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Top 10 Best North America Sailing Trips

Found 692 Sailing Trips activities in North America. Sort by Popularity. - Page 13
 

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

(5 of 33 reviews)

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More

Free Cancellation
Private Tour
Start From $599.00
 
Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

  • North America
  • Superb33 reviews5

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht ....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Boat ride to the Arch and Snorkel

(5 of 47 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 $74.58
 
Boat ride to the Arch and Snorkel

Boat ride to the Arch and Snorkel

  • North America
  • Superb47 reviews5

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 $74.58
 
 

Luxury Catamaran Whale Watch

(5 of 40 reviews)

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Class Yachts pro... More

Free Cancellation
Private Tour
Start From $159.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • North America
  • Superb40 reviews5

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

(4.9 of 21 reviews)

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More

Free Cancellation
Private Tour
Start From $59.95
 
Schooner Applejack Sunset Sail Tour in Boothbay Harbor Likely to Sell Out

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

  • North America
  • Superb21 reviews4.9

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Reef Snorkel + Sandbar & Sunset Sail-Small Groups with Honest Eco

(5 of 21 reviews)

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows yo... More

Free Cancellation
Private Tour
Start From $143.05
 
Reef Snorkel + Sandbar & Sunset Sail-Small Groups with Honest Eco Likely to Sell Out

Reef Snorkel + Sandbar & Sunset Sail-Small Groups with Honest Eco

  • North America
  • Superb21 reviews5

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....

    Free Cancellation
    Private Tour
    Start From $143.05
 
 

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

(5 of 16 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More

Free Cancellation
Private Tour
Start From $89.00
 
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise Likely to Sell Out

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

  • North America
  • Superb16 reviews5

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 93 reviews)

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Free Cancellation
Private Tour
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • North America
  • Superb93 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

(4.9 of 61 reviews)

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More

Free Cancellation
Private Tour
Start From $119.00
 
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak Likely to Sell Out

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

  • North America
  • Superb61 reviews4.9

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Tour to the Arch of Cabo San Lucas in a transparent glass boat

(4.5 of 8 reviews)

The end of the earth, the impressive union of two seas, the Sea of Cortez and the Pacific Sea, an incredible walk to the Arch of Cabo San Lucas where you can see the colony of sea lions and the wonderful rock formations, great att... More

Special Offer
Free Cancellation
Private Tour
Start From $45.00
(Saving 25% ) $60.00
 
-25% Tour to the Arch of Cabo San Lucas in a transparent glass boat Likely to Sell Out

Tour to the Arch of Cabo San Lucas in a transparent glass boat

  • North America
  • Exellent8 reviews4.5

The end of the earth, the impressive union of two seas, the Sea of Cortez and the Pacific Sea, an in....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $45.00
    (Saving 25% ) $60.00
 
 

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

(4.7 of 43 reviews)

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters... More

Free Cancellation
Private Tour
Start From $34.95
 
Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach Likely to Sell Out

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

  • North America
  • Superb43 reviews4.7

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Do....

    Free Cancellation
    Private Tour
    Start From $34.95
 
 

The Boat People Cruise Private Harbor Cruises

(5 of 34 reviews)

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an unforgettable evening with contagious laughter and panoramic views of the Newport Bay. Bring your plus one or ... More

Free Cancellation
Private Tour
Start From $100.00
 
The Boat People Cruise Private Harbor Cruises Likely to Sell Out

The Boat People Cruise Private Harbor Cruises

  • North America
  • Superb34 reviews5

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We ....

    Free Cancellation
    Private Tour
    Start From $100.00
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 7 reviews)

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Sunset Sail in Waikiki Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • North America
  • Superb7 reviews5

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

52' Yacht Rental in Miami Beach with Experienced Captain

(4 of 6 reviews)

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +950 reviews on Google with a 4.9 score guarantee our quality. Our Yacht & Captains are certified & licensed by the USCG, giving you a... More

Free Cancellation
Private Tour
Start From $1,500.00
 
52' Yacht Rental in Miami Beach with Experienced Captain Likely to Sell Out

52' Yacht Rental in Miami Beach with Experienced Captain

  • North America
  • Very Good6 reviews4

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +950 ....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
 

Private Catamaran Charter in Waikiki (7-12 Guests)

(4 of 6 reviews)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Private Catamaran Charter in Waikiki (7-12 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (7-12 Guests)

  • North America
  • Very Good6 reviews4

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Portland Tall Ship Private Charter on Casco Bay

(4 of 6 reviews)

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands. ... More

Free Cancellation
Private Tour
Start From $1,072.88
 
Portland Tall Ship Private Charter on Casco Bay Likely to Sell Out

Portland Tall Ship Private Charter on Casco Bay

  • North America
  • Very Good6 reviews4

What better way to see the delights than in the style of a private charter for you and five friends ....

    Free Cancellation
    Private Tour
    Start From $1,072.88
 
 

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

(5 of 4 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
Private Tour
Start From $91.23
 
Sail on Tall Ship Windy, join us for our Likely to Sell Out

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

  • North America
  • Superb4 reviews5

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

    Free Cancellation
    Private Tour
    Start From $91.23
 
 

Sailing Tour through the Laguna de los Siete Colores

(5 of 1,370 reviews)

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More

Special Offer
Free Cancellation
Private Tour
Start From $34.20
(Saving 10% ) $38.00
 
-10% Sailing Tour through the Laguna de los Siete Colores Likely to Sell Out

Sailing Tour through the Laguna de los Siete Colores

  • North America
  • Superb1,370 reviews5

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $34.20
    (Saving 10% ) $38.00
 
 

2-Hour Morning Sail in San Diego

(5 of 20 reviews)

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma, San Diego Bay and the downtown waterfront. This two-hour adventure on a Catalina sailboat is limited to a maximum of six (6) gues... More

Free Cancellation
Private Tour
Start From $95.00
 
2-Hour Morning Sail in San Diego Likely to Sell Out

2-Hour Morning Sail in San Diego

  • North America
  • Superb20 reviews5

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma,....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Private 2-Hour Sunset Sailing Tour on Lake Fairview

(5 of 29 reviews)

Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something different to do in Orlando besides theme parks? Escape the crowds and experience the hidden beauty of Central Florida with an unforgettabl... More

Free Cancellation
Private Tour
Start From $89.00
 
Private 2-Hour Sunset Sailing Tour on Lake Fairview Likely to Sell Out

Private 2-Hour Sunset Sailing Tour on Lake Fairview

  • North America
  • Superb29 reviews5

Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something differen....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 17 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
  • Superb17 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
 
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