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Top 10 Best North America Sailing Trips

Found 724 Sailing Trips activities in North America. Sort by Popularity. - Page 26
 

Private 2 Hour Sailboat Sunset Charter

(5 of 2 reviews)

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and your guests! You'll sail around Shell Island into the Gulf of Mexico, while you enjoy dol... More

Free Cancellation
Private Tour
Start From $699.00
 
Private 2 Hour Sailboat Sunset Charter Likely to Sell Out

Private 2 Hour Sailboat Sunset Charter

  • North America
  • Superb2 reviews5

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

(4.5 of 4 reviews)

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience is amazing for you to relax and have fun. ... More

Free Cancellation
Private Tour
Start From $1,199.00
 
Explore Turtle Canyons Waikiki Snorkel and Sail Adventure Likely to Sell Out

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

  • North America
  • Exellent4 reviews4.5

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience ....

    Free Cancellation
    Private Tour
    Start From $1,199.00
 
 

Chicago Air & Water Show

(5 of 2 reviews)

Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chicago’s Air & Water Show from the Best Seat on the Lake! 10AM SAIL: Our first sail will depart at 10am sharp. Our first event wil... More

Free Cancellation
Private Tour
Start From $154.00
 
Chicago Air & Water Show Likely to Sell Out

Chicago Air & Water Show

  • North America
  • Superb2 reviews5

Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chic....

    Free Cancellation
    Private Tour
    Start From $154.00
 
 

Key West Private Charter: Sandbar and Snorkeling

(5 of 5 reviews)

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you t... More

Free Cancellation
Private Tour
Start From $950.00
 
Key West Private Charter: Sandbar and Snorkeling Likely to Sell Out

Key West Private Charter: Sandbar and Snorkeling

  • North America
  • Superb5 reviews5

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who wa....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Friday Night Waikiki Fireworks Sail

(3 of 1 review)

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a spectacular Hawaiian sunset and the Friday Night Fireworks onboard a luxury private yacht.... More

Free Cancellation
Private Tour
Start From $699.00
 
Friday Night Waikiki Fireworks Sail Likely to Sell Out

Friday Night Waikiki Fireworks Sail

  • North America

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

Bacalar - Gourmet Tour in Private Catamaran with Cocktails Included

(5 of 43 reviews)

During this experience you will try star dishes from the best restaurants in the area aboard a comfortable private boat. You will enjoy a rich signature cocktail bar while navigating the crystal clear waters of Bacalar with a fine... More

Free Cancellation
Private Tour
Start From $525.00
 
Bacalar - Gourmet Tour in Private Catamaran with Cocktails Included Likely to Sell Out

Bacalar - Gourmet Tour in Private Catamaran with Cocktails Includ....

  • North America
  • Superb43 reviews5

During this experience you will try star dishes from the best restaurants in the area aboard a comfo....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Jungle Tour In Cancun, drive a speedboat through the lagoon with your companion

(4.3 of 3 reviews)

Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick way to know Cancun and all its beauty. Here you will know the Nichupte Lagoon that is a marvelous lagoon in Mexico, here you will... More

Free Cancellation
Private Tour
Start From $55.00
 
Jungle Tour In Cancun, drive a speedboat through the lagoon with your companion Likely to Sell Out

Jungle Tour In Cancun, drive a speedboat through the lagoon with ....

  • North America
  • Exellent3 reviews4.3

Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Half-Day Private Snorkel Sailing Adventure in Cabo San Lucas

(4.3 of 3 reviews)

A Private Adventure with a scent of exclusivity. Go snorkeling in style with Premium Open bar and fine exquisite snacks. Discover Marine Life or bath in the Sea of Cortes. A fantastic Private Adventure.... More

Free Cancellation
Private Tour
Start From $940.00
 
Half-Day Private Snorkel Sailing Adventure in Cabo San Lucas Likely to Sell Out

Half-Day Private Snorkel Sailing Adventure in Cabo San Lucas

  • North America
  • Exellent3 reviews4.3

A Private Adventure with a scent of exclusivity. Go snorkeling in style with Premium Open bar and fi....

    Free Cancellation
    Private Tour
    Start From $940.00
 
 

Whale Shark Snorkel Experience in Cancun (Snack Lunch included)

(5 of 1 review)

Live this unique experience swimming beside a Whale shark an immense animal in the underwater world of the Caribbean Sea. The whale shark is an amazing animal whose main food is the placton, the largest fish in the world, and it i... More

Free Cancellation
Private Tour
Start From $189.00
 
Whale Shark Snorkel Experience in Cancun (Snack Lunch included) Likely to Sell Out

Whale Shark Snorkel Experience in Cancun (Snack Lunch included)

  • North America
  • Superb1 review5

Live this unique experience swimming beside a Whale shark an immense animal in the underwater world ....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Private Cabo San Lucas Sunset Cruise

(4.9 of 58 reviews)

You will enjoy watching the sun set on the horizon from your very own private boat with our accommodating and knowledgeable crew. Every tour includes sightseeing along the spectacular Finisterra Rocky point where you will see the ... More

Free Cancellation
Private Tour
Start From $600.00
 
Private Cabo San Lucas Sunset Cruise Likely to Sell Out

Private Cabo San Lucas Sunset Cruise

  • North America
  • Superb58 reviews4.9

You will enjoy watching the sun set on the horizon from your very own private boat with our accommod....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Top Tour Sail To Isla Mujeres By Catamaran Buffet And Drinks Included

(3 of 1 review)

Stop looking for the perfect tour to Isla mujeres, we are the best option. Why? With us you´ll have: 1.No long lines, direct access 2.Quality food 3.Quality drinks 4.Best Service 5.We will take you to special reefs where on... More

Free Cancellation
Private Tour
Start From $55.00
 
Top Tour Sail To Isla Mujeres By Catamaran Buffet And Drinks Included Likely to Sell Out

Top Tour Sail To Isla Mujeres By Catamaran Buffet And Drinks Incl....

  • North America

Stop looking for the perfect tour to Isla mujeres, we are the best option. Why? With us you´ll hav....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Cabo Catamaran Tour: Snorkeling & Unlimited Drinks Included

(3 of 1 review)

Discover the magic of Cabo San Lucas on this exhilarating catamaran cruise! Glide across the sparkling waters of the Pacific Ocean and the Sea of Cortez, where you’ll have the chance to snorkel and explore vibrant underwater lif... More

Free Cancellation
Private Tour
Start From $99.00
 
Cabo Catamaran Tour: Snorkeling & Unlimited Drinks Included Likely to Sell Out

Cabo Catamaran Tour: Snorkeling & Unlimited Drinks Included

  • North America

Discover the magic of Cabo San Lucas on this exhilarating catamaran cruise! Glide across the sparkli....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

(5 of 1 review)

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite Tour to Isla Mujeres provides full sailing, snorkeling & enough time to visit Isla Mujeres for shopping or just enjoy this wonderf... More

Free Cancellation
Private Tour
Start From $79.00
 
Cancun Half Day Sailing Cataman Cruise to Isla Mujeres Likely to Sell Out

Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

  • North America
  • Superb1 review5

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite ....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Private Catamaran: Snorkel, Swim and Dolphin Watching

(5 of 1 review)

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast. ... More

Free Cancellation
Private Tour
Start From $465.00
 
Private Catamaran: Snorkel, Swim and Dolphin Watching Likely to Sell Out

Private Catamaran: Snorkel, Swim and Dolphin Watching

  • North America
  • Superb1 review5

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion....

    Free Cancellation
    Private Tour
    Start From $465.00
 
 

Private Whale Watching Sailing Adventure

(3.5 of 2 reviews)

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for maj... More

Free Cancellation
Private Tour
Start From $695.00
 
Private Whale Watching Sailing Adventure Likely to Sell Out

Private Whale Watching Sailing Adventure

  • North America
  • Good2 reviews3.5

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback ....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas

(5 of 1 review)

Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show which is the joy of children and adults alike. Our pirates dance, sing, climb the ropes, while you enjoy the beautiful sunset and li... More

Free Cancellation
Private Tour
Start From $136.59
 
Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas Likely to Sell Out

Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas

  • North America
  • Superb1 review5

Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show whi....

    Free Cancellation
    Private Tour
    Start From $136.59
 
 

Romantic private night yacht (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 $438.00
 
Romantic private night yacht (1 ticket covers 1-6 ppl) Likely to Sell Out

Romantic private night yacht (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 $438.00
 
 

Shared Day Sail along Historic St Augustine Bayfront

(5 of 5 reviews)

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories on the sea. Our cruise is perfect for all water-lovers: families, couples, and friends. Some guests interact with the USCG licensed... More

Free Cancellation
Private Tour
Start From $129.00
 
Shared Day Sail along Historic St Augustine Bayfront Likely to Sell Out

Shared Day Sail along Historic St Augustine Bayfront

  • North America
  • Superb5 reviews5

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories o....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Sunset Cruise Tequila Tasting

(5 of 4 reviews)

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the history of one of Mexico's most iconic drinks, brought to you by Tequila Cabo Único and Sunrider. You'll get to know the iconic Cabo S... More

Free Cancellation
Private Tour
Start From $110.00
 
Sunset Cruise Tequila Tasting Likely to Sell Out

Sunset Cruise Tequila Tasting

  • North America
  • Superb4 reviews5

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the histo....

    Free Cancellation
    Private Tour
    Start From $110.00
 
 

Sailing Charter

(5 of 5 reviews)

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More

Free Cancellation
Private Tour
Start From $195.00
 
Sailing Charter Likely to Sell Out

Sailing Charter

  • North America
  • Superb5 reviews5

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....

    Free Cancellation
    Private Tour
    Start From $195.00
 
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