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Top 10 Best North America Sailing Trips

Found 642 Sailing Trips activities in North America. Sort by Popularity. - Page 16
 

Fun Boat Rental with Captain in Miami Beach - up to 6 people

(4.9 of 43 reviews)

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straightforward bareboat charter. Now, let's talk logistics. The captain's compensation is a separate matter, settled directly at the ... More

Private Tour
Start From $330.00
 
Fun Boat Rental with Captain in Miami Beach - up to 6 people

Fun Boat Rental with Captain in Miami Beach - up to 6 people

  • North America
  • Superb43 reviews4.9

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straig....

    Private Tour
    Start From $330.00
 
 

New York Day Sail to the Statue of Liberty on Schooner America

(4.8 of 58 reviews)

Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable, elegant and smooth at 105-feet in length with 3600 square... More

Private Tour
Start From $65.72
 
New York Day Sail to the Statue of Liberty on Schooner America Likely to Sell Out

New York Day Sail to the Statue of Liberty on Schooner America

  • North America
  • Superb58 reviews4.8

Offering a premium sailing experience, the Schooner America is a tribute to the original America t....

    Private Tour
    Start From $65.72
 
 

The Finest Private Yacht Experience in Cabo

(4.8 of 17 reviews)

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some of the best things to do in Cabo such as whale watching and bathing on soothing crystal waters... More

Free Cancellation
Private Tour
Start From $651.60
 
The Finest Private Yacht Experience in Cabo Likely to Sell Out

The Finest Private Yacht Experience in Cabo

  • North America
  • Superb17 reviews4.8

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30....

    Free Cancellation
    Private Tour
    Start From $651.60
 
 

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

(4.7 of 67 reviews)

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above Honolulu to snorkeling off a catamaran off Waikiki. Explore lush rainforest and... More

Free Cancellation
Private Tour
Start From $196.63
 
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel Likely to Sell Out

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

  • North America
  • Superb67 reviews4.7

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....

    Free Cancellation
    Private Tour
    Start From $196.63
 
 

Kayak & Guided Snorkel hosted by Honest Eco

(5 of 142 reviews)

I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and bein... More

Free Cancellation
Private Tour
Start From $145.00
 
Kayak & Guided Snorkel hosted by Honest Eco Likely to Sell Out

Kayak & Guided Snorkel hosted by Honest Eco

  • North America
  • Superb142 reviews5

I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world w....

    Free Cancellation
    Private Tour
    Start From $145.00
 
 

Sea to Sky Afternoon Sail

(5 of 198 reviews)

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain ranges. We will depart from the docks in Squamish (about 40 minut... More

Free Cancellation
Private Tour
Start From $130.93
 
Sea to Sky Afternoon Sail Likely to Sell Out

Sea to Sky Afternoon Sail

  • North America
  • Superb198 reviews5

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds w....

    Free Cancellation
    Private Tour
    Start From $130.93
 
 

Private Morning Sailing/Dolphin & History Tours on Mystique

(5 of 72 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $499.00
 
Private Morning Sailing/Dolphin & History Tours on Mystique Likely to Sell Out

Private Morning Sailing/Dolphin & History Tours on Mystique

  • North America
  • Superb72 reviews5

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

    Free Cancellation
    Private Tour
    Start From $499.00
 
 

Polynesian Canoe Day Sail

(4.8 of 24 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
Private Tour
Start From $200.00
 
Polynesian Canoe Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • North America
  • Superb24 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Whale Shark Experience Lifetime Memory in Cancun (snack included)

(3.9 of 17 reviews)

Welcome to the Whale Shark experience, this is an unique activity in the world and is the most enigmatic activity in Mexico. Imagine swimming next to an immense fish like the whale shark. This animal is completely harmless since... More

Free Cancellation
Private Tour
Start From $189.00
 
Whale Shark Experience Lifetime Memory in Cancun (snack included) Likely to Sell Out

Whale Shark Experience Lifetime Memory in Cancun (snack included)

  • North America
  • Very Good17 reviews3.9

Welcome to the Whale Shark experience, this is an unique activity in the world and is the most enigm....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Party On Sailing Cruise to Isla Mujeres from Cancun

(3.8 of 15 reviews)

Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our national drinks onboard the catamaran. You will snorkel at one of the best reefs and see beautiful tropical fish, then eat lunch ... More

Free Cancellation
Private Tour
Start From $63.99
 
Party On Sailing Cruise to Isla Mujeres from Cancun Likely to Sell Out

Party On Sailing Cruise to Isla Mujeres from Cancun

  • North America
  • Very Good15 reviews3.8

Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our....

    Free Cancellation
    Private Tour
    Start From $63.99
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 71 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Private Tour
Start From $54.95
 
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor Likely to Sell Out

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

  • North America
  • Superb71 reviews4.6

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Private Tour
    Start From $54.95
 
 

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

(4.8 of 36 reviews)

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying on the bow relaxing under the stars, this moonlight sail is ultimate freedom! ... More

Free Cancellation
Private Tour
Start From $60.71
 
JFarwell Moonlight Yacht Cruise from Halifax Waterfront Likely to Sell Out

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

  • North America
  • Superb36 reviews4.8

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....

    Free Cancellation
    Private Tour
    Start From $60.71
 
 

Private Luxury 42ft Sailing with Snorkeling in Los Cabos

(5 of 115 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
  • Superb115 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
 
 

Visit Private Beaches around Puerto Vallarta in a Private Yacht

(4.9 of 66 reviews)

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain on the art of sailing. This is not a boat trip, this is an experience to enj... More

Free Cancellation
Private Tour
Start From $1,500.00
 
Visit Private Beaches around Puerto Vallarta in a Private Yacht Likely to Sell Out

Visit Private Beaches around Puerto Vallarta in a Private Yacht

  • North America
  • Superb66 reviews4.9

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours do....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
 

2hr Shared Sailing Experience in Toronto

(4.9 of 19 reviews)

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to be the shortest commercial one in the world. Below the water is a walking tunnel connecting the two for t... More

Free Cancellation
Private Tour
Start From $138.24
 
2hr Shared Sailing Experience in Toronto Likely to Sell Out

2hr Shared Sailing Experience in Toronto

  • North America
  • Superb19 reviews4.9

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out fo....

    Free Cancellation
    Private Tour
    Start From $138.24
 
 

Key West's Locals' Top Sailing and Sun Experience

(4.2 of 15 reviews)

Sebago's newest trip, the Locals Lounge, is designed to allow guests to experience the waters around Key West as so many locals do, visiting little known, breathtakingly beautiful spots with small groups of friends while enjoying ... More

Free Cancellation
Private Tour
Start From $129.00
 
Key West's Locals' Top Sailing and Sun Experience Likely to Sell Out

Key West's Locals' Top Sailing and Sun Experience

  • North America
  • Exellent15 reviews4.2

Sebago's newest trip, the Locals Lounge, is designed to allow guests to experience the waters around....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Catamaran with Open Bar through the Lagoon of the 7 Colors

(5 of 57 reviews)

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical landscapes. You will visit the most beautiful places in the lagoon where yo... More

Free Cancellation
Private Tour
Start From $96.00
 
Catamaran with Open Bar through the Lagoon of the 7 Colors Likely to Sell Out

Catamaran with Open Bar through the Lagoon of the 7 Colors

  • North America
  • Superb57 reviews5

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters i....

    Free Cancellation
    Private Tour
    Start From $96.00
 
 

All Inclusive Caribbean adventure, reef snorkeling with Food and Drinks

(3.7 of 33 reviews)

Admire the peaceful waters of the Caribbean Sea, aboard a catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience. Explore Isla Mujeres impressive sites are waiting for you. You will visit one of ... More

Free Cancellation
Skip The Line
Private Tour
Start From $49.00
 
All Inclusive Caribbean adventure, reef snorkeling with Food and Drinks Likely to Sell Out

All Inclusive Caribbean adventure, reef snorkeling with Food and ....

  • North America
  • Very Good33 reviews3.7

Admire the peaceful waters of the Caribbean Sea, aboard a catamaran and enjoy a spectacular day sail....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $49.00
 
 

New York City Skyline Lights Sail

(4.7 of 13 reviews)

Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights from the water and enjoy a peaceful setting as you escape the city and take to a quiet harbor at night. Key points about this activ... More

Free Cancellation
Skip The Line
Private Tour
Start From $76.32
 
New York City Skyline Lights Sail Likely to Sell Out

New York City Skyline Lights Sail

  • North America
  • Superb13 reviews4.7

Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights fro....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $76.32
 
 

Waikiki Friday Firework Catamaran Tour

(4.7 of 27 reviews)

The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breathtaking fireworks just outside the Hilton Hawaiian Village. Every Friday at 6:45pm, you have the opportunity to watch a spectacular ... More

Free Cancellation
Skip The Line
Private Tour
Start From $69.99
 
Waikiki Friday Firework Catamaran Tour Likely to Sell Out

Waikiki Friday Firework Catamaran Tour

  • North America
  • Superb27 reviews4.7

The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breatht....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $69.99
 
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