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Top 10 Best North America Sailing Trips

Found 705 Sailing Trips activities in North America. Sort by Popularity. - Page 10
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 922 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Free Cancellation
Start From $89.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • North America
  • Superb922 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Start From $89.99
 
 

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

(5 of 178 reviews)

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More

Free Cancellation
Private Tour
Start From $750.00
 
Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

  • North America
  • Superb178 reviews5

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....

    Free Cancellation
    Private Tour
    Start From $750.00
 
 

2-hour Private Luxury New York City Sunset Boat Tour

(5 of 25 reviews)

Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and reflects off of the city skyline on this magical 2-hour sunset cruise around lower Manhattan! Get an unobstructed view of the Man... More

Free Cancellation
Private Tour
Start From $599.99
 
2-hour Private Luxury New York City Sunset Boat Tour

2-hour Private Luxury New York City Sunset Boat Tour

  • North America
  • Superb25 reviews5

Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and....

    Free Cancellation
    Private Tour
    Start From $599.99
 
 

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

(5 of 19 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
  • Superb19 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
 
 

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

(4.9 of 24 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
  • Superb24 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
 
 

Polynesian Canoe Sunset Sail

(4.9 of 122 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

Special Offer
Free Cancellation
Private Tour
Start From $225.00
(Saving 10% ) $250.00
 
-10% Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • North America
  • Superb122 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $225.00
    (Saving 10% ) $250.00
 
 

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)

(4.9 of 73 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), 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 pal... More

Free Cancellation
Private Tour
Start From $69.00
 
2 hour Tiki Pub Sensational Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)

  • North America
  • Superb73 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $69.00
 
 

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos

(3.7 of 10 reviews)

Join us for an unforgettable sailboat tour to the stunning Puerto Morelos Reef, a part of the Mesoamerican Barrier Reef System, the second-largest coral reef in the world! Departing daily at 9 AM and 2 PM, our adventure begins wit... More

Free Cancellation
Private Tour
Start From $119.00
 
Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos Likely to Sell Out

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelo....

  • North America
  • Very Good10 reviews3.7

Join us for an unforgettable sailboat tour to the stunning Puerto Morelos Reef, a part of the Mesoam....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

(4.9 of 912 reviews)

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More

Special Offer
Free Cancellation
Private Tour
Start From $98.01
(Saving 10% ) $108.91
 
-10% Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses Likely to Sell Out

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

  • North America
  • Superb912 reviews4.9

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $98.01
    (Saving 10% ) $108.91
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 514 reviews)

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More

Free Cancellation
Private Tour
Start From $116.00
 
Small-Group San Diego Afternoon Sailing Excursion Likely to Sell Out

Small-Group San Diego Afternoon Sailing Excursion

  • North America
  • Superb514 reviews5

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....

    Free Cancellation
    Private Tour
    Start From $116.00
 
 

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

(4.7 of 298 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
  • Superb298 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
 
 

Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests

(5 of 40 reviews)

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a full restroom, as well as a... More

Free Cancellation
Private Tour
Start From $399.99
 
Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests Likely to Sell Out

Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests

  • North America
  • Superb40 reviews5

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....

    Free Cancellation
    Private Tour
    Start From $399.99
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.8 of 58 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
  • Superb58 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Luxury Camden Sailing Experience

(5 of 2 reviews)

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor... More

Free Cancellation
Private Tour
Start From $125.00
 
Luxury Camden Sailing Experience Likely to Sell Out

Luxury Camden Sailing Experience

  • North America
  • Superb2 reviews5

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 140 reviews)

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More

Free Cancellation
Private Tour
Start From $99.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • North America
  • Superb140 reviews4.9

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

(4.6 of 93 reviews)

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to fall in love again at the rhythm of the live sax with a sunset as enchanting as t... More

Free Cancellation
Private Tour
Start From $95.00
 
Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music Likely to Sell Out

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

  • North America
  • Superb93 reviews4.6

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

(3.7 of 203 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 $69.99
 
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar Likely to Sell Out

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

  • North America
  • Very Good203 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 $69.99
 
 

Bimini or Grand Bahama Island by Ferry

(3.6 of 13 reviews)

Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Florida! Picture this: pristine white beaches, crystal-clear turquoise waters, and tons of fun activities waiting for you. We'll pick... More

Free Cancellation
Private Tour
Start From $225.00
 
Bimini or Grand Bahama Island by Ferry Likely to Sell Out

Bimini or Grand Bahama Island by Ferry

  • North America
  • Very Good13 reviews3.6

Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Flor....

    Free Cancellation
    Private Tour
    Start From $225.00
 
 

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch

(4.8 of 293 reviews)

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a perfe... More

Free Cancellation
Private Tour
Start From $129.00
 
Puerto Vallarta Luxury Sailing with Premium Open bar & lunch Likely to Sell Out

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch

  • North America
  • Superb293 reviews4.8

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Sunset Sail Cruise in Key West

(4.9 of 235 reviews)

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Free Cancellation
Private Tour
Start From $95.00
 
Sunset Sail Cruise in Key West Likely to Sell Out

Sunset Sail Cruise in Key West

  • North America
  • Superb235 reviews4.9

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
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