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Top 10 Best North America Sailing Trips

Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 5
 

Private Sailing on the Miami Bay - Biscayne Bay

(4.9 of 74 reviews)

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish vessels in the company of experienced, but mostly fun, well traveled, passionate captains. A Private Sailing tour aboard Destino ... More

Free Cancellation
Private Tour
Start From $425.00
 
Private Sailing on the Miami Bay - Biscayne Bay Likely to Sell Out

Private Sailing on the Miami Bay - Biscayne Bay

  • North America
  • Superb74 reviews4.9

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish....

    Free Cancellation
    Private Tour
    Start From $425.00
 
 

Suncoast Sailing's Sunset Sailing Experience!

(4.9 of 246 reviews)

Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More

Free Cancellation
Private Tour
Start From $69.99
 
Suncoast Sailing's Sunset Sailing Experience! Likely to Sell Out

Suncoast Sailing's Sunset Sailing Experience!

  • North America
  • Superb246 reviews4.9

Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Waikiki Sunset Boat Cruise

(5 of 77 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
Private Tour
Start From $50.00
 
Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • North America
  • Superb77 reviews5

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

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

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

(4.2 of 5 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 Likely to Sell Out

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

  • North America
  • Exellent5 reviews4.2

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

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Key West Champagne Sunset Catamaran Cruise

(4.7 of 582 reviews)

Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy included wine, sparkling wine, beer, sangria or margaritas on board the boat. . As you sail thr... More

Free Cancellation
Private Tour
Start From $59.00
 
Key West Champagne Sunset Catamaran Cruise Likely to Sell Out

Key West Champagne Sunset Catamaran Cruise

  • North America
  • Superb582 reviews4.7

Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of t....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.8 of 165 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
Private Tour
Start From $79.00
 
Key West Sailing & Snorkeling: A Reef Adventure Likely to Sell Out

Key West Sailing & Snorkeling: A Reef Adventure

  • North America
  • Superb165 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

(3.7 of 205 reviews)

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More

Free Cancellation
Private Tour
Start From $69.99
 
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar Likely to Sell Out

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

  • North America
  • Very Good205 reviews3.7

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Panama City Beach Dolphin Sightseeing Sail

(4.8 of 124 reviews)

This cruise along the Gulf Coastline and Bay area offers a great opportunity to photograph local wildlife and scenery. At our onboard bar we have snacks and beverages available for purchase. Enjoy a variety of cocktails, including... More

Free Cancellation
Private Tour
Start From $35.00
 
Panama City Beach Dolphin Sightseeing Sail Likely to Sell Out

Panama City Beach Dolphin Sightseeing Sail

  • North America
  • Superb124 reviews4.8

This cruise along the Gulf Coastline and Bay area offers a great opportunity to photograph local wil....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 99 reviews)

Sail the stunning Kona-Kohala Coast aboard a spacious catamaran on this unforgettable Waikoloa snorkeling cruise. As you head out across the clear Pacific waters, enjoy panoramic views of volcanic mountains, golden coastline, and ... More

Free Cancellation
Private Tour
Start From $169.00
 
Waikoloa Catamaran Snorkel Sail Including Lunch Likely to Sell Out

Waikoloa Catamaran Snorkel Sail Including Lunch

  • North America
  • Superb99 reviews4.6

Sail the stunning Kona-Kohala Coast aboard a spacious catamaran on this unforgettable Waikoloa snork....

    Free Cancellation
    Private Tour
    Start From $169.00
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.5 of 70 reviews)

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Free Cancellation
Private Tour
Start From $49.00
 
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast Likely to Sell Out

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

  • North America
  • Exellent70 reviews4.5

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....

    Free Cancellation
    Private Tour
    Start From $49.00
 
 

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres

(4.4 of 297 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
  • Exellent297 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
 
 

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 77 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Private Tour
Start From $59.95
 
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

  • North America
  • Superb77 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Akialoa Mā’alaea Sunset Sail

(3.7 of 3 reviews)

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More

Free Cancellation
Private Tour
Start From $108.11
 
Akialoa Mā’alaea Sunset Sail Likely to Sell Out

Akialoa Mā’alaea Sunset Sail

  • North America
  • Very Good3 reviews3.7

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....

    Free Cancellation
    Private Tour
    Start From $108.11
 
 

Luxury Whale Watch Cruise to The Arch Los Cabos

(4.6 of 111 reviews)

Whale season is from mid-December thru mid-April, you can book this tour all year round but to travel only during the Whale Season (Dec 15 thru April 15th). Enjoy 2 hours spectacular adventure looking for whales, who travel thousa... More

Free Cancellation
Private Tour
Start From $95.00
 
Luxury Whale Watch Cruise to The Arch Los Cabos Likely to Sell Out

Luxury Whale Watch Cruise to The Arch Los Cabos

  • North America
  • Superb111 reviews4.6

Whale season is from mid-December thru mid-April, you can book this tour all year round but to trave....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 392 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
Private Tour
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
  • Superb392 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private Sailing Charter with Captain, BYOB

(5 of 64 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
  • Superb64 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
 
 

Sailing Tour through the Lagoon of the 7 Colors

(4.9 of 1,118 reviews)

Sail with people who share your passion for adventure! You will explore fascinating places along the lagoon of the 7 colors. Our small groups guarantee you excellent attention and service from our crew. Disconnect from the world ... More

Free Cancellation
Private Tour
Start From $37.00
 
Sailing Tour through the Lagoon of the 7 Colors Likely to Sell Out

Sailing Tour through the Lagoon of the 7 Colors

  • North America
  • Superb1,118 reviews4.9

Sail with people who share your passion for adventure! You will explore fascinating places along the....

    Free Cancellation
    Private Tour
    Start From $37.00
 
 

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

(5 of 197 reviews)

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More

Free Cancellation
Private Tour
Start From $1,102.00
 
Private Sailboat tour in Cabo San Lucas with Papillon Yachts Likely to Sell Out

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

  • North America
  • Superb197 reviews5

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....

    Free Cancellation
    Private Tour
    Start From $1,102.00
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 682 reviews)

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More

Free Cancellation
Private Tour
Start From $189.00
 
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • North America
  • Superb682 reviews5

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 199 reviews)

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More

Free Cancellation
Private Tour
Start From $109.00
 
Classic Key West Schooner Sunset Sail with Full Open Bar Likely to Sell Out

Classic Key West Schooner Sunset Sail with Full Open Bar

  • North America
  • Superb199 reviews4.9

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....

    Free Cancellation
    Private Tour
    Start From $109.00
 
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