Cruises & Sailing

(34 activities)
Reset Filters
  • Book Now

    Sunset Sail (Sun to Fri)

    (28)
    The maritime world of Boston has many great stories to offer, and on this classic sail through the Boston Harbor, as the Sun dips below the horizon, you'll get to see and hear it all. Experience the sights of the Boston Fish Pier, The Moakley Federal Courthouse at Fan Pier, Castle Island, the Donald McKay monument, the Charleston Navy Yard, and much more, on a sail aboard the Adirondack III, a classic 80 foot pilot schooner. Experience Boston like never before, on a schooner, a drink in hand, and a knowledgeable captain and crew to ask about all the stories behind some of Boston's most unforgettable sights.
    No available dates to book.
    Bucketlist to hear about new dates first!
    Sunset Sail (Sun to Fri)

    60 Rowes Wharf, Boston

    • Enjoy the historic scenery of the Boston Harbor aboard a classic 80 foot pilot schooner
    • Experience a beautiful Boston Harbor sunset on the water
    • Ask your knowledgeable staff and crew anything you'd like to know about the sights
    • Enjoy the ride, see the sights and have a drink onboard
    BOOK NOW ← Back
    28 positive reviews
  • Book Now

    Sunset Sail (Liberty Star)

    (20)
    Enjoy a Sunset sail aboard Boston's tall ship known as the Liberty Star. On your sunset sail, you'll view Boston and the Harbor Islands while enjoying the majestic experience of sailing through this beautiful area. There will also be a bar stocked with soda, water, Sam Adams on draft, mixed drinks, wine, and snacks. It will be a relaxing end to the day where you can look at onto the water and enjoy the natural beauty of the area. Expect a great experience on this peaceful sail with a gorgeous view.
    No available dates to book.
    Bucketlist to hear about new dates first!
    Sunset Sail (Liberty Star)

    67 Long Wharf, Boston

    • Set sail into the Boston Harbor on the magnificent schooner known as Liberty Star
    • Enjoy the beautiful nighttime views of the harbor while relaxing after a long day
    • Partake in delicious refreshments and a bar stocked with your favorite drinks
    BOOK NOW ← Back
    20 positive reviews
  • Book Now

    Introduction to Sailing

    Is sailing on your list of things you want to learn? Come sail out onto the Boston Harbor on either a Harbor 20 or Colgate 26 sailboat and enjoy the thrill of being out on the water. This is a great taste of sailing for anyone who is a beginner and wants to give the art of sailing a try. You'll learn the basics, see the beautiful city skyline, and explore the harbor. Come along and do as much or as little as you'd like.
    No available dates to book.
    Bucketlist to hear about new dates first!
    Introduction to Sailing

    56 E Service Rd, South Boston

    • Learn the basics of sailing or simply enjoy a captained cruise
    • Ride out into the scenic and historic Boston Harbor on a sailboat
    • Get a unique perspective of the city while enjoying the fresh wind and sea air
    • Sit back and relax or acquire impressive new skills
    BOOK NOW ← Back
  • Book Now

    Rum and Revelry Sail

    (20)
    Sail Boston Harbor at night and enjoy all facets of live entertainment on a tall ship! Actors dressed in period attire with play their fiddles or hornpipes as you sing and dance to sea shanties. You'll have a great time enjoying the entertainment and historic feel of the experience. The bar will be stocked with Madeira, Port, and the sailors favorite, the Dark 'n Stormy. This event will attract many singers and lovers of naval history and, of course, grog! Prepare for a rousing chorus of shanty singers and musicians of all sorts!
    No available dates to book.
    Bucketlist to hear about new dates first!
    Rum and Revelry Sail

    67 Long Wharf, Boston

    • Enjoy a sail out into the Boston Harbor with entertaining period actors and musicians
    • Sit back and relax with your favorite drink supplied by a well-stocked bar
    • Explore the naval history and prepare for a rousing chorus of shanty singers
    • Partake in the drinking festivities with Madeira, Port, Grog and delicious beverages
    BOOK NOW ← Back
    20 positive reviews
  • Book Now

    Fall Foliage Brunch Cruise on Yacht Northern Lights

    (28)
    Wake up and embark on an exciting sea voyage with a satisfying drink in hand! Start your day on the open water as you sail around the Boston Harbor while observing the fascinating and historic scenery. This 2-hour cruise on Yacht Northern Lights includes a freshly prepared gourmet buffet breakfast, included with each ticket. Drinks are available for purchase on-board by credit card only. Enjoy the sites around Boston's Inner Harbor Islands and the fall foliage. See the Boston Fish Pier, the Moakley Federal Courthouse at Fan Pier, and many more sights, firsthand! (Foliage is weather permitting, we cannot guarantee that guests will see foliage on this cruise)
    No available dates to book.
    Bucketlist to hear about new dates first!
    Fall Foliage Brunch Cruise on Yacht Northern Lights

    60 Rowes Wharf, Boston

    • Set out on an early and invigorating sail on the Boston Harbor
    • Experience the joy of a leisurely sailing cruise and the historic scenery of the Boston Harbor
    • Expect to forget the distractions of life on land within minutes of leaving the dock
    • Kick back, and enjoy seeing the historic sights of Boston with a drink in hand
    BOOK NOW ← Back
    28 positive reviews
  • Book Now

    Marys & Mimosas Cruise

    (28)
    Our Mary's & Mimosa Cruise aboard Northern Lights features a unique spot to enjoy your favorite morning cocktail with unique views of the Boston Skyline. It is recommended you pack a picnic for you and your guests to enjoy on this journey through Boston Harbor! We'll have the beverages aboard including a well-stocked bloody mary bar and seasonal mimosas!
    No available dates to book.
    Bucketlist to hear about new dates first!
    Marys & Mimosas Cruise

    60 Rowes Wharf, Boston

    • See historic sites along the harbor such as the harbor islands (Castle Island, Deer Island, Spectacle Island, Long Island, Lovells Island, Georges Island)
    • Keep an eye out for some of our harbor porpoises (early spring), harbor seals (early spring and fall), cormorants, oystercatchers, and other wildlife.
    • Expect to forget the distractions of life on land within minutes of leaving the dock
    BOOK NOW ← Back
    28 positive reviews
  • Give the gift of fun with a Vimbly gift card!
    Learn More
  • Book Now

    Sunday Barbecue & Beers Cruise

    (28)
    Gather friends and family and set your sites for the best views and barbecue you can find in Boston aboard Northern Lights. There's a little something for every meat lover on this cruise. Grab a plate, select your favorite from the buffet, walk around the boat to find your favorite viewing location for our cruise around the harbor. We'll pull out the corn hole and turn on some beach tunes as we create a unique summer event for you. Bring a few friends and grab a few seasonal beers from the bar and do summer like a pirate! Featured menu: Texas Style Brisket – Smoked and Braised in Beer, Boneless Country Pork Ribs, Smoked Linguica Sausages, BBQ Spiced Shrimp, North Carolina Style Fried Chicken with White BBQ Sauce, Seasonal Vegetable Roasted with Spices Sides: Seasonal Mixed Green Salad, Bacon Baked Beans, Creamy Mac and Cheese, Cole Slaw, Honey Cornbread.
    No available dates to book.
    Bucketlist to hear about new dates first!
    Sunday Barbecue & Beers Cruise

    60 Rowes Wharf, Boston

    • Set out on a midday sail on the Boston Harbor
    • Experience the joy of barbecue and beer cruise and the historic scenery of the Boston Harbor
    • Expect to forget the distractions of life on land within minutes of leaving the dock
    • Keep an eye out for some of our harbor porpoises, harbor seals, cormorants, ospreys, egrets, blue herons, oystercatchers, and other wildlife
    BOOK NOW ← Back
    28 positive reviews
  • Book Now

    Harbor Cruise

    Hoping to relieve yourself from the hectic city feeling without going too far? Try a two-hour cruise around Boston Harbor and its surrounding islands. Pack a lunch and set sail on a tour led by an experienced crew member; here, you'll be given an in-depth tour of this historical and exciting area. Let the sights and sounds fill your senses with nautical ruggedness and jubilation! As you explore the Boston harbor, a body of water revered by communities of passionate and experienced sailors, you'll be fascinated by its breathtaking storied history. Don't worry about a thing; the crew will do all the work as you sit back and enjoy the scenery.
    No available dates to book.
    Bucketlist to hear about new dates first!
    Harbor Cruise

    95 Marginal St, Boston

    • Take the afternoon off and set sail for a three-hour harbor cruise
    • Explore storied history of Boston Harbor with a knowledgeable guide
    • Relax as the crew takes you on a voyage on the open water
    BOOK NOW ← Back
  • Book Now

    Boston Harbor Sail (Liberty Star)

    (20)
    Set sail for the Boston Harbor on Liberty Star, a magnificent schooner! On your Boston sail, you'll see the sights in Boston Harbor and everything the ship has to offer. The crew will invite you to help hoist the sails and even to take a turn at the helm. There will also be a bar stocked with soda, water, Sam Adams on draft, mixed drinks, wine, and snacks. Take the wheel, set the sails, or just sit back and enjoy the sights and beauty of the Boston Harbor and her islands. The choice is yours!
    No available dates to book.
    Bucketlist to hear about new dates first!
    Boston Harbor Sail (Liberty Star)

    67 Long Wharf, Boston

    • Set sail into the Boston Harbor on the magnificent schooner known as Liberty Star
    • Enjoy the beautiful views of the harbor and have fun interacting with the knowledgeable crew
    • Partake in delicious refreshments and a bar stocked with your favorite drinks
    BOOK NOW ← Back
    20 positive reviews
  • Book Now

    Nantucket Seal Cruise

    If you don't sign up for this once-in-a-lifetime journey it will be the sealiest thing you ever do! Join Shearwater Excursions for a chance to see gray seals in their natural habitat. On this two-hour trip you'll learn about the life and ecology of these wonderful animals from an experienced naturalist on board, all while enjoying the beauty of Great Point. Don't forget to bring your camera -- this is the perfect chance to snap some memorable photos and make your social media followers green with envy! It's up to you of course, but this adventure certainly has OUR seal of approval!
    No available dates to book.
    Bucketlist to hear about new dates first!
    Nantucket Seal Cruise

    Slip 1011 Straight Wharf, Nantucket

    • See Gray Seals in their natural habitat
    • Learn about the life cycle of these amazing animals from a knowledgeable naturalist
    • Experience the serene beauty of Great Point
    • Take advantage of a great photography opportunity
    BOOK NOW ← Back

Page 2 of 4

Kind words from our customers