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Top 10 Best North America Sailing Trips

Found 719 Sailing Trips activities in North America. Sort by Popularity. - Page 2
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.8 of 1,575 reviews)

This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s local favorite ARVO Café, served with a selection of Anahola Granola bars—Original, Chocolate Chip, Tropical, and Mango & Ginger. ... More

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

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

  • North America
  • Superb1,575 reviews4.8

This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s loc....

    Free Cancellation
    Start From $89.56
 
 

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

(4.9 of 760 reviews)

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More

Free Cancellation
Start From $54.99
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

  • North America
  • Superb760 reviews4.9

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....

    Free Cancellation
    Start From $54.99
 
 
-8% Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 507 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 $43.10
(Saving 8% ) $47.00
 
-8% Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

  • North America
  • Superb507 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 $43.10
    (Saving 8% ) $47.00
 
 

Kona Catamaran Sunset Sail

(4.8 of 179 reviews)

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Free Cancellation
Start From $128.14
 
Kona Catamaran Sunset Sail

Kona Catamaran Sunset Sail

  • North America
  • Superb179 reviews4.8

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....

    Free Cancellation
    Start From $128.14
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 586 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

Free Cancellation
Start From $65.00
 
Evening Colors Sunset Sail Tour in Seattle

Evening Colors Sunset Sail Tour in Seattle

  • North America
  • Superb586 reviews4.8

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

    Free Cancellation
    Start From $65.00
 
 

Sunset Windjammer Cruise Along the Coast of Portland Maine

(4.8 of 136 reviews)

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

Free Cancellation
Start From $75.00
 
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

  • North America
  • Superb136 reviews4.8

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to exper....

    Free Cancellation
    Start From $75.00
 
 

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

(4.8 of 3,229 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 $149.00
 
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Likely to Sell Out

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

  • North America
  • Superb3,229 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 $149.00
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 588 reviews)

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Free Cancellation
Start From $99.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • North America
  • Superb588 reviews4.9

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....

    Free Cancellation
    Start From $99.00
 
 

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

(4.7 of 2,103 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

Free Cancellation
Start From $109.00
 
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed Likely to Sell Out

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

  • North America
  • Superb2,103 reviews4.7

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

    Free Cancellation
    Start From $109.00
 
 

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

(4.3 of 1,389 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 $59.00
 
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs Likely to Sell Out

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

  • North America
  • Exellent1,389 reviews4.3

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

    Free Cancellation
    Start From $59.00
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 508 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

Free Cancellation
Start From $263.82
 
Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Leila Na Pali Sunset Dinner Sail

  • North America
  • Superb508 reviews4.7

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

    Free Cancellation
    Start From $263.82
 
 

Sightseeing Day Sail around Boston Harbor

(4.8 of 539 reviews)

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

Free Cancellation
Start From $66.54
 
Sightseeing Day Sail around Boston Harbor Likely to Sell Out

Sightseeing Day Sail around Boston Harbor

  • North America
  • Superb539 reviews4.8

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....

    Free Cancellation
    Start From $66.54
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 218 reviews)

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

Special Offer
Free Cancellation
Start From $107.10
(Saving 10% ) $119.00
 
-10% Deluxe Sunset & Day Sail Small Group Likely to Sell Out

Deluxe Sunset & Day Sail Small Group

  • North America
  • Superb218 reviews5

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....

    Special Offer
    Free Cancellation
    Start From $107.10
    (Saving 10% ) $119.00
 
 

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(4.5 of 549 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

Free Cancellation
Start From $35.00
 
Key West Reef Morning Snorkeling with Breakfast and Mimosas Likely to Sell Out

Key West Reef Morning Snorkeling with Breakfast and Mimosas

  • North America
  • Exellent549 reviews4.5

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

    Free Cancellation
    Start From $35.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 874 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 Likely to Sell Out

Sunset Sail in Key West with Beverages Included

  • North America
  • Superb874 reviews4.9

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

    Free Cancellation
    Start From $79.00
 
 

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

(4.9 of 1,296 reviews)

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

Free Cancellation
Start From $115.00
 
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres Likely to Sell Out

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

  • North America
  • Superb1,296 reviews4.9

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....

    Free Cancellation
    Start From $115.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 516 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 Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb516 reviews4.9

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

    Free Cancellation
    Start From $177.73
 
 

50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party!

(4.3 of 43 reviews)

Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never before! Perfect for any special occasion, this VIP experience promises unforgettable memories Adventure Highlights Biscayne Bay ... More

Free Cancellation
Private Tour
Start From $599.99
 
50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party! Likely to Sell Out

50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party!

  • North America
  • Exellent43 reviews4.3

Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never....

    Free Cancellation
    Private Tour
    Start From $599.99
 
 

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

(4.8 of 2,117 reviews)

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes unlimited drinks from an open bar, accompanied by a delightful menu of small b... More

Free Cancellation
Private Tour
Start From $109.00
 
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar Likely to Sell Out

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

  • North America
  • Superb2,117 reviews4.8

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 33 reviews)

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Free Cancellation
Private Tour
Start From $183.08
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • North America
  • Superb33 reviews4.9

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Private Tour
    Start From $183.08
 
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