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Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 2
 

Key West's Favorite Afternoon Dolphin Sail

(4.6 of 151 reviews)

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More

Free Cancellation
Start From $59.00
 
Key West's Favorite Afternoon Dolphin Sail

Key West's Favorite Afternoon Dolphin Sail

  • North America
  • Superb151 reviews4.6

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....

    Free Cancellation
    Start From $59.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 540 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters a... More

Free Cancellation
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb540 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Free Cancellation
    Start From $177.73
 
 

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

(4.3 of 10 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

Free Cancellation
Start From $141.98
 
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

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

  • North America
  • Exellent10 reviews4.3

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

    Free Cancellation
    Start From $141.98
 
 

San Francisco Bay Cruise

(4.4 of 313 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

Free Cancellation
Start From $39.00
 
San Francisco Bay Cruise

San Francisco Bay Cruise

  • North America
  • Exellent313 reviews4.4

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

    Free Cancellation
    Start From $39.00
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,663 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

Free Cancellation
Start From $89.56
 
Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • North America
  • Superb1,663 reviews4.8

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

    Free Cancellation
    Start From $89.56
 
 
-10% Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

(4.7 of 2,112 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Special Offer
Free Cancellation
Start From $134.95
(Saving 10% ) $149.95
 
-10% Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

  • North America
  • Superb2,112 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Special Offer
    Free Cancellation
    Start From $134.95
    (Saving 10% ) $149.95
 
 

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

(4.3 of 1,471 reviews)

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

Free Cancellation
Start From $65.00
 
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

  • North America
  • Exellent1,471 reviews4.3

Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire th....

    Free Cancellation
    Start From $65.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 919 reviews)

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Free Cancellation
Start From $79.00
 
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

  • North America
  • Superb919 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Start From $79.00
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 823 reviews)

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

Free Cancellation
Start From $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • North America
  • Superb823 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $202.59
 
 

Puerto Vallarta, Luxury Sunset Sailing

(4.6 of 419 reviews)

Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium open bar, and top-tier service from our attentive crew. This i... More

Free Cancellation
Start From $99.00
 
Puerto Vallarta, Luxury Sunset Sailing Likely to Sell Out

Puerto Vallarta, Luxury Sunset Sailing

  • North America
  • Superb419 reviews4.6

Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamar....

    Free Cancellation
    Start From $99.00
 
 

Private Catamaran Escape for 2–6 Guests: Celebrate Your Way

(4.8 of 324 reviews)

Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re celebrating a bachelorette, a birthday, or simply enjoying time with your favorite people, this catamaran getaway for up to six gues... More

Free Cancellation
Private Tour
Start From $595.00
 
Private Catamaran Escape for 2–6 Guests: Celebrate Your Way Likely to Sell Out

Private Catamaran Escape for 2–6 Guests: Celebrate Your Way

  • North America
  • Superb324 reviews4.8

Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re ce....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 710 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Private Tour
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • North America
  • Superb710 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.7 of 556 reviews)

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This lively evening cruise invites solo travelers and groups alike to unwind with unlimited drinks—including Maui Brewing beers, wine... More

Free Cancellation
Private Tour
Start From $84.77
 
Waikiki Sunset Cocktail Sail with Open Bar Likely to Sell Out

Waikiki Sunset Cocktail Sail with Open Bar

  • North America
  • Superb556 reviews4.7

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This ....

    Free Cancellation
    Private Tour
    Start From $84.77
 
 

St. Augustine Live Music Cruise with Drinks and Sunset Option

(4.8 of 326 reviews)

**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** Sailing Catamaran tours will resume on March 2nd. Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all ... More

Free Cancellation
Private Tour
Start From $69.17
 
St. Augustine Live Music Cruise with Drinks and Sunset Option Likely to Sell Out

St. Augustine Live Music Cruise with Drinks and Sunset Option

  • North America
  • Superb326 reviews4.8

**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** S....

    Free Cancellation
    Private Tour
    Start From $69.17
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 621 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

Free Cancellation
Private Tour
Start From $45.00
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

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

  • North America
  • Exellent621 reviews4.5

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

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

Luxury Catamaran Whale Watch

(4.9 of 72 reviews)

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • North America
  • Superb72 reviews4.9

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 545 reviews)

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More

Free Cancellation
Private Tour
Start From $292.48
 
Kauai’s Na Pali Coast Snorkel and Sail Tour Likely to Sell Out

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • North America
  • Superb545 reviews4.8

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....

    Free Cancellation
    Private Tour
    Start From $292.48
 
 

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

(4.6 of 428 reviews)

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious catamaran, while Mother Nature prepares for her nightly performan... More

Free Cancellation
Private Tour
Start From $109.00
 
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar Likely to Sell Out

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

  • North America
  • Superb428 reviews4.6

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Half-Day Luxury Sailing Experience in Tulum with Open Bar

(4.2 of 250 reviews)

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More

Free Cancellation
Private Tour
Start From $149.00
 
Half-Day Luxury Sailing Experience in Tulum with Open Bar Likely to Sell Out

Half-Day Luxury Sailing Experience in Tulum with Open Bar

  • North America
  • Exellent250 reviews4.2

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Day's End Cocktail Sunset Sail

(4.7 of 71 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Free Cancellation
Private Tour
Start From $159.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • North America
  • Superb71 reviews4.7

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Private Tour
    Start From $159.00
 
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