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Top 10 Best North America Sailing Trips

Found 701 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

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

(4.6 of 273 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
Start From $72.00
 
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
  • Superb273 reviews4.6

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

    Free Cancellation
    Start From $72.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 850 reviews)

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Free Cancellation
Start From $79.00
 
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

  • North America
  • Superb850 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Start From $79.00
 
 

Key West Snorkeling with Breakfast and Unlimited Mimosas

(4.5 of 540 reviews)

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Free Cancellation
Start From $35.00
 
Key West Snorkeling with Breakfast and Unlimited Mimosas

Key West Snorkeling with Breakfast and Unlimited Mimosas

  • North America
  • Exellent540 reviews4.5

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....

    Free Cancellation
    Start From $35.00
 
 

Kona Catamaran Sunset Sail

(4.8 of 162 reviews)

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Free Cancellation
Start From $149.00
 
Kona Catamaran Sunset Sail

Kona Catamaran Sunset Sail

  • North America
  • Superb162 reviews4.8

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....

    Free Cancellation
    Start From $149.00
 
 

Newport Afternoon Sightseeing Sail on Classic Sailboat

(4.8 of 97 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
Start From $57.24
 
Newport Afternoon Sightseeing Sail on Classic Sailboat

Newport Afternoon Sightseeing Sail on Classic Sailboat

  • North America
  • Superb97 reviews4.8

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

    Free Cancellation
    Start From $57.24
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 150 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Start From $120.69
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • North America
  • Superb150 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Start From $120.69
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.6 of 45 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
Start From $49.00
 
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

  • North America
  • Superb45 reviews4.6

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

    Free Cancellation
    Start From $49.00
 
 

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way”

(4.9 of 308 reviews)

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

Free Cancellation
Private Tour
Start From $595.00
 
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way”

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way....

  • North America
  • Superb308 reviews4.9

Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re ce....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

(4.6 of 393 reviews)

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina and raise the sails, then it’s time to just chill out and relax. Get a... More

Free Cancellation
Private Tour
Start From $68.00
 
Sunset Sailing Cruise on a Tall Ship in Boston Harbor

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

  • North America
  • Superb393 reviews4.6

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise....

    Free Cancellation
    Private Tour
    Start From $68.00
 
 

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

(4.9 of 1,256 reviews)

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More

Free Cancellation
Private Tour
Start From $115.00
 
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

  • North America
  • Superb1,256 reviews4.9

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Panama City Beach Sunset Sail on The Footloose Catamaran

(4.8 of 413 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

Panama City Beach Sunset Sail on The Footloose Catamaran

  • North America
  • Superb413 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
 
 

New York City Sailboat Day Cruise to the Statue of Liberty

(4.9 of 128 reviews)

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides along the Hudson Rive... More

Free Cancellation
Private Tour
Start From $60.08
 
New York City Sailboat Day Cruise to the Statue of Liberty Likely to Sell Out

New York City Sailboat Day Cruise to the Statue of Liberty

  • North America
  • Superb128 reviews4.9

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by t....

    Free Cancellation
    Private Tour
    Start From $60.08
 
 

Sailing Experience on a 50’ sailboat

(5 of 81 reviews)

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More

Free Cancellation
Private Tour
Start From $111.19
 
Sailing Experience on a 50’ sailboat Likely to Sell Out

Sailing Experience on a 50’ sailboat

  • North America
  • Superb81 reviews5

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....

    Free Cancellation
    Private Tour
    Start From $111.19
 
 

New York Sunset Schooner Cruise on the Hudson River

(4.9 of 205 reviews)

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More

Free Cancellation
Private Tour
Start From $90.12
 
New York Sunset Schooner Cruise on the Hudson River Likely to Sell Out

New York Sunset Schooner Cruise on the Hudson River

  • North America
  • Superb205 reviews4.9

Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....

    Free Cancellation
    Private Tour
    Start From $90.12
 
 

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

(4.9 of 658 reviews)

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Dagger and set sail in search of treasure! But wait it's not... More

Free Cancellation
Private Tour
Start From $41.99
 
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger Likely to Sell Out

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

  • North America
  • Superb658 reviews4.9

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....

    Free Cancellation
    Private Tour
    Start From $41.99
 
 

Key West Dolphin and Snorkel Experience

(4.4 of 293 reviews)

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More

Free Cancellation
Private Tour
Start From $69.95
 
Key West Dolphin and Snorkel Experience Likely to Sell Out

Key West Dolphin and Snorkel Experience

  • North America
  • Exellent293 reviews4.4

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....

    Free Cancellation
    Private Tour
    Start From $69.95
 
 

2.5 Hours of Fun: Catamaran Sunset Sail

(4.9 of 185 reviews)

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride wit... More

Free Cancellation
Private Tour
Start From $119.00
 
2.5 Hours of Fun: Catamaran Sunset Sail Likely to Sell Out

2.5 Hours of Fun: Catamaran Sunset Sail

  • North America
  • Superb185 reviews4.9

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 659 reviews)

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

Free Cancellation
Private Tour
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • North America
  • Superb659 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Na Pali Coast Kauai Snorkel and Sail

(4.8 of 519 reviews)

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

Free Cancellation
Private Tour
Start From $292.48
 
Na Pali Coast Kauai Snorkel and Sail Likely to Sell Out

Na Pali Coast Kauai Snorkel and Sail

  • North America
  • Superb519 reviews4.8

Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....

    Free Cancellation
    Private Tour
    Start From $292.48
 
 

Monterey Bay Whale Watching

(4.7 of 289 reviews)

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

Free Cancellation
Private Tour
Start From $69.95
 
Monterey Bay Whale Watching Likely to Sell Out

Monterey Bay Whale Watching

  • North America
  • Superb289 reviews4.7

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....

    Free Cancellation
    Private Tour
    Start From $69.95
 
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