We Found These Experiences For You (22)
Sailing and Massachusetts
Adirondack Day Sail
Up to $74.20 | 1.5 or 2 hour Sail
Experience the timeless charm of Boston Harbor aboard our classic 2-hour or 1.5-hour afternoon day sails. Step aboard our schooners Adirondack III & IV for an unforgettable journey through the scenic beauty of the harbor. Our sailing vessels, both 80-foot pilot schooners, boast elegant designs with ...
Boston
1.5 or 2 hours
Adirondack Sailing, Boat Cruise, Boat Tour, Brewery, Castle, Cruise / Large Boat, Day Sail, Ferry, Sailing, Water Activities
Classic Harbor Line - Boston
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Labor Day Fireworks Cruise on Northern Lights
$79.50 | 2 Hour Cruise
Illuminate the Harbor Fireworks Cruise on Northern Lights Celebrate the last days of summer with friends and family on a 2-hour Illuminate the Harbor Fireworks Cruise aboard yacht Northern Lights, which offers a crowd-free alternative to the shore line! Avoid the crowds and get front row seats for Boston ...
Boston
2 hours
Boat Cruise, Cruise / Large Boat, Ferry, Fireworks Cruise, Sailing
Classic Harbor Line - Boston
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Labor Day Weekend Harbor Fireworks Cruise Aboard Adirondack
$95.40 | 1.5 hour Sail
Illuminate the Harbor Fireworks Cruise aboard Schooner Adirondack What better way to celebrate the end of summer, but with a stellar fireworks display from the waters of Boston Harbor? Join us aboard the historic and beautiful Adirondack for Illuminate the Harbor Fireworks hosted by Boston Harbor Now. ...
Boston
1.5 hours
Adirondack Sailing, Aquarium, Boat Cruise, Cruise / Large Boat, Day Sail, Evening Cruise, Ferry, Fireworks Cruise, Sailing, Water Activities
Classic Harbor Line - Boston
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Fall Brunch Cruise
Up to $93.28 | 2 Hour Cruise
Weekends are made for relaxing, and there’s no better way to unwind than with a two-hour Fall Brunch Cruise aboard the elegant Northern Lights. Step aboard our classic 1920s-style yacht, adorned with festive autumn décor, and ease into your weekend with a sparkling apple cider mimosa in hand. Savor ...
Boston
2 hours
Boat Cruise, Boat Tour, Brunch Cruise, Castle, Cruise / Large Boat, Ferry, Fishing, Party Boat, Party Fishing, Pirate Ship, Sailing, Wedding
Classic Harbor Line - Boston
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New Year's Day Brunch Cruise aboard 1920's Style Yacht Northern Lights
Up to $93.28 | 2 hour Cruise
Start the new year off right with a New Year's Day Brunch Cruise Aboard the yacht Northern Lights. While on the 2-hour cruise around the harbor warm up with a cup of hot cocoa and enjoy the sights in 2024! A tasty and hot three-course brunch is included with your ticket while beverages are available ...
Boston
2 hours
Boat Cruise, Boat Tour, Brunch Cruise, Castle, Chocolate Tour, Cruise / Large Boat, Ferry, Fishing, Food Tour, Harbor Tour, New Year's Eve Cruise, Sailing, Sightseeing Tour
Classic Harbor Line - Boston
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Brunch Cruise aboard Northern Lights
Up to $93.28 | 2 Hour Cruise
Spend your weekend unwinding in style with a delightful 2-hour Brunch Cruise aboard the elegant Northern Lights. From the moment you step aboard our luxurious ship, the bar is open, ready to kickstart your relaxation journey. Indulge in our gourmet brunch buffet while you settle into a cozy seat, soaking ...
Boston
2 hours
Boat Cruise, Boat Tour, Brunch Cruise, Castle, Cruise / Large Boat, Ferry, Fishing, Party Boat, Party Fishing, Sailing, Wedding
Classic Harbor Line - Boston
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Schooner Adirondack Oyster Sail
$76.32 | Classic Day Sail with Freshly Shucked Oysters
A Boston Harbor Sailing & Oyster Tour is a perfect blend of maritime adventure and culinary delight. Picture yourself aboard our classic sailboat, gliding across the waters of Boston Harbor with the city skyline as your backdrop. Tour Highlights: ⛵ Scenic Sailing: Depart from Rowes Wharf catching ...
Boston
2 hours
Adirondack Sailing, Beer Tour, Boat Tour, Brewery, City Tour, Day Sail, Ferry, Food Tour, Harbor Tour, History Tour, Party Boat, Party Fishing, Photography Tour, Sailing, Sightseeing Tour, Sunset Sail, Water Activities, Wine
Classic Harbor Line - Boston
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Sailboat Rentals at Natick
Boathouse open daily. Reserve your sailboat with our sailing season pass today!
Join us for a day of peaceful water exploration on the beautiful Lake Cochituate in Cochituate State Park. About Sailboats are great for family-oriented fun, learning the ropes, and enjoying the day. Boats We have Cape Cod Mercurys, RS Quests, Hobie Cats, and an RS Cat available for use by season pass ...
Natick
Up to 4 hours!
Kid-Friendly
Rentals, Sailing, Water Activities
Natick Boathouse
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Natick Boathouse Gift Card
Give an experience they'll remember! Purchase a Natick Boathouse Gift Card today.
Purchase the perfect gift: a gift card with a value of your choosing! Featured Natick Boathouse Offering Rates These are just our most popular items but gift cards are available for any amount! Hourly Paddle Rates and Class & Tour Prices Single Kayak or SUP- $22/hr Double Kayak or Canoe- $32/hr Pedalboat- ...
Natick
Canoe, Fishing, Gift Card, Kayak, Rentals, Sailing, SUP, Water Activities, Wildlife
Natick Boathouse
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Gloucester Schooner Festival on Malabar X
August 31st, 2025
Gloucester Schooner race onboard the historic racing schooner Malabar X. Lead the pack aboard this elegant Newport-Bermuda record breaker and enjoy the spectacular views of the Parade Of Sail and the Mayor's Cup race at Gloucester 2026! BOARD AND DISEMBARK AT GLOUCESTER, MA. Gloucester Schooner ...
2hr Sunset Sail on Malabar X
Schooner Malabar X Sunset Sail
Set sail on John Alden’s greatest creation! His personal yacht and 1930 and 1932 Bermuda Race winner. Enjoy a 2 hr sunset sail in elegance and style. Rum punch, select beers and wine available for purchase with complementary bottled water. Sit back and relax or lend a hand as the crew sets sail for ...
2hr Sunset Sail on When And If
Summer Sunsets on a Stunning Classic Schooner
2 HR. Sunset sail departing daily. Enjoy the sunset from the water aboard the gorgeous 1939 wooden schooner built for General George S. Patton. Built with the dream to sail around the world 'When the war is over, and If I live through it," When and If is over 80 years young with her destiny ...
Private Charter Sunset Sail on Malabar X
Classic Schooner Yacht Private Charter Day Sail
Set sail on a 2-hour private Daysail aboard the classic Schooner Malabar X and enjoy a truly unforgettable sailing experience on Salem Sound. This elegant 1930s John Alden-designed yacht offers a perfect blend of history, comfort, and adventure as the experienced crew hoists sails and glides you past ...
Salem
2hrs with option to add more time!
Private Tours
Sailing
Sunset Sail Salem
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2hr Day Sail on When And If
A Beautiful Sail on a Classic Yacht
Sail away on the gorgeous 1939 wooden schooner built for General George S. Patton. Built with the dream to sail around the world 'When the war is over, and If I live through it," When and If is over 80 years young with her destiny as yet unfulfilled. Come and be part of her story! Take a turn ...
2hr Day Sail on Malabar X
Classic Schooner Yacht Day Sail on Salem Sound
Step aboard our stunning classic schooner Malabar X (10). Built in 1930 for the private use of her designer, the famed John G. Alden of Boston, MA. Embark on a 2 hour sail through Salem sound under billowing canvas as we pass by up to 5 of the areas most beautiful lighthouses. Take in the sights of the ...
Salem
2 hours
Private Tours
Sailing
Sunset Sail Salem
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Private Charter Sunset Sail on When And If
From $1,163.44 • Private Sunset Sailing on the North Shore
Sail into the Summer Sunset on your own private classic yacht. With capacity for up to 32 guests, When And If is the last word in comfort and elegance for cruising away those long balmy evenings or catching the breeze for a little seafaring adventure. Call to talk about extending your trip - we know ...
Salem
Private Tours
Sailing
Sunset Sail Salem
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Private Charter Daysail on Malabar X
From $950.94 • Classic Schooner Yacht Day Sail Private Charter on Salem Sound
Have the ship to yourself for a summer afternoon of yachting in style as the captain and crew cater to your every needs. Perfect for any special occasion. Elegant. Sublime. Affordable.
Salem
2 Hour minimum
Private Tours
Sailing
Sunset Sail Salem
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Private Charter Daysail on When and If
From $950.94 • Up to 32 People • Price includes 12 people
Take to the glorious waters on the North Shore on your own private Classic. When And If is ready to take you and your party sailing as an exclusive group and whether you'd like to do our a-la-carte trip or customise it by adding hours, we're here to make your dream sail come true!
Salem
Private Tours
Sailing
Sunset Sail Salem
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Morning Mimosa Sail
Gourmet Yacht Mimosas!
What better way to start a Summer morning than with fully instagramable Mimosas and sailing on a classic yacht? Our star garnishes change from week to week so whether it's Elderflower and Mint, Blood Orange and Thyme or cheeky tropical Mango Basil, get ready to start your Sunday in style with Sunset ...
Corinthian Classic Regatta
Marblehead's Classic Yacht Regatta
Limited space available to participate in Marblehead's annual Corinthian Classic Yacht Regatta. Whether you prefer to join as a spectator to the the action or you wish to be enlisted to help the crew with sail handling, When And If is always competitive and easily the most photogenic yacht in a ...
Viewing 1 to 20 of 22 Experiences