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Top 10 Best North America Sailing Trips

Found 693 Sailing Trips activities in North America. Sort by Popularity. - Page 3
 

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

(4.9 of 762 reviews)

Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of Los Cabos’ Land’s End Arch! First, you’ll enjoy a beautiful sightseeing stop at Pelican’s Rock where you’ll have a cha... More

Free Cancellation
Start From $105.00
 
Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

  • North America
  • Superb762 reviews4.9

Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of....

    Free Cancellation
    Start From $105.00
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 488 reviews)

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More

Free Cancellation
Start From $85.00
 
Waikiki Sunset Cocktail Sail with Open Bar

Waikiki Sunset Cocktail Sail with Open Bar

  • North America
  • Superb488 reviews4.8

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....

    Free Cancellation
    Start From $85.00
 
 

Cabo San Lucas Sunset Sailing Shared Cruise

(4.9 of 720 reviews)

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

Free Cancellation
Start From $105.00
 
Cabo San Lucas Sunset Sailing Shared Cruise

Cabo San Lucas Sunset Sailing Shared Cruise

  • North America
  • Superb720 reviews4.9

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....

    Free Cancellation
    Start From $105.00
 
 

Small-Group Sunset Sailing Experience on San Diego Bay

(4.9 of 553 reviews)

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Free Cancellation
Start From $125.00
 
Small-Group Sunset Sailing Experience on San Diego Bay

Small-Group Sunset Sailing Experience on San Diego Bay

  • North America
  • Superb553 reviews4.9

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....

    Free Cancellation
    Start From $125.00
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 453 reviews)

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More

Free Cancellation
Start From $47.00
 
Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

  • North America
  • Superb453 reviews4.7

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....

    Free Cancellation
    Start From $47.00
 
 

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

(4.5 of 268 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 $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
  • Exellent268 reviews4.5

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

    Free Cancellation
    Start From $79.95
 
 

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

(4.6 of 398 reviews)

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious catamaran, while Mother Nature prepares for her nightly performan... More

Free Cancellation
Start From $109.00
 
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

  • North America
  • Superb398 reviews4.6

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....

    Free Cancellation
    Start From $109.00
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 17 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
Start From $172.85
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • North America
  • Superb17 reviews4.9

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

    Free Cancellation
    Start From $172.85
 
 

Toronto Tall Ship Boat Cruise

(4.2 of 571 reviews)

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the '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 from the re... More

Free Cancellation
Start From $32.33
 
Toronto Tall Ship Boat Cruise

Toronto Tall Ship Boat Cruise

  • North America
  • Exellent571 reviews4.2

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the 'Tall Ship K....

    Free Cancellation
    Start From $32.33
 
 

Na Pali Coast Kauai Snorkel and Sail

(4.8 of 515 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
Start From $292.48
 
Na Pali Coast Kauai Snorkel and Sail Likely to Sell Out

Na Pali Coast Kauai Snorkel and Sail

  • North America
  • Superb515 reviews4.8

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

    Free Cancellation
    Start From $292.48
 
 

Key West's Favorite Afternoon Dolphin Sail

(4.7 of 57 reviews)

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

Free Cancellation
Start From $59.00
 
Key West's Favorite Afternoon Dolphin Sail Likely to Sell Out

Key West's Favorite Afternoon Dolphin Sail

  • North America
  • Superb57 reviews4.7

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....

    Free Cancellation
    Start From $59.00
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 146 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 Likely to Sell Out

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • North America
  • Superb146 reviews4.8

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

    Free Cancellation
    Start From $120.69
 
 

Sunset Windjammer Cruise Along the Coast of Portland Maine

(4.8 of 78 reviews)

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. Pack a meal, bring your favorite wine or... More

Free Cancellation
Start From $75.00
 
Sunset Windjammer Cruise Along the Coast of Portland Maine Likely to Sell Out

Sunset Windjammer Cruise Along the Coast of Portland Maine

  • North America
  • Superb78 reviews4.8

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to exper....

    Free Cancellation
    Start From $75.00
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.8 of 363 reviews)

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More

Free Cancellation
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay Likely to Sell Out

2-Hour Sunset Sail on the San Francisco Bay

  • North America
  • Superb363 reviews4.8

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

    Free Cancellation
    Start From $129.00
 
 

Private Luxury Yacht Charters, BYOB & Dolphins

(5 of 363 reviews)

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

Free Cancellation
Private Tour
Start From $499.00
 
Private Luxury Yacht Charters, BYOB & Dolphins Likely to Sell Out

Private Luxury Yacht Charters, BYOB & Dolphins

  • North America
  • Superb363 reviews5

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....

    Free Cancellation
    Private Tour
    Start From $499.00
 
 

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

(4.8 of 1,856 reviews)

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes unlimited drinks from an open bar, accompanied by a delightful menu of small b... More

Free Cancellation
Private Tour
Start From $109.00
 
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar Likely to Sell Out

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

  • North America
  • Superb1,856 reviews4.8

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

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

(4.9 of 1,234 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

Special Offer
Free Cancellation
Private Tour
Start From $120.50
(Saving 10% ) $133.89
 
-10% Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres Likely to Sell Out

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

  • North America
  • Superb1,234 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $120.50
    (Saving 10% ) $133.89
 
 

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

(4.7 of 58 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
  • Superb58 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
 
 

Panama City Beach Sunset Catamaran Sail on The Privateer

(4.8 of 630 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More

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

Panama City Beach Sunset Catamaran Sail on The Privateer

  • North America
  • Superb630 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
 
 

Monterey Bay Whale Watching

(4.7 of 281 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
  • Superb281 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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