Experience Tuscany’s rolling hills by bike while savoring wine tastings and cooking classes at a historic vineyard farmhouse. Discover why this cultural cycling retreat is a standout in outdoor travel.
Experience Tuscany’s rolling hills by bike while savoring wine tastings and cooking classes at a historic vineyard farmhouse. Discover why this cultural cycling retreat is a standout in outdoor travel.
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Verified experiences and guided adventures in the surrounding area.
Operated by SUP YO · Siena, Tuscany
moderate.
3–5 hours per day.
Moderately fit riders comfortable with uphill cycling and long days
Yes, routes are chosen to accommodate varying skill levels with mostly moderate hills and plenty of breaks.
Due to the historic farmhouse and uneven terrain, full wheelchair access is limited.
Yes, all meals including cooking classes and wine tastings are included.
Late spring and early fall offer mild weather ideal for cycling and outdoor activities.
Basic cycling skills are recommended but the guides provide support throughout the trip.
Yes, the kitchen staff can accommodate most dietary needs with advance notice.
Tuscany’s vineyards trace back to Etruscan civilization, and Siena’s historic center is a UNESCO World Heritage site.
The retreat supports sustainable farming practices and encourages low-impact cycling to preserve the landscape.
SUP YO is a Seabrook, New Hampshire–based paddle sports provider offering stand up paddleboard yoga classes and guided paddle experiences along the New Hampshire coast and in nearby Massachusetts. The business runs 75-minute SUP Yoga sessions — including Rise & Shine and Sunset SUP Yoga — that blend traditional yoga with stand up paddleboarding to build balance, core strength, and focused breathing while practicing on the water. Rise & Shine SUP Yoga classes are limited to just 10 participants to maintain an intimate, focused setting. SUP YO also offers 60-minute Sunset Paddles and seasonal Full Moon Paddles (June through September). Sunset Paddles include provided stand-up paddleboards and beginner instruction, and guests are invited to bring snacks and drinks on board. Full Moon Paddles use Torch paddles for evening illumination and encourage glow accessories for a unique nighttime experience. Combo packages pair a 75-minute SUP Yoga class with a 60-minute sunset or Boston Harbor paddle, with all required equipment supplied for combo bookings. Outside Seabrook, SUP YO operates Boston Harbor paddles departing near Fort Point Pier and a one-hour Kids Paddleboarding Lesson in North Chelmsford, MA that teaches paddling techniques, equipment care, and includes games and swimming in a rain-or-shine format. Sessions are designed for all skill levels and include beginner instruction where noted, with small class sizes and clear session formats to make paddleboarding and SUP Yoga accessible and enjoyable for coastal visitors and local paddlers.
Book with SUP YO