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Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 11
 

Waikiki Fireworks Cocktail Cruise

(4.4 of 7 reviews)

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember. ... More

Free Cancellation
Start From $85.09
 
Waikiki Fireworks Cocktail Cruise

Waikiki Fireworks Cocktail Cruise

  • North America
  • Exellent7 reviews4.4

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....

    Free Cancellation
    Start From $85.09
 
 

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar

(3.7 of 35 reviews)

Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience where music, drinks and incredible views will never be lacking. ... More

Free Cancellation
Start From $55.00
 
Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar Likely to Sell Out

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar

  • North America
  • Very Good35 reviews3.7

Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a sp....

    Free Cancellation
    Start From $55.00
 
 

Cozumel Private Snorkeling and Charter Experience

(5 of 24 reviews)

We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting the famous 'El Cielo' and other amazing destinations to give you... More

Free Cancellation
Private Tour
Start From $900.00
 
Cozumel Private Snorkeling and Charter Experience Likely to Sell Out

Cozumel Private Snorkeling and Charter Experience

  • North America
  • Superb24 reviews5

We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On th....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Sunset Cocktail Cruise on our Sailing Catamaran

(4.8 of 62 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 on our Sailing Catamaran Likely to Sell Out

Sunset Cocktail Cruise on our Sailing Catamaran

  • North America
  • Superb62 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
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 36 reviews)

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Free Cancellation
Private Tour
Start From $192.17
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • North America
  • Superb36 reviews4.9

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Private Tour
    Start From $192.17
 
 

Private Sail of San Diego Bay Aboard a French Luxury Yacht

(4.9 of 36 reviews)

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully crafted French yacht, designed for comfort, performance, and elegan... More

Free Cancellation
Private Tour
Start From $1,499.00
 
Private Sail of San Diego Bay Aboard a French Luxury Yacht Likely to Sell Out

Private Sail of San Diego Bay Aboard a French Luxury Yacht

  • North America
  • Superb36 reviews4.9

What makes this experience truly unique is the combination of refined European luxury and a relaxed,....

    Free Cancellation
    Private Tour
    Start From $1,499.00
 
 

Private Catamaran Charter in Waikiki (7-12 Guests)

(4.9 of 36 reviews)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Private Catamaran Charter in Waikiki (7-12 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (7-12 Guests)

  • North America
  • Superb36 reviews4.9

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

San Diego Sunset or Afternoon Sail on Classic Yacht

(5 of 80 reviews)

Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of a 1904 gaff-rigged Friendship sloop. Our boat features highly-finished woodwork, bronze fixtures, and gaff rigging that showcase ... More

Free Cancellation
Private Tour
Start From $115.00
 
San Diego Sunset or Afternoon Sail on Classic Yacht Likely to Sell Out

San Diego Sunset or Afternoon Sail on Classic Yacht

  • North America
  • Superb80 reviews5

Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Fun Boat Rental with Captain in Miami Beach - up to 6 people

(4.9 of 51 reviews)

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straightforward bareboat charter. Now, let's talk logistics. The captain's compensation is a separate matter, settled directly at the ... More

Free Cancellation
Private Tour
Start From $260.00
 
Fun Boat Rental with Captain in Miami Beach - up to 6 people Likely to Sell Out

Fun Boat Rental with Captain in Miami Beach - up to 6 people

  • North America
  • Superb51 reviews4.9

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straig....

    Free Cancellation
    Private Tour
    Start From $260.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.7 of 60 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Private Tour
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • North America
  • Superb60 reviews4.7

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Private Key West Sandbar and Paddle by Boat

(4.9 of 36 reviews)

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More

Free Cancellation
Private Tour
Start From $600.00
 
Private Key West Sandbar and Paddle by Boat Likely to Sell Out

Private Key West Sandbar and Paddle by Boat

  • North America
  • Superb36 reviews4.9

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Best of Halifax Harbour Boat Tour

(4.9 of 77 reviews)

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed harbour tour as they share Halifax's history and present day facts!... More

Free Cancellation
Private Tour
Start From $44.14
 
Best of Halifax Harbour Boat Tour Likely to Sell Out

Best of Halifax Harbour Boat Tour

  • North America
  • Superb77 reviews4.9

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside ....

    Free Cancellation
    Private Tour
    Start From $44.14
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 465 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

Free Cancellation
Private Tour
Start From $108.91
 
Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • North America
  • Superb465 reviews4.6

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

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Reef Snorkel, underwater adventure in Puerto Morelos With Transportation & Lunch

(4.3 of 6 reviews)

Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a must activity in Cancun. You will visit one of the most bigger reef in the world, this is consider as the 2nd one worldwide. Imagi... More

Free Cancellation
Private Tour
Start From $44.25
 
Reef Snorkel, underwater adventure in Puerto Morelos With Transportation & Lunch Likely to Sell Out

Reef Snorkel, underwater adventure in Puerto Morelos With Transpo....

  • North America
  • Exellent6 reviews4.3

Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a mu....

    Free Cancellation
    Private Tour
    Start From $44.25
 
 

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

(5 of 42 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $550.00
 
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique Likely to Sell Out

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

  • North America
  • Superb42 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $550.00
 
 

Friday Night Catamaran Fireworks Sail with Open Bar

(4.8 of 55 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
 
Friday Night Catamaran Fireworks Sail with Open Bar Likely to Sell Out

Friday Night Catamaran Fireworks Sail with Open Bar

  • North America
  • Superb55 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
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(5 of 122 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 $485.00
 
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail Likely to Sell Out

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

  • North America
  • Superb122 reviews5

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

    Free Cancellation
    Private Tour
    Start From $485.00
 
 

Newport Afternoon Sightseeing Sail on Classic Sailboat

(4.8 of 142 reviews)

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, including Newport's historic lighthouses and landmarks, bridges, mansions a... More

Free Cancellation
Private Tour
Start From $57.24
 
Newport Afternoon Sightseeing Sail on Classic Sailboat Likely to Sell Out

Newport Afternoon Sightseeing Sail on Classic Sailboat

  • North America
  • Superb142 reviews4.8

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narraga....

    Free Cancellation
    Private Tour
    Start From $57.24
 
 

Polynesian Canoe Morning Sail

(5 of 18 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Special Offer
Free Cancellation
Private Tour
Start From $170.00
(Saving 15% ) $200.00
 
-15% Polynesian Canoe Morning Sail Likely to Sell Out

Polynesian Canoe Morning Sail

  • North America
  • Superb18 reviews5

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $170.00
    (Saving 15% ) $200.00
 
 

Chicago's Fireworks Show aboard Tall Ship Windy!

(4.8 of 14 reviews)

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Free Cancellation
Private Tour
Start From $113.73
 
Chicago's Fireworks Show aboard Tall Ship Windy! Likely to Sell Out

Chicago's Fireworks Show aboard Tall Ship Windy!

  • North America
  • Superb14 reviews4.8

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....

    Free Cancellation
    Private Tour
    Start From $113.73
 
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