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Set sail on a historic schooner with The Gloucester Adventure’s 99th Anniversary Sail. Enjoy lobster rolls and drinks as you glide through iconic Massachusetts waters on this special 2.5-hour evening voyage.
Set sail on a historic schooner with The Gloucester Adventure’s 99th Anniversary Sail. Enjoy lobster rolls and drinks as you glide through iconic Massachusetts waters on this special 2.5-hour evening voyage.
Book with The Gloucester Adventure, Inc.
Verified experiences and guided adventures in the surrounding area.
Operated by The Gloucester Adventure, Inc. · Gloucester, Massachusetts
Gloucester, Massachusetts, a historic seaport town on the North Shore, is known for its rugged coastline and deep maritime heritage. Here, The Gloucester Adventure, Inc. honors nearly a century of sailing tradition aboard a National Historic Landmark with its Adventure 99th Anniversary Sail — a unique 2.5-hour evening voyage that blends living history with coastal charm.
Launched in 1926 from Essex’s shipyards, the vintage vessel has weathered decades, evoking the spirit of the region’s fishing and sailing lineage. This anniversary sail is more than just a scenic cruise; it’s a celebration of the vessel’s legacy and the community’s ongoing commitment to preservation. Guests are invited to partake in an authentic maritime experience, feeling the sea breeze as the boat carves through Gloucester’s iconic harbor waters.
Onboard, the atmosphere is relaxed yet festive, with locally inspired lobster rolls, snacks, and drinks served throughout the sail, paying tribute to New England’s storied culinary staples. The intimate 2.5-hour itinerary offers plenty of time for snapping photographs that capture the wooden rigging against pastel twilight skies and the distant silhouettes of rocky islands and lighthouses that dot the harbor.
The Gloucester Adventure anchors itself firmly in the local outdoor recreation scene by offering a rare, tangible link to the maritime past that shaped the region. This isn’t just a boat tour; it’s a hands-on lesson in coastal culture, sea stewardship, and historic preservation uniquely available here on Massachusetts’ northeast coast.
Whether you’re a history buff, a sailing enthusiast, or a visitor eager to soak in authentic coastal vistas paired with hearty fare, this anniversary event is a standout experience. Aboard this historic schooner, you’re invited not only to witness but also to support the ongoing stewardship that keeps the vessel sailing toward its next century.
This is a distinctly Gloucester way to connect—with the water, history, and community united on a singular evening sail that honors 99 years of adventure.
easy.
2.5 hours.
Suitable for all fitness levels; minimal physical exertion required aboard the vessel.
Tickets include a 2.5-hour sail aboard a National Historic Landmark schooner, with lobster rolls, snacks, and drinks.
The sail departs from Gloucester, Massachusetts; exact boarding location details are provided upon booking.
Yes, the sail is family-friendly; however, children should be supervised on deck due to ship safety considerations.
Yes, all proceeds support the vessel’s 2025 preservation efforts to maintain this historic schooner.
Bring layered clothing, a camera, and comfortable shoes; all food and beverages are provided.
Due to the vessel’s historic design, there is limited wheelchair accessibility; contact the company for specific accommodations.
The schooner was launched in 1926 from Essex, a town famed for shipbuilding, reflecting Gloucester’s deep maritime roots.
The Gloucester Adventure emphasizes vessel preservation and sustainable tourism practices, helping protect the coastal environment and historic ship.
The Gloucester Adventure, Inc. organizes public sails and festival experiences aboard the Schooner Adventure, a vessel designated as a National Historic Landmark. Operating from Gloucester, Massachusetts, the business presents seasonal sails tied to the Schooner Festival and other maritime events, including the Schooner Challenge public sail and the Schooner Fest Race sail, plus a dedicated Adventure 99th Anniversary Sail. During Schooner Festival events, passengers can watch local captains compete on an obstacle course, join the Parade of Sail, or witness the Mayor’s Cup Race. The Schooner Fest Race sail includes a continental breakfast and lunch on race day. The anniversary cruise is a 2.5-hour commemorative sail offering lobster rolls, snacks, and drinks, with proceeds supporting vessel preservation efforts. The Gloucester Adventure, Inc. focuses on showcasing Gloucester Harbor, festival traditions, and maritime history while maintaining clear scheduling and passenger information. The business directs resources toward the Schooner Adventure’s preservation and public programming and encourages visitors to check for updated 2026 schedules for festival and race sails. All trip descriptions and on-board amenities are communicated up front so guests can prepare for weather, photography opportunities, and personal provisions when allowed. Described itinerary details, meal inclusions for race sails, and the anniversary sail’s 2.5-hour duration are provided in official trip summaries. The Gloucester Adventure, Inc. offers a reliable way to experience historic sailing, competitive festival racing, and milestone celebrations on Gloucester’s waterfront.
Book with The Gloucester Adventure, Inc.