Set sail aboard the historic Denis Sullivan and explore Boston Harbor up close. Enjoy skyline views, fresh sea air, and support ocean education programs with this private two-hour adventure.
Set sail aboard the historic Denis Sullivan and explore Boston Harbor up close. Enjoy skyline views, fresh sea air, and support ocean education programs with this private two-hour adventure.
Book with World Ocean School
Verified experiences and guided adventures in the surrounding area.
Operated by World Ocean School · Boston, Massachusetts
Discover the unique experience of sailing Boston Harbor aboard the historic schooner Denis Sullivan with World Ocean School. This private two-hour Harbor Sail invites you to engage hands-on by helping raise the sails or to simply relax while taking in breathtaking views of Boston’s iconic skyline. The vessel itself is a meticulously crafted replica of a Great Lakes cargo schooner, providing an authentic, nostalgic maritime ambiance that enhances your connection to the sea. Throughout the journey, a cash bar offers refreshments, making it easy to unwind as you glide past Boston’s historic waterfront landmarks. Beyond the beauty and adventure, every ticket supports educational programs dedicated to ocean stewardship, meaning your time on board directly benefits ocean conservation and youth learning initiatives. Whether you're a seasoned sailor or a first-timer, this accessible, engaging sail lets you enjoy fresh sea breezes, stunning panoramic vistas, and a memorable taste of Boston's maritime heritage.
easy.
2 hours.
Suitable for all fitness levels; most of the sail involves relaxed sitting, with optional light activity for sail-raising.
Yes! Passengers are welcome to participate in raising the sails with guidance from the crew.
Yes, the schooner has ample seating both on deck and below for your comfort.
A cash bar is on board offering drinks to enjoy during your journey.
We recommend dressing in layers with comfortable, closed-toe shoes and bringing a windbreaker.
Yes, children are welcome on board but must be supervised at all times.
A portion of each ticket sale funds World Ocean School’s marine education and ocean stewardship initiatives.
The Denis Sullivan is modeled after 19th-century Great Lakes cargo schooners, connecting Boston’s maritime past with modern sustainable sailing education.
World Ocean School emphasizes ocean stewardship, educating riders on marine ecosystems and minimizing environmental impact during each sail.
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.
Book with World Ocean School