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Top 10 Best North America Sailing Trips

Found 703 Sailing Trips activities in North America. Sort by Popularity. - Page 17
 

San Salvador Spanish Galleon Adventure Day Sail with General Admission

(4.5 of 2 reviews)

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. The San Salvador is a replica of Juan Rodriguez Cabrillo’s ship that arrived at the ... More

Start From $119.00
 
San Salvador Spanish Galleon Adventure Day Sail with General Admission

San Salvador Spanish Galleon Adventure Day Sail with General Admi....

  • North America
  • Exellent2 reviews4.5

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step o....

    Start From $119.00
 
 

Polynesian Canoe Day Sail

(4.9 of 28 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Start From $200.00
 
Polynesian Canoe Day Sail

Polynesian Canoe Day Sail

  • North America
  • Superb28 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Start From $200.00
 
 

Tour to The Arch and Lover's Beach (optional) from Cabo

(4.8 of 8 reviews)

This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, and through the Marina. See it all in one tour! During this awesome experience, you will be able to see a great variety of tropical... More

Free Cancellation
Start From $30.00
 
Tour to The Arch and Lover's Beach (optional) from Cabo

Tour to The Arch and Lover's Beach (optional) from Cabo

  • North America
  • Superb8 reviews4.8

This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, a....

    Free Cancellation
    Start From $30.00
 
 

4 hours Sailboat Tour for 2 people along the Los Angeles Coastline

(3.7 of 3 reviews)

The coastal line of Los Angeles. You will see Marina Del Rey, head for Santa Monica, sail past Venice Beach, Airport, Malibu beach, go into the open ocean, anchor (if desired) and return back to Marina Del Rey.... More

Free Cancellation
Private Tour
Start From $599.00
 
4 hours Sailboat Tour for 2 people along the Los Angeles Coastline

4 hours Sailboat Tour for 2 people along the Los Angeles Coastlin....

  • North America
  • Very Good3 reviews3.7

The coastal line of Los Angeles. You will see Marina Del Rey, head for Santa Monica, sail past Venic....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Luxury Private Yacht Charter in Cabo San Lucas Mexico

(5 of 4 reviews)

You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a capacity of up to 6 people maximum, remember that the trip is totally private, only your group and the crew (captain and first mat... More

Free Cancellation
Private Tour
Start From $400.00
 
Luxury Private Yacht Charter in Cabo San Lucas Mexico

Luxury Private Yacht Charter in Cabo San Lucas Mexico

  • North America
  • Superb4 reviews5

You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a ....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Let's Go Sail the York River in Gloucester Point, Virginia

(5 of 127 reviews)

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the cockpit or up on the bow of the boat for greater privacy. Great idea for engagement, bi... More

Free Cancellation
Private Tour
Start From $96.42
 
Let's Go Sail the York River in Gloucester Point, Virginia

Let's Go Sail the York River in Gloucester Point, Virginia

  • North America
  • Superb127 reviews5

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern ....

    Free Cancellation
    Private Tour
    Start From $96.42
 
 

San Diego Afternoon Sail

(5 of 127 reviews)

Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and military ves... More

Free Cancellation
Private Tour
Start From $120.00
 
San Diego Afternoon Sail Likely to Sell Out

San Diego Afternoon Sail

  • North America
  • Superb127 reviews5

Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna.....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

(4.8 of 18 reviews)

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Free Cancellation
Private Tour
Start From $99.00
 
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise Likely to Sell Out

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

  • North America
  • Superb18 reviews4.8

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private Morning Sail, Dolphin and History Tour on Mystique

(5 of 82 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing yachts are the highest quality and operated by two professional ... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Morning Sail, Dolphin and History Tour on Mystique Likely to Sell Out

Private Morning Sail, Dolphin and History Tour on Mystique

  • North America
  • Superb82 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

San Diego Private Morning Sail up to 12 guests

(5 of 33 reviews)

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More

Free Cancellation
Private Tour
Start From $235.00
 
San Diego Private Morning Sail up to 12 guests Likely to Sell Out

San Diego Private Morning Sail up to 12 guests

  • North America
  • Superb33 reviews5

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....

    Free Cancellation
    Private Tour
    Start From $235.00
 
 

New York City Skyline Night Sailboat Tour

(5 of 11 reviews)

Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New York. See the New York City skyline, the Statue of Liberty and Ellis Island lit up at night. Sit back and relax while enjoying a pe... More

Free Cancellation
Private Tour
Start From $67.01
 
New York City Skyline Night Sailboat Tour Likely to Sell Out

New York City Skyline Night Sailboat Tour

  • North America
  • Superb11 reviews5

Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New Y....

    Free Cancellation
    Private Tour
    Start From $67.01
 
 

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

(4.3 of 26 reviews)

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a c... More

Free Cancellation
Private Tour
Start From $54.95
 
Schooner Applejack 2-Hour Day Sail from Boothbay Harbor Likely to Sell Out

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

  • North America
  • Exellent26 reviews4.3

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

    Free Cancellation
    Private Tour
    Start From $54.95
 
 

Luxury Cruise with Dinner and Music in Los Cabos

(2.5 of 4 reviews)

Los Cabos offers unforgettable experiences and one not to be missed is to visit the famous Arch of Cabo San Lucas and to enjoy a sunset cruise. There are many similar options that offers this tour, but a few are unique and offers ... More

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Cruise with Dinner and Music in Los Cabos Likely to Sell Out

Luxury Cruise with Dinner and Music in Los Cabos

  • North America

Los Cabos offers unforgettable experiences and one not to be missed is to visit the famous Arch of C....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

2-Hour Rosé Luxury Day Sail

(5 of 1 review)

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expert captains leading the way. Keep an eye out for dolphins, seabirds, and Lowcountry landmarks as you relax, unwind, and enjoy the ... More

Free Cancellation
Private Tour
Start From $54.32
 
2-Hour Rosé Luxury Day Sail Likely to Sell Out

2-Hour Rosé Luxury Day Sail

  • North America
  • Superb1 review5

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expe....

    Free Cancellation
    Private Tour
    Start From $54.32
 
 

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

(4.9 of 56 reviews)

Let yourself be carried away by the wind on an unforgettable adventure through the wonderful Lagoon of 7 Colors. A unique experience to enjoy with family or friends, open bar and lunch. Without engine noises, the sounds of nature... More

Free Cancellation
Private Tour
Start From $70.51
 
Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch Likely to Sell Out

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

  • North America
  • Superb56 reviews4.9

Let yourself be carried away by the wind on an unforgettable adventure through the wonderful Lagoon ....

    Free Cancellation
    Private Tour
    Start From $70.51
 
 

Let’s do a morning sail on San Francisco Bay (semi private)

(5 of 6 reviews)

Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boat? Come sail with me, Captain John. Let me share my passion for sailing with you. I’m a U.S. certified sailing instructor and li... More

Free Cancellation
Private Tour
Start From $189.00
 
Let’s do a morning sail on San Francisco Bay (semi private) Likely to Sell Out

Let’s do a morning sail on San Francisco Bay (semi private)

  • North America
  • Superb6 reviews5

Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boa....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

(5 of 115 reviews)

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some goo... More

Free Cancellation
Private Tour
Start From $515.00
 
Private Hilton Head Sunset Sailing Tour with Dolphin Watching Likely to Sell Out

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

  • North America
  • Superb115 reviews5

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound ....

    Free Cancellation
    Private Tour
    Start From $515.00
 
 

Waikiki 3pm Tradewind Sail - Open Bar Included w/ General Ticket

(4.8 of 238 reviews)

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphin... More

Free Cancellation
Private Tour
Start From $42.88
 
Waikiki 3pm Tradewind Sail - Open Bar Included w/ General Ticket Likely to Sell Out

Waikiki 3pm Tradewind Sail - Open Bar Included w/ General Ticket

  • North America
  • Superb238 reviews4.8

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....

    Free Cancellation
    Private Tour
    Start From $42.88
 
 

2-Hour Sunset Sailing on San Diego Bay

(5 of 1 review)

Join Captain Doyle for an unforgettable 2-hour sunset sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and milit... More

Free Cancellation
Private Tour
Start From $120.00
 
2-Hour Sunset Sailing on San Diego Bay Likely to Sell Out

2-Hour Sunset Sailing on San Diego Bay

  • North America
  • Superb1 review5

Join Captain Doyle for an unforgettable 2-hour sunset sailing experience aboard our 35-foot sailboat....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Excursion to Reefs in a transparent boat from Cancun

(4.3 of 7 reviews)

It is the only tour that includes a visit to the lagoon, where we can appreciate 2 types of marine life, in addition, the colors of the blanquizal of Cancun are something spectacular and there is a great diversity of marine life... More

Free Cancellation
Private Tour
Start From $51.69
 
Excursion to Reefs in a transparent boat from Cancun Likely to Sell Out

Excursion to Reefs in a transparent boat from Cancun

  • North America
  • Exellent7 reviews4.3

It is the only tour that includes a visit to the lagoon, where we can appreciate 2 types of marine l....

    Free Cancellation
    Private Tour
    Start From $51.69
 
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