Experience Unforgettable Schooners & Boating Trips in Gloucester, MA

Cape Ann offers many schooner and boating opportunities. Whether you’re in Gloucester, Essex, or Rockport, you can explore cruise lines, schooners, boat tours, river cruises, and more. Experience the beautiful waters of Cape Ann and choose one of our many schooner and boating options today.  

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Artemis Sails LLC

Downtown

207-930-5873

Website

Are you looking for a way to get out on the water this summer with family and friends? Our sailing charters are all custom designed for those wanting to get away from it all and spend a glorious time out on the ocean, exploring the beautiful coastline of Cape Ann and the surrounding area.

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Maritime Gloucester

Downtown

(978) 281-0470

Website

Oceans of discovery at Maritime Gloucester, a working waterfront museum with hands-on maritime exhibits, aquarium, and schooner sails.

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Maritime Heritage Charters

Downtown

(978) 290-7168

Website

Enjoy fun and informative daily two-hour public sails aboard the Schooners Ardelle and Isabella! Open May to September.

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The Hotel at Cape Ann Marina

West Gloucester

(978) 283-2116

Website

Stay, Eat, Drink, Chill. Waterfront hotel rooms offer views of the river, salt marsh, “Wicked Tuna” boats and wildlife.

OPEN YEAR ROUND

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Tuna Hunter Fishing Charters

West Gloucester

(978) 407-1351

Website

Tuna Hunter offers full-service deep sea fishing charters for giant bluefin tuna, striped bass, cod and haddock, sharks, flounder, bluefish and more.

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Beauport Cruiselines

Downtown

(978) 282-9700 opt. 2

Website

Dine, dance, and cruise aboard the elegant Beauport Cruiseline while cruising around Gloucester harbor in true New England style.

OPEN YEAR ROUND

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Charlie’s Charters Fishing and Sightseeing

Downtown

(978) 281-8992

Website

Charlie’s Charters offers private charter fishing, sightseeing, lighthouse tours, photo charters, seal & bird watching, and ash scattering.

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Ocean Alliance Docks

East Gloucester

978-281-2814 ext. 100

Website

Lease a dock on Gloucester harbor with Ocean Alliance. Book your transient reservations for the upcoming season. Research, private, commercial, and education vessels are welcome!

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Schooner Adventure

Downtown

(978) 281-8079

Website

All aboard this 122′ National Historic Landmark schooner! Built in Essex in 1926.

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The Schooner Thomas E. Lannon

Downtown

(978) 281-6634

Website

Schooner sailing aboard the Lannon is relaxing, romantic, and fun. It’s an experience unlike any other.

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Gloucester Fleet Deep Sea Fishing & Charters

West Gloucester

(978) 559-1978

Website

Gloucester Fleet is a small family-owned and operated business. Fun and safe deep sea fishing trips for all ages!

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Cape Ann Cruises

Downtown

978-515-0484

Website

It all begins with a date. Maybe it’s a wedding date. Maybe it’s a birthday. Whatever date it may be, we would love for you to share it with us. Let us make your event a memorable one!

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Harbor Tours, Inc.

Downtown

(978) 283-1979

Website

Cape Ann’s longest running boat tour company offers the only tour that completely circles Cape Ann.

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Essex River Cruises & Charters

Essex

(978) 768-6981

Website

“Enjoy a river excursion that captures the essence of New England,” Boston Globe.

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North Shore Adventures and Outdoor Center

Rockport

978-546-5050

Website

The one stop shop to Adventure on Cape Ann. North Shore Adventures and Outdoor Center can equip and guide you for all your paddling, hiking, and biking needs around the beautiful North Shore.

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Agawam Boat & Fishing Charters

Essex

(978) 768-1114

Website

Enjoy a private boat with a Captain/guide for sightseeing, fishing, and exploring Cape Ann.

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Gloucester Boat Rental

Downtown

63 Rogers Street

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Gloucester Harbormaster

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19 Harbor Loop

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Amanda Marie Fishing Charters

Downtown

7 Parker St

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Cape Ann SUP at Beauport Hotel

Downtown

55 Commercial St

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Three Lantern Marine

Downtown

7 Parker St

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Patriot Wave Charters

Downtown

93 Western Ave

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Connemara Bay Charters

Downtown

47 Crafts Rd

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East Gloucester Marine

Downtown

8 Norwood Ct

Cruiseport Gloucester Marine Terminal

Downtown

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City of Gloucester Launch Service Operated by the Harbormaster

Downtown

19 Harbor Loop

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Gloucester Marine Railways

Rocky Neck

81 Rocky Neck Ave

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Seatronics Company

East Gloucester

171 E Main St

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Water Shuttle

East Gloucester

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Defiance Sail Charters/B&B Afloat

East Gloucester

211 E Main St

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Rose Marine

Downtown

375 E Main St

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Gloucester Charter Connection Deep Sea Fishing

West Gloucester

76 Essex Ave

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Cape Ann SUP

Essex

2 Southern Ave

Website