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Top 10 Best North America Sailing Trips

Found 673 Sailing Trips activities in North America. Sort by Popularity. - Page 16
 

Private 2-Hour Day Sailing Experience

(5 of 40 reviews)

As the first and only sailing tour in Central Florida, Sailing Orlando is committed to sharing the joy of sailing with our community and its visitors. From day sailing to sunset cruises or learning the ropes, our private tours off... More

Free Cancellation
Private Tour
Start From $85.00
 
Private 2-Hour Day Sailing Experience

Private 2-Hour Day Sailing Experience

  • North America
  • Superb40 reviews5

As the first and only sailing tour in Central Florida, Sailing Orlando is committed to sharing the j....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.7 of 334 reviews)

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More

Free Cancellation
Private Tour
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine

Windjammer Classic Day Sail from Camden, Maine

  • North America
  • Superb334 reviews4.7

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

New York City Sailboat Day Cruise to the Statue of Liberty

(4.9 of 118 reviews)

Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides a... More

Free Cancellation
Private Tour
Start From $65.72
 
New York City Sailboat Day Cruise to the Statue of Liberty Likely to Sell Out

New York City Sailboat Day Cruise to the Statue of Liberty

  • North America
  • Superb118 reviews4.9

Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted sc....

    Free Cancellation
    Private Tour
    Start From $65.72
 
 

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
Private Tour
Start From $115.00
 
An Unforgettable afternoon Aboard A Classic Sailing Yacht Likely to Sell Out

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
    Private Tour
    Start From $115.00
 
 

San Diego Bay Sailing Tour

(5 of 16 reviews)

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This group sail is li... More

Free Cancellation
Private Tour
Start From $95.00
 
San Diego Bay Sailing Tour Likely to Sell Out

San Diego Bay Sailing Tour

  • North America
  • Superb16 reviews5

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Sail Bainbridge Island & Seattle Waters - Luxury Classic Sailboat

(5 of 25 reviews)

Sailing Puget Sound is an unforgettable experience! We’ll set sail & soak up the panorama of these beautiful & inspiring waters. Departing daily from Bainbridge Island, a 30 min ferry ride from Seattle. This 2hr private sailing... More

Free Cancellation
Private Tour
Start From $475.00
 
Sail Bainbridge Island & Seattle Waters - Luxury Classic Sailboat Likely to Sell Out

Sail Bainbridge Island & Seattle Waters - Luxury Classic Sailboat

  • North America
  • Superb25 reviews5

Sailing Puget Sound is an unforgettable experience! We’ll set sail & soak up the panorama of these....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

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
Private Tour
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
    Private Tour
    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
Private Tour
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
    Private Tour
    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
Private Tour
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
    Private Tour
    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
Private Tour
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
    Private Tour
    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
 
 

Shared Day Sail along Historic St Augustine Bayfront

(5 of 3 reviews)

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories on the sea. Our cruise is perfect for all water-lovers: families, couples, and friends. Some guests interact with the USCG licensed... More

Free Cancellation
Private Tour
Start From $129.00
 
Shared Day Sail along Historic St Augustine Bayfront Likely to Sell Out

Shared Day Sail along Historic St Augustine Bayfront

  • North America
  • Superb3 reviews5

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories o....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

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
 
 

Pirate Ship Premium Dinner Cruise with Show

(4.4 of 31 reviews)

While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent views of Banderas Bay, take unforgettable photos of this amazing experience, while you taste a delicious dinner and have a good time ... More

Free Cancellation
Private Tour
Start From $211.00
 
Pirate Ship Premium Dinner Cruise with Show Likely to Sell Out

Pirate Ship Premium Dinner Cruise with Show

  • North America
  • Exellent31 reviews4.4

While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent vie....

    Free Cancellation
    Private Tour
    Start From $211.00
 
 

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
 
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