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Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 3
 

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

(4.9 of 47 reviews)

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing the beautiful ʻAuʻau Channel, surrounded by the s... More

Free Cancellation
Start From $126.82
 
Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

  • North America
  • Superb47 reviews4.9

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing ....

    Free Cancellation
    Start From $126.82
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 425 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

Free Cancellation
Start From $159.00
 
Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail

  • North America
  • Superb425 reviews4.7

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

    Free Cancellation
    Start From $159.00
 
 

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,518 reviews)

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either 55-ft open-style catamaran or 50-ft double-decker power catamaran and ... More

Free Cancellation
Start From $80.71
 
Waikiki 2 hour Turtle Canyon Snorkeling Adventure

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

  • North America
  • Superb1,518 reviews4.7

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cr....

    Free Cancellation
    Start From $80.71
 
 

San Diego Whale Watching Cruise

(4.8 of 2,544 reviews)

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we received a 100 percent success rate during winter whale watching when spotting the K... More

Free Cancellation
Start From $85.00
 
San Diego Whale Watching Cruise

San Diego Whale Watching Cruise

  • North America
  • Superb2,544 reviews4.8

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the opt....

    Free Cancellation
    Start From $85.00
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 372 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
Start From $119.00
 
Deluxe Sunset & Day Sail Small Group

Deluxe Sunset & Day Sail Small Group

  • North America
  • Superb372 reviews5

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

    Free Cancellation
    Start From $119.00
 
 

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

(4.9 of 2,145 reviews)

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More

Free Cancellation
Start From $41.73
 
Dolphin Sunset Cruise in Panama City Beach on the

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

  • North America
  • Superb2,145 reviews4.9

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....

    Free Cancellation
    Start From $41.73
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 661 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
  • Superb661 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
 
 

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

(4.5 of 310 reviews)

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and breeze on your face, dance ... More

Free Cancellation
Start From $199.00
 
Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef Likely to Sell Out

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

  • North America
  • Exellent310 reviews4.5

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quali....

    Free Cancellation
    Start From $199.00
 
 

2.5-Hour Small-Group Catamaran Sail with Drinks

(5 of 374 reviews)

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. Designed for comfort and stability, these modern catamarans featu... More

Free Cancellation
Start From $119.00
 
2.5-Hour Small-Group Catamaran Sail with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sail with Drinks

  • North America
  • Superb374 reviews5

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....

    Free Cancellation
    Start From $119.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 991 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
  • Superb991 reviews4.9

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

    Free Cancellation
    Start From $79.00
 
 

Shared Snorkeling Tour Playa El Cielo in Cozumel

(4.9 of 127 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

Free Cancellation
Start From $52.00
 
Shared Snorkeling Tour Playa El Cielo in Cozumel Likely to Sell Out

Shared Snorkeling Tour Playa El Cielo in Cozumel

  • North America
  • Superb127 reviews4.9

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

    Free Cancellation
    Start From $52.00
 
 

Cozumel ClearBoat Adventure with Snorkeling

(4.3 of 317 reviews)

Perfect For Families and Couples! Hope on aboard a unique experience in the only 100% transparent boat in the World. This is definitely a one of a kind snorkel tour in Cozumel. Discover shipwrecks, multicolored fish, coral reefs... More

Special Offer
Free Cancellation
Start From $39.15
(Saving 13% ) $45.00
 
-13% Cozumel ClearBoat Adventure with Snorkeling Likely to Sell Out

Cozumel ClearBoat Adventure with Snorkeling

  • North America
  • Exellent317 reviews4.3

Perfect For Families and Couples! Hope on aboard a unique experience in the only 100% transparent b....

    Special Offer
    Free Cancellation
    Start From $39.15
    (Saving 13% ) $45.00
 
 

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

(4.8 of 2,435 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

Special Offer
Free Cancellation
Start From $82.00
(Saving inf% ) $0.00
 
-inf% 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
  • Superb2,435 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $82.00
    (Saving inf% ) $0.00
 
 

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

(4.9 of 40 reviews)

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More

Special Offer
Free Cancellation
Start From $203.16
(Saving inf% ) $0.00
 
-inf% Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali Likely to Sell Out

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

  • North America
  • Superb40 reviews4.9

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Special Offer
    Free Cancellation
    Start From $203.16
    (Saving inf% ) $0.00
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.7 of 437 reviews)

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More

Special Offer
Free Cancellation
Start From $129.00
(Saving inf% ) $0.00
 
-inf% 2-Hour Sunset Sail on the San Francisco Bay Likely to Sell Out

2-Hour Sunset Sail on the San Francisco Bay

  • North America
  • Superb437 reviews4.7

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

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

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

(4.9 of 1,484 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

Special Offer
Free Cancellation
Start From $135.00
(Saving inf% ) $0.00
 
-inf% 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
  • Superb1,484 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $135.00
    (Saving inf% ) $0.00
 
 

Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

(4.9 of 138 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Special Offer
Free Cancellation
Start From $269.00
(Saving inf% ) $0.00
 
-inf% Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion Likely to Sell Out

Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

  • North America
  • Superb138 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Special Offer
    Free Cancellation
    Start From $269.00
    (Saving inf% ) $0.00
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 376 reviews)

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More

Special Offer
Free Cancellation
Start From $84.15
(Saving 15% ) $99.00
 
-15% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon Likely to Sell Out

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • North America
  • Superb376 reviews4.8

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....

    Special Offer
    Free Cancellation
    Start From $84.15
    (Saving 15% ) $99.00
 
 

Cabo San Lucas Sunset Sailing Shared Cruise

(4.9 of 825 reviews)

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San Lucas amazing waters. This is a family-friendly tour and includes... More

Special Offer
Free Cancellation
Start From $96.00
(Saving 20% ) $120.00
 
-20% Cabo San Lucas Sunset Sailing Shared Cruise Likely to Sell Out

Cabo San Lucas Sunset Sailing Shared Cruise

  • North America
  • Superb825 reviews4.9

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....

    Special Offer
    Free Cancellation
    Start From $96.00
    (Saving 20% ) $120.00
 
 

Boat to Isla Espíritu Santo and Balandra

(4.9 of 38 reviews)

Nothing with sea lions and get to know Espíritu Santo Island and Balandra from another perspective accompanied by MARINE BIOLOGISTS guides on a super comfortable yacht-type boat, with a full bathroom and not in a small boat, whic... More

Special Offer
Free Cancellation
Start From $142.82
(Saving inf% ) $0.00
 
-inf% Boat to Isla Espíritu Santo and Balandra Likely to Sell Out

Boat to Isla Espíritu Santo and Balandra

  • North America
  • Superb38 reviews4.9

Nothing with sea lions and get to know Espíritu Santo Island and Balandra from another perspective ....

    Special Offer
    Free Cancellation
    Start From $142.82
    (Saving inf% ) $0.00
 
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