Cruises & Sailing

(34 activities)
Reset Filters
  • 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)
    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

    Brunch Cruise

    (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. See the USS Constitution,Bunker Hill Monument, USS Cassin Young, and many more sights, firsthand! This cruise features a freshly prepared gourmet buffet brunch included with each ticket. Drinks are available for purchase on-board by credit card only. You will be so refreshed, even the morning people will want to channel your energy!
    Brunch Cruise

    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
    • 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

    Brunch Cruise

    (1)
    Admire the unforgettable sights of Boston on board this breathtaking climate controlled yacht. This cruise offers the most unique brunch setting on Boston's famous harbor. Relax and be captivated by the city skyline while enjoying a delectable buffet brunch menu. Your cruise experience begins as you board the luxury yacht at Rowes Wharf. After a quick stop for a commemorative boarding photo, one of the hosts will greet you and escort you to your private table. Enjoy a complimentary glass of champagne or tour the ship's three climate controlled decks. A great way to start your day is by watching the boat castoff from one of the observation decks. Bring your appetite when you return to your private table, the Executive Chef and galley staff present you with an imaginative buffet of appetizers, entrees, salads and desserts that is sure to please any number of tastes. Enjoy live entertainment while boarding and dance to music from the DJ on board. Return, 2 hours later. Relaxed. Refreshed. As you depart, you'll find your boarding photo ready for purchase. Cruise Route: Departing from Rowes Wharf, it cruises along Historic Boston Harbor from Castle Island to George's Island, then east to the Boston Light on Little Brewster Island, and back north to Charlestown Naval Yard before returning to the Wharf. Cruise Route may vary depending on weather.
    Brunch Cruise

    200 Seaport Blvd, Boston

    • Hop aboard a luxury yacht at Rowes Wharf for a relaxing brunch out on the water
    • Sip champagne and explore three climate-controlled decks while on board
    • Dance to a live DJ and have fun with the sights and entertainment to go along with your meal
    • Return to land relaxed and refreshed
    BOOK NOW ← Back
    1 positive reviews
  • Book Now

    Sunset Dinner Cruise with Buffet

    (6)
    See Boston's waterfront sights from the deck of a luxury sunset dinner cruise. Enjoy a fabulous fine-dining buffet with a carving station and hit the dance floor while one of Boston's top DJs spins your favorite songs. Join the sunset party on the ship's exterior deck for the biggest patio party in Boston! This two-hour Boston sunset dinner cruise is a fun and unique way to see some of Boston's famous attractions, as you start a night out on the town. Purchase a cocktail on board and watch as the sun sinks below the horizon. You'll see breathtaking nighttime views of Boston sights like the Bunker Hill Monument, USS Constitution (known as "Old Ironsides") and the site of the Boston Tea Party.

    Get in line for a decadent all-you-can-eat buffet, complete with a carving station. While enjoying your dinner in the elegant setting of the ship's dining room, you'll be entertained by the colorful characters of the ship's cabaret. After dinner, the DJ turns up the heat with the sounds of your favorite songs. Show your moves off on the dance floor, or take a romantic stroll with that special someone around the ship's decks.

    The dance party continues all the way across the harbor, as you take in the sparkling views of the Boston skyline.
    Sunset Dinner Cruise with Buffet

    200 Seaport Blvd, Boston

    • Immerse yourself in Boston's waterfront sights with a two hour dinner cruise
    • Enjoy live entertainment and a buffet for fine dining and dancing on the ship's exterior deck
    • Take in beautiful views of the skyline, Bunker HIll Monument, and USS Constitution
    • Purchase a cocktail on board and watch as the sun sinks below the horizon
    BOOK NOW ← Back
    6 positive reviews
  • No available dates to book.
    Bucketlist to hear about new dates first!
    Your Bucketlist
  • Book Now

    Boston City Lights Sail

    (20)
    Step on board a tallship for a night cruise through Boston. If you're wondering what the heck a tallship is, we'll give you a hint: Pirates of the Caribbean. Yes, you'll be sailing past the scenic city lights on a traditionally-rigged ship with huge, billowing sails and towering masts. Although the boat itself is beautiful, you'll also have breathtaking views of Boston and its historical points of interest. Help yourself to a cocktail or two and enjoy the view of the stars and skyline with a scenic tour on an even more splendid sailing craft.
    No available dates to book.
    Bucketlist to hear about new dates first!
    Boston City Lights Sail

    67 Long Wharf, Boston

    • Take a scenic night cruise on a traditionally styled boat
    • Experience Boston's city skyline from on board a tallship
    • Help yourself to a cocktail or two while relaxing on board
    • Relax and take in the stars on this beautiful night cruise
    BOOK NOW ← Back
    20 positive reviews
  • Book Now

    BYOB Spectacle Island Picnic

    Set sail from Fan Pier for an adventure that includes dramatic views of Boston, time to explore the hills and beaches of Spectacle Island, and whimsical visits from the ghost of John Adams clad in fishing gear. You'll spend approximately 1 hour on the water, with 2 hours in between to hike the island, fly kites, check out the small museum, or even swim, weather-dependent. It's a fun getaway for kids, groups, dates and entertaining out-of-town visitors. Hop aboard a speed boat for a unique way to take in the sights of the city!
    No available dates to book.
    Bucketlist to hear about new dates first!
    BYOB Spectacle Island Picnic

    1 Marina Park Dr, Boston

    • Hop aboard power boat Precious Time for a sail to Spectacle Island
    • Spend two hours exploring the island, its museum, and all of its glorious views
    • Go kite flying, sea-glass hunting, or even swimming with your time on the island
    BOOK NOW ← Back
  • Give the gift of fun with a Vimbly gift card!
    Learn More
  • Book Now

    Boston Tea Party Sail

    (20)
    Come aboard Liberty Clipper (named after John Hancock's ship) to discover the Boston Tea Party and sail through the Boston Harbor. You'll be welcomed aboard by a professional reenactor dressed in period attire as you prepare to hoist sail. On this Boston Tea Party experience, expect to host a town hall meeting, fire the ship's cannon, and toss the tea into the sea! You will also have the opportunity to help set the sails and even take a turn at the helm with the ship's captain!
    No available dates to book.
    Bucketlist to hear about new dates first!
    Boston Tea Party Sail

    67 Long Wharf, Boston

    • Sail through Boston Harbor for an interactive reenactment of the Boston Tea Party
    • Enjoy professional reenactors dressed in period attire for the full experience
    • Participate in a mock town hall meeting, prepare to fire cannons, and toss tea into the water
    • Have fun helping the crew with setting the sails or take a turn at the helm with the captain
    BOOK NOW ← Back
    20 positive reviews
  • Book Now

    City Lights Sail

    (28)
    The maritime world of Boston has many great stories to offer, and on this classic sail through the Boston Harbor, with an evening sea breeze and all of Boston at your back, 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, and 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!
    City Lights Sail

    60 Rowes Wharf, Boston

    • Enjoy the historic scenery of the Boston Harbor aboard a classic 80 foot pilot schooner
    • Experience the beautiful Boston Harbor at night
    • 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

Page 1 of 4

Kind words from our customers