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Top 10 Best North America Sailing Trips

Found 689 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests

(5 of 31 reviews)

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a full restroom, as well as a... More

Free Cancellation
Private Tour
Start From $399.99
 
Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests

Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests

  • North America
  • Superb31 reviews5

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....

    Free Cancellation
    Private Tour
    Start From $399.99
 
 

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

(5 of 53 reviews)

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore pristine beaches and beautiful sights while savoring fresh guacamole and a selection of delicious snacks. This pe... More

Free Cancellation
Private Tour
Start From $655.80
 
Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

  • North America
  • Superb53 reviews5

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....

    Free Cancellation
    Private Tour
    Start From $655.80
 
 

Sunset Sail from Ma'alaea Harbor

(4.6 of 205 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our  luxury sailing catamaran, Ocean Spirit. It’s the perfect way to ex... More

Free Cancellation
Private Tour
Start From $151.00
 
Sunset Sail from Ma'alaea Harbor

Sunset Sail from Ma'alaea Harbor

  • North America
  • Superb205 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Private Tour
    Start From $151.00
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 416 reviews)

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut the engine down and enjoy the quiet of our beautiful schooner cutting through the tranquil Puget So... More

Free Cancellation
Private Tour
Start From $65.00
 
Evening Colors Sunset Sail Tour in Seattle

Evening Colors Sunset Sail Tour in Seattle

  • North America
  • Superb416 reviews4.8

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Sunset Sip and Sail Key West with Open Bar and Live Music

(4.5 of 258 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Free Cancellation
Private Tour
Start From $79.95
 
Sunset Sip and Sail Key West with Open Bar and Live Music

Sunset Sip and Sail Key West with Open Bar and Live Music

  • North America
  • Exellent258 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. ....

    Free Cancellation
    Private Tour
    Start From $79.95
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 492 reviews)

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More

Free Cancellation
Private Tour
Start From $116.00
 
Small-Group San Diego Afternoon Sailing Excursion Likely to Sell Out

Small-Group San Diego Afternoon Sailing Excursion

  • North America
  • Superb492 reviews5

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....

    Free Cancellation
    Private Tour
    Start From $116.00
 
 

Key West Rum and Reggae:Reef Snorkel Adventure and Sunset Sail

(4.4 of 346 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Free Cancellation
Private Tour
Start From $59.07
 
Key West Rum and Reggae:Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae:Reef Snorkel Adventure and Sunset Sail

  • North America
  • Exellent346 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Free Cancellation
    Private Tour
    Start From $59.07
 
 

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

(4.9 of 1,407 reviews)

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More

Free Cancellation
Private Tour
Start From $29.00
 
1-Hour Interactive Pirate Cruise (arrive 30 minutes early) Likely to Sell Out

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

  • North America
  • Superb1,407 reviews4.9

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....

    Free Cancellation
    Private Tour
    Start From $29.00
 
 

BYOB Waikiki Sunset Swim and Diamond Head Sailing

(5 of 144 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Private Tour
Start From $79.00
 
BYOB Waikiki Sunset Swim and Diamond Head Sailing Likely to Sell Out

BYOB Waikiki Sunset Swim and Diamond Head Sailing

  • North America
  • Superb144 reviews5

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Buccaneer Pirate Cruise

(5 of 40 reviews)

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More

Free Cancellation
Private Tour
Start From $55.00
 
Buccaneer Pirate Cruise Likely to Sell Out

Buccaneer Pirate Cruise

  • North America
  • Superb40 reviews5

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Adults only Sunset Cruise from Key West with Champagne

(4.9 of 887 reviews)

Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are the house champagne Chandon Brut, 7 premium red and whit... More

Free Cancellation
Private Tour
Start From $108.91
 
Adults only Sunset Cruise from Key West with Champagne Likely to Sell Out

Adults only Sunset Cruise from Key West with Champagne

  • North America
  • Superb887 reviews4.9

Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Ch....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

(3.7 of 200 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 Good200 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
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 105 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Free Cancellation
Private Tour
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks Likely to Sell Out

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb105 reviews4.9

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Private Tour
    Start From $61.50
 
 

Sail Splash and Sailing Excursion in Ft. Lauderdale

(4.8 of 263 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 $89.00
 
Sail Splash and Sailing Excursion in Ft. Lauderdale Likely to Sell Out

Sail Splash and Sailing Excursion in Ft. Lauderdale

  • North America
  • Superb263 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

(4.7 of 51 reviews)

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Free Cancellation
Private Tour
Start From $119.00
 
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor Likely to Sell Out

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

  • North America
  • Superb51 reviews4.7

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

(4.8 of 264 reviews)

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to immerse yourself in an authentic, action-packed fishing experience, wit... More

Free Cancellation
Private Tour
Start From $625.00
 
Private Fishing Trip Likely to Sell Out

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

  • North America
  • Superb264 reviews4.8

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 146 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Free Cancellation
Private Tour
Start From $39.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast Likely to Sell Out

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • North America
  • Superb146 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Private Tour
    Start From $39.99
 
 

52' Yacht Rental in Miami Beach with Experienced Captain

(4 of 6 reviews)

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +950 reviews on Google with a 4.9 score guarantee our quality. Our Yacht & Captains are certified & licensed by the USCG, giving you a... More

Free Cancellation
Private Tour
Start From $1,500.00
 
52' Yacht Rental in Miami Beach with Experienced Captain Likely to Sell Out

52' Yacht Rental in Miami Beach with Experienced Captain

  • North America
  • Very Good6 reviews4

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +950 ....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
 

Panama City Beach Sunset Sail on The Footloose Catamaran

(4.8 of 390 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More

Free Cancellation
Private Tour
Start From $45.00
 
Panama City Beach Sunset Sail on The Footloose Catamaran Likely to Sell Out

Panama City Beach Sunset Sail on The Footloose Catamaran

  • North America
  • Superb390 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

Sunset Sail in Miami: Complimentary Champagne Toast

(4.8 of 214 reviews)

Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for sun dresses, sandals and chilled wine. Take advantage of one of Florida's finest highlights upon our comfortable 80 ft catamaran a... More

Free Cancellation
Private Tour
Start From $89.00
 
Sunset Sail in Miami: Complimentary Champagne Toast Likely to Sell Out

Sunset Sail in Miami: Complimentary Champagne Toast

  • North America
  • Superb214 reviews4.8

Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
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