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

Sunset & Dinner Cruises in Westbrook, CT- BoatBooker

Westbrook

Westbrook, United States

westbrook

Enjoy the beautiful sunset in Montauk, wine or champagne available with advance notice.

United States

VitaminSea Voyages

Montauk

Set sail with VitaminSea Voyages, a premium boating experience departing from the scenic shores of Montauk aboard a 2011 Steiger Craft Miami Cuddy Cabin. This sturdy and stylish vessel comfortably hosts up to six guests and is powered by twin 300 HP Yamah

Evening trip to the Thimble Islands to enjoy the Sunset!  (Grill, utensils, pans, two burner stove provided - you provide the food and cooking expertise!)

Nightjack

Branford

Discover the perfect getaway on the water aboard Nightjack, a 2002 Levy 32sc Cruiser docked in Branford. This beautiful vessel offers ample space for up to six guests, making it an ideal choice for a day out with friends or family. Powered by a 330 HP Cum

Step aboard and immerse yourself in a truly unforgettable experience. There's nothing quite like the breathtaking beauty of a Montauk sunset — where the sky ignites and the ocean shimmers beneath it. Whether you're planning a laid-back gathering with friends or a romantic escape, this is the ultimate setting to let the magic of golden hour unfold.

Crunch Time Sport Fishing

Step aboard CrunchTime Sport Fishing, a fully restored 1978 Rose Brothers Custom Charter Headboat, designed for comfort and performance. Based in Montauk, this spacious vessel accommodates up to 27 guests, making it perfect for group excursions, corporate

Pack a cooler and take out your friends for a relaxing cruise around the bay to view the sights and take in a spectacular sunset.

North Fork Adventures Charters

Southold

Set sail with North Fork Adventures Charters, a 2001 Parker 2510 Pilothouse offering unforgettable boating experiences from Southold! With room for up to six guests, this sturdy and well-equipped vessel is powered by twin 150 HP Yamaha outboard engines, c

Unwind on a peaceful 2-hour Sunset Sail departing from Westbrook, CT, and experience the magic of golden hour on the water. As the sun dips below the horizon, enjoy stunning views of the coastline bathed in warm light and the gentle rhythm of the sailboat. It’s the perfect way to end your day on the Sound.

Joyride Charters

Come Sail with Captain Joy! Looking for an unforgettable experience on the water? Step aboard with Captain Joy &mdash; a USCG Master Captain with 40+ years of sailing adventures across the globe. Now docked in Westbrook, CT, she&rsquo;s ready to share the

Set sail on an unforgettable 8-hour custom cruise from Montauk, where you call the shots! Whether you're into island hopping, sightseeing, or relaxing on the water, we'll tailor the perfect day just for you. Pricing varies based on time and distance—let’s plan your dream day on the water!

Montauk Charterboat CUJO

Step aboard the legendary CUJO, a beautifully restored 1977 Bertram Sportfish Sportfishing yacht, now better than ever after a full 2025 refit. Departing from iconic Montauk, this classic vessel combines vintage charm with modern comfort, perfect for an u

Experience the magic of golden hour on our 3-Hour Montauk Lighthouse Sunset Cruise. Set sail along the scenic coast as the sun dips behind the iconic lighthouse, painting the sky in vibrant hues. It's the perfect way to unwind, snap stunning photos, and soak in the beauty of Montauk from the water.

Montauk Venture Charters

Experience timeless elegance and adventure aboard Montauk Venture Charters, a beautifully restored 1961 Hatteras Sportfish Motor Yacht, fully refreshed in 2020. Nestled in the heart of Montauk, this classic yacht comfortably welcomes up to six guests for 

Set out on a scenic cruise from Sag Harbor and take in the beauty of the Hamptons from the water. Drop anchor at a serene spot to swim, relax, and soak up the sun, or follow your own desired itinerary for a personalized adventure. Whether it’s a leisurely day on the bay or a custom route, this trip is all about your perfect on-the-water experience.

July Special 4 Hours $3200 53" Luxury Yacht

Sag Harbor

&nbsp; &nbsp; Galeon 510 Sky Deck is a stunning 2019 Galeon 510 Sky Deck Motor Yacht (restored in 2025), available for unforgettable private charters from Sag Harbor. Designed for both relaxation and adventure, this sleek yacht accommodates up to 10 guest

Join us aboard the Kopis, a 30-foot Grady White, where your group of up to six people will enjoy a 2-hour tour of Montauk Harbor and the surrounding sights. During this experience you will relax, unwind and enjoy the tranquility of Montauk on the water. You will enjoy a spectacular sunset, all of the sights/sounds, plus I will put your group in position for some amazing photos. If you so choose, you can be dropped off at several local bars or restaurants/restaurants or back at Marlena's Marina.

Kopis Charters

Experience Montauk from the water with a Grady-White 30 and enjoy a private charter designed entirely around your group. Whether you&rsquo;re planning a relaxing harbor cruise, a romantic sunset outing, a family adventure, or a fun evening with friends, K

3-Hour Sightseeing Tour of Fishers Island Sound, including Latimer’s Light, Watch Hill Lighthouse, Fishers Island, the Dumpling Islands, Race Rock Light, New London Ledge Light, and Avery Point.

Don’t forget that a 20% tip is customary to show your appreciation!

FV Kelly Marie Boat Cruises

Groton

FV Kelly Marie Boat Cruises is a classic 2004 Terry Jason Lobster Downeast vessel, beautifully suited for comfortable and intimate private charters departing from Groton, Connecticut. Designed for small groups, she accommodates up to 6 guests, making her 

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