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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 20
 

Clear Boat to Cabo Lands End, The Arch and more

(4.5 of 17 reviews)

Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most uniquely, in a clear boat. You will take a tour just where the Pacific Ocean meets the Sea of Cortez, the famous Lands End. In our... More

Free Cancellation
Start From $39.00
 
Clear Boat to Cabo Lands End, The Arch and more

Clear Boat to Cabo Lands End, The Arch and more

  • North America
  • Exellent17 reviews4.5

Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most ....

    Free Cancellation
    Start From $39.00
 
 

Pirate Ship Premium Dinner Cruise with Show

(4.4 of 34 reviews)

While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent views of Banderas Bay, take unforgettable photos of this amazing experience, while you taste a delicious dinner and have a good time ... More

Free Cancellation
Start From $150.00
 
Pirate Ship Premium Dinner Cruise with Show

Pirate Ship Premium Dinner Cruise with Show

  • North America
  • Exellent34 reviews4.4

While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent vie....

    Free Cancellation
    Start From $150.00
 
 

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

(4 of 3 reviews)

Welcome to an incredible adventure, if what you like is getting to know new places and being in contact with nature, then this activity is for you. We will take you to know the second largest coral reef in the world, the first one... More

Free Cancellation
Start From $44.25
 
Guided Tour of Puerto Morelos Reefs with Snorkeling Experience Likely to Sell Out

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

  • North America
  • Very Good3 reviews4

Welcome to an incredible adventure, if what you like is getting to know new places and being in cont....

    Free Cancellation
    Start From $44.25
 
 

All Inclusive Full Day and Sunset Private Catamaran in St. Pete

(4 of 3 reviews)

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks,... More

Free Cancellation
Private Tour
Start From $2,200.00
 
All Inclusive Full Day and Sunset Private Catamaran in St. Pete Likely to Sell Out

All Inclusive Full Day and Sunset Private Catamaran in St. Pete

  • North America
  • Very Good3 reviews4

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and cr....

    Free Cancellation
    Private Tour
    Start From $2,200.00
 
 

Bacalar Private Sailing Tour : cervezas & Snack with Pickup

(5 of 20 reviews)

Discover Bacalar Lagoon like no other tour. Our experiences are responsibly crafted to offer a truly unique adventure. Visit hidden, less-explored spots and enjoy the lagoon with skilled captains and crew fluent in Spanish, Englis... More

Free Cancellation
Private Tour
Start From $252.25
 
Bacalar Private Sailing Tour : cervezas & Snack with Pickup Likely to Sell Out

Bacalar Private Sailing Tour : cervezas & Snack with Pickup

  • North America
  • Superb20 reviews5

Discover Bacalar Lagoon like no other tour. Our experiences are responsibly crafted to offer a truly....

    Free Cancellation
    Private Tour
    Start From $252.25
 
 

Captain Steve's Sailing Experience on Long Island

(5 of 11 reviews)

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, you can experience the beauty of the area from a unique perspecti... More

Free Cancellation
Private Tour
Start From $550.00
 
Captain Steve's Sailing Experience on Long Island Likely to Sell Out

Captain Steve's Sailing Experience on Long Island

  • North America
  • Superb11 reviews5

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best ....

    Free Cancellation
    Private Tour
    Start From $550.00
 
 

Afternoon Ali'i Adventure

(5 of 6 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Free Cancellation
Private Tour
Start From $276.00
 
Afternoon Ali'i Adventure Likely to Sell Out

Afternoon Ali'i Adventure

  • North America
  • Superb6 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Free Cancellation
    Private Tour
    Start From $276.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 127 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and bec... More

Special Offer
Free Cancellation
Private Tour
Start From $225.00
(Saving 10% ) $250.00
 
-10% Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • North America
  • Superb127 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $225.00
    (Saving 10% ) $250.00
 
 

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

(5 of 6 reviews)

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in the picturesque views of St. Michaels, MD. Your journey includes gliding throu... More

Special Offer
Free Cancellation
Private Tour
Start From $160.00
(Saving inf% ) $0.00
 
-inf% 2-Hour Relaxing Chesapeake Day Sail on Lady Patty Likely to Sell Out

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

  • North America
  • Superb6 reviews5

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise of....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $160.00
    (Saving inf% ) $0.00
 
 

Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar

(5 of 1 review)

Experience Cabo San Lucas like never before on your private catamaran at sunset. Unlike crowded group tours, this 2-hour cruise is exclusive to your party, giving you space to relax, celebrate, and enjoy the views in privacy. Sai... More

Special Offer
Free Cancellation
Private Tour
Start From $1,200.00
(Saving inf% ) $0.00
 
-inf% Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar Likely to Sell Out

Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar

  • North America
  • Superb1 review5

Experience Cabo San Lucas like never before on your private catamaran at sunset. Unlike crowded grou....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,200.00
    (Saving inf% ) $0.00
 
 

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

(5 of 125 reviews)

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some goo... More

Special Offer
Free Cancellation
Private Tour
Start From $525.00
(Saving inf% ) $0.00
 
-inf% Private Hilton Head Sunset Sailing Tour with Dolphin Watching Likely to Sell Out

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

  • North America
  • Superb125 reviews5

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $525.00
    (Saving inf% ) $0.00
 
 

Fort Lauderdale Sailing Charter

(5 of 401 reviews)

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a beautiful blend of natural mangroves, luxurious waterfront homes, and ... More

Special Offer
Free Cancellation
Private Tour
Start From $200.00
(Saving inf% ) $0.00
 
-inf% Fort Lauderdale Sailing Charter Likely to Sell Out

Fort Lauderdale Sailing Charter

  • North America
  • Superb401 reviews5

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $200.00
    (Saving inf% ) $0.00
 
 

Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres

(5 of 401 reviews)

Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise departing from the historic Key West Seaport. As the sails are raised and the breeze carries you across the sparkling Gulf waters, unwi... More

Special Offer
Free Cancellation
Private Tour
Start From $129.99
(Saving inf% ) $0.00
 
-inf% Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres Likely to Sell Out

Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres

  • North America
  • Superb401 reviews5

Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise depar....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $129.99
    (Saving inf% ) $0.00
 
 

2 Hour Sailing Lesson in Wrightsville Beach

(5 of 8 reviews)

Experience the thrill of sailing a 26' performance keelboat! Our knowledgeable captains will take you around the waterways of Wrightsville Beach and out into the Atlantic Ocean. You have the freedom to make this a learning experie... More

Special Offer
Free Cancellation
Private Tour
Start From $360.00
(Saving inf% ) $0.00
 
-inf% 2 Hour Sailing Lesson in Wrightsville Beach Likely to Sell Out

2 Hour Sailing Lesson in Wrightsville Beach

  • North America
  • Superb8 reviews5

Experience the thrill of sailing a 26' performance keelboat! Our knowledgeable captains will take yo....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $360.00
    (Saving inf% ) $0.00
 
 

Whale Watching Sailboat Tour in San Jose del Cabo

(5 of 3 reviews)

Join us at the marina for a brief orientation before boarding the vessel. As we set sail, you'll cruise past the iconic landmarks of San José del Cabo. Like the Estuary a bird sanctuary and the amazing coastline of the Sea of Cor... More

Special Offer
Free Cancellation
Private Tour
Start From $149.00
(Saving inf% ) $0.00
 
-inf% Whale Watching Sailboat Tour in San Jose del Cabo Likely to Sell Out

Whale Watching Sailboat Tour in San Jose del Cabo

  • North America
  • Superb3 reviews5

Join us at the marina for a brief orientation before boarding the vessel. As we set sail, you'll cru....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $149.00
    (Saving inf% ) $0.00
 
 

Old Plank Adventures: Sail into Deep Tranquility

(5 of 2 reviews)

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica Bay and beyond. Founded by Captain & Chef Matthew Manc... More

Special Offer
Free Cancellation
Private Tour
Start From $400.00
(Saving inf% ) $0.00
 
-inf% Old Plank Adventures: Sail into Deep Tranquility Likely to Sell Out

Old Plank Adventures: Sail into Deep Tranquility

  • North America
  • Superb2 reviews5

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, de....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $400.00
    (Saving inf% ) $0.00
 
 

Afternoon Sail With the Whales from Lahaina Harbor

(5 of 1 review)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Special Offer
Free Cancellation
Private Tour
Start From $100.22
(Saving inf% ) $0.00
 
-inf% Afternoon Sail With the Whales from Lahaina Harbor Likely to Sell Out

Afternoon Sail With the Whales from Lahaina Harbor

  • North America
  • Superb1 review5

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $100.22
    (Saving inf% ) $0.00
 
 

Sunset Yacht Cruise | Champagne Included | San Diego Bay

(5 of 1 review)

What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group tour. You will be sailing aboard a beautifully crafted French yacht designed for... More

Special Offer
Free Cancellation
Private Tour
Start From $300.00
(Saving inf% ) $0.00
 
-inf% Sunset Yacht Cruise | Champagne Included | San Diego Bay Likely to Sell Out

Sunset Yacht Cruise | Champagne Included | San Diego Bay

  • North America
  • Superb1 review5

What makes this experience truly special is the blend of refined European luxury and a relaxed, inti....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $300.00
    (Saving inf% ) $0.00
 
 

Private Sunset Sail in San Diego Up to 6 guests

(5 of 73 reviews)

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking to experience the bay from the water. Relax while our licensed captain handles... More

Special Offer
Free Cancellation
Private Tour
Start From $297.50
(Saving inf% ) $0.00
 
-inf% Private Sunset Sail in San Diego Up to 6 guests Likely to Sell Out

Private Sunset Sail in San Diego Up to 6 guests

  • North America
  • Superb73 reviews5

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perf....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $297.50
    (Saving inf% ) $0.00
 
 

Luxury Snorkel Adventure in Cabo

(4.8 of 57 reviews)

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at either one of this beach areas is where boat captain will make a stop for snorkeling at one ... More

Special Offer
Free Cancellation
Private Tour
Start From $134.10
(Saving 10% ) $149.00
 
-10% Luxury Snorkel Adventure in Cabo Likely to Sell Out

Luxury Snorkel Adventure in Cabo

  • North America
  • Superb57 reviews4.8

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $134.10
    (Saving 10% ) $149.00
 
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