Is prior sailing experience necessary?

No prior sailing experience is needed. The crew guides guests through the basics and can assist with raising sails.

Are there any age restrictions for this activity?

This sail is family-friendly and suitable for all ages, though children should be supervised at all times.

Can I bring my own beverages or food on board?

Outside beverages or food are not permitted, but complimentary wine is provided during the sail.

What happens in case of bad weather?

If the weather causes safety concerns, the trip will be rescheduled or refunded, with notifications provided promptly.

Is the schooner wheelchair accessible?

Due to the historic vessel's design, accessibility is limited. Please contact World Ocean School for accommodations.

How do I book this experience?

You can book directly through the World Ocean School website or via the provided referral link for availability.

Father's Day Sailing Adventure with Free Wine in Boston | Sailing | Boat Tour

Experience a unique Father's Day celebration aboard the historic Schooner Denis Sullivan in Boston Harbor. This private two-hour sail offers an unforgettable way to honor Dad, combining scenic waterfront views with hands-on sailing opportunities. Guests can participate by raising the sails alongside the knowledgeable crew or simply relax on deck, savoring complimentary wine provided by 90+ Cellars. The schooner’s traditional rig and classic wooden design create a charming maritime atmosphere that enhances the experience. Beyond the fun and relaxation, your adventure supports educational programs by World Ocean School, contributing to ocean literacy and stewardship. Whether you’re a seasoned sailor or a curious first-timer, this excursion offers an approachable, memorable outing perfect for families. The fresh sea breeze, panoramic views of Boston's skyline, and the chance to connect with maritime heritage make this Father's Day sail an extraordinary gift. Make lasting memories while enjoying a thoughtful blend of relaxation, education, and celebration.

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.