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Top 10 Best North America Sailing Trips

Found 642 Sailing Trips activities in North America. Sort by Popularity. - Page 9
 

Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience

(3 of 2 reviews)

Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan that can accommodate up to 25 passengers. It's decked out with a kitchen, bedroom, bathroom, and even water sports gear like kayak... More

Free Cancellation
Private Tour
Start From $1,250.00
 
Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience Likely to Sell Out

Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience

  • North America

Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan ....

    Free Cancellation
    Private Tour
    Start From $1,250.00
 
 

Private Sailboat Charter on San Francisco Bay

(5 of 7 reviews)

3 hour PRIVATE Charter with a unique experience aboard Carmelita, our beautiful and pristine Catalina 42 sailboat. We provide our clients with upscale beverages and have your interest, destination and comfort in mind, while tourin... More

Free Cancellation
Private Tour
Start From $995.00
 
Private Sailboat Charter on San Francisco Bay Likely to Sell Out

Private Sailboat Charter on San Francisco Bay

  • North America
  • Superb7 reviews5

3 hour PRIVATE Charter with a unique experience aboard Carmelita, our beautiful and pristine Catalin....

    Free Cancellation
    Private Tour
    Start From $995.00
 
 

Deluxe Turtle Snorkeling Escapade at Waikiki

(4.8 of 4 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Private Tour
Start From $99.00
 
Deluxe Turtle Snorkeling Escapade at Waikiki Likely to Sell Out

Deluxe Turtle Snorkeling Escapade at Waikiki

  • North America
  • Superb4 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

2-Hour Interactive Sailing Experience on San Francisco Bay

(5 of 43 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

Free Cancellation
Private Tour
Start From $149.00
 
2-Hour Interactive Sailing Experience on San Francisco Bay Likely to Sell Out

2-Hour Interactive Sailing Experience on San Francisco Bay

  • North America
  • Superb43 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

2.5-hour Guided Sailboat Tour

(4.9 of 163 reviews)

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor's Island and M... More

Free Cancellation
Private Tour
Start From $98.00
 
2.5-hour Guided Sailboat Tour Likely to Sell Out

2.5-hour Guided Sailboat Tour

  • North America
  • Superb163 reviews4.9

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, ....

    Free Cancellation
    Private Tour
    Start From $98.00
 
 

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline

(4.7 of 11 reviews)

Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Miami Beach experience. Connect with nature, discover new landscapes, & create lasting memories as you explore the stunning coastline... More

Free Cancellation
Private Tour
Start From $600.00
 
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline Likely to Sell Out

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline

  • North America
  • Superb11 reviews4.7

Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

'Alihilani Sunset Sail from Ma'alaea Harbor

(5 of 66 reviews)

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands while wa... More

Free Cancellation
Private Tour
Start From $112.90
 
'Alihilani Sunset Sail from Ma'alaea Harbor Likely to Sell Out

'Alihilani Sunset Sail from Ma'alaea Harbor

  • North America
  • Superb66 reviews5

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....

    Free Cancellation
    Private Tour
    Start From $112.90
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(4.9 of 112 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 $493.25
 
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail Likely to Sell Out

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

  • North America
  • Superb112 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $493.25
 
 

Half-Day Private Snorkel Sailing Adventure in Cabo San Lucas

(4.9 of 112 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
  • Superb112 reviews4.9

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
 
 

#1 eFoil, wing foil, windsurf or kiteboard lesson in Kailua, Oahu

(5 of 3 reviews)

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed so you learn faster and safer. We will share with you the best locations to launch f... More

Free Cancellation
Private Tour
Start From $175.00
 
#1 eFoil, wing foil, windsurf or kiteboard lesson in Kailua, Oahu Likely to Sell Out

#1 eFoil, wing foil, windsurf or kiteboard lesson in Kailua, Oahu

  • North America
  • Superb3 reviews5

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets he....

    Free Cancellation
    Private Tour
    Start From $175.00
 
 

Suncoast Sailing's Day Sailing Experience!

(4.9 of 94 reviews)

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. Feel the wind as it glides us through the picturesque waters of Treasure Island and Gulf of Mexico. Come face to face with nature a... More

Free Cancellation
Private Tour
Start From $59.99
 
Suncoast Sailing's Day Sailing Experience! Likely to Sell Out

Suncoast Sailing's Day Sailing Experience!

  • North America
  • Superb94 reviews4.9

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. F....

    Free Cancellation
    Private Tour
    Start From $59.99
 
 

Romantic Dinner Touring the Nichupté Lagoon in Galeón

(4.9 of 94 reviews)

Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard the Columbus Romantic Dinner Cruise. This is a unique romance tour in Cancun, as it offers a very special evening, surrounded by ... More

Free Cancellation
Private Tour
Start From $125.00
 
Romantic Dinner Touring the Nichupté Lagoon in Galeón Likely to Sell Out

Romantic Dinner Touring the Nichupté Lagoon in Galeón

  • North America
  • Superb94 reviews4.9

Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Deluxe Day Sail in San Diego

(5 of 46 reviews)

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More

Free Cancellation
Private Tour
Start From $109.00
 
Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • North America
  • Superb46 reviews5

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Private sailing tour of Bacalar Lagoon

(5 of 204 reviews)

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More

Free Cancellation
Private Tour
Start From $205.00
 
Private sailing tour of Bacalar Lagoon Likely to Sell Out

Private sailing tour of Bacalar Lagoon

  • North America
  • Superb204 reviews5

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....

    Free Cancellation
    Private Tour
    Start From $205.00
 
 

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

(4 of 386 reviews)

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More

Free Cancellation
Private Tour
Start From $70.00
 
2-Hour Windjammer Sailing Trip in Maine with Licensed Captain Likely to Sell Out

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

  • North America
  • Very Good386 reviews4

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Key West Ultimate Beach Pass with Parasailing

(4.6 of 18 reviews)

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass. ... More

Free Cancellation
Private Tour
Start From $109.95
 
Key West Ultimate Beach Pass with Parasailing Likely to Sell Out

Key West Ultimate Beach Pass with Parasailing

  • North America
  • Superb18 reviews4.6

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are....

    Free Cancellation
    Private Tour
    Start From $109.95
 
 

JFarwell Sunset Wine and Cheese Yacht Sailing

(4.9 of 116 reviews)

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More

Free Cancellation
Private Tour
Start From $136.92
 
JFarwell Sunset Wine and Cheese Yacht Sailing Likely to Sell Out

JFarwell Sunset Wine and Cheese Yacht Sailing

  • North America
  • Superb116 reviews4.9

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....

    Free Cancellation
    Private Tour
    Start From $136.92
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 331 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Private Tour
Start From $64.95
 
Windjammer Classic Sunset Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Sunset Sail from Camden, Maine

  • North America
  • Superb331 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Private Tour
    Start From $64.95
 
 

Beach Day Tour with Horseback Ride Water Sports and City Tour

(3 of 2 reviews)

Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transported in a luxurious, air-conditioned vehicle, complete with complimentary beverages. Our tour includes visits to the stunning cathe... More

Free Cancellation
Private Tour
Start From $79.00
 
Beach Day Tour with Horseback Ride Water Sports and City Tour Likely to Sell Out

Beach Day Tour with Horseback Ride Water Sports and City Tour

  • North America

Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transpor....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Hilton Hawaiian Village Sunset Cocktail Cruise

(3 of 2 reviews)

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More

Free Cancellation
Private Tour
Start From $151.00
 
Hilton Hawaiian Village Sunset Cocktail Cruise Likely to Sell Out

Hilton Hawaiian Village Sunset Cocktail Cruise

  • North America

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Free Cancellation
    Private Tour
    Start From $151.00
 
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