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Top 10 Best North America Sailing Trips

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

Official Miami Millionaires Sightseeing Cruise

(4.3 of 1,186 reviews)

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More

Free Cancellation
Start From $18.00
 
Official Miami Millionaires Sightseeing Cruise

Official Miami Millionaires Sightseeing Cruise

  • North America
  • Exellent1,186 reviews4.3

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....

    Free Cancellation
    Start From $18.00
 
 

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

(4.7 of 3,341 reviews)

Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — with the option to choose between an Adults Only or Family Friendly experience. Snorkel in warm, crystalline waters, then savor a del... More

Free Cancellation
Start From $129.00
 
Isla Mujeres Luxury Sailing: Adults Only or Family Friendly Likely to Sell Out

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

  • North America
  • Superb3,341 reviews4.7

Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — wit....

    Free Cancellation
    Start From $129.00
 
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 1,420 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

Special Offer
Free Cancellation
Start From $200.57
(Saving 10% ) $222.86
 
-10% Deluxe Na Pali Sunset Tour on the Lucky Lady Likely to Sell Out

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • North America
  • Superb1,420 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $200.57
    (Saving 10% ) $222.86
 
 

Hear the whales! World class whale watching!

(4.8 of 5 reviews)

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky to get the rare opportunity to hear the whale songs live! Our RABEN (Me... More

Free Cancellation
Start From $99.00
 
Hear the whales! World class whale watching! Likely to Sell Out

Hear the whales! World class whale watching!

  • North America
  • Superb5 reviews4.8

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade h....

    Free Cancellation
    Start From $99.00
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,342 reviews)

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and enjoy the best of what Panama City Beach has to offer! Cruise over to Shell Island where you and the... More

Free Cancellation
Start From $57.59
 
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....

  • North America
  • Superb4,342 reviews4.9

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....

    Free Cancellation
    Start From $57.59
 
 

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

(4.9 of 2,112 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Free Cancellation
Start From $89.99
 
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast Likely to Sell Out

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

  • North America
  • Superb2,112 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Free Cancellation
    Start From $89.99
 
 

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

(4.7 of 3,395 reviews)

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More

Free Cancellation
Start From $79.00
 
Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres Likely to Sell Out

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

  • North America
  • Superb3,395 reviews4.7

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....

    Free Cancellation
    Start From $79.00
 
 

Waikiki Turtle Snorkeling Boat Tour and Adventure

(4.7 of 1,189 reviews)

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **Waikiki coastlin... More

Free Cancellation
Start From $68.60
 
Waikiki Turtle Snorkeling Boat Tour and Adventure Likely to Sell Out

Waikiki Turtle Snorkeling Boat Tour and Adventure

  • North America
  • Superb1,189 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-ho....

    Free Cancellation
    Start From $68.60
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,188 reviews)

2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURSION in the US!! Best value in Waikiki! See turtles GUARANTEED or receive a FULL REFUND! Brand new PREMIUM snorkel equipment inclu... More

Free Cancellation
Start From $44.95
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • North America
  • Superb1,188 reviews4.9

2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURS....

    Free Cancellation
    Start From $44.95
 
 

Key West Signature Sunset Sail with Live Music, Open Bar & Food

(4.5 of 292 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Special Offer
Free Cancellation
Start From $64.80
(Saving 10% ) $72.00
 
-10% Key West Signature Sunset Sail with Live Music, Open Bar & Food Likely to Sell Out

Key West Signature Sunset Sail with Live Music, Open Bar & Food

  • North America
  • Exellent292 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....

    Special Offer
    Free Cancellation
    Start From $64.80
    (Saving 10% ) $72.00
 
 

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

(4.6 of 258 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
  • Superb258 reviews4.6

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

    Free Cancellation
    Start From $199.00
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 588 reviews)

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More

Free Cancellation
Start From $44.00
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....

  • North America
  • Exellent588 reviews4.5

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....

    Free Cancellation
    Start From $44.00
 
 

Sunset & Dolphin Catamaran Cruise with Island Time

(4.9 of 1,855 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 $57.59
 
Sunset & Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Sunset & Dolphin Catamaran Cruise with Island Time

  • North America
  • Superb1,855 reviews4.9

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

    Free Cancellation
    Start From $57.59
 
 

St. Augustine Live Music Sunset Sail with Drinks Included

(4.8 of 254 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 Likely to Sell Out

St. Augustine Live Music Sunset Sail with Drinks Included

  • North America
  • Superb254 reviews4.8

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

    Free Cancellation
    Start From $69.17
 
 

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

(4.6 of 413 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
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
  • Superb413 reviews4.6

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....

    Free Cancellation
    Start From $109.00
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.8 of 77 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 $199.00
 
Turtles & Tacos Luxury Catamaran Snorkel Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • North America
  • Superb77 reviews4.8

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

    Free Cancellation
    Start From $199.00
 
 

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

(4.1 of 599 reviews)

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More

Free Cancellation
Start From $70.00
 
1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain Likely to Sell Out

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

  • North America
  • Exellent599 reviews4.1

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....

    Free Cancellation
    Start From $70.00
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 380 reviews)

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More

Free Cancellation
Start From $149.00
 
Waikoloa Signature Catamaran Sunset Sail Likely to Sell Out

Waikoloa Signature Catamaran Sunset Sail

  • North America
  • Superb380 reviews4.7

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....

    Free Cancellation
    Start From $149.00
 
 

Day's End Cocktail Sunset Sail

(4.7 of 52 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
Start From $159.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • North America
  • Superb52 reviews4.7

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

    Free Cancellation
    Start From $159.00
 
 

San Francisco Bay Cruise

(4.4 of 301 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
Start From $39.00
 
San Francisco Bay Cruise Likely to Sell Out

San Francisco Bay Cruise

  • North America
  • Exellent301 reviews4.4

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

    Free Cancellation
    Start From $39.00
 
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