woodshed, a barn, a pigsty, a winery and an olive-oil press. In 1984 it was purchased in poor conditions, almost unsuitable to live in, by a man named Sestilio. However, the unique view of San Gimignano and the sweeping panorama over the vineyards and hills held an irresistible attraction. Sestilio’s intention was to rediscover the spirit of country life with his family. In 1997, his daughter, Susan, decided to start making wine from her own grapes in the winery built and fitted out by her father, producing wines and extra-virgin olive oil under the brand Sovestro in Poggio. In 2003 she began renovation works on the house, and after four years of work she endowed Guardastelle with its current appearance. It is impossible not to fall in love with its rolling hills, the fruits of which become the wine and olive oil that the whole world envies. Guardastelle Villa will immerse you into a fairytale atmosphere as the fireflies accompany you along the road leading to the gates of San Gimignano, with its enchanting towers, cobblestone streets and centuries old history. Join us in October and experience for yourself the magic that makes this villa and this village so incredibly special that you will want to return again and again.

Package Includes

• 8 Days/7 nights in a shared or single room
• 7 Breakfasts, 3 Lunches, 5 Dinners
• 2 Cooking Classes
• Wine Tasting & Tour of Property
• Siena city tour
• San Gimignano tour
• Florence city tour
• Cycling through the Vineyards Tour
• Yoga Daily
• Unlimited Use of Pool
• Entrance Fees (tours)
• English Speaking Private Guides
• Airport Transfers

Not Included

• Airfare
• Meals not mentioned above
• Additional tours, excursions or other not included in the above itinerary

Payment Options

• CC: Pay deposit only or in full at check out
• Check: Use promo code paybycheck at check out
• If Mailing Check, mail to: SUP YO, PO BOX 273, N. Andover MA 01845

Arrival & Departure

• Please plan to arrive in Florence (FLR) before noon on October 18, 2025
• Depart on October 25, 2025 from Florence (FLR) anytime.
• If you require assistance with booking airfare please contact us via email

Ground Transfers

• Private Group Transfers are included and will be provided for you.
• Everyone will be on the same coach transfer to/from the airport. (If your flight arrives later than noon, you will be required to take your own transportation to the villa)
• On the return, the group coach transfer is included OR you may take a taxi to the airport at your leisure.

Cancellation Policy

Full payment is due 90 days prior to retreat start date.

In the event a customer needs to cancel:

-more than 90 days before the retreat start date – $1,000 penalty (your non-refundable deposit)

-89-60 days before the retreat start date – 50% refund minus the $1000 penalty

-59-0 days no refunds.

If a customer cancels and we are able to fill their spot, the customer will be refunded in full minus a $200 admin fee and the 6% FareHarbor booking fee.

Travel Insurance

Cancel for any reason trip insurance is recommended. We recommend contacting Allianz.