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Top 10 Best North America Sailing Trips

Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 33
 

Private Sunset Sail for 3-6 People

(4.7 of 12 reviews)

Experience a private group charter with up to six passengers while sailing along the San Diego Bay. If you’re looking for a night of family fun, or to celebrate with your friends look no further. Leave your worries behind as yo... More

Free Cancellation
Private Tour
Start From $776.00
 
Private Sunset Sail for 3-6 People

Private Sunset Sail for 3-6 People

  • North America
  • Superb12 reviews4.7

Experience a private group charter with up to six passengers while sailing along the San Diego Bay.....

    Free Cancellation
    Private Tour
    Start From $776.00
 
 

Key West Haunted Night Sail on Schooner America 2.0

(4.7 of 12 reviews)

Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under the Key West night sky. During this night boat ride, we'll cruise through the waters of Key West while listening to mysterious t... More

Free Cancellation
Private Tour
Start From $88.15
 
Key West Haunted Night Sail on Schooner America 2.0

Key West Haunted Night Sail on Schooner America 2.0

  • North America
  • Superb12 reviews4.7

Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under....

    Free Cancellation
    Private Tour
    Start From $88.15
 
 

San Diego Private Morning Sail up to 12 guests

(5 of 30 reviews)

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More

Free Cancellation
Private Tour
Start From $235.00
 
San Diego Private Morning Sail up to 12 guests

San Diego Private Morning Sail up to 12 guests

  • North America
  • Superb30 reviews5

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....

    Free Cancellation
    Private Tour
    Start From $235.00
 
 

Private Charter Snorkel Sail Adventure off Kaanapali Beach

(5 of 30 reviews)

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘H... More

Free Cancellation
Private Tour
Start From $6,301.24
 
Private Charter Snorkel Sail Adventure off Kaanapali Beach

Private Charter Snorkel Sail Adventure off Kaanapali Beach

  • North America
  • Superb30 reviews5

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....

    Free Cancellation
    Private Tour
    Start From $6,301.24
 
 

Private Long Island Sound Sailing Experience

(5 of 30 reviews)

Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled between Great Neck's Kings Point and Port Washington's Sands Point. Oogle at the multi million dollar Mansions lining the coast un... More

Free Cancellation
Private Tour
Start From $650.00
 
Private Long Island Sound Sailing Experience

Private Long Island Sound Sailing Experience

  • North America
  • Superb30 reviews5

Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled ....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

Private Sailing for up to 10 people 4 hrs

(5 of 30 reviews)

Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to have fun with your friends in private. It is a charming classic-style sailboat, where you can enjoy the pleasure of sailing thro... More

Free Cancellation
Private Tour
Start From $1,216.00
 
Private Sailing for up to 10 people 4 hrs

Private Sailing for up to 10 people 4 hrs

  • North America
  • Superb30 reviews5

Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to....

    Free Cancellation
    Private Tour
    Start From $1,216.00
 
 

Luxury Yacht 58 ft for up to 20 people 4 hrs

(5 of 30 reviews)

Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard this luxury yacht along the coast of Bahía de Banderas. You will enjoy every moment and every place in this tropical paradise. L... More

Free Cancellation
Private Tour
Start From $4,100.00
 
Luxury Yacht 58 ft for up to 20 people 4 hrs Likely to Sell Out

Luxury Yacht 58 ft for up to 20 people 4 hrs

  • North America
  • Superb30 reviews5

Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard ....

    Free Cancellation
    Private Tour
    Start From $4,100.00
 
 

3-Night Private Charter in Lake Clark National Park

(5 of 2 reviews)

An exciting private adventure exploring Lake Clark in the luxury of our 50ft sailing catamaran, the only live aboard yacht on Lake Clark. Enjoy meals prepared by your onboard chef. Relax in our beanbags and hammocks while enjoyin... More

Free Cancellation
Private Tour
Start From $17,000.00
 
3-Night Private Charter in Lake Clark National Park Likely to Sell Out

3-Night Private Charter in Lake Clark National Park

  • North America
  • Superb2 reviews5

An exciting private adventure exploring Lake Clark in the luxury of our 50ft sailing catamaran, the ....

    Free Cancellation
    Private Tour
    Start From $17,000.00
 
 

Monday Ladies Night Sail- Charleston's Luxury Catamaran w/Bar

(5 of 2 reviews)

Mermaid Monday Ladies’ Night Sail: Fun, Friends & Fabulous Harbor Views Calling all ladies! Mermaid Monday is Charleston’s hottest ladies' night, and you’re invited to join the fun. With $10 off regular tickets and irresisti... More

Free Cancellation
Private Tour
Start From $50.00
 
Monday Ladies Night Sail- Charleston's Luxury Catamaran w/Bar Likely to Sell Out

Monday Ladies Night Sail- Charleston's Luxury Catamaran w/Bar

  • North America
  • Superb2 reviews5

Mermaid Monday Ladies’ Night Sail: Fun, Friends & Fabulous Harbor Views Calling all ladies! Mermai....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

Private tour at Sea of Cortés: Sunset tour or Snorkel

(5 of 2 reviews)

We kick off our day with the best available transportation service for our clients, featuring brand-new, fully-equipped vehicles for your comfort. Upon arriving at Puerto Los Cabos Marina, our sailboat will be waiting to begin the... More

Free Cancellation
Private Tour
Start From $1,019.00
 
Private tour at Sea of Cortés: Sunset tour or Snorkel Likely to Sell Out

Private tour at Sea of Cortés: Sunset tour or Snorkel

  • North America
  • Superb2 reviews5

We kick off our day with the best available transportation service for our clients, featuring brand-....

    Free Cancellation
    Private Tour
    Start From $1,019.00
 
 

Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats

(5 of 2 reviews)

Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water toys. Relax and listen to music in the shade. Barbecue lunch or dinner and watch the sunset. Swim off the Slide Boat or relax on o... More

Free Cancellation
Private Tour
Start From $350.00
 
Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats Likely to Sell Out

Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats

  • North America
  • Superb2 reviews5

Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water ....

    Free Cancellation
    Private Tour
    Start From $350.00
 
 

Scientific and Cultural Tour in Bacalar with an Expert

(5 of 1 review)

Embark on an exclusive journey to the enchanting Bacalar Lagoon with our private tour, guided by a local expert and dedicated naturalist committed to the preservation and study of this unique ecosystem. Our guide, fluent in Englis... More

Free Cancellation
Private Tour
Start From $313.71
 
Scientific and Cultural Tour in Bacalar with an Expert Likely to Sell Out

Scientific and Cultural Tour in Bacalar with an Expert

  • North America
  • Superb1 review5

Embark on an exclusive journey to the enchanting Bacalar Lagoon with our private tour, guided by a l....

    Free Cancellation
    Private Tour
    Start From $313.71
 
 

Platinum Private Catamaran Sailing Tour

(5 of 3 reviews)

If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the dates of December 15th thru April 15th, you can enjoy this amazing adventure for 2 hours departing at 09:00 am in the morning. If... More

Free Cancellation
Private Tour
Start From $237.00
 
Platinum Private Catamaran Sailing Tour Likely to Sell Out

Platinum Private Catamaran Sailing Tour

  • North America
  • Superb3 reviews5

If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the....

    Free Cancellation
    Private Tour
    Start From $237.00
 
 

Adult Only - Cabo San Lucas Romantic Sunset Cruise

(3 of 1 review)

Finding the right for you Sunset Cruise experience can be sometimes overwhelming and more in a destination as diverse as Los Cabos. This experience offers the perfect blend of relaxation, not crowded, Adult only, laid-back fun, de... More

Free Cancellation
Private Tour
Start From $199.00
 
Adult Only - Cabo San Lucas Romantic Sunset Cruise Likely to Sell Out

Adult Only - Cabo San Lucas Romantic Sunset Cruise

  • North America

Finding the right for you Sunset Cruise experience can be sometimes overwhelming and more in a desti....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Private Sunset Sail for Two

(5 of 5 reviews)

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More

Free Cancellation
Private Tour
Start From $462.00
 
Private Sunset Sail for Two Likely to Sell Out

Private Sunset Sail for Two

  • North America
  • Superb5 reviews5

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....

    Free Cancellation
    Private Tour
    Start From $462.00
 
 

Nights of Lights Sailboat Tour St Augustine Sailing

(5 of 3 reviews)

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More

Free Cancellation
Private Tour
Start From $774.00
 
Nights of Lights Sailboat Tour St Augustine Sailing Likely to Sell Out

Nights of Lights Sailboat Tour St Augustine Sailing

  • North America
  • Superb3 reviews5

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....

    Free Cancellation
    Private Tour
    Start From $774.00
 
 

Private 3 hour Bird Watching Tour in Monterey Bay

(5 of 1 review)

Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail is much quieter and therefore up close encounters with seabirds are common. This tour is great for birders who are looking for an ... More

Free Cancellation
Private Tour
Start From $950.00
 
Private 3 hour Bird Watching Tour in Monterey Bay Likely to Sell Out

Private 3 hour Bird Watching Tour in Monterey Bay

  • North America
  • Superb1 review5

Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail ....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Magic Night Boat Dinner with Show & Speedboat Experience at Cancun (1 day tour)

(5 of 1 review)

Discover the magic of the Caribbean Sea with two of the most popular tours in Cancun. If you are looking for an exciting activity, experience an intrepid adventure in our guided speed boat and snorkeling tour. Our speed boats ar... More

Free Cancellation
Private Tour
Start From $180.00
 
Magic Night Boat Dinner with Show & Speedboat Experience at Cancun (1 day tour) Likely to Sell Out

Magic Night Boat Dinner with Show & Speedboat Experience at Cancu....

  • North America
  • Superb1 review5

Discover the magic of the Caribbean Sea with two of the most popular tours in Cancun. If you are l....

    Free Cancellation
    Private Tour
    Start From $180.00
 
 

Waikiki private Day Tour and Sunset sail for couples

(5 of 12 reviews)

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples on their honeymoon, celebrating an Anniversary, or just in love, celebrating ... More

Free Cancellation
Private Tour
Start From $300.00
 
Waikiki private Day Tour and Sunset sail for couples Likely to Sell Out

Waikiki private Day Tour and Sunset sail for couples

  • North America
  • Superb12 reviews5

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

Public Schooner Sail in Greenport

(5 of 12 reviews)

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. U... More

Free Cancellation
Private Tour
Start From $130.00
 
Public Schooner Sail in Greenport Likely to Sell Out

Public Schooner Sail in Greenport

  • North America
  • Superb12 reviews5

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands d....

    Free Cancellation
    Private Tour
    Start From $130.00
 
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