Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 719 Sailing Trips activities in North America. Sort by Popularity. - Page 4Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
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North America
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Superb136 reviews4.6
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....
Sunset Catamaran Cruise in Ft. Lauderdale
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Sunset Catamaran Cruise in Ft. Lauderdale
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North America
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Superb685 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....
Private Luxury Yacht Charters, BYOB & Dolphins
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More
Private Tour

Private Luxury Yacht Charters, BYOB & Dolphins
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North America
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Superb392 reviews5
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....
Private Tour
Cabo San Lucas Sunset Sailing Shared Cruise
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San Lucas amazing waters. This is a family-friendly tour and includes... More
Private Tour

Cabo San Lucas Sunset Sailing Shared Cruise
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North America
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Superb739 reviews4.9
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....
Private Tour
Na Pali Coast Kauai Snorkel and Sail
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and comfortable 50’ Kauai-built sailing catamaran, Leila. Let’s explore the cliffs, valleys, sea caves and wildlife of the Napali... More
Private Tour

Na Pali Coast Kauai Snorkel and Sail
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North America
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Superb526 reviews4.8
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....
Private Tour
Half-Day Luxury Sailing Experience in Tulum with Open Bar
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More
Private Tour

Half-Day Luxury Sailing Experience in Tulum with Open Bar
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North America
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Exellent244 reviews4.2
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Private Tour
Monterey Bay Whale Watching
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More
Private Tour

Monterey Bay Whale Watching
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North America
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Superb302 reviews4.7
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....
Private Tour
Waikiki Sunset Boat Cruise
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
Private Tour

Waikiki Sunset Boat Cruise
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North America
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Superb59 reviews5
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
Private Tour
Day Sails and Sunset tours on Schooner Surprise in Camden Maine
Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board for all. Experienced crew will point out wild life, tell you history of our area and show... More
Private Tour

Day Sails and Sunset tours on Schooner Surprise in Camden Maine
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North America
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Superb74 reviews4.9
Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at ....
Private Tour
Toronto Tall Ship Boat Cruise
This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat, and sit back and relax with a cold drink from the bar or order fr... More
Private Tour

Toronto Tall Ship Boat Cruise
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North America
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Exellent674 reviews4.3
This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Ta....
Private Tour
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way”
Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re celebrating a bachelorette, a birthday, or simply enjoying time with your favorite people, this catamaran getaway for up to six gues... More
Private Tour

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way....
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North America
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Superb316 reviews4.9
Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re ce....
Private Tour
'Alihilani Sunset Sail
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands while wa... More
Private Tour

'Alihilani Sunset Sail
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North America
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Superb79 reviews5
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
Private Tour
Luxury Catamaran Whale Watch
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
Private Tour

Luxury Catamaran Whale Watch
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North America
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Superb40 reviews5
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
Private Tour
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More
Private Tour

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
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North America
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Superb670 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
Private Tour
Key West's Favorite Afternoon Dolphin Sail
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More
Private Tour

Key West's Favorite Afternoon Dolphin Sail
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North America
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Superb93 reviews4.7
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
Private Tour
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More
Private Tour

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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North America
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Superb255 reviews4.8
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Private Tour

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
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
Free Cancellation
Private Tour
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America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
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North America
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Superb498 reviews4.6
Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....
Free Cancellation
Private Tour
(Saving 10% )
Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
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
Private Tour

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
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North America
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Superb338 reviews4.8
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....
Private Tour

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More
Free Cancellation
Private Tour
(Saving 10% )

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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North America
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Superb146 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
Free Cancellation
Private Tour
(Saving 10% )
Buccaneer Pirate Cruise in Destin
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
Private Tour

Buccaneer Pirate Cruise in Destin
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North America
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Superb89 reviews4.9
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....
Private Tour