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Top 10 Best North America Sailing Trips

Found 705 Sailing Trips activities in North America. Sort by Popularity. - Page 9
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 296 reviews)

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Start From $165.00
 
4-Hour Fort Lauderdale Sailing Charter

4-Hour Fort Lauderdale Sailing Charter

  • North America
  • Superb296 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Start From $165.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 788 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Start From $148.57
 
Sunset and Manta Ray Snorkel Adventure

Sunset and Manta Ray Snorkel Adventure

  • North America
  • Superb788 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Start From $148.57
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.7 of 144 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Start From $79.00
 
Key West Sailing & Snorkeling: A Reef Adventure Likely to Sell Out

Key West Sailing & Snorkeling: A Reef Adventure

  • North America
  • Superb144 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Start From $79.00
 
 

Waikiki Sunset Boat Cruise

(5 of 31 reviews)

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Free Cancellation
Start From $50.00
 
Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • North America
  • Superb31 reviews5

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....

    Free Cancellation
    Start From $50.00
 
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 384 reviews)

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

Free Cancellation
Start From $99.00
 
1.5-Hour San Francisco Bay Sailing Tour Likely to Sell Out

1.5-Hour San Francisco Bay Sailing Tour

  • North America
  • Superb384 reviews4.8

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....

    Free Cancellation
    Start From $99.00
 
 

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat

(5 of 30 reviews)

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More

Free Cancellation
Private Tour
Start From $899.00
 
Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat Likely to Sell Out

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat

  • North America
  • Superb30 reviews5

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....

    Free Cancellation
    Private Tour
    Start From $899.00
 
 

Wrightsville Beach Sunset Cocktail Sail

(5 of 7 reviews)

Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while you cruise our local waterways and watch the sunset. Wind permitting, we'll turn off the engines and enjoy the beauty of sailing!... More

Free Cancellation
Private Tour
Start From $150.00
 
Wrightsville Beach Sunset Cocktail Sail Likely to Sell Out

Wrightsville Beach Sunset Cocktail Sail

  • North America
  • Superb7 reviews5

Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Sailing on Historic Schooner Yacht in Salem, MA

(4.9 of 136 reviews)

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More

Free Cancellation
Private Tour
Start From $55.00
 
Sailing on Historic Schooner Yacht in Salem, MA Likely to Sell Out

Sailing on Historic Schooner Yacht in Salem, MA

  • North America
  • Superb136 reviews4.9

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Casco Bay Morning Windjammer Sail

(4.9 of 12 reviews)

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a ... More

Free Cancellation
Private Tour
Start From $59.00
 
Casco Bay Morning Windjammer Sail Likely to Sell Out

Casco Bay Morning Windjammer Sail

  • North America
  • Superb12 reviews4.9

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the per....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

JFarwell Adventure Yacht Sailing in the Halifax Harbour

(4.9 of 133 reviews)

Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged to be as hands on with the sailing process as they would... More

Free Cancellation
Private Tour
Start From $81.34
 
JFarwell Adventure Yacht Sailing in the Halifax Harbour Likely to Sell Out

JFarwell Adventure Yacht Sailing in the Halifax Harbour

  • North America
  • Superb133 reviews4.9

Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....

    Free Cancellation
    Private Tour
    Start From $81.34
 
 

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

(4.9 of 35 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

Free Cancellation
Private Tour
Start From $350.00
 
Private Luxury Daytime Boat Tour in New York City - 1 Hour Likely to Sell Out

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

  • North America
  • Superb35 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $350.00
 
 

Sunset Cocktail Cruise from Anaeho'omalu Bay

(4.8 of 57 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Free Cancellation
Private Tour
Start From $165.00
 
Sunset Cocktail Cruise from Anaeho'omalu Bay Likely to Sell Out

Sunset Cocktail Cruise from Anaeho'omalu Bay

  • North America
  • Superb57 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 76 reviews)

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More

Free Cancellation
Private Tour
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • North America
  • Superb76 reviews5

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Sail & Splash Excursion in Ft. Lauderdale

(4.8 of 267 reviews)

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran, the Spirit of Lauderdale. Enjoy one of the best cruise Ft Lauderdale has to offer . Sit back... More

Free Cancellation
Private Tour
Start From $99.00
 
Sail & Splash Excursion in Ft. Lauderdale Likely to Sell Out

Sail & Splash Excursion in Ft. Lauderdale

  • North America
  • Superb267 reviews4.8

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private Customizable Sailing Tour in Cancun

(4.7 of 119 reviews)

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers the opportunity to visit wonderful places that can only be known by the sea. From a relaxing private sailing tour in the bay of Can... More

Free Cancellation
Private Tour
Start From $549.34
 
Private Customizable Sailing Tour in Cancun Likely to Sell Out

Private Customizable Sailing Tour in Cancun

  • North America
  • Superb119 reviews4.7

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers th....

    Free Cancellation
    Private Tour
    Start From $549.34
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 455 reviews)

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Special Offer
Free Cancellation
Private Tour
Start From $98.01
(Saving 10% ) $108.91
 
-10% Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • North America
  • Superb455 reviews4.6

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $98.01
    (Saving 10% ) $108.91
 
 

Brunch Cruise with Buffet in Washington

(4.1 of 8 reviews)

Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer three public sailing tours daily from Seattle’s downtown waterfront. Our beautiful sailing ship, the Bay Lady, evokes the romanc... More

Free Cancellation
Private Tour
Start From $98.21
 
Brunch Cruise with Buffet in Washington Likely to Sell Out

Brunch Cruise with Buffet in Washington

  • North America
  • Exellent8 reviews4.1

Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer ....

    Free Cancellation
    Private Tour
    Start From $98.21
 
 

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres

(4.4 of 293 reviews)

Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a delicious drink and the entertainment from the crew. Unique and quality service is our priority. We are sure that you will love all... More

Free Cancellation
Private Tour
Start From $62.00
 
Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres Likely to Sell Out

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres

  • North America
  • Exellent293 reviews4.4

Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....

    Free Cancellation
    Private Tour
    Start From $62.00
 
 

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

(4.8 of 22 reviews)

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More

Free Cancellation
Private Tour
Start From $63.00
 
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms Likely to Sell Out

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

  • North America
  • Superb22 reviews4.8

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....

    Free Cancellation
    Private Tour
    Start From $63.00
 
 

Private Sailing Charter with Captain, BYOB

(5 of 59 reviews)

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More

Free Cancellation
Private Tour
Start From $500.00
 
Private Sailing Charter with Captain, BYOB Likely to Sell Out

Private Sailing Charter with Captain, BYOB

  • North America
  • Superb59 reviews5

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....

    Free Cancellation
    Private Tour
    Start From $500.00
 
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