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Popular Sunset & Dinner Cruises Charters in Gloucester  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Sunset & Dinner Cruises in Gloucester, MA- BoatBooker

Gloucester

Gloucester, United States

gloucester

Experience the charm of Gloucester, a picturesque coastal town in Massachusetts, with our exceptional Gloucester Boat Tours. Located on historic Cape Ann, Gloucester offers a blend of maritime heritage, stunning natural beauty, and vibrant culture. Whether you're interested in exploring the bustling harbor, witnessing majestic lighthouses, or enjoying the thrill of lobstering, Gloucester has something for everyone.

Choose from a variety of tours that cater to different interests. Take a Lighthouse Cruise to admire six iconic lighthouses, including those at Eastern Point, and enjoy the scenic views of Cape Ann's rugged coastline. Alternatively, join a Harbor Tour to discover the famous fishing fleet, historic landmarks like Stage Fort Park and Norman's Woe, and artistic hotspots like Rocky Neck Art Colony.

For a more leisurely experience, opt for a Sunset Cruise aboard unique boats like the Friki Tiki, offering an "island vibe" amidst Gloucester Harbor's stunning scenery. If you prefer a more traditional sailing experience, board the Schooner Thomas E. Lannon and enjoy a relaxing sail while absorbing the rich maritime history of the area.

No matter which tour you choose, you'll be surrounded by the beauty of Gloucester's shores, rich history, and vibrant community. Let your Gloucester boat tour be an unforgettable adventure amidst New England's most captivating coastal scenery.

Enjoy your own Private Cruise through Boston Harbor & it's many Islands. Witness stunning views of the many Boston sites. You'll have a clear & picturesque view of the city, It's Skyline, Numerous Historic Sites & Landmarks. This Cruise is a perfect way to relax & enjoy the city's beauty. Cruise can be structured to your specific needs. Bring your favorite Snacks & Beverages. We offer this cruise in 2,4,6 & 8 hour options, for Island Excursions, Swimming or lighthouse cruises book a 6 or 8 hour cruise. 

United States

Trinacria Cruising Boston

Boston

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

Enjoy the sunset over the beautiful city of Boston as we slowly cruise around the inner harbor taking in the local waterfront. This is NOT a fishing trip! 
BYOB

Fishbucket Sportfishing – Boston

The Fishbucket is a Wellcraft 3200 coastal sportfishing boat based out of Boston. It can take up to six guests. The boat is powered by two 260 HP diesel inboard Yanmar engines, offering a maximum cruising speed of 20 knots. The vessel comes equipped with 

Enjoy a relaxing cruise through the scenic Annisquam River as you head out into Ipswich Bay for an absolutley breathtaking view of the sunset out on the water!

Lyla Rose Charters

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

Departing from Fan Pier in Boston's Seaport, we'll embark on a scenic journey around the harbor and outer islands. Along the way, we'll pass three historic lighthouses, and I’ll share insights into the rich history of the islands and their landmarks. For those looking to step ashore, several islands offer docking opportunities to explore their natural beauty up close.

Boston Fish Charters

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

Experience Boston’s stunning waterfront aboard Motor Yacht Atlas, a custom-built 50-foot fantail yacht designed for intimate private events. Whether you're celebrating a special occasion or simply enjoying time on the water with friends and family, Atlas offers a comfortable and elegant setting. Relax on the spacious teak-furnished aft deck, mix a cocktail at the beautifully varnished teak bar, and take in breathtaking views of the Boston skyline.

Boston Boat Charters – Atlas

Quincy

Embark on a luxurious, unforgettable journey through Boston&rsquo;s breathtaking waterfront aboard the stunning Motor Yacht, Atlas. This custom-built 50-foot fantail yacht is the perfect choice for those looking to host intimate, private events or simply 

We do it all—and some activities just take a little more time than others. With years of experience (longer than it takes whale bones to decompose!), we’ll tailor your trip exactly to what you want to do. Trips are a la carte at $180/hr—contact us to plan your adventure!

Central NH Guides

Hampton

Experience the ultimate boating adventure with Central NH Guides, a 2017 Duffy Downeast based in Hampton. Perfect for up to six guests, this powerful vessel is equipped with a 650 HP diesel inboard Mack engine, reaching speeds up to 35 knots, ensuring bot

Experience Boston’s stunning waterfront aboard Beacon, a custom-built 50-foot fantail yacht designed for intimate private events. Whether you're celebrating a special occasion or simply enjoying time on the water with friends and family, Beacon offers a comfortable and elegant setting. Relax on the spacious aft deck and take in breathtaking views of the Boston skyline.

Boston Boat Charters – Beacon

Boston Boat Charters &ndash; Beacon is a classic 1991 Willard 50&#039; Custom Downeast vessel, offering an exceptional cruising experience from the scenic Quincy waters. Designed to accommodate up to 36 guests, it&rsquo;s the perfect choice for unforgetta

Sunset cruise on the beautiful Merrimack River. Relax in comfort as we cruise the Newburyport waterfront and explore upriver to Amesbury and West Newbury.

30 Fathom Charters

Newburyport

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

Departure times are flexible between 8 AM - 6 PM.
Cruise down the Essex River, travel through the Great Salt Marsh estuary, where you will likely encounter wildlife up close on your private cruise for up to 6 passengers.  Pass scenic Cross Island, Conomo Point, Hog Island, and see the gulls over Crane Beach in Ipswich. You may encounter clammers, colorful kayaks, or sailboats in the Essex River or bay. Bring your own food, appetizers, beer, wine, or soft drinks.  Captain Ted will provide coolers and ice.

Agawam Boat & Fishing Charters

Essex

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 

Set out on a two‑hour sailing escape that reveals Gloucester Harbor from a fresh, adventurous perspective. Aboard our spacious, stable catamaran, you’ll explore the working waterfront, historic lighthouses, and the rugged edges of Cape Ann — all at an easy, unhurried pace. With Capt. Lu at the helm, you’ll experience a calm, knowledgeable guide who brings local insight and a warm personal touch to every trip.


Private Catamaran Sailing Adventure

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

Sunset & Dinner Cruises in Gloucester

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