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Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 2
 

Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu

(4.7 of 625 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 $58.64
 
Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu

Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu

  • North America
  • Superb625 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 $58.64
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 748 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 $65.22
 
Evening Colors Sunset Sail Tour in Seattle

Evening Colors Sunset Sail Tour in Seattle

  • North America
  • Superb748 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 $65.22
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,793 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
  • Superb1,793 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
 
 

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

(4.9 of 1,022 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
  • Superb1,022 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
 
 

Sunset Windjammer Cruise Along the Coast of Portland Maine

(4.7 of 225 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 $77.00
 
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

  • North America
  • Superb225 reviews4.7

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

    Free Cancellation
    Start From $77.00
 
 

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

(4.7 of 627 reviews)

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Spacious 45-foot catamaran with near 360 degree view -Families welcome: Keiki ra... More

Free Cancellation
Start From $84.77
 
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

  • North America
  • Superb627 reviews4.7

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boardi....

    Free Cancellation
    Start From $84.77
 
 

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(4.5 of 743 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 $53.70
 
Key West Reef Morning Snorkeling with Breakfast and Mimosas

Key West Reef Morning Snorkeling with Breakfast and Mimosas

  • North America
  • Exellent743 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 $53.70
 
 

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

(4.6 of 88 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
 
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

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

  • North America
  • Superb88 reviews4.6

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

    Free Cancellation
    Start From $141.98
 
 

City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

(4.5 of 580 reviews)

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such as Seaport Village, Shelter Island, and the ship-building docks. Gaze at the scenic... More

Free Cancellation
Start From $38.33
 
City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

  • North America
  • Exellent580 reviews4.5

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, thi....

    Free Cancellation
    Start From $38.33
 
 

Monterey Bay Whale Watching

(4.6 of 397 reviews)

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More

Free Cancellation
Start From $69.95
 
Monterey Bay Whale Watching

Monterey Bay Whale Watching

  • North America
  • Superb397 reviews4.6

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....

    Free Cancellation
    Start From $69.95
 
 

St. Augustine Live Music Sail with Drinks & Sunset Option

(4.8 of 425 reviews)

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised, or unwind on a 90-minute After Dark Live Music Cruise (no sailin... More

Free Cancellation
Start From $66.49
 
St. Augustine Live Music Sail with Drinks & Sunset Option

St. Augustine Live Music Sail with Drinks & Sunset Option

  • North America
  • Superb425 reviews4.8

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience!....

    Free Cancellation
    Start From $66.49
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.5 of 491 reviews)

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

Free Cancellation
Start From $59.07
 
Key West Afternoon Reef Snorkeling with Open Bar

Key West Afternoon Reef Snorkeling with Open Bar

  • North America
  • Exellent491 reviews4.5

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....

    Free Cancellation
    Start From $59.07
 
 

Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

(5 of 95 reviews)

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More

Free Cancellation
Start From $242.60
 
Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

  • North America
  • Superb95 reviews5

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....

    Free Cancellation
    Start From $242.60
 
 

Afternoon Windjammer Cruise Along the Coast of Portland Maine

(4.7 of 309 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
Start From $69.00
 
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

  • North America
  • Superb309 reviews4.7

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

    Free Cancellation
    Start From $69.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 221 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views ... More

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb221 reviews4.9

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $61.50
 
 

Sailing on Historic Schooner Yacht in Salem, MA

(4.9 of 326 reviews)

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More

Free Cancellation
Start From $58.44
 
Sailing on Historic Schooner Yacht in Salem, MA

Sailing on Historic Schooner Yacht in Salem, MA

  • North America
  • Superb326 reviews4.9

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....

    Free Cancellation
    Start From $58.44
 
 

Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

(4.9 of 591 reviews)

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Red Hill Area lava arches — underwater volcanic terrain, weather per... More

Free Cancellation
Start From $178.72
 
Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

  • North America
  • Superb591 reviews4.9

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 â....

    Free Cancellation
    Start From $178.72
 
 

Happy Hour Sunset Sail on Maui's Luxury Catamaran

(4.8 of 102 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted drinks, vibrant music, and a relaxed-yet-refined vibe that turns every pour ... More

Free Cancellation
Start From $169.00
 
Happy Hour Sunset Sail on Maui's Luxury Catamaran

Happy Hour Sunset Sail on Maui's Luxury Catamaran

  • North America
  • Superb102 reviews4.8

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

    Free Cancellation
    Start From $169.00
 
 

El Cielo Snorkel by Private Boat

(4.8 of 377 reviews)

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine white sandy beach away from the crowds - Taste a delicious fish ceviche and co... More

Free Cancellation
Private Tour
Start From $499.99
 
El Cielo Snorkel by Private Boat

El Cielo Snorkel by Private Boat

  • North America
  • Superb377 reviews4.8

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 862 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
Private Tour
Start From $213.41
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • North America
  • Superb862 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $213.41
 
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