Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 15Friday Night Firework Cruise in Waikiki
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More
Friday Night Firework Cruise in Waikiki
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North America
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Superb23 reviews4.7
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
Sailing on Historic Schooner Yacht in Salem, MA
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More
Likely to Sell Out Sailing on Historic Schooner Yacht in Salem, MA
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North America
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Superb172 reviews4.9
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....
3 Hours Ultimate Watersports Excursion in Miami
All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable and stable Catamaran for an unforgettable all-inclusive water experience. Highlights: - Extreme Watersports: Feel the thrill wi... More
Likely to Sell Out 3 Hours Ultimate Watersports Excursion in Miami
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North America
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Superb172 reviews4.9
All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable....
Whale Watching with Lunch and transportation included
Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll have front-row seats to witness the playful and majestic antics of whales in their natural habitat. Setting sail from the Marina, you... More
Likely to Sell Out Whale Watching with Lunch and transportation included
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North America
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Exellent20 reviews4.4
Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll hav....
Sunset sail Aboard Manakai Catamaran
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More
Likely to Sell Out Sunset sail Aboard Manakai Catamaran
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North America
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Superb14 reviews5
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More
Likely to Sell Out Schooner Applejack Sunset Sail Tour in Boothbay Harbor
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North America
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Superb42 reviews4.9
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....
Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More
Likely to Sell Out Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15
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North America
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Exellent31 reviews4.5
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More
Likely to Sell Out Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
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North America
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Superb46 reviews4.9
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....
Deluxe Turtle Snorkeling Escapade at Waikiki
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More
Likely to Sell Out Deluxe Turtle Snorkeling Escapade at Waikiki
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North America
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Superb8 reviews4.9
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Slow Sailing Bacalar Experience with snack and drinks
Step aboard our sailboat and experience Bacalar in most authentic and sustainable way - powered mainly by the wind. By choosing to sail, you help protect the lagoon's fragile ecosystem while enjoying a peaceful and unforgettable j... More
Likely to Sell Out Slow Sailing Bacalar Experience with snack and drinks
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North America
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Superb21 reviews4.9
Step aboard our sailboat and experience Bacalar in most authentic and sustainable way - powered main....
Catamaran Sailing Cruise in Monterey
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More
Likely to Sell Out Catamaran Sailing Cruise in Monterey
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North America
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Superb30 reviews4.8
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....
Pirates Sunset Cruise at the Cabo San Lucas Arch
You'll love visiting the Arch of Cabo San Lucas! - Experience breathtaking views of the stunning sunset where the Sea of Cortez meets the Pacific Ocean. - If you visit during the winter months, you might catch a glimpse of whales ... More
Likely to Sell Out Pirates Sunset Cruise at the Cabo San Lucas Arch
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North America
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Superb1 review5
You'll love visiting the Arch of Cabo San Lucas! - Experience breathtaking views of the stunning sun....
Likely to Sell Out
Tour Sailing boat 4 Hours
We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat equipped with bathroom for emergencies. Surrounded by lush nature and crystal clear waters of the most beautiful lagoon in the wor... More
Free Cancellation
(Saving 15% )
Likely to Sell Out Tour Sailing boat 4 Hours
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North America
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Superb10 reviews5
We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat ....
Free Cancellation
(Saving 15% )
Romantic Dinner Touring the Nichupté Lagoon in Galeón
Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard the Columbus Romantic Dinner Cruise. This is a unique romance tour in Cancun, as it offers a very special evening, surrounded by ... More
Likely to Sell Out Romantic Dinner Touring the Nichupté Lagoon in Galeón
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North America
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Superb1 review5
Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard....
Your Private Miami Yacht Charter with Music and Fun
Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is designed for fun, style, and unforgettable memories with your group. Adventure Highlig... More
Private Tour
Likely to Sell Out Your Private Miami Yacht Charter with Music and Fun
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North America
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Superb65 reviews4.6
Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate....
Private Tour
New York City Sailboat Day Cruise to the Statue of Liberty
Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides along the Hudson Rive... More
Private Tour
Likely to Sell Out New York City Sailboat Day Cruise to the Statue of Liberty
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North America
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Superb152 reviews4.8
Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by t....
Private Tour
Los Cabos Sunset Sailing Adventure
Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete with delicious appetizers and an international open bar. After being picked up from your hotel, embark from the Cabo San Lucas Mar... More
Private Tour
Likely to Sell Out Los Cabos Sunset Sailing Adventure
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North America
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Superb152 reviews4.8
Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete ....
Private Tour
The Boat People Cruise Private Harbor Cruises
Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an unforgettable evening with contagious laughter and panoramic views of the Newport Bay. Bring your plus one or ... More
Private Tour
Likely to Sell Out The Boat People Cruise Private Harbor Cruises
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North America
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Superb44 reviews5
Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We ....
Private Tour
Escape from the Rock! Cruise around Alcatraz
Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an in-depth view of the prison. Take in the sights and sounds of ... More
Private Tour
Likely to Sell Out Escape from the Rock! Cruise around Alcatraz
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North America
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Exellent157 reviews4.2
Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and ....
Private Tour
Sail San Francisco Bay on the Historic Brigantine Matthew Turner
Set sail on the San Francisco Bay aboard the historic brigantine Matthew Turner, the largest sailboat in the area. Experience the beauty of the bay as you glide past iconic landmarks like the Golden Gate Bridge, Alcatraz, and Ange... More
Private Tour
Likely to Sell Out Sail San Francisco Bay on the Historic Brigantine Matthew Turner
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North America
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Superb2 reviews5
Set sail on the San Francisco Bay aboard the historic brigantine Matthew Turner, the largest sailboa....
Private Tour