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Top 10 Best North America Sailing Trips

Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 12
 

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

(5 of 88 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

Free Cancellation
Private Tour
Start From $499.99
 
Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

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

  • North America
  • Superb88 reviews5

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

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Sunset Sail in the Gulf of Mexico for up to 6 Guests

(5 of 3 reviews)

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the sun dips below the horizon. For two and a half hours, enjoy the stunning views along Fort ... More

Free Cancellation
Private Tour
Start From $149.00
 
Sunset Sail in the Gulf of Mexico for up to 6 Guests Likely to Sell Out

Sunset Sail in the Gulf of Mexico for up to 6 Guests

  • North America
  • Superb3 reviews5

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the roman....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor

(4.7 of 158 reviews)

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More

Free Cancellation
Private Tour
Start From $159.00
 
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor Likely to Sell Out

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....

  • North America
  • Superb158 reviews4.7

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Waikiki 3pm Tradewind Sail - Open Bar Included

(4.8 of 245 reviews)

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphin... More

Free Cancellation
Private Tour
Start From $53.36
 
Waikiki 3pm Tradewind Sail - Open Bar Included Likely to Sell Out

Waikiki 3pm Tradewind Sail - Open Bar Included

  • North America
  • Superb245 reviews4.8

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....

    Free Cancellation
    Private Tour
    Start From $53.36
 
 

Sail & Splash Excursion in Ft. Lauderdale

(4.8 of 270 reviews)

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran, the Spirit of Lauderdale. Enjoy one of the best cruise Ft Lauderdale has to offer . Sit back... More

Free Cancellation
Private Tour
Start From $99.00
 
Sail & Splash Excursion in Ft. Lauderdale Likely to Sell Out

Sail & Splash Excursion in Ft. Lauderdale

  • North America
  • Superb270 reviews4.8

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

(4.9 of 45 reviews)

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More

Free Cancellation
Private Tour
Start From $63.00
 
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms Likely to Sell Out

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

  • North America
  • Superb45 reviews4.9

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....

    Free Cancellation
    Private Tour
    Start From $63.00
 
 

LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

(5 of 2 reviews)

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and the Captain. Enjoy a stunning 1 hr private romantic night cruise and sea life discovery aboard... More

Free Cancellation
Private Tour
Start From $134.00
 
LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl Likely to Sell Out

LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

  • North America
  • Superb2 reviews5

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht....

    Free Cancellation
    Private Tour
    Start From $134.00
 
 

Sunset Sail Tour

(4.9 of 90 reviews)

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, engage on this classic 42 ft yacht, that accommodates a 6 passenger maximum for an intimate cruise through the waters of Wrightsvill... More

Free Cancellation
Private Tour
Start From $115.00
 
Sunset Sail Tour Likely to Sell Out

Sunset Sail Tour

  • North America
  • Superb90 reviews4.9

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, enga....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Tall Ship Silva Sailing Cruise Ft. a Live Musician

(4.2 of 289 reviews)

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More

Free Cancellation
Private Tour
Start From $39.89
 
Tall Ship Silva Sailing Cruise Ft. a Live Musician Likely to Sell Out

Tall Ship Silva Sailing Cruise Ft. a Live Musician

  • North America
  • Exellent289 reviews4.2

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....

    Free Cancellation
    Private Tour
    Start From $39.89
 
 

NYC Statue of Liberty Tall Ship Sail aboard Clipper City

(4.3 of 265 reviews)

Step aboard the majestic Clipper City and feel the city fade into the background as the wind fills the sails. Glide through New York Harbor in style, with the Brooklyn Bridge, Statue of Liberty, Ellis Island, and the glittering Ma... More

Free Cancellation
Private Tour
Start From $68.00
 
NYC Statue of Liberty Tall Ship Sail aboard Clipper City Likely to Sell Out

NYC Statue of Liberty Tall Ship Sail aboard Clipper City

  • North America
  • Exellent265 reviews4.3

Step aboard the majestic Clipper City and feel the city fade into the background as the wind fills t....

    Free Cancellation
    Private Tour
    Start From $68.00
 
 

Romantic Dinner on a Spanish Galeon in Cancun

(4.3 of 23 reviews)

Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner with the most wonderful scenary. This is the perfect opportunity to enjoy a delicious dinner while you fall in love with the liv... More

Free Cancellation
Private Tour
Start From $95.00
 
Romantic Dinner on a Spanish Galeon in Cancun Likely to Sell Out

Romantic Dinner on a Spanish Galeon in Cancun

  • North America
  • Exellent23 reviews4.3

Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Jungle Tour

(5 of 1 review)

This boat and snorkeling tour from Cancun gives you a 2-for-1 value—take a speedboat ride through Nichupte Lagoon and snorkel in the El Angel coral reef. Choose to take the driver’s seat or ride shotgun in a 2-seat speedboat a... More

Free Cancellation
Private Tour
Start From $70.00
 
Jungle Tour Likely to Sell Out

Jungle Tour

  • North America
  • Superb1 review5

This boat and snorkeling tour from Cancun gives you a 2-for-1 value—take a speedboat ride through ....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Suncoast Sailing's Day Sailing Experience!

(4.9 of 104 reviews)

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. Feel the wind as it glides us through the picturesque waters of Treasure Island and Gulf of Mexico. Come face to face with nature a... More

Free Cancellation
Private Tour
Start From $64.99
 
Suncoast Sailing's Day Sailing Experience! Likely to Sell Out

Suncoast Sailing's Day Sailing Experience!

  • North America
  • Superb104 reviews4.9

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. F....

    Free Cancellation
    Private Tour
    Start From $64.99
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 516 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
Private Tour
Start From $263.82
 
Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Leila Na Pali Sunset Dinner Sail

  • North America
  • Superb516 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $263.82
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 810 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Private Tour
Start From $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • North America
  • Superb810 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Private Tour
    Start From $202.59
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 708 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
Private Tour
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
  • Superb708 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Mexico City: Xochimilco at sunrise + Breakfast and transportation

(5 of 97 reviews)

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for the environment. This is not the traditional Xochimilco of the trajineras;... More

Free Cancellation
Private Tour
Start From $162.72
 
Mexico City: Xochimilco at sunrise + Breakfast and transportation Likely to Sell Out

Mexico City: Xochimilco at sunrise + Breakfast and transportation

  • North America
  • Superb97 reviews5

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural....

    Free Cancellation
    Private Tour
    Start From $162.72
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.7 of 147 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
Private Tour
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
  • Superb147 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 245 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 adve... More

Free Cancellation
Private Tour
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
  • Superb245 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

El Cielo Cozumel Snorkeling trip by Catamaran

(4.4 of 275 reviews)

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More

Free Cancellation
Private Tour
Start From $95.00
 
El Cielo Cozumel Snorkeling trip by Catamaran Likely to Sell Out

El Cielo Cozumel Snorkeling trip by Catamaran

  • North America
  • Exellent275 reviews4.4

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....

    Free Cancellation
    Private Tour
    Start From $95.00
 
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