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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 8
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 740 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling a... More

Free Cancellation
Start From $135.64
 
Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb740 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Free Cancellation
    Start From $135.64
 
 

2-Hour Private Sailboat Charter in the San Francisco Bay

(4.8 of 22 reviews)

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the romance of sail. Private sailboat charters are a great way to celebrate you... More

Free Cancellation
Private Tour
Start From $695.00
 
2-Hour Private Sailboat Charter in the San Francisco Bay

2-Hour Private Sailboat Charter in the San Francisco Bay

  • North America
  • Superb22 reviews4.8

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Jus....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

New York City Sailboat Day Cruise to the Statue of Liberty

(4.9 of 179 reviews)

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides along the Hudson Rive... More

Free Cancellation
Private Tour
Start From $60.08
 
New York City Sailboat Day Cruise to the Statue of Liberty

New York City Sailboat Day Cruise to the Statue of Liberty

  • North America
  • Superb179 reviews4.9

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by t....

    Free Cancellation
    Private Tour
    Start From $60.08
 
 

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

(4.8 of 61 reviews)

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More

Free Cancellation
Private Tour
Start From $90.01
 
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

  • North America
  • Superb61 reviews4.8

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....

    Free Cancellation
    Private Tour
    Start From $90.01
 
 

Public Daytime Sailing Cruise

(5 of 26 reviews)

Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, Friend Ship and Wild Rose. With a maximum of 10 guests, this intimate sailing adventure is perfect for anyone looking to escape th... More

Free Cancellation
Private Tour
Start From $85.00
 
Public Daytime Sailing Cruise Likely to Sell Out

Public Daytime Sailing Cruise

  • North America
  • Superb26 reviews5

Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, ....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Midday Whale Watch: Mā’alaea Harbor

(4.9 of 104 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Private Tour
Start From $100.22
 
Midday Whale Watch: Mā’alaea Harbor Likely to Sell Out

Midday Whale Watch: Mā’alaea Harbor

  • North America
  • Superb104 reviews4.9

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Private Tour
    Start From $100.22
 
 

Two Hour Coastal Sailing Cruise

(5 of 84 reviews)

What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one of the largest and most stable sailing vessels in Savannah. Unlike crowded tour boats, our open-deck layout offers plenty of room... More

Free Cancellation
Private Tour
Start From $134.99
 
Two Hour Coastal Sailing Cruise Likely to Sell Out

Two Hour Coastal Sailing Cruise

  • North America
  • Superb84 reviews5

What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one....

    Free Cancellation
    Private Tour
    Start From $134.99
 
 

Mexico City: Xochimilco at sunrise + Breakfast and transportation

(5 of 123 reviews)

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for the environment. This is not the traditional Xochimilco of the trajineras;... More

Free Cancellation
Private Tour
Start From $174.94
 
Mexico City: Xochimilco at sunrise + Breakfast and transportation Likely to Sell Out

Mexico City: Xochimilco at sunrise + Breakfast and transportation

  • North America
  • Superb123 reviews5

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural....

    Free Cancellation
    Private Tour
    Start From $174.94
 
 

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

(4.6 of 1,335 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Free Cancellation
Private Tour
Start From $53.31
 
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu Likely to Sell Out

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

  • North America
  • Superb1,335 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Free Cancellation
    Private Tour
    Start From $53.31
 
 

Portland Tall Ship Cruise on Casco Bay

(4.6 of 242 reviews)

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More

Free Cancellation
Private Tour
Start From $101.92
 
Portland Tall Ship Cruise on Casco Bay Likely to Sell Out

Portland Tall Ship Cruise on Casco Bay

  • North America
  • Superb242 reviews4.6

What better way to see the delights of Portland than from the sea in one of the famous schooner tall....

    Free Cancellation
    Private Tour
    Start From $101.92
 
 

Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!

(5 of 137 reviews)

Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in the Puget Sound. This personalized voyage is designed for up to six passengers, offering an intimate and unforgettable experience ... More

Free Cancellation
Private Tour
Start From $549.00
 
Seattle's Best Private Sailing Adventure on the Puget Sound BYOB! Likely to Sell Out

Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!

  • North America
  • Superb137 reviews5

Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in ....

    Free Cancellation
    Private Tour
    Start From $549.00
 
 

The Legendary Canadian Coastal Sail

(5 of 282 reviews)

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain ranges. We will depart from the docks in Squamish (about 40 minut... More

Special Offer
Free Cancellation
Private Tour
Start From $99.56
(Saving 15% ) $117.13
 
-15% The Legendary Canadian Coastal Sail Likely to Sell Out

The Legendary Canadian Coastal Sail

  • North America
  • Superb282 reviews5

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds w....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.56
    (Saving 15% ) $117.13
 
 

Boat Ride to the Arch with Snorkeling in Cabo

(5 of 181 reviews)

Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a smooth ride through the Sea of ​​Cortez Our guide and captain who are biologists will share interesting and professional infor... More

Special Offer
Free Cancellation
Private Tour
Start From $83.25
(Saving inf% ) $0.00
 
-inf% Boat Ride to the Arch with Snorkeling in Cabo Likely to Sell Out

Boat Ride to the Arch with Snorkeling in Cabo

  • North America
  • Superb181 reviews5

Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a s....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $83.25
    (Saving inf% ) $0.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 254 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More

Special Offer
Free Cancellation
Private Tour
Start From $135.64
(Saving inf% ) $0.00
 
-inf% Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb254 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $135.64
    (Saving inf% ) $0.00
 
 

San Diego Harbor Cruise on the Largest Catamaran in San Diego

(4.9 of 54 reviews)

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by all of the amazing San Diego harbor monuments while enjoying the smooth sailing of San Diego's... More

Special Offer
Free Cancellation
Private Tour
Start From $55.00
(Saving inf% ) $0.00
 
-inf% San Diego Harbor Cruise on the Largest Catamaran in San Diego Likely to Sell Out

San Diego Harbor Cruise on the Largest Catamaran in San Diego

  • North America
  • Superb54 reviews4.9

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our gu....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $55.00
    (Saving inf% ) $0.00
 
 

HipHop Catamaran Party from Cancun to Isla Mujeres

(3.9 of 20 reviews)

Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snorkeling in one of the Caribbean's top reefs, surrounded by vibrant marine life. Then, head to a secluded sandbank—a hidden gem pe... More

Special Offer
Free Cancellation
Private Tour
Start From $65.00
(Saving inf% ) $0.00
 
-inf% HipHop Catamaran Party from Cancun to Isla Mujeres Likely to Sell Out

HipHop Catamaran Party from Cancun to Isla Mujeres

  • North America
  • Very Good20 reviews3.9

Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snor....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $65.00
    (Saving inf% ) $0.00
 
 

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

(4.6 of 564 reviews)

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More

Special Offer
Free Cancellation
Private Tour
Start From $55.00
(Saving inf% ) $0.00
 
-inf% America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head Likely to Sell Out

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

  • North America
  • Superb564 reviews4.6

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $55.00
    (Saving inf% ) $0.00
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $119.00
(Saving inf% ) $0.00
 
-inf% 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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $119.00
    (Saving inf% ) $0.00
 
 

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

(5 of 43 reviews)

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a relaxing and comfortable journey around lower Manhattan. En... More

Special Offer
Free Cancellation
Private Tour
Start From $350.00
(Saving inf% ) $0.00
 
-inf% Best Private Luxury Daytime Boat Tour in New York City - 1 Hour Likely to Sell Out

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

  • North America
  • Superb43 reviews5

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $350.00
    (Saving inf% ) $0.00
 
 

Seattle Golden Gardens Sunset Sail 70ft Boat Tour

(5 of 9 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
  • Superb9 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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