Top New England On the Water

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.

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.

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.

Cruise through the scenic waters of Frenchman Bay during a leisurely sailing trip. Admire views of Acadia National Park in Maine during this sightseeing boat tour. Keep an eye out for wildlife including eagles, seals, and porpoises during the sail. Check out views of the Porcupine Islands from the spacious decks on board a Windjammer. Picnics are welcome on board.

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.

Take in Rhode Island’s scenic shoreline on a scenic sightseeing cruise through Newport Harbor and Narragansett Bay. Aboard an open-air, fully restored lobster boat, enjoy a narrated tour as you pass Newport and Jamestown harbor fronts, and see landmarks like Fort Adams, Newport Bridge, and the famous Clingstone house. Your afternoon trip includes a Rhode Island-styled refreshment, as well as a cash bar.

Experience the scenic coastline of Casco Bay in Portland, aboard a traditional Maine windjammer. Sail past lighthouses, rocky islands, and wildlife while enjoying the peaceful pace of a classic schooner cruise. Bring your own picnic and drinks to enjoy on board as you take in the views. Suitable for all ages, this relaxing sailing experience offers an authentic way to discover the beauty of the coast.

Experience the beauty of Casco Bay and set sail from Portland, Maine for an unforgettable sunset cruise. Bring your own snacks and drinks, kick back, and relax as your captain sails towards incredible views. Feel free to ask your captain and crew questions about the scenery, and remember to keep your eyes peeled for seals and seabirds.

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.

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.

Scenic Narragansett Bay isn’t just great for sailing—it’s the ideal vantage point for taking in the region’s best sights, beloved landmarks, and fascinating history. On this tour, you’ll hop aboard a 57-foot cruiser, nabbing panoramic views from your comfy seat. Your guide will detail 300+ years of history, from the Jamestown village to Fort Hamilton, Fort Wetherill State Park, Newport’s opulent harbor estates, the region’s vintage lighthouses, and more.

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.

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.

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.

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, including Newport's historic lighthouses and landmarks, bridges, mansions and more! We'll even see Newport Bridge, New England's largest suspension bridge from the water. Relax on deck of Schooner Madeleine, a beautiful classic sailboat, as the crew raises sail. Drinks are available for purchase onboard and guests are welcome to bring a snack. This sightseeing sailing experience is great for locals and those visiting Newport in the spring, summer and fall.

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 Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, lighthouses and more during this 1.5-hour experience!

Step back in time and immerse yourself in Maine's maritime heritage on a sailing trip onboard the only historic day sailing schooner out of Camden. Soak up views of Maine's lighthouse-dotted coastline while the crew points out wildlife, tells you the history of the area, and shows you local landmarks. Get hands on by learning to haul sails or just relax with a bottle of wine and a picnic (byob).

Get the best chance of seeing whales off the coast of Gloucester, Massachusetts, by booking this half-day whale-watch cruise. Your experienced captain and crew know the whales’ feeding and swimming patterns and keep close tabs on where they’re hanging out. Spread out on the deck of the boat and enjoy being out in the open air while you find whales, then get ready to snap photos of breaching, spouts, and tail slaps.

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including historic lighthouses and landmarks, other classic vessels, bridges, mansions, and more! We'll sail from historic downtown Newport and arrive back at the same meeting point.

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.

This isn’t a typical boat tour—it’s a hands-on Maine lobster fishing experience rooted in real working-waterfront traditions. Choose from three ways to experience it: Lobster Fishing Only — NO MEAL INCLUDED Head onto Penobscot Bay and haul real lobster traps while learning the tools, techniques and traditions of Maine’s iconic fishery. See what comes up—lobsters, crabs and the occasional surprise. Lobster Fishing + Feast Enjoy the full hands-on fishing experience, then step ashore for a VIP stop at Young’s Lobster Pound and a classic Maine lobster feast. From trap to table, this is the real thing. The Ultimate Maine Experience — Lobster Feast + Sunset Cruise Haul real traps, feast at Young’s, then head back onto the bay and cruise into a spectacular Maine sunset. Lobsters, feast and sunset—all in one unforgettable experience. Whichever you choose, expect small groups, real participation, local knowledge and a genuine taste of Maine’s working waterfront.

Newport, Rhode Island, is an absolute hotspot of history, and on this tour, you’ll get to experience the city’s wild past from the water. Sit back with a mimosa as your guide tells you the story of the region’s classic lighthouses, relays the tales behind the harbor mansions and churches, and dives behind the scenes of Fort Adams, Jamestown Village, Hammersmith Farm, and beyond.