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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 14
 

Maui Turtle Snorkel & Sail with Lunch & Open Bar

(4.8 of 39 reviews)

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear waters teeming with vibrant coral reefs a... More

Free Cancellation
Start From $122.40
 
Maui Turtle Snorkel & Sail with Lunch & Open Bar

Maui Turtle Snorkel & Sail with Lunch & Open Bar

  • North America
  • Superb39 reviews4.8

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine lan....

    Free Cancellation
    Start From $122.40
 
 

Private sailing tour of Bacalar Lagoon

(5 of 463 reviews)

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More

Free Cancellation
Private Tour
Start From $240.00
 
Private sailing tour of Bacalar Lagoon

Private sailing tour of Bacalar Lagoon

  • North America
  • Superb463 reviews5

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....

    Free Cancellation
    Private Tour
    Start From $240.00
 
 

Maui Snorkel and Sunset Sail Lahaina

(5 of 463 reviews)

Embark on a once-in-a-lifetime family adventure, where sun, sea, and stunning sunsets come together for the perfect day on the water! Whether you’re snorkeling or simply soaking in the views, there’s something for everyone to ... More

Free Cancellation
Private Tour
Start From $129.75
 
Maui Snorkel and Sunset Sail Lahaina Likely to Sell Out

Maui Snorkel and Sunset Sail Lahaina

  • North America
  • Superb463 reviews5

Embark on a once-in-a-lifetime family adventure, where sun, sea, and stunning sunsets come together ....

    Free Cancellation
    Private Tour
    Start From $129.75
 
 

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

(5 of 2 reviews)

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yacht designe... More

Free Cancellation
Private Tour
Start From $675.00
 
2 Hours Sunset Private Charter on Heart's Desire in Casco Bay Likely to Sell Out

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

  • North America
  • Superb2 reviews5

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - com....

    Free Cancellation
    Private Tour
    Start From $675.00
 
 

Tiki Pub Amazing Dolphin Eco Adventure

(4.4 of 8 reviews)

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and a myriad of sea creatures and incredible Birds! The best part is that then y... More

Free Cancellation
Private Tour
Start From $49.95
 
Tiki Pub Amazing Dolphin Eco Adventure Likely to Sell Out

Tiki Pub Amazing Dolphin Eco Adventure

  • North America
  • Exellent8 reviews4.4

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water i....

    Free Cancellation
    Private Tour
    Start From $49.95
 
 

Spectacular Afternoon Sail on San Diego Bay

(5 of 20 reviews)

A unique small group two-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy spectacular views as your fun-loving, informative Captain shares his knowledge of sailing and San Diego. Get hands-on or sit back and enjoy ... More

Free Cancellation
Private Tour
Start From $108.00
 
Spectacular Afternoon Sail on San Diego Bay Likely to Sell Out

Spectacular Afternoon Sail on San Diego Bay

  • North America
  • Superb20 reviews5

A unique small group two-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy spectacula....

    Free Cancellation
    Private Tour
    Start From $108.00
 
 

Brunch Cruise with Buffet in Washington

(3.9 of 11 reviews)

Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer three public sailing tours daily from Seattle’s downtown waterfront. Our beautiful sailing ship, the Bay Lady, evokes the romanc... More

Free Cancellation
Private Tour
Start From $89.00
 
Brunch Cruise with Buffet in Washington Likely to Sell Out

Brunch Cruise with Buffet in Washington

  • North America
  • Very Good11 reviews3.9

Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Private Swim, Snorkel & Sail on the Daydreams Sailboat

(5 of 32 reviews)

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More

Free Cancellation
Private Tour
Start From $899.00
 
Private Swim, Snorkel & Sail on the Daydreams Sailboat Likely to Sell Out

Private Swim, Snorkel & Sail on the Daydreams Sailboat

  • North America
  • Superb32 reviews5

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....

    Free Cancellation
    Private Tour
    Start From $899.00
 
 

San Diego Sailing Sunset and Afternoon Classic Yacht

(5 of 6 reviews)

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More

Free Cancellation
Private Tour
Start From $125.00
 
San Diego Sailing Sunset and Afternoon Classic Yacht Likely to Sell Out

San Diego Sailing Sunset and Afternoon Classic Yacht

  • North America
  • Superb6 reviews5

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Wednesday Happy Hour Sunset Sail - Drinks Included

(5 of 7 reviews)

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha Wednesday Sunset Sail. This midweek escape combines tropical charm with st... More

Free Cancellation
Private Tour
Start From $76.00
 
Wednesday Happy Hour Sunset Sail - Drinks Included Likely to Sell Out

Wednesday Happy Hour Sunset Sail - Drinks Included

  • North America
  • Superb7 reviews5

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit....

    Free Cancellation
    Private Tour
    Start From $76.00
 
 

Public Sunset Sailing Cruise on Lake Champlain

(5 of 4 reviews)

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendship Sloop. This two-hour cruise offers an unparalleled view of the Adirondack Mountains as you relax and enjoy the charming atmosphe... More

Free Cancellation
Private Tour
Start From $95.00
 
Public Sunset Sailing Cruise on Lake Champlain Likely to Sell Out

Public Sunset Sailing Cruise on Lake Champlain

  • North America
  • Superb4 reviews5

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendshi....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

(5 of 2 reviews)

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on board sound system with Tiki-Oki, and the friendliest most fun captains around. You'll be sure to have... More

Free Cancellation
Private Tour
Start From $349.00
 
Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise Likely to Sell Out

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

  • North America
  • Superb2 reviews5

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, b....

    Free Cancellation
    Private Tour
    Start From $349.00
 
 

Adults Only Party Cruise to Isla Mujeres Free one-way pickup

(3.7 of 210 reviews)

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More

Free Cancellation
Private Tour
Start From $89.99
 
Adults Only Party Cruise to Isla Mujeres Free one-way pickup Likely to Sell Out

Adults Only Party Cruise to Isla Mujeres Free one-way pickup

  • North America
  • Very Good210 reviews3.7

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....

    Free Cancellation
    Private Tour
    Start From $89.99
 
 

Xoximilco Flaoting Fiesta in Canals of Cancun

(5 of 7 reviews)

Celebrate Mexican culture like never before at Xoximilco by Xcaret—a one-of-a-kind floating fiesta through the canals of Cancun! Step aboard a colorful trajinera (traditional gondola-style boat) and get ready for a night full of... More

Free Cancellation
Private Tour
Start From $155.00
 
Xoximilco Flaoting Fiesta in Canals of Cancun Likely to Sell Out

Xoximilco Flaoting Fiesta in Canals of Cancun

  • North America
  • Superb7 reviews5

Celebrate Mexican culture like never before at Xoximilco by Xcaret—a one-of-a-kind floating fiesta....

    Free Cancellation
    Private Tour
    Start From $155.00
 
 

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

(4.9 of 85 reviews)

This sailing tour is born of our love of the 7 Colors Lagoon and the desire to share it in an authentic and relaxed way. It’s not just a walk – it’s a space to live together, laugh, toast and connect, whether you come with f... More

Free Cancellation
Private Tour
Start From $76.20
 
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
  • Superb85 reviews4.9

This sailing tour is born of our love of the 7 Colors Lagoon and the desire to share it in an authen....

    Free Cancellation
    Private Tour
    Start From $76.20
 
 

Friday Night Firework Cruise in Waikiki

(4.8 of 34 reviews)

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More

Free Cancellation
Private Tour
Start From $69.99
 
Friday Night Firework Cruise in Waikiki Likely to Sell Out

Friday Night Firework Cruise in Waikiki

  • North America
  • Superb34 reviews4.8

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

(5 of 203 reviews)

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More

Free Cancellation
Private Tour
Start From $870.00
 
Private Sailboat tour in Cabo San Lucas with Papillon Yachts Likely to Sell Out

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

  • North America
  • Superb203 reviews5

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....

    Free Cancellation
    Private Tour
    Start From $870.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.6 of 63 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Private Tour
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • North America
  • Superb63 reviews4.6

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Romantic Sunset Dinner Cruise in Cancun with Open Bar

(4.6 of 12 reviews)

Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to an amazing romantic experience and an exquisite 3-course dinner. Following you check-in, get aboard the spectacular ship under t... More

Free Cancellation
Private Tour
Start From $112.00
 
Romantic Sunset Dinner Cruise in Cancun with Open Bar Likely to Sell Out

Romantic Sunset Dinner Cruise in Cancun with Open Bar

  • North America
  • Superb12 reviews4.6

Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to ....

    Free Cancellation
    Private Tour
    Start From $112.00
 
 

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

(5 of 2 reviews)

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for fu... More

Free Cancellation
Private Tour
Start From $120.00
 
Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams Likely to Sell Out

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

  • North America
  • Superb2 reviews5

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow....

    Free Cancellation
    Private Tour
    Start From $120.00
 
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