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.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
3–5 hours per day
Fitness Level
Moderately fit riders comfortable with uphill cycling and long days
Wildlife
History
Tuscany’s vineyards trace back to Etruscan civilization, and Siena’s historic center is a UNESCO World Heritage site.
Conservation
The retreat supports sustainable farming practices and encourages low-impact cycling to preserve the landscape.
SUP YO
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.
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.
Small Classes
10 max
Intimate sessions for focus
Locations
Seabrook & Boston
Coastal paddles and harbor tours
Session Lengths
60–75 min
Efficient, full experiences
Equipment
Provided
Boards and paddles provided
Limited spots available for Sunrise, Sunset, Full Moon, Boston Harbor, and kids lessons — book a session and enjoy boards and paddles provided on applicable trips.
Stay Hydrated on the Hilly Routes
Carry plenty of water, especially on warmer days, as Tuscan hills can be deceptively demanding.
Bring a Comfortable Bike Seat
Smooth but sometimes uneven roads mean comfort is key for enjoying long rides through the countryside.
Reserve Cooking Classes Early
Popular classes fill quickly; book ahead to secure your spot and enjoy hands-on Tuscan cuisine preparation.
Wear Sunscreen and Protective Clothing
Tuscany’s sun can be strong during midday rides; protect skin and eyes to stay comfortable.
Road or Hybrid Bike
Reliable bike suited for mixed paved and gravel roads typical of Tuscany.
spring
Padded Cycling Shorts
Enhances comfort during extended rides over varied terrain.
Lightweight Rain Jacket
Spring showers are possible; stay dry without overheating.
spring
Reusable Water Bottle
Keeps you hydrated throughout cycling and vineyard tours.