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Top 10 Best North America Sailing Trips

Found 701 Sailing Trips activities in North America. Sort by Popularity. - Page 5
 

Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included

(4.9 of 307 reviews)

Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica of a 1904 gaff rigged friendship sloop. She is an elegant sight under sail, featuring; highly finished woodwork, bronze fixtures, a... More

Free Cancellation
Start From $125.00
 
 Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included

Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included

  • North America
  • Superb307 reviews4.9

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

    Free Cancellation
    Start From $125.00
 
 

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

(4.7 of 11 reviews)

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Free Cancellation
Start From $91.23
 
Sail on Tall Ship Windy, join us for our

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

  • North America
  • Superb11 reviews4.7

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....

    Free Cancellation
    Start From $91.23
 
 

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

(4.8 of 320 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

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

  • North America
  • Superb320 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
 
 

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

(4.4 of 357 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

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

  • North America
  • Exellent357 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
 
 
-6% 2-Hour Private Sailing Experience in San Diego Bay

2-Hour Private Sailing Experience in San Diego Bay

(5 of 157 reviews)

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More

Special Offer
Free Cancellation
Private Tour
Start From $550.00
(Saving 6% ) $585.00
 
-6% 2-Hour Private Sailing Experience in San Diego Bay

2-Hour Private Sailing Experience in San Diego Bay

  • North America
  • Superb157 reviews5

Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $550.00
    (Saving 6% ) $585.00
 
 

Half-Day Luxury Sailing Experience in Tulum with Open Bar

(4.2 of 242 reviews)

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

Free Cancellation
Private Tour
Start From $149.00
 
Half-Day Luxury Sailing Experience in Tulum with Open Bar

Half-Day Luxury Sailing Experience in Tulum with Open Bar

  • North America
  • Exellent242 reviews4.2

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 371 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Private Tour
Start From $64.95
 
Windjammer Classic Sunset Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Sunset Sail from Camden, Maine

  • North America
  • Superb371 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Private Tour
    Start From $64.95
 
 

Schooner Fame Sailing Tour

(4.9 of 543 reviews)

FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per TripAdvisor. Don't miss the very best of what Salem has to offer! There's more to our town than witches! FAME is a full-scale replica... More

Free Cancellation
Private Tour
Start From $50.65
 
Schooner Fame Sailing Tour Likely to Sell Out

Schooner Fame Sailing Tour

  • North America
  • Superb543 reviews4.9

FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....

    Free Cancellation
    Private Tour
    Start From $50.65
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.5 of 377 reviews)

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

Free Cancellation
Private Tour
Start From $59.95
 
Key West Afternoon Reef Snorkeling with Open Bar Likely to Sell Out

Key West Afternoon Reef Snorkeling with Open Bar

  • North America
  • Exellent377 reviews4.5

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Dolphin Adventure Sail in Cocoa Beach

(4.9 of 151 reviews)

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter pla... More

Free Cancellation
Private Tour
Start From $50.85
 
Dolphin Adventure Sail in Cocoa Beach Likely to Sell Out

Dolphin Adventure Sail in Cocoa Beach

  • North America
  • Superb151 reviews4.9

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....

    Free Cancellation
    Private Tour
    Start From $50.85
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 32 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Private Tour
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) Likely to Sell Out

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • North America
  • Superb32 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Private Tour
    Start From $289.00
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 521 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Private Tour
Start From $79.00
 
Key West Reef Snorkel & Sail Adventure Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • North America
  • Superb521 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 129 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
  • Superb129 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
 
 

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

(4.7 of 135 reviews)

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
Start From $69.95
 
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine Likely to Sell Out

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

  • North America
  • Superb135 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
    Start From $69.95
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 650 reviews)

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More

Free Cancellation
Private Tour
Start From $177.65
 
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • North America
  • Superb650 reviews5

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....

    Free Cancellation
    Private Tour
    Start From $177.65
 
 

Day Sail from Traverse City with Food, Wine, & Cocktails

(4.9 of 140 reviews)

For a full description please visit our website at https://www.winddancertc.com/ where you can learn about the vessel, crew, local history and make your bookings!... More

Free Cancellation
Private Tour
Start From $169.00
 
Day Sail from Traverse City with Food, Wine, & Cocktails Likely to Sell Out

Day Sail from Traverse City with Food, Wine, & Cocktails

  • North America
  • Superb140 reviews4.9

For a full description please visit our website at https://www.winddancertc.com/ where you can learn....

    Free Cancellation
    Private Tour
    Start From $169.00
 
 

El Cielo Snorkel by Private Boat

(4.8 of 317 reviews)

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine white sandy beach away from the crowds - Taste a delicious fish ceviche and co... More

Free Cancellation
Private Tour
Start From $499.99
 
El Cielo Snorkel by Private Boat Likely to Sell Out

El Cielo Snorkel by Private Boat

  • North America
  • Superb317 reviews4.8

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 87 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Private Tour
Start From $54.95
 
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor Likely to Sell Out

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

  • North America
  • Superb87 reviews4.6

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Private Tour
    Start From $54.95
 
 

Buccaneer Pirate Cruise in Destin

(4.9 of 78 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 in Destin Likely to Sell Out

Buccaneer Pirate Cruise in Destin

  • North America
  • Superb78 reviews4.9

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
 
 

Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting

(4.7 of 56 reviews)

DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews on Google. What you will get: Nature Immersion: Encounter dolphins, turtles, manatees, and more as you explore Miami's waters Cel... More

Free Cancellation
Private Tour
Start From $65.00
 
Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting Likely to Sell Out

Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting

  • North America
  • Superb56 reviews4.7

DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews ....

    Free Cancellation
    Private Tour
    Start From $65.00
 
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