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Top 10 Best North America Sailing Trips

Found 639 Sailing Trips activities in North America. Sort by Popularity.
 

Isla Mujeres Luxury Catamaran Sailing plus Lunch and Open Bar

(4.7 of 3,061 reviews)

Join us for the Luxury Sailing Adventure to Isla Mujeres onboard a state of the art sailing catamaran. You'll explore some of the most beautiful locations along Cancun’s stunning Caribbean coastline where you will go snorkeling... More

Free Cancellation
Start From $149.00
 
Isla Mujeres Luxury Catamaran Sailing plus Lunch and Open Bar Likely to Sell Out

Isla Mujeres Luxury Catamaran Sailing plus Lunch and Open Bar

  • North America
  • Superb3,061 reviews4.7

Join us for the Luxury Sailing Adventure to Isla Mujeres onboard a state of the art sailing catamar....

    Free Cancellation
    Start From $149.00
 
 

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

(4.7 of 2,895 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 Full Bar, Live Music and Hors D'oeuvres Likely to Sell Out

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

  • North America
  • Superb2,895 reviews4.7

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

    Free Cancellation
    Start From $79.00
 
 

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

(4.8 of 2,392 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 $139.00
 
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Likely to Sell Out

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

  • North America
  • Superb2,392 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 $139.00
 
 

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

(4.9 of 1,713 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 $84.99
 
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
  • Superb1,713 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 $84.99
 
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 1,129 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 $211.99
 
Deluxe Na Pali Sunset Tour on the Lucky Lady Likely to Sell Out

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • North America
  • Superb1,129 reviews4.7

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

    Free Cancellation
    Start From $211.99
 
 

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

(4.3 of 1,168 reviews)

TRAVELER’S FAVORITE SNORKELING TRIP! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the ... More

Free Cancellation
Start From $65.00
 
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs Likely to Sell Out

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

  • North America
  • Exellent1,168 reviews4.3

TRAVELER’S FAVORITE SNORKELING TRIP! Set off for a great Adventure to the Caribbean and admire t....

    Free Cancellation
    Start From $65.00
 
 

Cabo San Lucas Sunset Sailing Shared Cruise

(4.9 of 663 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

Free Cancellation
Start From $105.00
 
Cabo San Lucas Sunset Sailing Shared Cruise Likely to Sell Out

Cabo San Lucas Sunset Sailing Shared Cruise

  • North America
  • Superb663 reviews4.9

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

    Free Cancellation
    Start From $105.00
 
 

OAHU CATAMARAN Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!!

(4.9 of 536 reviews)

Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985 and are proud to boast a perfect safety record. Passengers are limited to 50% of Coast Guard rated capacity for... More

Free Cancellation
Start From $54.95
 
OAHU CATAMARAN Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!! Likely to Sell Out

OAHU CATAMARAN Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!!

  • North America
  • Superb536 reviews4.9

Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island ....

    Free Cancellation
    Start From $54.95
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.7 of 1,304 reviews)

This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea turtle cleaning station. Our crew shows you not only turtles but also hidden creatures such as he’e (octopus) and ka hoku kai (st... More

Free Cancellation
Start From $84.77
 
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran Likely to Sell Out

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

  • North America
  • Superb1,304 reviews4.7

This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea t....

    Free Cancellation
    Start From $84.77
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 640 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling a... More

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb640 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Free Cancellation
    Start From $136.19
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 419 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 $240.86
 
Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Leila Na Pali Sunset Dinner Sail

  • North America
  • Superb419 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 $240.86
 
 

Na Pali Coast Kauai Snorkel and Sail

(4.8 of 487 reviews)

Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and comfortable 50’ Kauai-built sailing catamaran, Leila. Let’s explore the cliffs, valleys, sea caves and wildlife of the Napali... More

Free Cancellation
Start From $275.28
 
Na Pali Coast Kauai Snorkel and Sail Likely to Sell Out

Na Pali Coast Kauai Snorkel and Sail

  • North America
  • Superb487 reviews4.8

Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....

    Free Cancellation
    Start From $275.28
 
 

Puerto Vallarta, Luxury Sunset Sailing

(4.6 of 301 reviews)

Puerto Vallarta is known for beautiful sunsets and there is nothing more tranquil and romantic than sailing across Banderas Bay as the crimson sun dips into the deep blue waters of the Pacific. Imagine relaxing on the deck of a lu... More

Free Cancellation
Start From $79.00
 
Puerto Vallarta, Luxury Sunset Sailing Likely to Sell Out

Puerto Vallarta, Luxury Sunset Sailing

  • North America
  • Superb301 reviews4.6

Puerto Vallarta is known for beautiful sunsets and there is nothing more tranquil and romantic than ....

    Free Cancellation
    Start From $79.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 702 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
  • Superb702 reviews4.9

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

    Free Cancellation
    Start From $79.00
 
 

Invisible Boat Snorkeling Tour

(4.5 of 264 reviews)

PERFECT FOR ALL TRAVELERS! Hope on aboard a unique experience in the only 100% transparent boat in the World. This is definitely one of the most original snorkeling tours in Cozumel. Discover shipwrecks, multicoloured fish, cora... More

Free Cancellation
Start From $49.99
 
Invisible Boat Snorkeling Tour Likely to Sell Out

Invisible Boat Snorkeling Tour

  • North America
  • Exellent264 reviews4.5

PERFECT FOR ALL TRAVELERS! Hope on aboard a unique experience in the only 100% transparent boat in ....

    Free Cancellation
    Start From $49.99
 
 

2-Hour Whale Watching from Oahu

(4.5 of 583 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

Free Cancellation
Start From $47.00
 
2-Hour Whale Watching from Oahu Likely to Sell Out

2-Hour Whale Watching from Oahu

  • North America
  • Exellent583 reviews4.5

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

    Free Cancellation
    Start From $47.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 410 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters a... More

Free Cancellation
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb410 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Free Cancellation
    Start From $177.73
 
 

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

(4.7 of 1,992 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Start From $108.62
 
Waikiki Catamaran Adventure: Snorkel with Sea Turtles Likely to Sell Out

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

  • North America
  • Superb1,992 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Start From $108.62
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 555 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • North America
  • Superb555 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Start From $89.00
 
 

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

(4.9 of 560 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 $116.10
 
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
  • Superb560 reviews4.9

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

    Free Cancellation
    Start From $116.10
 
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