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The top boating charters in Gloucester

Gloucester

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Step aboard Lyla Rose Fishing Charters, a beautifully restored 28&rsquo; BHM Downeast vessel, based in the historic fishing hub of Gloucester. With a 2022 restoration, this 1987 classic blends vintage charm with modern amenities, providing an unforgettabl

Lyla Rose Charters

Step aboard Tuna Tail Charters for an unforgettable adventure out of Gloucester. This beautiful 2008 Duffy 35 Downeast cruiser comfortably accommodates up to six guests, making it perfect for intimate whale watching trips, scenic eco tours, or relaxing bo

Tuna Tail Charters

Set sail on a 1976 Harris Custom Sportboat, fully restored in 2023, and based out of Gloucester. This sleek, powerful vessel offers a thrilling experience for up to six guests. Powered by twin 400 HP Caterpillar diesel inboard engines, it boasts a cruisin

10 Point Charters

Step aboard Cape Ann Cruises&mdash;a beautifully restored 1967 Royal Lowell-designed Phil Fessenden Custom Headboat, now modernized in 2023 for comfort, charm, and performance. Departing from Gloucester, this spacious vessel welcomes up to 46 guests, maki

Cape Ann Cruises

Set sail on a private catamaran adventure crafted for small groups who want to explore Cape Ann with intention and a spirit of discovery. Halcyon Days offers exclusive 6‑guest charters aboard a wide, stable sailing catamaran designed for comfort, curiosit

Private Catamaran Sailing Adventure

Take a Cruise with Trinacria Cruising Boston for an unforgettable adventure through the scenic waters of Boston Harbor, the Gulf of Maine, and Cape Cod Bay. Aboard the luxurious 38&rsquo; Stamas yacht, you&#039;ll be guided by Captain Riccardo, a seasoned

Trinacria Cruising Boston

Step aboard Keepin It Reel Charters for an unforgettable day on the water. This sleek 2015 Sea Hunt Gamefish 25 Center Console, based out of scenic Marblehead, is the perfect choice for up to six guests looking to explore in comfort and style. Powered by 

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Set sail with 30 Fathom Charters aboard a beautifully restored 1999 Stamas Tarpon 29 Center Console, docked in scenic Newburyport. Fully refurbished in 2023, this vessel blends classic reliability with modern comfort, powered by twin 300 HP Suzuki outboar

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Climb aboard Agawam Boat &amp; Fishing Charters, a sleek 2015 Parker 2510 Sportfish Walkaround ready to take you on an unforgettable adventure from Essex! Designed for comfort and performance, this vessel accommodates up to six guests and is powered by a 

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Boston Fish Charters invites you on an unforgettable adventure in Boston Harbor! Our 1988 Wellcraft V20 Steplift Cuddy Cabin, beautifully restored in 2023, offers an intimate and thrilling experience for up to three guests&mdash;but come mid-June 2025, ou

Gloucester: 21 boats available

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Gloucester: 21 boats available