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Top 10 Best North America Sailing Trips

Found 673 Sailing Trips activities in North America. Sort by Popularity. - Page 15
 

An Unforgettable afternoon Aboard A Classic Sailing Yacht

(5 of 66 reviews)

Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica of a 1904 gaff rigged friendship sloop. She is an elegant sight under sail, featuring; highly finished woodwork, bronze fixtures, a... More

Free Cancellation
Start From $115.00
 
An Unforgettable afternoon Aboard A Classic Sailing Yacht

An Unforgettable afternoon Aboard A Classic Sailing Yacht

  • North America
  • Superb66 reviews5

Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....

    Free Cancellation
    Start From $115.00
 
 

1.5-Hour Koa Kai Adventure Whale Watch

(5 of 2 reviews)

Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful creatures return to Maui every year to birth their young. During this trip, you will get a chance to hear the whale’s unique songs a... More

Free Cancellation
Start From $79.00
 
1.5-Hour Koa Kai Adventure Whale Watch Likely to Sell Out

1.5-Hour Koa Kai Adventure Whale Watch

  • North America
  • Superb2 reviews5

Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful crea....

    Free Cancellation
    Start From $79.00
 
 

Luxury Catamaran tour to isla mujeres with transportation from Tulum

(3.5 of 62 reviews)

Excellent service on board Professional crew members Safety measures in all our activities Sanitary prevention protocols for all our guests and staff Once in a lifetime experience Delicious buffet lunch and drinks Beach club (beac... More

Free Cancellation
Start From $110.77
 
Luxury Catamaran tour to isla mujeres with transportation from Tulum Likely to Sell Out

Luxury Catamaran tour to isla mujeres with transportation from Tu....

  • North America
  • Good62 reviews3.5

Excellent service on board Professional crew members Safety measures in all our activities Sanitary ....

    Free Cancellation
    Start From $110.77
 
 

Private Luxury Adventure Tours in Cabo San Lucas

(4.9 of 8 reviews)

Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy this amazing adventure for 2 hours departing at 09:00 am in the morning. Or you prefer more for a special day in the water that i... More

Free Cancellation
Start From $149.00
 
Private Luxury Adventure Tours in Cabo San Lucas Likely to Sell Out

Private Luxury Adventure Tours in Cabo San Lucas

  • North America
  • Superb8 reviews4.9

Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy....

    Free Cancellation
    Start From $149.00
 
 

Sailing Snorkel Adventure

(4.4 of 5 reviews)

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sailing Boat Adventure is unbeatable Value. ... More

Free Cancellation
Start From $145.00
 
Sailing Snorkel Adventure Likely to Sell Out

Sailing Snorkel Adventure

  • North America
  • Exellent5 reviews4.4

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sa....

    Free Cancellation
    Start From $145.00
 
 

Private Luxury 42ft Sailing with Snorkeling in Los Cabos

(5 of 118 reviews)

Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful white beaches. Your yacht and crew will provide you with all the ameni... More

Free Cancellation
Private Tour
Start From $990.00
 
Private Luxury 42ft Sailing with Snorkeling in Los Cabos Likely to Sell Out

Private Luxury 42ft Sailing with Snorkeling in Los Cabos

  • North America
  • Superb118 reviews5

Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Sno....

    Free Cancellation
    Private Tour
    Start From $990.00
 
 

Snorkeling Adventure in Isla Mujeres

(3.8 of 12 reviews)

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum is a unique activity in the world since there is no such thing anywhere. This activity is cataloged as mandatory for all traveler... More

Free Cancellation
Private Tour
Start From $55.00
 
Snorkeling Adventure in Isla Mujeres Likely to Sell Out

Snorkeling Adventure in Isla Mujeres

  • North America
  • Very Good12 reviews3.8

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Skagway Trail and Sail

(5 of 3 reviews)

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More

Free Cancellation
Private Tour
Start From $265.00
 
Skagway Trail and Sail Likely to Sell Out

Skagway Trail and Sail

  • North America
  • Superb3 reviews5

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....

    Free Cancellation
    Private Tour
    Start From $265.00
 
 

Romantic Dinner on a Spanish Galeon in Cancun

(4.2 of 22 reviews)

Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner with the most wonderful scenary. This is the perfect opportunity to enjoy a delicious dinner while you fall in love with the liv... More

Free Cancellation
Private Tour
Start From $95.00
 
Romantic Dinner on a Spanish Galeon in Cancun Likely to Sell Out

Romantic Dinner on a Spanish Galeon in Cancun

  • North America
  • Exellent22 reviews4.2

Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

The Boat People Cruise Private Harbor Cruises

(5 of 26 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
  • Superb26 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
 
 

Day Sailing Adventure in the Florida Marine Sanctuary

(5 of 7 reviews)

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose a 3-hour Day Sail or our popular Sunset Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailbo... More

Free Cancellation
Private Tour
Start From $99.00
 
Day Sailing Adventure in the Florida Marine Sanctuary Likely to Sell Out

Day Sailing Adventure in the Florida Marine Sanctuary

  • North America
  • Superb7 reviews5

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar

(3.7 of 33 reviews)

Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience where music, drinks and incredible views will never be lacking. ... More

Free Cancellation
Private Tour
Start From $55.00
 
Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar Likely to Sell Out

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar

  • North America
  • Very Good33 reviews3.7

Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a sp....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

San Francisco City Lights Sail

(5 of 5 reviews)

The Golden Gate isn’t the only bridge in town! Once the sun sets and the lights come on, join us for a city-front cruise to enjoy the majestic sites of San Francisco in the night sky. See the Bay Bridge lit in all its glory, alo... More

Free Cancellation
Private Tour
Start From $85.00
 
San Francisco City Lights Sail Likely to Sell Out

San Francisco City Lights Sail

  • North America
  • Superb5 reviews5

The Golden Gate isn’t the only bridge in town! Once the sun sets and the lights come on, join us f....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 6 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
  • Superb6 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
 
 

Palancar, Columbia and El Cielo Reef Snorkeling by Catamaran

(4.1 of 48 reviews)

Get yourself in the mood for fun in this guided Catamaran snorkeling trip and enjoy one of the Caribbean wonders as you visit El Cielo Beach and its shallow waters surrounded by starfish, baby rays and a sandy bottom. Included on... More

Free Cancellation
Skip The Line
Private Tour
Start From $110.00
 
Palancar, Columbia and El Cielo Reef Snorkeling by Catamaran Likely to Sell Out

Palancar, Columbia and El Cielo Reef Snorkeling by Catamaran

  • North America
  • Exellent48 reviews4.1

Get yourself in the mood for fun in this guided Catamaran snorkeling trip and enjoy one of the Carib....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $110.00
 
 

Deluxe Turtle Snorkeling Escapade at Waikiki

(4.8 of 4 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Skip The Line
Private Tour
Start From $110.00
 
Deluxe Turtle Snorkeling Escapade at Waikiki Likely to Sell Out

Deluxe Turtle Snorkeling Escapade at Waikiki

  • North America
  • Superb4 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $110.00
 
 

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

(4.7 of 286 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
Skip The Line
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
  • Superb286 reviews4.7

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

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $66.67
 
 

Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

(5 of 1 review)

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite Tour to Isla Mujeres provides full sailing, snorkeling & enough time to visit Isla Mujeres for shopping or just enjoy this wonderf... More

Free Cancellation
Skip The Line
Private Tour
Start From $79.00
 
Cancun Half Day Sailing Cataman Cruise to Isla Mujeres Likely to Sell Out

Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

  • North America
  • Superb1 review5

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite ....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $79.00
 
 

Pastries and Prosecco in Boston Harbor

(5 of 7 reviews)

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. F... More

Free Cancellation
Skip The Line
Private Tour
Start From $75.00
 
Pastries and Prosecco in Boston Harbor Likely to Sell Out

Pastries and Prosecco in Boston Harbor

  • North America
  • Superb7 reviews5

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable v....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $75.00
 
 

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 49 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
Skip The Line
Private Tour
Start From $59.95
 
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

  • North America
  • Superb49 reviews4.9

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

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $59.95
 
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