Top Massachusetts Sightseeing Cruises

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 catamaran that gets to and from the whales in the least amount of time possible. See 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.

Experience one of the best whale-sighting destinations in the world on this guided, 4-hour whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed catamaran that gets to and from the whales in the least amount of time possible. See humpback and fin whales, plus Atlantic white-sided dolphins and harbour porpoises with the help of a naturalist guide. The on-board galley offers hot meals, snacks and beverages for purchase during the trip.

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.

Take an evening cruise on Boston Harbor to watch the sunset from the water. Glide out to the Old North Church and Historic Site, the Charlestown Navy Yard, Leonard P. Zakim Bunker Hill Memorial Bridge, and the USS Cassin Young. As a bonus, listen to the cannon fire of the USS Constitution, which marks the sunset each night.

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.

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.

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.

Try a unique alternative to a typical night out in downtown Boston with an exciting dinner cruise along the city’s waterfront. This 2-hour expedition on Boston Harbor features a three-course 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. Bring that special someone or a whole group of friends for a night to remember.

From the country's oldest lighthouse to the world's oldest commissioned warship afloat and everything in between, you'll see and hear about it all on this unique two-hour cruise through Boston Harbor's history and present day. We'll journey up close for photo ops of Boston Light, originally built in 1716, and Graves Light, the only privately owned lighthouse on Boston Harbor, with two additional lighthouse views. We'll sail past historic forts, learn about how Boston built the land upon which it sits, the bridges that span the rivers that flow into the harbor, and view the Boston Harbor Islands, the Old North Church, the USS Constitution and much more. This tour is hosted by Boston area raconteur, David Coffin, who has been leading Boston Harbor tours since 2000. He is also well known as a chanty singer so you never know what might happen on any given tour!

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.

Enjoy the beauty of dusk along Boston Harbor on this sunset sightseeing cruise. See all the historic attractions that Boston Harbor has to offer and witness the USS Constitution’s traditional sunset ritual — ceremoniously firing her cannon and lowering her flag, signaling the end of the day.

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.

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.

Explore Boston by boat with this cruise on the Liberty Star. Help the crew hoist the sails or simply find a spot on deck to enjoy the views. Your captain creates a route depending on wind direction, heading toward the outer harbor for a glimpse of Fort Independence, or sailing toward East Boston for views of the Charlestown Navy Yard, home to the USS Constitution.

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 the city’s history from live narration onboard and relax during Boston’s long summer days in the company of your dog.

Grab a drink and settle into the heated, main observation cabin to enjoy a seasonal experience on this beautiful 1920s-style yacht. During the cruise, grab a hot cocoa or festive libation from the bar and take in the sights as the boat cruises around Boston's waterfront neighborhoods, such as North End. Enjoy cruising under the Tobin Bridge for a unique perspective of this iconic landmark. Watch the sky as it changes from blues to oranges behind the outline of Boston's city skyline while listening to classic Holiday hits.

Immerse yourself in the autumn season while exploring beautiful Boston Harbor on a relaxing sightseeing cruise. Step aboard the Northern Lights vessel and catch spectacular views of colorful seasonal foliage on the Boston Harbor Islands. Then, enjoy a delicious gourmet lunch and sip a hot cider.

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.

Come aboard for an Alive after Five Cruise sure to be an unforgettable evening of good times on the water with your crew. Whether it's after a long day at work or a great day of play, this cruise is the perfect way to wind down or get pumped up as the Boston skyline views breeze by.

Join Captain Riccardo aboard the Trinacria for a Private tour of Boston Harbor & The Harbor Islands. Choices include Sightseeing, Fishing, Lobstering or just Cruising. This unique tour is one of the very few available that you & your guests have the boat to yourselves. Most Boston tours are shared. We also allow you to bring your own Food & Beverages on-board, making your trip ultra personalized. We are flexible on pick up locations & are happy to entertain special requests. Book with us & we will do everything we can to exceed your expectations. Tours can last up to 5 Hours depending on activities chosen. Inner Harbor Tours take 2-3 Hours, Fishing adds time. Plan on being on-board a minimum of 4 Hours for Fishing/Lobstering or Lighthouse tours. We also can preform an Ash Scattering in a burial at sea ceremony for loved ones remains. We attend to filing all required notifications with the US Government free of charge As a reminder Gratuities are not included in your fare.

The yacht Ponemah is a luxurious 42 foot picnic style yacht with plenty of enclosed and open seating for up to 6 guests. The main salon is heated or air conditioned if necessary, providing dry and comfortable enclosed viewing in all weather conditions. There's a complete galley, head and dinette area for your use. A trip around Cape Ann including seal sightings, the Annisquam Canal and Gloucester Harbor, will take about 3 hours. Alternative routes to Jefferies Ledge for whale watching or Manchester By the Sea for real estate viewing can be arranged in a 3 hour tour. Full day bookings can be customized to include lunch stops, Isle of Shoals, or Marblehead and Salem Harbors.

Hop into a duck boat—renovated World War II amphibious vehicle—for a comprehensive tour of Boston. Pass Boston Common, Quincy Market, and the Celtics' home turf at TD Garden. 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.