Top Massachusetts Water Tours - page 2

Experience Boston Harbor on a sunset cruise aboard a historic tall ship. Depart from Fan Pier Marina on the 67-foot Liberty Star enjoy views of the outer harbor, Fort Independence, East Boston, the Charlestown Navy Yard, and beyond. Relax and let the crew handle the sails or jump in the action and a grab a line on this fun and affordable outing.

Set sail on the historic Lobster Tales for a memorable evening on the "Sounds and Sunsets" cruise in Plymouth. Relish the picturesque sunset views while enjoying live music from top local artists. Sip on refreshing margaritas, cold beer, and champagne, accompanied by complimentary appetizers. Perfect for couples or friends looking to unwind, this 2-hour cruise is all about good vibes, great music, and stunning views. Celebrate summer nights on the water and create unforgettable memories with the sounds of Plymouth. - 2-hour sunset cruise with live music and scenic views - Complimentary appetizers and unlimited drinks included - Perfect for all ages, especially couples and friends - Departure from Plymouth, with a spacious sunset viewing area

Cruise Boston Harbor aboard a luxury yacht, complete with superb city views and a buffet brunch featuring both breakfast and lunch offerings. For 2-hours you'll explore the waters from Rowes Wharf to the Charlestown Naval Yard and back, sailing past sights such as Castle Island and Boston Light. Spend some time enjoying the yacht's three climate-controlled decks or dancing to the sounds of a live DJ mix.

Enjoy the beauty of Boston illuminated on this 1-hour evening cruise. Coast past sights like the Old North Church, Independence Wharf, the U.S.S. Constitution, the New England Aquarium, and more. Choose between open-air seating on the top deck, with blankets available, or stay cozy in the interior cabin. Alcohol, water, soda, and snacks are available for sale.

Beat the Boston heat and get out on the water on this dog-friendly harbor cruise. With your group and your canine companion, board the cruise boat and set sail. Learn about Boston's history and sights including the Seaport District, Castle Island, USS Constitution, and North End from live narration onboard, and relax during Boston’s long summer days in the company of your dog.

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. Feel free to bring your own food along if you prefer, but please no outside beverages and no coolers. Mimosas are $5 all morning! We also have our full drink menu available including local craft beers, cocktails, wine, soda, juice, and water. We accept Apple Pay, credit cards, or cash onboard.

Take a cruise along the Charles River for a chance to see some of Boston’s most beautiful historic and contemporary architecture. Pass important landmarks such as Marriott’s Custom House, the Prudential Building, and the Hancock tower and listen to live commentary onboard about the history, architecture, and design of these buildings.

Make this holiday season one to remember with this cocoa and carols holiday cruise on Boston Harbor. With dates offered throughout December, you can add a magical touch to your holiday, and easily find a date that works for you. Plus, you’ll cruise the harbor aboard a classic yacht with live music as you take in beautiful views of Boston.

Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed boat in Boston that gets to and from the whales in the least amount of time possible. Look out for humpback and fin whales, plus Atlantic white-sided dolphins, with the help of a naturalist guide. The on-board galley offers food and beverages for purchase during the trip.

Learn about Boston's history while enjoying beer and snacks with a guide who will provide insider details on the city's history and culinary scene. Step inside several historic pubs and grab a cold one (or two) along with some of the city's best tavern snacks. Explore some of the city’s oldest neighborhoods, including the Blackstone Block, the North End, and Charlestown, and enjoy a ferry ride in Boston Harbor.

Explore the stunning Gloucester Harbor and Annisquam River on a guided kayak tour from Boston. Paddle past historic landmarks, catch a glimpse of the famous Wicked Tuna boats, and even hunt for sea glass on Ten Pound Island. This adventure is perfect for both seasoned kayakers and beginners, blending sightseeing with relaxation. Enjoy free time for dinner in Gloucester before returning to Boston via a private van shuttle. - Guided 4-hour kayak tour suitable for all skill levels - Visit Ten Pound Island for the best sea glass collecting - Spot Wicked Tuna boats while paddling through the harbor - Includes transportation from Boston and free time for dinner

Discover some of Boston’s deepest, darkest secrets that lots of tourists miss out on by joining this “frightseeing” tour aboard the Trolley of the Doomed, which roams around the haunted streets and burial grounds of Boston. Your costumed host provides illuminating insights into the history of the city's spookiest sights, such as Copp’s Hill Burying Ground.

Enjoy Boston from the water while dining on a delicious buffet lunch on this cruise. See an array of top landmarks including Bunker Hill, the World Trade Center, and the site of the 1773 Boston Tea Party. After lunch, head up to the top deck—the largest outdoor patio deck in town.

Explore the best of Boston at your own pace on a hop-on hop-off trolley tour of the city. Choose from a 1- or 2-day pass and see Boston’s top attractions, including the USS Constitution, the original bar from TV show “Cheers,” and the Faneuil Hall Marketplace, to name a few. The pass includes discounted admission to the Boston Tea Party Ships and Museum, to enjoy during or after the tour.

Enjoy lunch on the waters of Boston Harbor during this cruise aboard the "Odyssey Boston." You'll have the chance to admire views of the city skyline and seaport from the boat decks, plus listen to live music. The 3-course lunch includes a starter, main course, and dessert. This is a relaxing way to see the city from another perspective.

Unlike typical kayak tours, North of Boston Island Lighthouse Tour is a refined, personalized coastal experience. Your expertly trained guides combine deep knowledge of local history, wildlife, and island landscapes with the freedom to tailor each outing to the day’s conditions and your group’s interests. Expect a relaxed pace, intimate storytelling, and exclusive moments among iconic lighthouses and pristine island scenery—no scripts, no crowds, just a truly elevated adventure.

Our Clambake at Sea is more than a boat ride—it’s a full sensory experience. Dine on a traditional New England clambake while cruising past historic landmarks, remote beaches, and lighthouses. With a local captain narrating the region’s rich history and coastal lore, guests enjoy both education and indulgence. There’s simply no better way to taste and explore Plymouth than by sea—with fresh lobster in hand and harbor breezes in your hair.

Discover Boston in the evening on a guided night tour that combines city highlights with a scenic sunset harbor cruise, all with convenient downtown hotel pickup and drop-off. Begin your experience with pickup from your downtown Boston hotel and set out on a narrated driving tour through the city’s most iconic neighbourhoods and landmarks. As you explore, your local guide will share stories of Boston’s history and culture while you take in the city illuminated at night. Then, head to the waterfront and board a relaxing sunset cruise through Boston Harbor. From the water, enjoy panoramic views of the skyline, historic sites, and bustling harbor as the sun sets and the city begins to glow. After the cruise, sit back and relax as you’re transported back to your downtown Boston hotel, completing a seamless and memorable evening experience.

The Haunted Harbor Tour isn’t just a boat ride—it’s a journey into the shadowy side of America’s oldest seaport. While other tours skim the surface, we take you deeper, blending true local history with spine-tingling ghost lore you won’t hear anywhere else. From the deck of our vessel, you’ll see Plymouth’s most storied landmarks—Plymouth Rock, the Mayflower II, Burial Hill, Cole’s Hill, Bug Light, and more—exactly as they appear under the cover of night. Every stop along our route comes alive through vivid storytelling, researched local legends, and the natural drama of the harbor after dark. You’ll feel the sea breeze, hear the lap of waves against the hull, and see the silhouettes of centuries-old landmarks as their ghost stories unfold. Our small-group setting ensures a more personal, immersive experience—plenty of time to soak in the eerie atmosphere between tales. It’s equal parts history, mystery, and pure New England coastal magic.

Celebrate a special occasion or just enjoy the company of your family and friends on this leaf-peeping Boston Harbor brunch cruise. On board a 1920s-style yacht, the Northern Lights, you’ll sail through Boston Harbor, cruise past the Harbor Islands, and spot landmarks and beautiful fall scenery along the way. Indulge in a fresh, gourmet brunch prepared by the onboard chef as you take in the waterfront views.

This cruise is a perfect end to your day. Sit back, relax and breathe in the sea air while taking in the sights and sounds of Boston harbor under the Full Moon.

Set sail on the Bear Tide Oyster Tasting Cruise for a unique culinary adventure in Plymouth Bay. This 1.5-hour narrated cruise offers the chance to savor fresh oysters directly from a local farm, while enjoying a cash bar and live music. Meet the oyster farmer who shares insights about the aquaculture industry, enriching your tasting experience with local stories and knowledge. Relax on the open deck, take in stunning harbor views, and celebrate the flavors of the coast with friends or a special date. - 1.5-hour narrated cruise featuring fresh Bear Tide oysters - Meet the oyster farmer and learn about local aquaculture - Cash bar available with beer, wine, and cocktails - Maximum capacity of 50 guests for an intimate experience

Enjoy a relaxing evening on the Charles River with our Cocktail and Sunset Cruises. Experience the vibrant scenery of Boston and Cambridge as you unwind with a refreshing drink from our full bar while listening to cocktail music. Choose between our charming riverboat or the festive Tiki boat for a unique perspective of the sunset over the city. Perfect for both casual outings and special celebrations, our cruises offer a serene escape for everyone. - 90-minute evening cruises featuring stunning views of Boston. - Full bar service available on board with a variety of cocktails. - Departures from Lechmere Canal at the Cambridge Side Mall. - Ideal for groups, parties, or a romantic evening out.

Join our wonderful, professionally trained guides for an unforgettable evening adventure designed to beautifully wrap up your day. From the moment you set out, our knowledgeable guides are there to ensure your safety, comfort, and confidence on the water. More than just expert paddlers, they are passionate storytellers and local experts who bring the surroundings to life. As you glide across calm waters under the changing colors of the sunset, they will share fascinating insights about the islands, marine life, local ecosystem, and natural wonders you encounter along the way. Whether you’re spotting wildlife, learning about the area’s history, or simply soaking in the peaceful atmosphere, our guides make sure the experience is engaging, educational, and truly memorable.