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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 18
 

New York City Skyline Lights Sail

(4.6 of 14 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
Start From $67.01
 
New York City Skyline Lights Sail Likely to Sell Out

New York City Skyline Lights Sail

  • North America
  • Superb14 reviews4.6

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

    Free Cancellation
    Start From $67.01
 
 

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

(4.9 of 120 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
Start From $55.00
 
Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon Likely to Sell Out

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

  • North America
  • Superb120 reviews4.9

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

    Free Cancellation
    Start From $55.00
 
 

Romantic Sunset Dinner Cruising Experience

(4.2 of 42 reviews)

Sail away on Cancun's only romantic dinner cruise, a magnificent way to pamper your loved one or to enjoy a classy supper with your friends. With the magnificent backdrop that no restaurant can provide, indulge in a fine meal unde... More

Free Cancellation
Start From $109.00
 
Romantic Sunset Dinner Cruising Experience Likely to Sell Out

Romantic Sunset Dinner Cruising Experience

  • North America
  • Exellent42 reviews4.2

Sail away on Cancun's only romantic dinner cruise, a magnificent way to pamper your loved one or to ....

    Free Cancellation
    Start From $109.00
 
 

2-Hour Morning Sail in San Diego

(4.9 of 32 reviews)

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma, San Diego Bay and the downtown waterfront. This two-hour adventure on a Catalina sailboat is limited to a maximum of six (6) gues... More

Free Cancellation
Start From $95.00
 
2-Hour Morning Sail in San Diego Likely to Sell Out

2-Hour Morning Sail in San Diego

  • North America
  • Superb32 reviews4.9

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma,....

    Free Cancellation
    Start From $95.00
 
 

Sunset Sailing Seattle

(4.9 of 32 reviews)

I've been doing sailing tours for 10 years, and compared to the bigger boats, with more passengers, I offer more intimate setting with great history on an antique modern sailing yacht.... More

Free Cancellation
Start From $125.00
 
Sunset Sailing Seattle Likely to Sell Out

Sunset Sailing Seattle

  • North America
  • Superb32 reviews4.9

I've been doing sailing tours for 10 years, and compared to the bigger boats, with more passengers, ....

    Free Cancellation
    Start From $125.00
 
 

Private Sailing Tour in Valle de Bravo

(4.7 of 27 reviews)

Enjoy the beauty of sailing in the waters of the magical town through a sailboat ride in Velero in Valle de Bravo, crossing the lake to observe its beautiful panoramic views of its different places such as the rock in the company ... More

Free Cancellation
Private Tour
Start From $99.14
 
Private Sailing Tour in Valle de Bravo Likely to Sell Out

Private Sailing Tour in Valle de Bravo

  • North America
  • Superb27 reviews4.7

Enjoy the beauty of sailing in the waters of the magical town through a sailboat ride in Velero in V....

    Free Cancellation
    Private Tour
    Start From $99.14
 
 

Introduction to Sailing in Saint John, NB

(5 of 8 reviews)

Set sail on the tranquil waters of the Saint John River aboard our O'Day 34 sailing yacht, for a 2.5 to 3-hour introduction to boating experience. Led by a certified Sail Canada instructor, this cruise offers first-time boaters a ... More

Free Cancellation
Private Tour
Start From $65.55
 
Introduction to Sailing in Saint John, NB Likely to Sell Out

Introduction to Sailing in Saint John, NB

  • North America
  • Superb8 reviews5

Set sail on the tranquil waters of the Saint John River aboard our O'Day 34 sailing yacht, for a 2.5....

    Free Cancellation
    Private Tour
    Start From $65.55
 
 

Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar

(3.6 of 17 reviews)

Set off on a sun-and-fun-packed day trip to charming Isla Mujeres, a must-see attraction just off the Cancun coast. Cruise on a modern catamaran while sipping a drink or two from the open bar on your way to and from the scenic isl... More

Free Cancellation
Private Tour
Start From $79.00
 
Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar Likely to Sell Out

Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar

  • North America
  • Very Good17 reviews3.6

Set off on a sun-and-fun-packed day trip to charming Isla Mujeres, a must-see attraction just off th....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks

(5 of 14 reviews)

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel at the beauty that makes Los Cabos a unique destination and enjoy this adventure aboard our luxurious French-made sailboats and cat... More

Free Cancellation
Private Tour
Start From $180.00
 
Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks Likely to Sell Out

Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Dr....

  • North America
  • Superb14 reviews5

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel a....

    Free Cancellation
    Private Tour
    Start From $180.00
 
 

Sunrise by Paddle or Kayak with Floating Picnic

(5 of 394 reviews)

Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic in a natural environment while you immerse yourself in warm and crystal clear w... More

Free Cancellation
Private Tour
Start From $29.33
 
Sunrise by Paddle or Kayak with Floating Picnic Likely to Sell Out

Sunrise by Paddle or Kayak with Floating Picnic

  • North America
  • Superb394 reviews5

Dare to live a new experience! During this activity you will connect with your ecological SELF as yo....

    Free Cancellation
    Private Tour
    Start From $29.33
 
 

Sailing Tour through the Lagoon of the 7 Colors

(4.9 of 1,232 reviews)

Sail with people who share your passion for adventure! You will explore fascinating places along the lagoon of the 7 colors. Our small groups guarantee you excellent attention and service from our crew. Disconnect from the world ... More

Free Cancellation
Private Tour
Start From $44.00
 
Sailing Tour through the Lagoon of the 7 Colors Likely to Sell Out

Sailing Tour through the Lagoon of the 7 Colors

  • North America
  • Superb1,232 reviews4.9

Sail with people who share your passion for adventure! You will explore fascinating places along the....

    Free Cancellation
    Private Tour
    Start From $44.00
 
 

Maui Sunset Sail

(4.6 of 220 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to expe... More

Free Cancellation
Private Tour
Start From $137.82
 
Maui Sunset Sail Likely to Sell Out

Maui Sunset Sail

  • North America
  • Superb220 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Private Tour
    Start From $137.82
 
 

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

(4.9 of 54 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

Free Cancellation
Private Tour
Start From $260.00
 
Fun Boat Rental with Captain in Miami Beach - up to 6 people Likely to Sell Out

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

  • North America
  • Superb54 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $260.00
 
 

Cabo Yacht Tour to Lovers or Pelícano Beach with Beach Time

(4.3 of 6 reviews)

Set sail for a day of relaxation on our yacht tour to Lovers Beach. This 45-minute journey offers you the chance to unwind on the beautiful sands of Pelícano Beach, where you can enjoy a minimum of 2 hours of free time to soak up... More

Free Cancellation
Private Tour
Start From $35.00
 
Cabo Yacht Tour to Lovers or Pelícano Beach with Beach Time Likely to Sell Out

Cabo Yacht Tour to Lovers or Pelícano Beach with Beach Time

  • North America
  • Exellent6 reviews4.3

Set sail for a day of relaxation on our yacht tour to Lovers Beach. This 45-minute journey offers yo....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

BYOB Friday Night Fireworks Cruise

(4.3 of 6 reviews)

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More

Free Cancellation
Private Tour
Start From $138.95
 
BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • North America
  • Exellent6 reviews4.3

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Free Cancellation
    Private Tour
    Start From $138.95
 
 

Whale Watching, Kraken Chase and Cabo Arch

(4.3 of 6 reviews)

Embark on an exciting Kraken chase across the Pacific Ocean and the Sea of Cortez! We begin the adventure by exploring the iconic Cabo San Lucas Arch, where you will have the opportunity to capture images of the sea lion colony. ... More

Free Cancellation
Private Tour
Start From $140.79
 
Whale Watching, Kraken Chase and Cabo Arch Likely to Sell Out

Whale Watching, Kraken Chase and Cabo Arch

  • North America
  • Exellent6 reviews4.3

Embark on an exciting Kraken chase across the Pacific Ocean and the Sea of Cortez! We begin the adv....

    Free Cancellation
    Private Tour
    Start From $140.79
 
 

Harbor Sail Aboard the Tall Ship Denis Sullivan

(4.3 of 6 reviews)

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views, this pub... More

Free Cancellation
Private Tour
Start From $55.00
 
Harbor Sail Aboard the Tall Ship Denis Sullivan Likely to Sell Out

Harbor Sail Aboard the Tall Ship Denis Sullivan

  • North America
  • Exellent6 reviews4.3

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique oppor....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Bacalar : Sailing Tour with Beers & Guacamole

(4.9 of 109 reviews)

Let's go, adventurers! Join a unique shared sailing tour across the Bacalar Lagoon, where we’ll explore the area’s incredible cenotes. Feel the magic of each spot as we sail without engines — just the sound of the wind and w... More

Free Cancellation
Private Tour
Start From $50.33
 
Bacalar : Sailing Tour with Beers & Guacamole Likely to Sell Out

Bacalar : Sailing Tour with Beers & Guacamole

  • North America
  • Superb109 reviews4.9

Let's go, adventurers! Join a unique shared sailing tour across the Bacalar Lagoon, where we’ll ex....

    Free Cancellation
    Private Tour
    Start From $50.33
 
 

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

(4.7 of 68 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
  • Superb68 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
 
 

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

(4.9 of 107 reviews)

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More

Free Cancellation
Private Tour
Start From $119.00
 
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak Likely to Sell Out

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

  • North America
  • Superb107 reviews4.9

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....

    Free Cancellation
    Private Tour
    Start From $119.00
 
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