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Top 10 Best North America Sailing Trips

Found 770 Sailing Trips activities in North America. Sort by Popularity.
 

Miami Millionaires Sightseeing Cruise

(4.3 of 1,799 reviews)

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

Free Cancellation
Start From $18.00
 
Miami Millionaires Sightseeing Cruise

Miami Millionaires Sightseeing Cruise

  • North America
  • Exellent1,799 reviews4.3

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....

    Free Cancellation
    Start From $18.00
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,639 reviews)

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes approximately 1 hour of snorkeling at Shell Island, where... More

Free Cancellation
Start From $57.59
 
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....

  • North America
  • Superb4,639 reviews4.9

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboa....

    Free Cancellation
    Start From $57.59
 
 

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

(4.8 of 3,692 reviews)

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

Free Cancellation
Start From $112.00
 
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Likely to Sell Out

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

  • North America
  • Superb3,692 reviews4.8

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time t....

    Free Cancellation
    Start From $112.00
 
 

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,435 reviews)

**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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Free Cancellation
Start From $68.60
(Saving 15% ) $80.71
 
-15% Waikiki: 2-hour Turtle Canyon Snorkeling Adventure Likely to Sell Out

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

  • North America
  • Superb1,435 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join ....

    Special Offer
    Free Cancellation
    Start From $68.60
    (Saving 15% ) $80.71
 
 

San Francisco Bay Cruise

(4.4 of 355 reviews)

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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Free Cancellation
Start From $39.00
(Saving inf% ) $0.00
 
-inf% San Francisco Bay Cruise Likely to Sell Out

San Francisco Bay Cruise

  • North America
  • Exellent355 reviews4.4

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....

    Special Offer
    Free Cancellation
    Start From $39.00
    (Saving inf% ) $0.00
 
 

Kona Signature Catamaran Sunset Sail

(4.8 of 267 reviews)

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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Free Cancellation
Start From $109.00
(Saving inf% ) $0.00
 
-inf% Kona Signature Catamaran Sunset Sail Likely to Sell Out

Kona Signature Catamaran Sunset Sail

  • North America
  • Superb267 reviews4.8

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....

    Special Offer
    Free Cancellation
    Start From $109.00
    (Saving inf% ) $0.00
 
 

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

(4.7 of 3,739 reviews)

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

Special Offer
Free Cancellation
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres Likely to Sell Out

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

  • North America
  • Superb3,739 reviews4.7

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....

    Special Offer
    Free Cancellation
    Start From $79.00
    (Saving inf% ) $0.00
 
 

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

(4.7 of 569 reviews)

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More

Special Offer
Free Cancellation
Start From $47.60
(Saving 15% ) $56.00
 
-15% Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure Likely to Sell Out

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

  • North America
  • Superb569 reviews4.7

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....

    Special Offer
    Free Cancellation
    Start From $47.60
    (Saving 15% ) $56.00
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 622 reviews)

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut the engine down and enjoy the quiet of our beautiful schooner cutting through the tranquil Puget So... More

Special Offer
Free Cancellation
Start From $65.00
(Saving inf% ) $0.00
 
-inf% Evening Colors Sunset Sail Tour in Seattle Likely to Sell Out

Evening Colors Sunset Sail Tour in Seattle

  • North America
  • Superb622 reviews4.8

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....

    Special Offer
    Free Cancellation
    Start From $65.00
    (Saving inf% ) $0.00
 
 

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

(4.6 of 3,483 reviews)

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

Special Offer
Free Cancellation
Start From $55.00
(Saving inf% ) $0.00
 
-inf% Isla Mujeres Luxury Sailing: Adults Only or Family Friendly Likely to Sell Out

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

  • North America
  • Superb3,483 reviews4.6

Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — wit....

    Special Offer
    Free Cancellation
    Start From $55.00
    (Saving inf% ) $0.00
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 713 reviews)

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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Free Cancellation
Start From $48.00
(Saving inf% ) $0.00
 
-inf% Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....

  • North America
  • Exellent713 reviews4.5

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....

    Special Offer
    Free Cancellation
    Start From $48.00
    (Saving inf% ) $0.00
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.8 of 131 reviews)

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

Special Offer
Free Cancellation
Start From $199.00
(Saving inf% ) $0.00
 
-inf% Turtles & Tacos Luxury Catamaran Snorkel Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • North America
  • Superb131 reviews4.8

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....

    Special Offer
    Free Cancellation
    Start From $199.00
    (Saving inf% ) $0.00
 
 

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(4.5 of 655 reviews)

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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Free Cancellation
Start From $49.95
(Saving inf% ) $0.00
 
-inf% Key West Reef Morning Snorkeling with Breakfast and Mimosas Likely to Sell Out

Key West Reef Morning Snorkeling with Breakfast and Mimosas

  • North America
  • Exellent655 reviews4.5

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....

    Special Offer
    Free Cancellation
    Start From $49.95
    (Saving inf% ) $0.00
 
 

Kauai: Leila Na Pali Sunset Dinner Sail

(4.7 of 558 reviews)

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

Special Offer
Free Cancellation
Start From $263.82
(Saving inf% ) $0.00
 
-inf% Kauai: Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Kauai: Leila Na Pali Sunset Dinner Sail

  • North America
  • Superb558 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Special Offer
    Free Cancellation
    Start From $263.82
    (Saving inf% ) $0.00
 
 

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,321 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Special Offer
Free Cancellation
Start From $89.99
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cocktail Sail on the Moana Catamaran Likely to Sell Out

Waikiki Sunset Cocktail Sail on the Moana Catamaran

  • North America
  • Superb2,321 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Special Offer
    Free Cancellation
    Start From $89.99
    (Saving inf% ) $0.00
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,704 reviews)

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More

Special Offer
Free Cancellation
Start From $89.56
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkel and Sail on Hawea Catamaran Likely to Sell Out

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • North America
  • Superb1,704 reviews4.8

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....

    Special Offer
    Free Cancellation
    Start From $89.56
    (Saving inf% ) $0.00
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,640 reviews)

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

Special Offer
Free Cancellation
Start From $59.99
(Saving inf% ) $0.00
 
-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • North America
  • Superb1,640 reviews4.9

The water is clean, clear, and safe following the recent storms! Experience one Viator's 2025 Top 2....

    Special Offer
    Free Cancellation
    Start From $59.99
    (Saving inf% ) $0.00
 
 

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

(4.5 of 42 reviews)

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

Special Offer
Free Cancellation
Start From $141.98
(Saving inf% ) $0.00
 
-inf% Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar Likely to Sell Out

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

  • North America
  • Exellent42 reviews4.5

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....

    Special Offer
    Free Cancellation
    Start From $141.98
    (Saving inf% ) $0.00
 
 

Pirate Ship Sunset Dinner and Show in Los Cabos

(4.3 of 727 reviews)

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

Special Offer
Free Cancellation
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Pirate Ship Sunset Dinner and Show in Los Cabos Likely to Sell Out

Pirate Ship Sunset Dinner and Show in Los Cabos

  • North America
  • Exellent727 reviews4.3

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....

    Special Offer
    Free Cancellation
    Start From $99.00
    (Saving inf% ) $0.00
 
 

Key West Signature Sunset Sail with Live Music, Open Bar & Food

(4.5 of 376 reviews)

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

Special Offer
Free Cancellation
Start From $72.00
(Saving inf% ) $0.00
 
-inf% Key West Signature Sunset Sail with Live Music, Open Bar & Food Likely to Sell Out

Key West Signature Sunset Sail with Live Music, Open Bar & Food

  • North America
  • Exellent376 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....

    Special Offer
    Free Cancellation
    Start From $72.00
    (Saving inf% ) $0.00
 
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