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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 17
 

Sunset Sail Experience by Catamaran in Waikiki

(4.8 of 6 reviews)

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More

Free Cancellation
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki

Sunset Sail Experience by Catamaran in Waikiki

  • North America
  • Superb6 reviews4.8

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....

    Free Cancellation
    Start From $92.31
 
 

Sunday Brunch Sail in Greenport

(5 of 9 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
Start From $175.00
 
Sunday Brunch Sail in Greenport

Sunday Brunch Sail in Greenport

  • North America
  • Superb9 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
    Start From $175.00
 
 

Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

(5 of 8 reviews)

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, and set sail for a relaxing and refreshing 2-hour cruise through Charleston’s histor... More

Free Cancellation
Start From $75.00
 
Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

  • North America
  • Superb8 reviews5

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard ou....

    Free Cancellation
    Start From $75.00
 
 

Boat Fishing Tour, Puerto Morelos CIPREA, 25'

(5 of 2 reviews)

We are a team with 20 years of experience in sport fishing tour only. Newbies and experts are welcome. Come and enjoy the beauties of the Caribbean Sea, the setting where we fish We have the best boats in Puerto Morelos. Come an... More

Free Cancellation
Private Tour
Start From $310.92
 
Boat Fishing Tour, Puerto Morelos CIPREA, 25'

Boat Fishing Tour, Puerto Morelos CIPREA, 25'

  • North America
  • Superb2 reviews5

We are a team with 20 years of experience in sport fishing tour only. Newbies and experts are welco....

    Free Cancellation
    Private Tour
    Start From $310.92
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(4.7 of 27 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... More

Free Cancellation
Private Tour
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks

South Shore Open Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb27 reviews4.7

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Private Tour
    Start From $47.50
 
 

Private Sailboat Charter from San Pedro: Port of Los Angeles

(4.7 of 27 reviews)

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a sunset sailing adventure on a Beneteau Oceanis (39ft) sailing yacht, perfect for couples or small groups looking for a memorable out... More

Free Cancellation
Private Tour
Start From $380.00
 
Private Sailboat Charter from San Pedro: Port of Los Angeles

Private Sailboat Charter from San Pedro: Port of Los Angeles

  • North America
  • Superb27 reviews4.7

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a su....

    Free Cancellation
    Private Tour
    Start From $380.00
 
 

All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks

(3.8 of 15 reviews)

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatable experience with unlimited drinks, mouth-watering lunch, and your choice of two exciting activities. Whether you want to ride ho... More

Free Cancellation
Private Tour
Start From $59.00
 
All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks

All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks

  • North America
  • Very Good15 reviews3.8

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatab....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

(4.9 of 73 reviews)

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Free Cancellation
Private Tour
Start From $114.00
 
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise Likely to Sell Out

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

  • North America
  • Superb73 reviews4.9

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....

    Free Cancellation
    Private Tour
    Start From $114.00
 
 

Detroit Sunset Sail on the River

(4.9 of 73 reviews)

Our sunset sail is designed to feel effortless, intimate, and elevated from the moment you step aboard. This is not a crowded cruise. It’s a small group sailing experience where guests can truly relax, connect, and take in Detro... More

Free Cancellation
Private Tour
Start From $115.00
 
Detroit Sunset Sail on the River Likely to Sell Out

Detroit Sunset Sail on the River

  • North America
  • Superb73 reviews4.9

Our sunset sail is designed to feel effortless, intimate, and elevated from the moment you step aboa....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

6 Hour Private Fishing Charter in the Riviera Maya

(4.9 of 13 reviews)

Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully private experience, not a shared tour. The itinerary is flexible ... More

Free Cancellation
Private Tour
Start From $1,050.00
 
6 Hour Private Fishing Charter in the Riviera Maya Likely to Sell Out

6 Hour Private Fishing Charter in the Riviera Maya

  • North America
  • Superb13 reviews4.9

Unlike many destinations, your fishing time starts within minutes of departure—no long boat ridesâ....

    Free Cancellation
    Private Tour
    Start From $1,050.00
 
 

Luxury Catamaran Whale Watch

(4.9 of 89 reviews)

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • North America
  • Superb89 reviews4.9

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

4-Hour Sailing Adventure on The Strait of Juan de Fuca

(4.7 of 27 reviews)

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water birds there is always something to see while you are learning the skills to sail one... More

Free Cancellation
Private Tour
Start From $131.12
 
4-Hour Sailing Adventure on The Strait of Juan de Fuca Likely to Sell Out

4-Hour Sailing Adventure on The Strait of Juan de Fuca

  • North America
  • Superb27 reviews4.7

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbac....

    Free Cancellation
    Private Tour
    Start From $131.12
 
 

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar

(4.4 of 75 reviews)

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More

Free Cancellation
Private Tour
Start From $149.00
 
Half Day Luxury Sailing Experience in Riviera Maya with Open Bar Likely to Sell Out

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar

  • North America
  • Exellent75 reviews4.4

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Afternoon Schooner Clearwater Beach Cruise Sailing

(5 of 2 reviews)

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

Free Cancellation
Private Tour
Start From $65.00
 
Afternoon Schooner Clearwater Beach Cruise Sailing Likely to Sell Out

Afternoon Schooner Clearwater Beach Cruise Sailing

  • North America
  • Superb2 reviews5

Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable vi....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Polynesian Canoe Day Sail

(4.9 of 29 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $180.00
(Saving 10% ) $200.00
 
-10% Polynesian Canoe Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • North America
  • Superb29 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $180.00
    (Saving 10% ) $200.00
 
 

Whale Shark Experience Lifetime Memory in Cancun (snack included)

(3.9 of 17 reviews)

Join one of the most wonderful wildlife experiences in Cancun during the whale shark season! Explore the Caribbean Sea aboard a small-group boat for a more exclusive adventure. Experience a memorable whale shark encounter featuri... More

Special Offer
Free Cancellation
Private Tour
Start From $159.00
(Saving inf% ) $0.00
 
-inf% Whale Shark Experience Lifetime Memory in Cancun (snack included) Likely to Sell Out

Whale Shark Experience Lifetime Memory in Cancun (snack included)

  • North America
  • Very Good17 reviews3.9

Join one of the most wonderful wildlife experiences in Cancun during the whale shark season! Explor....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $159.00
    (Saving inf% ) $0.00
 
 

90 Minute Sailing Tour of Portland

(3.8 of 5 reviews)

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate channel on Portland's own "Jungle Cruise" to the spectacular city riverfront wh... More

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% 90 Minute Sailing Tour of Portland Likely to Sell Out

90 Minute Sailing Tour of Portland

  • North America
  • Very Good5 reviews3.8

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamet....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
 

Experience Maalaea Harbor Sailing Snorkeling Adventure

(3.8 of 5 reviews)

Spend a leisurely afternoon sailing aboard the widest and most stable and luxurious catamaran in Maui, where your adventure takes you to the stunning waters of Molokini or a secret turtle sanctuary. Enjoy hand-shaken Mai Tais and ... More

Special Offer
Free Cancellation
Private Tour
Start From $149.00
(Saving inf% ) $0.00
 
-inf% Experience Maalaea Harbor Sailing Snorkeling Adventure Likely to Sell Out

Experience Maalaea Harbor Sailing Snorkeling Adventure

  • North America
  • Very Good5 reviews3.8

Spend a leisurely afternoon sailing aboard the widest and most stable and luxurious catamaran in Mau....

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

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

(4.9 of 112 reviews)

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel safe sailing with highly trained and bilingual staff in this beautiful freshwater paradise. Our years of experience back us up. Qua... More

Special Offer
Free Cancellation
Private Tour
Start From $252.25
(Saving inf% ) $0.00
 
-inf% Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks Likely to Sell Out

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

  • North America
  • Superb112 reviews4.9

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel s....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $252.25
    (Saving inf% ) $0.00
 
 

Seattle Golden Gardens Sunset Sail 70ft Boat Tour

(5 of 2 reviews)

Experience a beautiful Seattle evening on this 2-hour sunset sailing cruise departing from Shilshole Bay Marina near the iconic Golden Gardens Park. Step aboard a classic 70-foot former ocean racing yacht and head out onto Puget S... More

Special Offer
Free Cancellation
Private Tour
Start From $76.00
(Saving inf% ) $0.00
 
-inf% Seattle Golden Gardens Sunset Sail 70ft Boat Tour Likely to Sell Out

Seattle Golden Gardens Sunset Sail 70ft Boat Tour

  • North America
  • Superb2 reviews5

Experience a beautiful Seattle evening on this 2-hour sunset sailing cruise departing from Shilshole....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $76.00
    (Saving inf% ) $0.00
 
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