Top Massachusetts Water Tours

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff on Cape Cod. Our tours stay at low numbers so that it is a fun and unique experience for every participant. Our equipment is always top of the line and this area is perfect for all levels of kayakers.

Spend two hours sailing on the Boston Harbor as the sun goes down, taking in the sights of the city skyline. Your captain will set sail and take you on a smooth cruise along the waterfront in a comfortable schooner, with a friendly and informative crew who’s happy to help you have the best possible experience while you’re on the water.

See some of the top attractions in Boston from the waterfront on this narrated sightseeing cruise. Explore the world-famous Boston Harbor and see the city’s historic sites while listening to live commentary on board, from tales of the Revolutionary War to local legends. While you cruise, enjoy views of the city skyline as well as the Boston Harbor Islands, USS Constitution (“Old Ironsides”), and the Bunker Hill Monument.

Enjoy unparalleled views of the Boston Harbor from the water during this 90-minute sightseeing cruise. Set sail aboard a classic tall-ship schooner. Enjoy plenty of time to ask the captain and crew about local landmarks and Boston’s history. You'll also have plenty of time to relax. Soft drinks and alcoholic beverages are available to purchase, including several beers brewed right in South Boston.

Experience Boston and Cambridge on a narrated morning or afternoon cruise. After boarding at Lechmere Canal Park, embark on a journey down the Charles River and check out Beacon Hill, Esplanade Park, the Back Bay, Boston University, Fenway Park, M.I.T., Harvard, and other important landmarks. Hear entertaining stories about the region from your captain and crew and enjoy a snack or drink on board.

See the landmarks and highlights of Boston from the water on this sightseeing cruise in Boston Harbor aboard a 1920s-style yacht. Snap photos and enjoy a unique perspective of the harbor, very different than a typical walking or driving tour through Boston. Highlights include the USS Constitution, Bunker Hill Monument, Old North Church, and the USS Cassin Young.

Explore Boston on a trolley tour that’s timed to catch sunset over the Charles River. Many Boston sites are illuminated—and uncrowded—at night, making this an ideal time to explore Boston Harbor, Cambridge, the Public Garden, and more. Live narration from an experienced guide showcases the stories and culture behind each place you visit, from stylish seaside neighborhoods to revolutionary war–era landmarks.

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.

Hop into a duck boat—s renovated World War II amphibious vehicle—for a comprehensive city sightseeing tour of Boston. Pass Boston Common, Quincy Market, the Celtics' home turf at TD Garden, and much more. Then splashdown into the Charles River for a view of the city by boat. Learn all about Boston's history and landmarks as you go.

See Boston Harbor’s sights from the water on this day sail aboard a replica of a pilot schooner. Step aboard the boat and sail off through the harbor, bound for Spectacle Island, Fort Independence, Castle Island, and Long Island. Snap photos of Boston's coast from the water and feel free to ask the captain or crew questions about the passing landmarks.

Set sail at along the Massachusetts' North Shore, during your visit to Salem. Board the historic schooner yacht What and If and drift along the coastline, taking in the sights of Salem. Relax on the deck or take a turn at the wheel of this beautifully restored classic sailing yacht, which was built in 1939 by General George Patton. Soft drinks and bottled water are provided, and a cash bar is available on board.

Enjoy a private seal-watching crossing with only your group aboard. We’ll explore at a relaxed pace, with time to linger when conditions allow and observe gray and harbor seals from a respectful distance. Each trip is shaped by the tide, weather, and wildlife, making every outing a little different. A great choice for families, photographers, and anyone looking for a quieter, more personal experience on the water. Up to 6 passengers.

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff on Cape Cod. Our tours are small and intimate so that it is a fun and unique experience for every participant. Our equipment is always top of the line and this area is perfect for all levels of kayakers. RideAway Adventures is the highest rated outdoor company on Cape Cod and we are committed to creating ocean ambassadors through education and active environmental awareness.

End a day in Boston the right way with a sunset sightseeing cruise on Boston Harbor. See all of the harbor’s historic attractions as well as the city’s modern skyline, and witness the USS Constitution’s traditional sunset ritual: a ceremonial firing of the cannon of the oldest commissioned sailing ship in the US, and a lowering of her flag, signaling the end of the day.

Enjoy views of beautiful Boston with this 90-minute sunset cruise. Watch the sun sink over the sparkling water as your guides point out the USS Constitution and other historic sights. Once the sun goes down, you’ll have a chance to see the city skyline illuminated. There is a full bar on every boat, with snacks and other beverages available for purchase.

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.

See Boston from a whole new angle aboard a Boston Harbor evening cruise. Watch the sunset from the water, and glide out to the Old North Church and Historic Site, the Charlestown Navy Yard, the USS Cassin Young, and more. As a bonus, listen to the cannon fire of the USS Constitution, which marks the sunset each night, and sip a cocktail (own expense) from the onboard bar as you relax and enjoy the views.

This Lobstering Eco Tour will immerse you in the vibrant culture of New England! Join our lively cruise and dive headfirst into the world of lobster harvesting, right from the heart of the sea. As a brave crew of volunteers lends a claw to haul in those lobster traps, all passengers will have a front-row seat to witness the mesmerizing marine life of Plymouth Harbor. Prepare yourself to see (and hold) all kinds of animals; from lively crabs and curious snails to the occasional fishy friend. But fear not, fellow ocean enthusiasts! We’re committed to safeguarding the future of our magnificent marine world. Every incredible creature we encounter is given a one-way ticket back to their salty sanctuary. We believe in cherishing and preserving the wonders of our watery wonderland for generations to come.

Try a unique alternative to a typical night out in downtown Boston with an exciting dinner cruise along the city’s waterfront. This expedition on Boston Harbor features a meal with live entertainment and dancing. Watch the sun set, then take a stroll under the stars and enjoy the view of the illuminated Boston skyline at night, or head to the dance floor for music and fun in the ship’s nightclub.

While many tours help you explore Boston’s Freedom Trail, not many also continue the story with a boat ride on Boston Harbor. On this half-day combination walking and boat tour, witness historic landmarks such as the Boston Massacre Site, Quincy Market, and Blackstone Block before heading to the harbor to see the USS Constitution and float by Boston Tea Party replica ships.

Get ready for a mouthwatering ice cream sundae cruise in Plymouth, MA. Become the master dessert architect and load up your sundae with all the toppings your heart desires. Enjoy great music, limbo, and an awesome ride through Plymouth’s most famous landmarks. Board the boat and get ready to create your own ice cream sundae. Proudly serving Giffords Ice Cream, you can load up your sundae with all the toppings your heart desires. Enjoy great music, limbo, and an awesome ride through Plymouth’s most famous landmarks. Great for all ages, bring your family and friends with you.

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 a gourmet brunch on this scenic cruise of the Boston Harbor. Set sail aboard the Northern Lights at Rowes Wharf and settle in for a buffet filled with eggs, bacon, fresh fruit, and more. View popular Boston highlights such as Bunker Hill Monument, the USS Constitution, Old North Church, and Sea Castle Island. This brunch cruise offers a great overview of Boston and a lovely morning on the water.