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Top 10 Best North America Sailing Trips

Found 705 Sailing Trips activities in North America. Sort by Popularity. - Page 12
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 83 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Free Cancellation
Start From $289.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • North America
  • Superb83 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Free Cancellation
    Start From $289.00
 
 

Sailing Tour through the Lagoon of the 7 Colors

(4.9 of 1,056 reviews)

Sail with people who share your passion for adventure! You will explore fascinating places along the lagoon of the 7 colors. Our small groups guarantee you excellent attention and service from our crew. Disconnect from the world ... More

Free Cancellation
Start From $37.00
 
Sailing Tour through the Lagoon of the 7 Colors

Sailing Tour through the Lagoon of the 7 Colors

  • North America
  • Superb1,056 reviews4.9

Sail with people who share your passion for adventure! You will explore fascinating places along the....

    Free Cancellation
    Start From $37.00
 
 

El Cielo Cozumel Snorkeling by Private Boat

(4.8 of 134 reviews)

TRAVELER'S FAVORITE EXPERIENCE! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private tour will take you out to the most renowned r... More

Special Offer
Free Cancellation
Private Tour
Start From $710.10
(Saving 10% ) $789.00
 
-10% El Cielo Cozumel Snorkeling by Private Boat Likely to Sell Out

El Cielo Cozumel Snorkeling by Private Boat

  • North America
  • Superb134 reviews4.8

TRAVELER'S FAVORITE EXPERIENCE! Have fun aboard your Private boat and experience Cozumel water trea....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $710.10
    (Saving 10% ) $789.00
 
 

Marina Del Rey Luxury Yacht Experience

(4.8 of 134 reviews)

Step aboard a privately chartered yacht and explore the tranquil beauty of Marina del Rey from the water. This curated experience blends the ease of smooth, wave-free cruising with the timeless appeal of golden sunsets, marine wil... More

Free Cancellation
Private Tour
Start From $125.00
 
Marina Del Rey Luxury Yacht Experience Likely to Sell Out

Marina Del Rey Luxury Yacht Experience

  • North America
  • Superb134 reviews4.8

Step aboard a privately chartered yacht and explore the tranquil beauty of Marina del Rey from the w....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Sunset Sail Aboard the 47 ft Daydreams Sailboat

(4.9 of 17 reviews)

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Sail Aboard the 47 ft Daydreams Sailboat Likely to Sell Out

Sunset Sail Aboard the 47 ft Daydreams Sailboat

  • North America
  • Superb17 reviews4.9

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

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

(4.9 of 729 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
Private Tour
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
  • Superb729 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $116.10
 
 

Snorkel & Millionaire Row - Private Miami Boat Tour w/ Drinks

(4.8 of 266 reviews)

Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of friends, bachelorette parties, and anyone looking to celebrate in style. Cruise the sparkling waters of Miami while enjoying your ... More

Free Cancellation
Private Tour
Start From $375.00
 
Snorkel & Millionaire Row - Private Miami Boat Tour w/ Drinks Likely to Sell Out

Snorkel & Millionaire Row - Private Miami Boat Tour w/ Drinks

  • North America
  • Superb266 reviews4.8

Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of f....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

(4.8 of 45 reviews)

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying on the bow relaxing under the stars, this moonlight sail is ultimate freedom! ... More

Free Cancellation
Private Tour
Start From $73.95
 
JFarwell Moonlight Yacht Cruise from Halifax Waterfront Likely to Sell Out

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

  • North America
  • Superb45 reviews4.8

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....

    Free Cancellation
    Private Tour
    Start From $73.95
 
 

Chicago Air & Water Show

(4.8 of 45 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
  • Superb45 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $154.00
 
 

BYOB Friday Night Fireworks Cruise

(4.3 of 6 reviews)

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More

Free Cancellation
Private Tour
Start From $138.95
 
BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • North America
  • Exellent6 reviews4.3

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Free Cancellation
    Private Tour
    Start From $138.95
 
 

52' Yacht Rental in Miami Beach with Experienced Captain

(3.6 of 7 reviews)

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +950 reviews on Google with a 4.9 score guarantee our quality. Our Yacht & Captains are certified & licensed by the USCG, giving you a... More

Free Cancellation
Private Tour
Start From $1,500.00
 
52' Yacht Rental in Miami Beach with Experienced Captain Likely to Sell Out

52' Yacht Rental in Miami Beach with Experienced Captain

  • North America
  • Very Good7 reviews3.6

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +950 ....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
 

6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beaches

(5 of 13 reviews)

Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer you to make... More

Free Cancellation
Private Tour
Start From $1,432.54
 
6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beaches Likely to Sell Out

6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beac....

  • North America
  • Superb13 reviews5

Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 passengers. We are sure ....

    Free Cancellation
    Private Tour
    Start From $1,432.54
 
 

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 Likely to Sell Out

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
 
 

Schooner Clearwater- Afternoon Sailing Cruise-Clearwater Beach

(4.9 of 209 reviews)

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Parti... More

Free Cancellation
Private Tour
Start From $85.00
 
Schooner Clearwater- Afternoon Sailing Cruise-Clearwater Beach Likely to Sell Out

Schooner Clearwater- Afternoon Sailing Cruise-Clearwater Beach

  • North America
  • Superb209 reviews4.9

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wi....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

(4.9 of 77 reviews)

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More

Free Cancellation
Private Tour
Start From $119.00
 
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak Likely to Sell Out

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

  • North America
  • Superb77 reviews4.9

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Experience Oceanside Sailing with Whales and dolphins!

(5 of 12 reviews)

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the Oceanside harbor. We cater to guests from many of the five star hotels in the area. We serve an up... More

Free Cancellation
Private Tour
Start From $130.00
 
Experience Oceanside Sailing with Whales and dolphins! Likely to Sell Out

Experience Oceanside Sailing with Whales and dolphins!

  • North America
  • Superb12 reviews5

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and mo....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $85.50
(Saving 10% ) $95.00
 
-10% 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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $85.50
    (Saving 10% ) $95.00
 
 

Private Therapy Sailing Adventure

(4.8 of 35 reviews)

WHO WE ARE? Old Plank is a boutique luxury sailing charter & aquatic expedition company with gourmet 5 star cuisine. Founded by Captain Matthew Mancini, we live by the currents, plan by the tides, and follow the sun. WHAT DO WE D... More

Free Cancellation
Private Tour
Start From $400.00
 
Private Therapy Sailing Adventure Likely to Sell Out

Private Therapy Sailing Adventure

  • North America
  • Superb35 reviews4.8

WHO WE ARE? Old Plank is a boutique luxury sailing charter & aquatic expedition company with gourmet....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Skagway Trail and Sail

(5 of 3 reviews)

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More

Free Cancellation
Private Tour
Start From $265.00
 
Skagway Trail and Sail Likely to Sell Out

Skagway Trail and Sail

  • North America
  • Superb3 reviews5

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....

    Free Cancellation
    Private Tour
    Start From $265.00
 
 

Luxury Snorkel Adventure in Cabo

(4.8 of 44 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

Free Cancellation
Private Tour
Start From $149.00
 
Luxury Snorkel Adventure in Cabo Likely to Sell Out

Luxury Snorkel Adventure in Cabo

  • North America
  • Superb44 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $149.00
 
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