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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

Akialoa Mā’alaea Sunset Sail

(4.9 of 30 reviews)

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More

Free Cancellation
Start From $108.11
 
Akialoa Mā’alaea Sunset Sail

Akialoa Mā’alaea Sunset Sail

  • North America
  • Superb30 reviews4.9

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....

    Free Cancellation
    Start From $108.11
 
 

Best of Halifax Harbour Boat Tour

(4.9 of 104 reviews)

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed harbour tour as they share Halifax's history and present day facts!... More

Free Cancellation
Start From $43.46
 
Best of Halifax Harbour Boat Tour

Best of Halifax Harbour Boat Tour

  • North America
  • Superb104 reviews4.9

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside ....

    Free Cancellation
    Start From $43.46
 
 

New York Sunset Schooner Cruise on the Hudson River

(4.9 of 234 reviews)

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More

Free Cancellation
Start From $90.12
 
New York Sunset Schooner Cruise on the Hudson River

New York Sunset Schooner Cruise on the Hudson River

  • North America
  • Superb234 reviews4.9

Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....

    Free Cancellation
    Start From $90.12
 
 
-10% Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 417 reviews)

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More

Special Offer
Free Cancellation
Start From $143.10
(Saving 10% ) $159.00
 
-10% Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail

  • North America
  • Superb417 reviews4.7

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....

    Special Offer
    Free Cancellation
    Start From $143.10
    (Saving 10% ) $159.00
 
 
-inf% Kauai’s Na Pali Coast Snorkel and Sail Tour

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 572 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

Special Offer
Free Cancellation
Start From $292.48
(Saving inf% ) $0.00
 
-inf% Kauai’s Na Pali Coast Snorkel and Sail Tour

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • North America
  • Superb572 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $292.48
    (Saving inf% ) $0.00
 
 
-6% Shared Snorkeling Tour Playa El Cielo in Cozumel

Shared Snorkeling Tour Playa El Cielo in Cozumel

(4.9 of 96 reviews)

We offer a tour with all security measures Our Guides are fully certified Visits to the Palancar reefs, Arrecife Colombia, as well as the visit to the Sea Turtle Sanctuary is one of the best experiences you can have. Our staff wil... More

Special Offer
Free Cancellation
Start From $46.92
(Saving 6% ) $49.68
 
-6% Shared Snorkeling Tour Playa El Cielo in Cozumel

Shared Snorkeling Tour Playa El Cielo in Cozumel

  • North America
  • Superb96 reviews4.9

We offer a tour with all security measures Our Guides are fully certified Visits to the Palancar ree....

    Special Offer
    Free Cancellation
    Start From $46.92
    (Saving 6% ) $49.68
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 649 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

Special Offer
Free Cancellation
Start From $109.00
(Saving inf% ) $0.00
 
-inf% Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • North America
  • Superb649 reviews4.9

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

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

Key West Dolphin and Snorkel Experience

(4.4 of 370 reviews)

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More

Special Offer
Free Cancellation
Start From $69.82
(Saving inf% ) $0.00
 
-inf% Key West Dolphin and Snorkel Experience Likely to Sell Out

Key West Dolphin and Snorkel Experience

  • North America
  • Exellent370 reviews4.4

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....

    Special Offer
    Free Cancellation
    Start From $69.82
    (Saving inf% ) $0.00
 
 

Chicago's Fireworks Show aboard Tall Ship Windy!

(4.7 of 25 reviews)

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Special Offer
Free Cancellation
Start From $113.73
(Saving inf% ) $0.00
 
-inf% Chicago's Fireworks Show aboard Tall Ship Windy! Likely to Sell Out

Chicago's Fireworks Show aboard Tall Ship Windy!

  • North America
  • Superb25 reviews4.7

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....

    Special Offer
    Free Cancellation
    Start From $113.73
    (Saving inf% ) $0.00
 
 

Seattle's Original Sunset Sail (Est. 1984) - 70ft Boat - BYOB

(4.9 of 226 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

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Free Cancellation
Start From $71.00
(Saving inf% ) $0.00
 
-inf% Seattle's Original Sunset Sail (Est. 1984) - 70ft Boat - BYOB Likely to Sell Out

Seattle's Original Sunset Sail (Est. 1984) - 70ft Boat - BYOB

  • North America
  • Superb226 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $71.00
    (Saving inf% ) $0.00
 
 

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

(4.4 of 392 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Special Offer
Free Cancellation
Start From $57.32
(Saving inf% ) $0.00
 
-inf% Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

  • North America
  • Exellent392 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Special Offer
    Free Cancellation
    Start From $57.32
    (Saving inf% ) $0.00
 
 

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

(5 of 40 reviews)

Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and a beautiful Hawaiian sunset in one unforgettable trip. Start your adventure at Turtle Canyon, where you c... More

Special Offer
Free Cancellation
Start From $119.00
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise Likely to Sell Out

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

  • North America
  • Superb40 reviews5

Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adv....

    Special Offer
    Free Cancellation
    Start From $119.00
    (Saving inf% ) $0.00
 
 

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

(4.8 of 53 reviews)

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More

Special Offer
Free Cancellation
Start From $57.24
(Saving inf% ) $0.00
 
-inf% Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport Likely to Sell Out

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

  • North America
  • Superb53 reviews4.8

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....

    Special Offer
    Free Cancellation
    Start From $57.24
    (Saving inf% ) $0.00
 
 

Buccaneer Pirate Cruise in Destin

(4.8 of 143 reviews)

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger buccaneers into pirate training, sword fights, water gun battles, and a search for un... More

Special Offer
Free Cancellation
Start From $55.00
(Saving inf% ) $0.00
 
-inf% Buccaneer Pirate Cruise in Destin Likely to Sell Out

Buccaneer Pirate Cruise in Destin

  • North America
  • Superb143 reviews4.8

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew ....

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

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

(4.9 of 121 reviews)

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More

Special Offer
Free Cancellation
Start From $163.20
(Saving inf% ) $0.00
 
-inf% Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar Likely to Sell Out

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

  • North America
  • Superb121 reviews4.9

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....

    Special Offer
    Free Cancellation
    Start From $163.20
    (Saving inf% ) $0.00
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.5 of 37 reviews)

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More

Special Offer
Free Cancellation
Start From $101.95
(Saving 15% ) $119.95
 
-15% Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village Likely to Sell Out

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

  • North America
  • Exellent37 reviews4.5

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Special Offer
    Free Cancellation
    Start From $101.95
    (Saving 15% ) $119.95
 
 

BOAT to Espiritu Santo Island and Balandra

(4.8 of 22 reviews)

Swim with sea lions and get to know Isla Espiritu Santo and Balandra from another perspective accompanied by MARINE BIOLOGISTS guides in a super comfortable yacht, with full bath and not by boat, which gives a plus to your adventu... More

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Free Cancellation
Start From $156.84
(Saving inf% ) $0.00
 
-inf% BOAT to Espiritu Santo Island and Balandra Likely to Sell Out

BOAT to Espiritu Santo Island and Balandra

  • North America
  • Superb22 reviews4.8

Swim with sea lions and get to know Isla Espiritu Santo and Balandra from another perspective accomp....

    Special Offer
    Free Cancellation
    Start From $156.84
    (Saving inf% ) $0.00
 
 

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

(4.9 of 133 reviews)

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board for all. Experienced crew will point out wild life, tell you history of our area and show... More

Special Offer
Free Cancellation
Start From $78.00
(Saving inf% ) $0.00
 
-inf% Day Sails and Sunset tours on Schooner Surprise in Camden Maine Likely to Sell Out

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

  • North America
  • Superb133 reviews4.9

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at ....

    Special Offer
    Free Cancellation
    Start From $78.00
    (Saving inf% ) $0.00
 
 

Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

(5 of 106 reviews)

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view of the Manhattan skyline, Freedom Tower, Brooklyn Bridge, Empire ... More

Special Offer
Free Cancellation
Private Tour
Start From $499.99
(Saving inf% ) $0.00
 
-inf% Best Private Luxury Daytime Boat Tour in New York City - 2 Hour Likely to Sell Out

Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

  • North America
  • Superb106 reviews5

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manh....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $499.99
    (Saving inf% ) $0.00
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 711 reviews)

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Special Offer
Free Cancellation
Private Tour
Start From $129.00
(Saving inf% ) $0.00
 
-inf% Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • North America
  • Superb711 reviews4.8

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $129.00
    (Saving inf% ) $0.00
 
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