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Top 10 Best North America Sailing Trips

Found 721 Sailing Trips activities in North America. Sort by Popularity. - Page 8
 

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
Start From $43.04
 
Best of Halifax Harbour Boat Tour

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
    Start From $43.04
 
 

Private Family Catamaran From Isla Mujeres

(5 of 1 review)

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time? Affordable Private Catamaran, avoid crowded vessels Half-day fun catamaran, with a guided sn... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Family Catamaran From Isla Mujeres

Private Family Catamaran From Isla Mujeres

  • North America
  • Superb1 review5

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 17 reviews)

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More

Free Cancellation
Private Tour
Start From $80.00
 
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • North America
  • Superb17 reviews4.7

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....

    Free Cancellation
    Private Tour
    Start From $80.00
 
 

2hr. SUNSET Sailing Experience on San Francisco Bay

(5 of 21 reviews)

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get the full experience of sailing so you'll have an opportunity to tak... More

Free Cancellation
Private Tour
Start From $149.00
 
2hr. SUNSET Sailing Experience on San Francisco Bay

2hr. SUNSET Sailing Experience on San Francisco Bay

  • North America
  • Superb21 reviews5

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sail....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Sunset Catamaran Sail in Cocoa Beach

(4.9 of 165 reviews)

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Florida... More

Free Cancellation
Private Tour
Start From $55.37
 
Sunset Catamaran Sail in Cocoa Beach

Sunset Catamaran Sail in Cocoa Beach

  • North America
  • Superb165 reviews4.9

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....

    Free Cancellation
    Private Tour
    Start From $55.37
 
 

Premium Isla Mujeres Tour by Private Catamaran

(5 of 278 reviews)

We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, as we offer 2 options to our customers. Our trained team is always there to pro... More

Free Cancellation
Private Tour
Start From $950.00
 
Premium Isla Mujeres Tour by Private Catamaran

Premium Isla Mujeres Tour by Private Catamaran

  • North America
  • Superb278 reviews5

We specialize in making this all-day trip unique, a unique and beautiful experience for all our gues....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 423 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

Windjammer Classic Sunset Sail from Camden, Maine

  • North America
  • Superb423 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
 
 

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

(4.7 of 302 reviews)

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More

Free Cancellation
Private Tour
Start From $66.67
 
4-Hour St. Pete Pier to Egmont Key Experience by Ferry Likely to Sell Out

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

  • North America
  • Superb302 reviews4.7

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....

    Free Cancellation
    Private Tour
    Start From $66.67
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.8 of 408 reviews)

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More

Free Cancellation
Private Tour
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Day Sail from Camden, Maine

  • North America
  • Superb408 reviews4.8

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 79 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

Free Cancellation
Private Tour
Start From $149.00
 
2hr. INTERACTIVE Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

  • North America
  • Superb79 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Diamond Head Sunset Sail

(4.7 of 15 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More

Free Cancellation
Private Tour
Start From $695.00
 
Diamond Head Sunset Sail Likely to Sell Out

Diamond Head Sunset Sail

  • North America
  • Superb15 reviews4.7

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 153 reviews)

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More

Free Cancellation
Private Tour
Start From $70.00
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans Likely to Sell Out

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • North America
  • Superb153 reviews4.9

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Private Sailing Charter with Captain, BYOB

(5 of 62 reviews)

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More

Free Cancellation
Private Tour
Start From $500.00
 
Private Sailing Charter with Captain, BYOB Likely to Sell Out

Private Sailing Charter with Captain, BYOB

  • North America
  • Superb62 reviews5

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....

    Free Cancellation
    Private Tour
    Start From $500.00
 
 

Boat ride to the Arch and Snorkel

(4.9 of 109 reviews)

Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a smooth ride through the Sea of ​​Cortez Our guide and captain who are biologists will share interesting and professional infor... More

Free Cancellation
Private Tour
Start From $77.00
 
Boat ride to the Arch and Snorkel Likely to Sell Out

Boat ride to the Arch and Snorkel

  • North America
  • Superb109 reviews4.9

Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a s....

    Free Cancellation
    Private Tour
    Start From $77.00
 
 

2-Hour Private Sailboat Charter in the San Francisco Bay

(4.9 of 20 reviews)

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the romance of sail. Private sailboat charters are a great way to celebrate you... More

Free Cancellation
Private Tour
Start From $695.00
 
2-Hour Private Sailboat Charter in the San Francisco Bay Likely to Sell Out

2-Hour Private Sailboat Charter in the San Francisco Bay

  • North America
  • Superb20 reviews4.9

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Jus....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 21 reviews)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Charter in Waikiki (1-6 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (1-6 Guests)

  • North America
  • Superb21 reviews5

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 190 reviews)

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More

Free Cancellation
Private Tour
Start From $109.00
 
Classic Key West Schooner Sunset Sail with Full Open Bar Likely to Sell Out

Classic Key West Schooner Sunset Sail with Full Open Bar

  • North America
  • Superb190 reviews4.9

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 390 reviews)

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

Free Cancellation
Private Tour
Start From $99.00
 
1.5-Hour San Francisco Bay Sailing Tour Likely to Sell Out

1.5-Hour San Francisco Bay Sailing Tour

  • North America
  • Superb390 reviews4.8

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Sailing Charters in Wilmington

(5 of 183 reviews)

After a successful first season I am happy to be here for back to back seasons. Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for publ... More

Free Cancellation
Private Tour
Start From $89.00
 
Sailing Charters in Wilmington Likely to Sell Out

Sailing Charters in Wilmington

  • North America
  • Superb183 reviews5

After a successful first season I am happy to be here for back to back seasons. Sail in style on the....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 265 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Private Tour
Start From $84.77
 
9am Turtle Canyon Snorkel Adventure Likely to Sell Out

9am Turtle Canyon Snorkel Adventure

  • North America
  • Superb265 reviews4.9

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Private Tour
    Start From $84.77
 
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