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Top 10 Best North America Sailing Trips

Found 701 Sailing Trips activities in North America. Sort by Popularity. - Page 2
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 1,358 reviews)

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

Free Cancellation
Start From $222.86
 
Deluxe Na Pali Sunset Tour on the Lucky Lady

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • North America
  • Superb1,358 reviews4.7

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....

    Free Cancellation
    Start From $222.86
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 48 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

Free Cancellation
Start From $169.00
 
Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel

  • North America
  • Superb48 reviews4.7

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

    Free Cancellation
    Start From $169.00
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 468 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

Free Cancellation
Start From $47.00
 
Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

  • North America
  • Superb468 reviews4.7

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

    Free Cancellation
    Start From $47.00
 
 

St. Augustine Live Music Sunset Sail with Drinks Included

(4.7 of 207 reviews)

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

Free Cancellation
Start From $69.17
 
St. Augustine Live Music Sunset Sail with Drinks Included

St. Augustine Live Music Sunset Sail with Drinks Included

  • North America
  • Superb207 reviews4.7

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....

    Free Cancellation
    Start From $69.17
 
 

Tall Ship Silva Sailing Cruise Ft. a Live Musician

(4.2 of 229 reviews)

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More

Free Cancellation
Start From $40.36
 
Tall Ship Silva Sailing Cruise Ft. a Live Musician

Tall Ship Silva Sailing Cruise Ft. a Live Musician

  • North America
  • Exellent229 reviews4.2

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....

    Free Cancellation
    Start From $40.36
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 800 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
  • Superb800 reviews4.7

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

    Free Cancellation
    Start From $202.59
 
 

Seattle Sunset Sail BYOB

(4.9 of 137 reviews)

Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunset Sail is powered by the wind, so it is extremally Eco-Friendly. We are one of the only cruises in the area that allow you to brin... More

Free Cancellation
Start From $71.00
 
Seattle Sunset Sail BYOB Likely to Sell Out

Seattle Sunset Sail BYOB

  • North America
  • Superb137 reviews4.9

Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunse....

    Free Cancellation
    Start From $71.00
 
 

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

(4.5 of 40 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
  • Exellent40 reviews4.5

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
 
 

Waikiki Catamaran Turtle Snorkel Sail

(4.7 of 2,095 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
Private Tour
Start From $109.00
 
Waikiki Catamaran Turtle Snorkel Sail Likely to Sell Out

Waikiki Catamaran Turtle Snorkel Sail

  • North America
  • Superb2,095 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Boston Harbor Sunset Sail Tour

(4.8 of 93 reviews)

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

Free Cancellation
Private Tour
Start From $82.27
 
Boston Harbor Sunset Sail Tour Likely to Sell Out

Boston Harbor Sunset Sail Tour

  • North America
  • Superb93 reviews4.8

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....

    Free Cancellation
    Private Tour
    Start From $82.27
 
 

Classic Tall Ship Cruise in Boston Harbor

(4.7 of 533 reviews)

Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeatable views of the ci... More

Free Cancellation
Private Tour
Start From $35.00
 
Classic Tall Ship Cruise in Boston Harbor Likely to Sell Out

Classic Tall Ship Cruise in Boston Harbor

  • North America
  • Superb533 reviews4.7

Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Ge....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 171 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

Free Cancellation
Private Tour
Start From $119.00
 
Deluxe Sunset & Day Sail Small Group Likely to Sell Out

Deluxe Sunset & Day Sail Small Group

  • North America
  • Superb171 reviews5

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

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Day's End Cocktail Sunset Sail

(4.7 of 41 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 $149.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • North America
  • Superb41 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 $149.00
 
 

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

(4.3 of 1,356 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
Private Tour
Start From $65.00
 
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs Likely to Sell Out

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

  • North America
  • Exellent1,356 reviews4.3

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

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

(4.6 of 400 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
  • Superb400 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
 
 

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

(4.9 of 698 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
Private Tour
Start From $64.98
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB Likely to Sell Out

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

  • North America
  • Superb698 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $64.98
 
 

Afternoon Windjammer Cruise Along the Coast of Portland Maine

(4.7 of 126 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,... More

Free Cancellation
Private Tour
Start From $67.00
 
Afternoon Windjammer Cruise Along the Coast of Portland Maine Likely to Sell Out

Afternoon Windjammer Cruise Along the Coast of Portland Maine

  • North America
  • Superb126 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $67.00
 
 

San Francisco Bay Cruise

(4.4 of 278 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
Private Tour
Start From $39.00
 
San Francisco Bay Cruise Likely to Sell Out

San Francisco Bay Cruise

  • North America
  • Exellent278 reviews4.4

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

    Free Cancellation
    Private Tour
    Start From $39.00
 
 

Sunset Sail from Traverse City with Food, Wine & Cocktails

(4.8 of 198 reviews)

Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stories about the history of the lands, people, and waters of the Grand Traverse Bay area. Enjoy complimentary locally sourced food, w... More

Free Cancellation
Private Tour
Start From $199.00
 
Sunset Sail from Traverse City with Food, Wine & Cocktails Likely to Sell Out

Sunset Sail from Traverse City with Food, Wine & Cocktails

  • North America
  • Superb198 reviews4.8

Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stor....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 495 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
Private Tour
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
  • Superb495 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $177.73
 
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