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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

Departure time can be flexible between 6-8 PM, depending on the time of sunset.

Steal Your Fish Charters, LLC

New London

Step aboard Steal Your Fish Charters, LLC, a sleek and powerful 2015 Boston Whaler Outrage Center Console based out of New London. Perfect for intimate outings, this premium vessel comfortably accommodates up to four guests and is powered by twin 300 HP M

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

Enjoy the beautiful Montauk sunset on your way back from your trip to the Montauk Lighthouse.

Four C's

Step aboard Four C&#039;s, a well-appointed 2002 Pursuit 3000 Offshore Sportfishing vessel based in Montauk, and get ready for an unforgettable day on the water. Powered by twin 315 HP YANMAR diesel inboards, this boat cruises comfortably at 25 knots&mdas

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.

Sea Lover – Galeon 510 Sky Deck

Sag Harbor

Sea Lover &ndash; 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 g

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