Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 756 Sailing Trips activities in North America. Sort by Popularity.Miami Millionaires Sightseeing Cruise
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More
Miami Millionaires Sightseeing Cruise
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North America
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Exellent1,688 reviews4.3
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....
Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More
Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings
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North America
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Superb1,319 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and enjoy the best of what Panama City Beach has to offer! Cruise over to Shell Island where you and the... More
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....
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North America
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Superb4,502 reviews4.9
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....
Isla Mujeres Luxury Sailing: Adults Only or Family Friendly
Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — with the option to choose between an Adults Only or Family Friendly experience. Snorkel in warm, crystalline waters, then savor a del... More
Likely to Sell Out Isla Mujeres Luxury Sailing: Adults Only or Family Friendly
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North America
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Superb3,458 reviews4.6
Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — wit....
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
Likely to Sell Out Key West Signature Sunset Sail with Live Music, Open Bar & Food
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North America
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Exellent356 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. ....
Kauai: Deluxe Nā 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
Likely to Sell Out Kauai: Deluxe Nā Pali Sunset Cruise - aboard Lucky Lady
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North America
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Superb1,554 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
Likely to Sell Out
San Francisco Bay Cruise
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the cit... More
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Likely to Sell Out San Francisco Bay Cruise
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North America
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Exellent328 reviews4.4
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....
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Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More
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Likely to Sell Out Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
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North America
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Superb3,663 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
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Turtles & Tacos Luxury Catamaran Snorkel
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More
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Likely to Sell Out Turtles & Tacos Luxury Catamaran Snorkel
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North America
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Superb114 reviews4.7
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
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Los Cabos Luxury Sailing, Snorkel and Lunch Cruise
Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time to hang out in the pristine water and take it easy aboard the sailboat – you can snorkel with tropical fish, stand atop a paddleb... More
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Likely to Sell Out Los Cabos Luxury Sailing, Snorkel and Lunch Cruise
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North America
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Superb3,608 reviews4.8
Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time t....
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Kona Signature Catamaran Sunset Sail
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on d... More
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Likely to Sell Out Kona Signature Catamaran Sunset Sail
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North America
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Superb249 reviews4.8
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....
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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
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Likely to Sell Out Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....
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North America
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Exellent649 reviews4.5
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....
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Pirate 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
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Likely to Sell Out Pirate Ship Sunset Dinner and Show in Los Cabos
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North America
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Exellent702 reviews4.3
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....
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Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the C... More
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Likely to Sell Out Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
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North America
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Exellent1,502 reviews4.3
Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire th....
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Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
The water is clean, clear, and safe following the recent storms! Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. ... More
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Likely to Sell Out Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
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North America
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Superb1,543 reviews4.9
The water is clean, clear, and safe following the recent storms! Experience one Viator's 2025 Top 2....
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Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More
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Likely to Sell Out Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
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North America
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Superb22 reviews4.6
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
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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
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Likely to Sell Out Key West Reef Morning Snorkeling with Breakfast and Mimosas
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North America
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Exellent613 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
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Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **W... More
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Likely to Sell Out Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure
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North America
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Superb1,395 reviews4.7
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join ....
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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
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Likely to Sell Out Kauai: Leila Na Pali Sunset Dinner Sail
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North America
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Superb538 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
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Buccaneer Pirate Cruise in Destin
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More
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Likely to Sell Out Buccaneer Pirate Cruise in Destin
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North America
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Superb110 reviews4.9
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....
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