Is prior sailing experience required?

No prior experience is needed; you can choose to relax or help the crew.

Are there age restrictions for this experience?

Guests of all ages are welcome, but those under 21 cannot partake in wine tasting.

What happens if the weather is bad?

Trips may be rescheduled or canceled for safety; you will be notified promptly.

Can I bring my own wine onboard?

Outside alcohol is not permitted; complimentary wine is provided by 90+ Cellars.

Is parking available near the dock?

Yes, there are public parking options within walking distance of the departure point.

Are snacks or food provided during the sail?

Light snacks are available for purchase or you can bring your own picnic.

Wine on the Weekend Sail in Boston Harbor | Sailing | Boat Tour

Discover a unique blend of relaxation and adventure with "Wine on the Weekend" aboard the historic schooner Denis Sullivan in Boston Harbor. This private experience, hosted by World Ocean School, invites you to savor complimentary wine from 90+ Cellars while soaking in panoramic waterfront views. Whether you're joining the crew to learn the ropes or simply lounging on deck with friends and family, each moment offers a refreshing escape from the city’s bustle. The Denis Sullivan provides an authentic maritime atmosphere, enhancing the charm of your voyage through the harbor's rich history and stunning skyline. This trip is perfect for wine lovers, outdoor enthusiasts, and anyone looking for a memorable weekend activity that combines the peaceful rhythm of sailing with flavorful tasting. With every sip and sea breeze, you’ll enjoy new perspectives of Boston from the water, creating lasting memories in an unparalleled setting.

About World Ocean School

World Ocean School delivers hands-on ocean education and community sails based in St. Croix, U.S. Virgin Islands. The organization operates public and private sails aboard historic vessels including the Denis Sullivan and the Roseway, combining cultural interpretation, ecology programming, and seasonal events. Sails range from two-hour educational trips that highlight local ecology and wildlife to gala fundraisers, holiday parties, and appreciation sails that raise funds for student programs.

Programming partners include local historians from CHANT and the St. Croix Environmental Association, who lead cultural and ecological discussions onboard. These collaborations reinforce curriculum quality and ensure accurate, locally rooted storytelling. Tickets, events, and fundraising galas support school scholarships, in-classroom materials, and experiential learning for St. Croix students.

Staff and volunteer crew include trained educators and experienced sailors who supervise hands-on activities such as raising sails and observing marine life, maintaining safety standards while promoting active learning. Vessel operations adhere to standard safety and hospitality practices, with refreshment services provided during public sails.

Community engagement is central: the organization hosts public holiday events like the St. Croix Christmas Boat Parade viewing, family-focused end-of-season sails, and donor appreciation evenings. Annual signature events—gala fundraisers and sunset send-offs—connect supporters directly to educational impact.

Through documented partnerships, recurring public events, and targeted fundraising, World Ocean School positions itself as a credible provider of maritime education and community experiences. Prospective guests and donors can expect professionally run sails that blend cultural history, environmental education, and memorable island views. Booking information, schedules, and tickets are available online today.