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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2.5 hours
Fitness Level
Suitable for all fitness levels; minimal physical exertion required aboard the vessel.
Wildlife
History
The schooner was launched in 1926 from Essex, a town famed for shipbuilding, reflecting Gloucester’s deep maritime roots.
Conservation
The Gloucester Adventure emphasizes vessel preservation and sustainable tourism practices, helping protect the coastal environment and historic ship.
The Gloucester Adventure, Inc.
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.
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.
Location
Gloucester, MA
Historic New England harbor city
National Landmark
Schooner Adventure
Designated National Historic Landmark
Anniversary Sail
99 years
2.5-hour commemorative anniversary sail
Tours Offered
3 distinct sails
Challenge, Race, Anniversary sails
Check the 2026 schedule for Schooner Festival sails, race participation, and the Adventure 99th Anniversary Sail — spaces fill quickly for festival weekends.
Bring a Camera
The evening light and historic vessel provide excellent photo opportunities—don’t miss capturing the wooden schooner against the coastal skyline.
Dress in Layers
Coastal weather can shift quickly; bring a windbreaker or warm layer to stay comfortable during the sail.
Arrive Early
Plan to arrive at least 15 minutes before the scheduled departure to check in and settle aboard comfortably.
Mind the Railings
The historic schooner has wooden railings and rigging—stay aware and avoid leaning too far over the edge for safety.
Windbreaker or Light Jacket
Protects from brisk spring sea breezes during the evening sail.
spring
Sun Hat
Shields your face from potential late afternoon sun while aboard.
summer
Camera or Smartphone
Captures memorable views of the historic schooner and Gloucester’s coastline.
Non-slip Footwear
Ensures stable footing on the wooden deck and rigging areas.