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

Sunset & Dinner Cruises in Nantucket Sound- BoatBooker

Nantucket Sound

Nantucket Sound, United States

nantucket-sound

Enjoy a 3-hour sailing adventure aboard Tandemeer, our 60-foot luxury Ketch, exploring Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound. Feel the wind in your hair, take in stunning views, and dive in for a swim whenever you like.

Charters can start at any time between 10 AM and 4 PM—just give us a call to schedule your preferred departure.

United States

Island Sailing Tours

Martha's Vineyard

Set sail on the beautifully restored 1980 Nautical Development 56 Sailing yacht, refreshed in 2024, and based out of picturesque Martha&#039;s Vineyard. Accommodating up to six guests, this classic sailing vessel combines timeless charm with modern comfor

Come spend a few hours touring beautiful Chatham. 

Stage Harbor Lighthouse, The Chatham Fish Pier, Coast Guard Light, Morris Island, Oyster River, Oyster Pond, the North end of Monomoy Island, Monomoy’s clam flats, Tern Island, and The world-renowned Chatham Outer Bars are all with a short boat rides reach. Besides some of the most beautiful and scenic places on Cape Cod, we will be treated to some amazing wildlife along the way! Chatham’s inner waterways are full of birds, fish, and seals!!!

Got Stryper’s Chatham Eco Tours

Chatham

Did you know that the world-famous &ldquo;Elbow of Cape Cod&rdquo; has three lighthouses, over 60 miles of shoreline, acres of pristine sand bars to explore or relax on, and is home to the largest grey seal colony in New England? Did you also know that Ch

Spend a few hours touring Chatham’s stunning sights. Stage Harbor Lighthouse, the Chatham Fish Pier, Coast Guard Light, Morris Island, Oyster River, Oyster Pond, Monomoy’s north end and clam flats, Tern Island, and the world-renowned Chatham Outer Bars are all within a short boat ride. Along the way, enjoy breathtaking scenery and incredible wildlife. Chatham’s inner waterways are alive with birds, fish, and seals, making this an unforgettable Cape Cod experience.

Got Stryper’s Chatham Adventure Tours

Did you know that Chatham, located on Cape Cod&rsquo;s famous &ldquo;Elbow,&rdquo; is home to three iconic lighthouses, over 60 miles of breathtaking shoreline, and expansive sandbars perfect for exploring or relaxing? It&rsquo;s also home to New England&

This is a four-hour sail around the bay. This will allow ample time for a mix of sailing, swimming, exploring, and byob/food dining. We can cater to your desires and make a custom itinerary that 

works for you and your guests.

Martha’s Vineyard Charter Company

Set sail around the scenic waters of Martha&rsquo;s Vineyard aboard Our Passion, a beautifully maintained 1983 Pearson 422 Sailing Yacht operated by Martha&rsquo;s Vineyard Charter Company. Departing from charming Vineyard Haven, this classic sailing vess

Our most popular trip! Cruise through beautiful Popponesset Bay and enjoy scenic views of Popponesset Island and its stunning waterfront homes. This relaxing boat tour offers a unique look at one of Cape Cod’s most exclusive coastal areas, blending natural beauty with local history and insight. Perfect for families, couples, and anyone looking to experience Cape Cod from the water.

The trip provides time for anchoring and swimming or beaching on the spit.

We can pick up from private docks in the area.

Popponesset Bay Tours & Sunset Cruises

Mashpee

Experience the beauty of Cape Cod from the water with our scenic boat tours and sunset cruises through the pristine waters of Popponesset Bay in Mashpee, Massachusetts. Cruise past sandy beaches, hidden coves, wildlife habitats, and the iconic Popponesset

Enjoy a relaxing 2-hour sunset tour aboard Sandy Bottom, departing from Hyannis Harbor. Take in the beautiful Cape Cod coastline, feel the refreshing ocean breeze, and admire stunning sunset views as you cruise in comfort with family and friends. Perfect for a romantic evening, a special occasion, or simply unwinding on the water.

Sandy Bottom Yacht Charters

Barnstable

Sandy Bottom Yacht Charters offers an unforgettable private boating experience aboard a 2009 Sea Ray Sundancer Cruiser, based in Barnstable. Perfect for groups of up to 6 guests, this well-equipped yacht combines comfort, performance, and coastal adventur

Sunset tour with stops at sandbars and sightseeing.

In The Net Sportfishing

Step aboard In The Net Sportfishing, a 2021 Grady-White Fisherman 257 center console designed for speed, comfort, and serious on-the-water adventure out of Barnstable. Powered by twin 200 HP Yamaha outboards, this high-performance vessel reaches up to 45 

Sightseeing cruise around Martha’s Vineyard and nearby islands. Enjoy scenic coastal views, wildlife spotting, and relaxed cruising along the island’s shoreline. Optional trips to Cuttyhunk Island available on request. Short 2-hour tour perfect for exploring the beauty of Massachusetts’ coastline from the water.

Obsession Tours – Martha's Vineyard

Obsession Tours is a beautifully restored 1989 Blackfin 1 Sportfishing (refitted in 2011), operating out of Falmouth and offering an unforgettable private boating experience for up to 6 guests. Powered by twin 370 HP Cummins engines, she delivers a smooth

Cruise through the scenic waters of Waquoit Bay and experience one of Cape Cod's most beautiful and ecologically significant coastal environments. This relaxing boat tour showcases expansive salt marshes, barrier beaches, pristine shoreline habitats, and abundant wildlife, offering a unique perspective on the region's natural beauty and maritime heritage. 
Perfect for families, couples, nature enthusiasts, and anyone looking to experience Cape Cod from the water. We can pick up from private area docks.

Waquoit Bay & Washburn Island Boat Cruises

Discover the natural beauty and rich coastal heritage of Waquoit Bay on one of our relaxing boat tours and sunset cruises in Mashpee, Massachusetts. Explore the calm waters of this protected estuary as you cruise past salt marshes, barrier beaches, and sc

Most trips are at 8 am, back to the dock around 10, but if you prefer, I can arrange an afternoon or sunset trip based on availability. You can simply message me through BoatBooker, and we can choose what is right for you.

Vineyard Boat Charters with Capt. John Hobby

A fun time to cruise up and down the north shore of the Vineyard and see the island from a water view. We leave from Tahmoo Harbor and cruise down the North shore coast or over the the Elizabeth Islands. Sunsets are great and its fun for families or coupl

Sunset & Dinner Cruises in Nantucket Sound

Top Sunset & Dinner Cruises in Nantucket Sound