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Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity.
 
-11% Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

(4.6 of 1,152 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

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Free Cancellation
Start From $45.31
(Saving 11% ) $50.71
 
-11% Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

  • North America
  • Superb1,152 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Special Offer
    Free Cancellation
    Start From $45.31
    (Saving 11% ) $50.71
 
 

Miami Millionaires Sightseeing Cruise

(4.3 of 1,547 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
 
Miami Millionaires Sightseeing Cruise

Miami Millionaires Sightseeing Cruise

  • North America
  • Exellent1,547 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
 
 
-15% Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

(4.7 of 1,343 reviews)

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

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Free Cancellation
Start From $68.60
(Saving 15% ) $80.71
 
-15% Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

  • North America
  • Superb1,343 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join ....

    Special Offer
    Free Cancellation
    Start From $68.60
    (Saving 15% ) $80.71
 
 

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

(4.6 of 3,430 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
  • Superb3,430 reviews4.6

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 1,527 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 Likely to Sell Out

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • North America
  • Superb1,527 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
 
 

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

(4.7 of 3,591 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
  • Superb3,591 reviews4.7

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

    Free Cancellation
    Start From $79.00
 
 

Kona Signature Catamaran Sunset Sail

(4.8 of 229 reviews)

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on d... More

Free Cancellation
Start From $109.00
 
Kona Signature Catamaran Sunset Sail Likely to Sell Out

Kona Signature Catamaran Sunset Sail

  • North America
  • Superb229 reviews4.8

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....

    Free Cancellation
    Start From $109.00
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,463 reviews)

Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. Swim alongside Hawaiian green sea turtles and vibrant tropical fis... More

Free Cancellation
Start From $49.95
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • North America
  • Superb1,463 reviews4.9

Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour....

    Free Cancellation
    Start From $49.95
 
 

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

(4.9 of 823 reviews)

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More

Free Cancellation
Start From $122.59
 
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres Likely to Sell Out

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

  • North America
  • Superb823 reviews4.9

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....

    Free Cancellation
    Start From $122.59
 
 

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

(4.9 of 2,219 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
 
Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail Likely to Sell Out

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

  • North America
  • Superb2,219 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 Small-Group Sunset Sail with Wine and Hors d'oeuvres

(4.9 of 1,386 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

Free Cancellation
Start From $135.00
 
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
  • Superb1,386 reviews4.9

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

    Free Cancellation
    Start From $135.00
 
 

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

(4.8 of 3,543 reviews)

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time to hang out in the pristine water and take it easy aboard the sailboat – you can snorkel with tropical fish, stand atop a paddleb... More

Free Cancellation
Start From $149.00
 
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Likely to Sell Out

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

  • North America
  • Superb3,543 reviews4.8

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time t....

    Free Cancellation
    Start From $149.00
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 108 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
  • Superb108 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 $199.00
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,367 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

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Free Cancellation
Start From $46.07
(Saving 20% ) $57.59
 
-20% 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
  • Superb4,367 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $46.07
    (Saving 20% ) $57.59
 
 

Pirate Ship Sunset Dinner and Show in Los Cabos

(4.3 of 677 reviews)

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that is the joy for children and grown-ups alike. Our pirates, dance, chant, climb the ropes, while you... More

Free Cancellation
Start From $99.00
 
Pirate Ship Sunset Dinner and Show in Los Cabos Likely to Sell Out

Pirate Ship Sunset Dinner and Show in Los Cabos

  • North America
  • Exellent677 reviews4.3

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....

    Free Cancellation
    Start From $99.00
 
 

Kauai: Leila Na Pali Sunset Dinner Sail

(4.7 of 530 reviews)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Free Cancellation
Start From $263.82
 
Kauai: Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Kauai: Leila Na Pali Sunset Dinner Sail

  • North America
  • Superb530 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Free Cancellation
    Start From $263.82
 
 

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

(4.5 of 329 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

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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
  • Exellent329 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
 
 

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(4.5 of 583 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 $35.00
 
Key West Reef Morning Snorkeling with Breakfast and Mimosas Likely to Sell Out

Key West Reef Morning Snorkeling with Breakfast and Mimosas

  • North America
  • Exellent583 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 $35.00
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.7 of 214 reviews)

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More

Free Cancellation
Start From $79.00
 
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed Likely to Sell Out

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • North America
  • Superb214 reviews4.7

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....

    Free Cancellation
    Start From $79.00
 
 

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

(4.9 of 855 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 $49.99
 
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
  • Superb855 reviews4.9

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

    Free Cancellation
    Start From $49.99
 
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