Top Massachusetts Sailing Tours

Embark on an interactive sailing excursion off the coast of Salem on a replica historic privateer schooner. Great for families and anyone who gets bored easily, this adventure keeps you engaged by offering opportunities to help with tasks such as raising the sails and steering the boat. Plus, the crew shares stories about the history of Salem and the role played by privateers.

Experience a beautiful 2-hour Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. You will be aboard the most elegant sailing yacht in town, Adirondack III, a classically styled, 80-foot pilot schooner. Adirondack III is the fastest and most elegant schooner in Boston Harbor. She offers a smooth and gentle sailing experience to her passengers as well as top-notch customer service by her captain and crew. Enjoy a comfortable and relaxing ride for you and your loved ones. Within minutes of leaving the dock, you'll forget the distractions of life on land, as you experience the ambiance of a sunset sailing cruise aboard a stellar vessel.

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.

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.

Experience Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound on this sailing tour of Martha's Vineyard. Hop aboard a classic 60-foot (18-meter) ketch (a two-masted sailboat), which was made famous in the hit movie "Trading Places.” Along the way, take in views of the historic West and East Chop Lighthouses and soak up the sun while on the water.

Set sail at one of the best times of day—sunset—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 guests can tote their own adult beverages.

Go sailing in Martha’s Vineyard with this half-day private tour. Explore Nantucket Sound by water during this outdoor adventure aboard a 1980 classic 60-foot ketch sailboat. Experience the Martha’s Vineyard tradition of sailing and see local landmarks from a fresh perspective. Customize the itinerary according to your interests and maximize time in Martha’s Vineyard.

Go sailing in Martha’s Vineyard with this 6-hour private cruise for you and your group of up to 12 people. Climb aboard the classic 60-foot (18-meter) ketch sailboat made famous by the movie “Trading Places” and soak up the sun, sea, and views as you sail around Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.

Go sailing in Martha’s Vineyard with this 4-hour private cruise for you and your group of up to six people. Climb aboard the classic 60-foot (18-meter) ketch sailboat made famous by the movie “Trading Places” and soak up the views as you sail around Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.

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, tea, 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, wine, soda, juice, and water. We accept Apple Pay, credit cards, or cash onboard.

Skip the bridge traffic and toursit traps and come spend the day in picturesque Mattapoisett Harbor, a quaint New England coastal village. Your day on Buzzards Bay will be designed to fulfill your interest in spending the day on the water. Wehter you want to go for a sail or cruise the shoreline, we're happy to make suggestions and craft an itinerary to make you visit to Boston or the Cape complete. For longer charters, picnics at Hadley's Harbor or Tarpolin Cove are favorites as well as visiting Cuttyhunk Island. BBYC also specializes in Engagement and bachelorette parties, wedding launch, regattas and spectator fleet services.