sailing

(40 activities)
Reset Filters
  • 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!
    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

    Sunset Sail (Saturday)

    (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.
    Sunset Sail (Saturday)

    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

    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

    Newport Mansions Tour

    Escape to the lovely coastal city of Newport, Rhode Island, on this day trip that includes both a guided tour and free time. Explore The Breakers mansion, the summer home of Cornelius Vanderbilt II's family. See top Newport attractions such as St Mary's Parish, Ocean Drive and the Naval War College on a narrated city tour. Then spend the afternoon exploring more of this quaint and historic city on your own. This small-group tour is limited to 14 people for a more intimate, interactive experience. After pickup from your central Boston hotel in a minibus, enjoy a morning snack during the 1.5-hour drive to Newport, Rhode Island. Listen to your informative guide provide historical commentary about Newport, which has been called 'America's First Resort'; feel free to ask questions in the relaxed company of your small group. Arrive at The Breakers, the elegant summer home of Cornelius Vanderbilt II and his family, to explore for 2-hours. Tour the remarkable mansion, which covers a full acre of the 13-acre (5.2-hectare) oceanfront estate. It's one of many local mansions that served as getaways for America's rich and famous during the 20th century. During this time, you may take part in a 1.5-hour self-guided audio tour (available in 9 languages). Directly behind The Breakers, take in gorgeous ocean views at the Newport Cliff Walk for great photo opportunities. After, embark on a 1-hour narrated city tour of Newport sights. See St Mary's Parish, where President John F Kennedy wed Jacqueline Bouvier in 1953. Drive by Touro Synagogue, the oldest synagogue in the US, and see Fort Adams and the Naval War College. Learn why Newport is considered a sailing mecca and admire lovely waterfront vistas from Ocean Drive. Finish your guided city tour at the Newport Visitors Center, where you can plan out your 3.5 hours of free time. Public transportation makes it easy to get around the city from this location. Use your free time to visit another Newport mansion of your choice, you may choose to see the International Tennis Hall of Fame (at a discounted price) orr take a lunchtime cruise, dine on the oceanfront and browse the shops on the city's boardwalk (all at own expense). Take advantage of the guidebook and discount card included with your tour during your free time in Newport. In the late afternoon, you will meet back at the Newport Visitors Center for the drive back to Boston.
    Newport Mansions Tour

    8 N Market St, Boston

    • Escape to the lovely coastal city of Newport, Rhode Island on this day trip
    • Navigate through The Breakers mansion, the summer home of Cornelius Vanderbilt II's family
    • See top Newport attractions such as St Mary's Parish, Ocean Drive and the Naval War College
    • Enjoy both a narrated city tour and free time to check out more of this quaint and historic city on your own
    BOOK NOW ← Back
  • 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.
    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

    Community Boating Orientation Workshop

    Having trouble keeping your dreams of boating afloat? It's a-boat time you took this class! This orientation introduces you to the Community Boating Inc. facilities and benefits that it offers. The session will introduce you to the organization, hopefully kicking off a long and fruitful relationship. You'll learn the workings of the docks, the facilities and the boats -- in short, everything you need to know to decide if Community Boating is right for you. Seas the day and sign up now!
    Community Boating Orientation Workshop

    21 David G Mugar Way, Boston

    • Get oriented with everything that Community Boating Inc. has to offer, perfect for sailors new or experienced
    • Ask questions about the sailing community and topics that matter to you as a sailor
    • Learn about classes and programs offered, as well as boats and facilities available at the site
    • Meet new friends with similar interests, and have fun!
    BOOK NOW ← Back
  • Give the gift of fun with a Vimbly gift card!
    Learn More
  • No available dates to book.
    Bucketlist to hear about new dates first!
    Your Bucketlist
  • 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.
    No available dates to book.
    Bucketlist to hear about new dates first!
    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
  • Book Now

    Dinner Cruise

    (5)
    As you are boarding, the ship's photographer records the moment for your entire party. The Captain and crew greet you as you step onto the ship. Step inside your deck, the hostess will greet you and escort you to your private table where your wait staff will introduce themselves and give you the opportunity to decide for yourself how to pace your service. Serving begins. From each of her three climate-controlled dining decks to the Observation deck, Boston Dinner Cruise offers a singularly unique setting that begs to be explored. Understated art-deco accents. Enticing dance floors. And a distinctive atmosphere reminiscent of the classic ocean liners. Be sure to visit the Captain's bridge, open to all passengers throughout most of the cruise. Enjoy live entertainment for boarding and food service paired with an entertaining DJ that will get you up and dancing after their meal. Return, hours later. Relaxed. Refreshed. As you depart, you'll find your Souvenir photo ready for purchase. Classic Dinner Menu (subject to change) FRESH SALADS Organic Mixed Field Green Salad Organic Spinach and Kale Salad Mediterranean Couscous and Chickpea Salad MAIN COURSE Roast Salmon & Tilapia Chicken Parmesan Meatballs Twice Cooked Beef Short Ribs Baked Ziti Roast Broccoli DESSERTS Mini Pastries Cookies Brownies Seasonal Fruit
    Dinner Cruise

    Rowes Wharf, Boston

    • Enjoy a three hour dinner cruise out into Boston Harbor for a relaxing meal
    • Listen to the waves as you enjoy fine dining, delicious wine, and plenty of entertainment
    • Dance to a live DJ and explore the unique and understated aspects of the boat
    • Return relaxed and refreshed with an option to buy a souvenir photo ready for purchase
    BOOK NOW ← Back
    5 positive reviews
  • Book Now

    Ales and Tales Tour

    (1)
    Who would you trust on a Gloucester pub crawl? It's gotta be a fishing boat captain. Join the captain, grab a drink, pull up a chair, and listen to the tales of the brave men and women who make their living off the fierce fishing grounds of the North Atlantic. On this tour, you'll visit two local watering holes and sip on a few brews. Can you think of a better way to experience the stories of America's oldest working seaport?
    Ales and Tales Tour

    11 Rogers St, Gloucester

    • Listen to the stories behind the brave men and women who make a living fishing off the North Atlantic
    • Visit two local watering holes for some tales and ales
    • Experience Gloucester from the pleasantries of a local
    BOOK NOW ← Back
    1 positive reviews
  • Book Now

    Day Sail

    (28)
    The maritime world of Boston has many great stories to offer, and on this classic afternoon sail through the Boston Harbor, 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.
    Day Sail

    60 Rowes Wharf, Boston

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

Page 1 of 4

Kind words from our customers