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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Featured Business Listings

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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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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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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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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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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Schooner Adventure

Downtown

(978) 281-8079

Website

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

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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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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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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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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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Essex Heritage Lighthouse & Harbor Tours

North of Boston

978-212-9227

Website

Explore the treasures of Salem’s islands and coastlines! From June-September trips to Bakers Island Light, Misery Island, and specialty tours are available. Overnight stays and camping also available… Read more »

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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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Business Listings

Cape Ann Marina

Downtown

Website

(On the water: between the Blynman Bridge and railroad bridge). Dock & Dine, fuel-dock, 265 boat slips, boatyard and marine sales & services. Fishing, diving and site seeing… Read more »

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Friki Tiki of Gloucester Harbor

Downtown

Solomon Jacobs Landing

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Gloucester Boat Rental

Downtown

63 Rogers Street

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Gloucester Harbormaster

Downtown

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

Website

Gloucester Marine Railways

Rocky Neck

81 Rocky Neck Ave

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Seatronics Company

East Gloucester

171 E Main St

Website

Water Shuttle

East Gloucester

Website

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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Charlie’s Charters Fishing and Sightseeing

Downtown

415 Main Street

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Gloucester Fleet Deep Sea Fishing & Charters

West Gloucester

75 Essex Ave

Website

Cape Ann SUP

Essex

2 Southern Ave

Website

Featured Business: Minglewood Harborside

Discover Gloucester Spotlight

Minglewood Harborside is open 7 nights a week plus lunch Friday, Saturday, Sunday and Monday for outdoor and indoor dining and takeout. Waterfront dining with a heated, enclosed oversized deck and retractable glass walls that create an al fresco experience both inside and out.

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