Menu

Top 10 Best North America Sailing Trips

Found 715 Sailing Trips activities in North America. Sort by Popularity. - Page 21
 

Private Charleston Harbor Catamaran Sail

(5 of 29 reviews)

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Charleston Harbor Catamaran Sail

Private Charleston Harbor Catamaran Sail

  • North America
  • Superb29 reviews5

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing cata....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos

(3.8 of 12 reviews)

Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Barrier Reef System, the world’s second-largest coral reef. Departing daily at 9:00 a.m. and 2:00 p.m., your journey begins with a... More

Free Cancellation
Private Tour
Start From $129.00
 
Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelo....

  • North America
  • Very Good12 reviews3.8

Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Ba....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Guided Seattle Sailing Adventure from Bainbridge Island

(5 of 85 reviews)

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we could see a nuclear submarine, inbound container ships, or century-old schooners... More

Free Cancellation
Private Tour
Start From $360.00
 
Guided Seattle Sailing Adventure from Bainbridge Island

Guided Seattle Sailing Adventure from Bainbridge Island

  • North America
  • Superb85 reviews5

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning wa....

    Free Cancellation
    Private Tour
    Start From $360.00
 
 

Key West Dolphin Watch and Sunset Sail on Catamaran

(4.7 of 43 reviews)

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unobs... More

Free Cancellation
Private Tour
Start From $117.17
 
Key West Dolphin Watch and Sunset Sail on Catamaran

Key West Dolphin Watch and Sunset Sail on Catamaran

  • North America
  • Superb43 reviews4.7

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the ligh....

    Free Cancellation
    Private Tour
    Start From $117.17
 
 

Deluxe private Sunset & Day Sail

(5 of 3 reviews)

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More

Free Cancellation
Private Tour
Start From $714.00
 
Deluxe private Sunset & Day Sail

Deluxe private Sunset & Day Sail

  • North America
  • Superb3 reviews5

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....

    Free Cancellation
    Private Tour
    Start From $714.00
 
 

Private Sailing Excursions, Nice Spacious Sailboats

(4.9 of 41 reviews)

Bacalar's lagoon is explored by sailboat with up to six guests, giving families and friends space to tailor the trip. Sail to cenotes, Bird Island, and Pirate Channel, use snorkeling equipment to explore underwater rock formations... More

Free Cancellation
Private Tour
Start From $274.66
 
Private Sailing Excursions, Nice Spacious Sailboats

Private Sailing Excursions, Nice Spacious Sailboats

  • North America
  • Superb41 reviews4.9

Bacalar's lagoon is explored by sailboat with up to six guests, giving families and friends space to....

    Free Cancellation
    Private Tour
    Start From $274.66
 
 

Party On Sailing Cruise to Isla Mujeres from Cancun

(3.9 of 19 reviews)

Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our national drinks onboard the catamaran. You will snorkel at one of the best reefs and see beautiful tropical fish, then eat lunch ... More

Free Cancellation
Private Tour
Start From $59.99
 
Party On Sailing Cruise to Isla Mujeres from Cancun

Party On Sailing Cruise to Isla Mujeres from Cancun

  • North America
  • Very Good19 reviews3.9

Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our....

    Free Cancellation
    Private Tour
    Start From $59.99
 
 

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(5 of 2 reviews)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More

Free Cancellation
Private Tour
Start From $1,200.00
 
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

  • North America
  • Superb2 reviews5

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Wrightsville Beach Day Sail Private Catamaran Charter

(5 of 1 review)

On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islands and local spots. Upon anchoring, the crew will dinghy you around wherever you'd like to go! The boat is fully equipped with ai... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Wrightsville Beach Day Sail Private Catamaran Charter

Wrightsville Beach Day Sail Private Catamaran Charter

  • North America
  • Superb1 review5

On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islan....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Private 90-Minute Harbor Sailing Charter in Key West

(4.9 of 20 reviews)

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility. You may even get to see some fri... More

Free Cancellation
Private Tour
Start From $424.62
 
Private 90-Minute Harbor Sailing Charter in Key West

Private 90-Minute Harbor Sailing Charter in Key West

  • North America
  • Superb20 reviews4.9

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-mi....

    Free Cancellation
    Private Tour
    Start From $424.62
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(5 of 125 reviews)

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More

Free Cancellation
Private Tour
Start From $485.00
 
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

  • North America
  • Superb125 reviews5

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....

    Free Cancellation
    Private Tour
    Start From $485.00
 
 

Okanagan Lake Sailing Tour from Penticton & Naramata BC

(5 of 52 reviews)

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More

Free Cancellation
Private Tour
Start From $182.09
 
Okanagan Lake Sailing Tour from Penticton & Naramata BC

Okanagan Lake Sailing Tour from Penticton & Naramata BC

  • North America
  • Superb52 reviews5

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....

    Free Cancellation
    Private Tour
    Start From $182.09
 
 

Baltimore Inner Harbor Sail on the Unforgettable

(4.8 of 25 reviews)

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling city from the water. Explore the Inner Harbor and the joy of sailing on t... More

Free Cancellation
Private Tour
Start From $65.00
 
Baltimore Inner Harbor Sail on the Unforgettable Likely to Sell Out

Baltimore Inner Harbor Sail on the Unforgettable

  • North America
  • Superb25 reviews4.8

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authe....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound

(5 of 36 reviews)

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole Bay Marina we sail west across Puget Sound toward the magnificent Olympic Mountains. A... More

Free Cancellation
Private Tour
Start From $125.00
 
Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound Likely to Sell Out

Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound

  • North America
  • Superb36 reviews5

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these wate....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar

(3.6 of 17 reviews)

Set off on a sun-and-fun-packed day trip to charming Isla Mujeres, a must-see attraction just off the Cancun coast. Cruise on a modern catamaran while sipping a drink or two from the open bar on your way to and from the scenic isl... More

Special Offer
Free Cancellation
Private Tour
Start From $69.52
(Saving 12% ) $79.00
 
-12% Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar Likely to Sell Out

Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar

  • North America
  • Very Good17 reviews3.6

Set off on a sun-and-fun-packed day trip to charming Isla Mujeres, a must-see attraction just off th....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $69.52
    (Saving 12% ) $79.00
 
 

Key West Private Charter: Sandbar and Snorkeling

(5 of 20 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

Special Offer
Free Cancellation
Private Tour
Start From $950.00
(Saving inf% ) $0.00
 
-inf% Key West Private Charter: Sandbar and Snorkeling Likely to Sell Out

Key West Private Charter: Sandbar and Snorkeling

  • North America
  • Superb20 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $950.00
    (Saving inf% ) $0.00
 
 

Deluxe Catamaran Tour to Isla Mujeres, Drinks, Snorkeling, Buffet

(3.8 of 28 reviews)

Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will board the catamaran and we will begin our tour together with our guides and entertainers so that you have a pleasant time. You can as... More

Special Offer
Free Cancellation
Private Tour
Start From $38.90
(Saving inf% ) $0.00
 
-inf% Deluxe Catamaran Tour to Isla Mujeres, Drinks, Snorkeling, Buffet Likely to Sell Out

Deluxe Catamaran Tour to Isla Mujeres, Drinks, Snorkeling, Buffet

  • North America
  • Very Good28 reviews3.8

Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will boa....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $38.90
    (Saving inf% ) $0.00
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $138.95
(Saving inf% ) $0.00
 
-inf% 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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $138.95
    (Saving inf% ) $0.00
 
 

Los Cabos Seasonal Whale Watch and Snorkel Tour

(4.7 of 21 reviews)

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the Santa Maria or Chileno Bay, will ride along the Sea of Cortes, and you will ... More

Special Offer
Free Cancellation
Private Tour
Start From $239.00
(Saving inf% ) $0.00
 
-inf% Los Cabos Seasonal Whale Watch and Snorkel Tour Likely to Sell Out

Los Cabos Seasonal Whale Watch and Snorkel Tour

  • North America
  • Superb21 reviews4.7

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful M....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $239.00
    (Saving inf% ) $0.00
 
 

Hidden Beach - Marietas Islands

(4.3 of 46 reviews)

Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursion, departing from Puerto Vallarta. Even those without experience can feel comfortable participating in guided snorkeling excursion... More

Special Offer
Free Cancellation
Private Tour
Start From $205.00
(Saving inf% ) $0.00
 
-inf% Hidden Beach - Marietas Islands Likely to Sell Out

Hidden Beach - Marietas Islands

  • North America
  • Exellent46 reviews4.3

Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursio....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $205.00
    (Saving inf% ) $0.00
 
Booking.com
Booking.com
Booking.com