Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 2Pirate Ship Sunset Dinner and Show in Los Cabos
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that is the joy for children and grown-ups alike. Our pirates, dance, chant, climb the ropes, while you... More
Pirate Ship Sunset Dinner and Show in Los Cabos
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North America
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Exellent764 reviews4.3
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....
Cabo Boat Ride to El Arco & Lover’s Beach with Swimming
Enjoy the perfect combination of sightseeing and beach time on this Cabo San Lucas boat ride to El Arco and Lover’s Beach. Cruise along the stunning coastline as you pass iconic landmarks like the Arch, Sea Lion Colony, and Peli... More
Cabo Boat Ride to El Arco & Lover’s Beach with Swimming
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North America
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Exellent523 reviews4.5
Enjoy the perfect combination of sightseeing and beach time on this Cabo San Lucas boat ride to El A....
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour,... More
Afternoon Windjammer Cruise Along the Coast of Portland Maine
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North America
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Superb262 reviews4.7
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to e....
Sightseeing Day Sail around Boston Harbor
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More
Sightseeing Day Sail around Boston Harbor
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North America
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Superb632 reviews4.8
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Spacious 45-foot catamaran with near 360 degree view -Families welcome: Keiki ra... More
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
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North America
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Superb599 reviews4.7
-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boardi....
Deluxe Sunset & Day Sail Small Group
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More
Deluxe Sunset & Day Sail Small Group
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North America
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Superb346 reviews5
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....
San Diego Whale Watching Cruise
Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we received a 100 percent success rate during winter whale watching when spotting the K... More
San Diego Whale Watching Cruise
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North America
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Superb2,508 reviews4.8
Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the opt....
Sunset Windjammer Cruise Along the Coast of Portland Maine
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a narrated tour, bu... More
Sunset Windjammer Cruise Along the Coast of Portland Maine
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North America
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Superb194 reviews4.7
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to exper....
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....
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North America
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Exellent803 reviews4.5
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....
Key West Reef Morning Snorkeling with Breakfast and Mimosas
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More
Key West Reef Morning Snorkeling with Breakfast and Mimosas
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North America
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Exellent728 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
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North America
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Superb1,609 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
Key West Signature Sunset Sail with Live Music, Open Bar & Food
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More
Key West Signature Sunset Sail with Live Music, Open Bar & Food
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North America
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Exellent401 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....
Newport Afternoon Sightseeing Sail on Classic Sailboat
Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, including Newport's historic lighthouses and landmarks, bridges, mansions a... More
Newport Afternoon Sightseeing Sail on Classic Sailboat
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North America
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Superb191 reviews4.9
Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narraga....
Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More
Waikiki Sunset Boat Cruise
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North America
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Superb231 reviews4.9
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
Kauai: Leila Na Pali Sunset Dinner Sail
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More
Kauai: Leila Na Pali Sunset Dinner Sail
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North America
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Superb592 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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North America
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Superb854 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
'Alihilani Lahaina Sunset Sail
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More
'Alihilani Lahaina Sunset Sail
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North America
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Superb192 reviews4.9
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
Boston Harbor Sunset Sail Tour
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More
Boston Harbor Sunset Sail Tour
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North America
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Superb180 reviews4.8
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
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North America
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Superb348 reviews4.8
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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North America
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Superb1,476 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....