Sail aboard Adventure's Sail Boston 250 maiden voyage!
Step aboard Adventure for a once-in-a-generation transit sail from Gloucester to Boston during Sail Boston 250. Help raise sails, learn traditional seamanship, and watch Cape Ann's granite coast give way to the Boston skyline.
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Difficulty
easy
Duration
6–8 hours
Fitness Level
Able to stand and move on a heaving deck for several hours; basic balance and stamina for boarding and moving on deck.
Wildlife
History
Adventure is a roughly 100-year-old dory fishing schooner and a designated National Historic Landmark representing New England's fishing fleet heritage.
Conservation
Passengers are requested to pack out all trash, avoid glass containers, and respect wildlife; the crew follows best practices to minimize disturbance to seabirds and marine mammals.
The Gloucester Adventure, Inc.
Sail aboard Adventure's Sail Boston 250 maiden 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.
Plan your return
This is a point-to-point passage to Boston; arrange your return trip to Gloucester in advance.
Pack a picnic
Passengers supply food and non-glass beverages—bring soft-sided coolers and trash bags to pack out waste.
Dress in layers
Wind off the water can be much colder than onshore—bring a windproof jacket and insulating mid-layer.
Prevent seasickness
If you're prone to motion sickness, take remedies before boarding and sit midship where motion is reduced.
Soft-soled shoes
Protects the deck and gives better footing while moving around the schooner.
Windproof jacket and layers
Sea breeze can be chilly even on summer days; layers let you adjust to changing conditions.
Binoculars
Helps spot seals, seabirds, and coastline details during the transit.
Sun hat and sunscreen
Sun reflects off the water; protect exposed skin during long hours on deck.
summer