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Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 25
 

All Inclusive St Pete Private Half Day Catamaran Charter

(5 of 1 review)

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks,... More

Free Cancellation
Private Tour
Start From $1,700.00
 
All Inclusive St Pete Private Half Day Catamaran Charter

All Inclusive St Pete Private Half Day Catamaran Charter

  • North America
  • Superb1 review5

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and cr....

    Free Cancellation
    Private Tour
    Start From $1,700.00
 
 

Sunset Sailing Cruise on San Diego Bay | Champagne Included

(5 of 1 review)

What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group tour. You will be sailing aboard a beautifully crafted French yacht designed for... More

Free Cancellation
Private Tour
Start From $199.00
 
Sunset Sailing Cruise on San Diego Bay | Champagne Included

Sunset Sailing Cruise on San Diego Bay | Champagne Included

  • North America
  • Superb1 review5

What makes this experience truly special is the blend of refined European luxury and a relaxed, inti....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Afternoon Ali'i Adventure

(5 of 6 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Free Cancellation
Private Tour
Start From $276.00
 
Afternoon Ali'i Adventure

Afternoon Ali'i Adventure

  • North America
  • Superb6 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Free Cancellation
    Private Tour
    Start From $276.00
 
 

Private Luxury Adventure Tours in Cabo San Lucas

(4.9 of 16 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

Private Luxury Adventure Tours in Cabo San Lucas

  • North America
  • Superb16 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
 
 

Private Morning Sail in San Diego up to 12 guests $975

(5 of 33 reviews)

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More

Free Cancellation
Private Tour
Start From $487.50
 
Private Morning Sail in San Diego up to 12 guests $975

Private Morning Sail in San Diego up to 12 guests $975

  • North America
  • Superb33 reviews5

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....

    Free Cancellation
    Private Tour
    Start From $487.50
 
 

Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

(5 of 3 reviews)

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and your guests! You'll sail around Shell Island into the Gulf of Mexico, while you enjoy dol... More

Free Cancellation
Private Tour
Start From $759.96
 
Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

  • North America
  • Superb3 reviews5

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you....

    Free Cancellation
    Private Tour
    Start From $759.96
 
 

Private Catamaran: Snorkel, Swim and Dolphin Watching

(5 of 1 review)

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast.... More

Free Cancellation
Private Tour
Start From $465.00
 
Private Catamaran: Snorkel, Swim and Dolphin Watching

Private Catamaran: Snorkel, Swim and Dolphin Watching

  • North America
  • Superb1 review5

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion....

    Free Cancellation
    Private Tour
    Start From $465.00
 
 

Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos

(3.7 of 75 reviews)

Prepare for a thrilling day trip to Isla Mujeres from Cancun, tailored for nature lovers and fun-seekers with our two exciting options: Option 1: All-Inclusive Adventure We'll take you from your Cancun hotel to two incredible sno... More

Free Cancellation
Private Tour
Start From $93.50
 
Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos

Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos

  • North America
  • Very Good75 reviews3.7

Prepare for a thrilling day trip to Isla Mujeres from Cancun, tailored for nature lovers and fun-see....

    Free Cancellation
    Private Tour
    Start From $93.50
 
 

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
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
    Private Tour
    Start From $79.00
 
 

Isla Mujeres Sailing Adventure from Cancun

(3.7 of 6 reviews)

Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard of an exclusive catamaran...!! This tour is recommended for those who like to have fun, with music for all tastes and open-bar on... More

Free Cancellation
Private Tour
Start From $149.00
 
Isla Mujeres Sailing Adventure from Cancun Likely to Sell Out

Isla Mujeres Sailing Adventure from Cancun

  • North America
  • Very Good6 reviews3.7

Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Los Cabos Snorkeling Tour by Boat with Open Bar and Music

(3.7 of 6 reviews)

One moment you’re sailing past Lover’s Beach, the Arch and the Sea Lion Colony; the next, you’re jumping into the warm waters of Santa Maria Bay or Chileno Bay with your snorkel gear ready to explore beneath the surface. Sw... More

Free Cancellation
Private Tour
Start From $129.00
 
Los Cabos Snorkeling Tour by Boat with Open Bar and Music Likely to Sell Out

Los Cabos Snorkeling Tour by Boat with Open Bar and Music

  • North America
  • Very Good6 reviews3.7

One moment you’re sailing past Lover’s Beach, the Arch and the Sea Lion Colony; the next, you’....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Baltimore Harbor Evening Sail on the Unforgettable

(4.6 of 5 reviews)

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorgeous scenery of the skyline as the city lights up. Treat yourself and a loved one on this elegant sailing experience.  It's BYOB,... More

Free Cancellation
Private Tour
Start From $75.00
 
Baltimore Harbor Evening Sail on the Unforgettable Likely to Sell Out

Baltimore Harbor Evening Sail on the Unforgettable

  • North America
  • Superb5 reviews4.6

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorg....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Private luxury sailing catamaran experience in Bacalar lagoon

(5 of 5 reviews)

Our Stiletto catamaran stands out due to several unique features: 1. Speed and Stability : Unlike traditional catamarans, the Stiletto combines the thrill of speed with exceptional stability, ensuring a smooth and exciting ride,... More

Free Cancellation
Private Tour
Start From $302.13
 
Private luxury sailing catamaran experience in Bacalar lagoon Likely to Sell Out

Private luxury sailing catamaran experience in Bacalar lagoon

  • North America
  • Superb5 reviews5

Our Stiletto catamaran stands out due to several unique features: 1. Speed and Stability : Unlike ....

    Free Cancellation
    Private Tour
    Start From $302.13
 
 

2hr Luxury Private Sailing Catamaran for 7-12 People

(5 of 4 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,495.00
 
2hr Luxury Private Sailing Catamaran for 7-12 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran for 7-12 People

  • North America
  • Superb4 reviews5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,495.00
 
 

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

(5 of 37 reviews)

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions for sailing). During the MORNING, this is generally a calm - light wind relaxing sail, a... More

Free Cancellation
Private Tour
Start From $465.00
 
2 - Hour Private Hilton Head Morning Dolphin Watching / Sail Likely to Sell Out

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

  • North America
  • Superb37 reviews5

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side ....

    Free Cancellation
    Private Tour
    Start From $465.00
 
 

Private Sunset Sailing

(5 of 1 review)

A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premium Open Bar and a Cheese and Cold Cuts table as snacks. Go in style and go Private. Since Covid-19 additional measures and precauti... More

Free Cancellation
Private Tour
Start From $999.00
 
Private Sunset Sailing Likely to Sell Out

Private Sunset Sailing

  • North America
  • Superb1 review5

A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premiu....

    Free Cancellation
    Private Tour
    Start From $999.00
 
 

Sailing Charter

(5 of 9 reviews)

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More

Free Cancellation
Private Tour
Start From $240.00
 
Sailing Charter Likely to Sell Out

Sailing Charter

  • North America
  • Superb9 reviews5

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....

    Free Cancellation
    Private Tour
    Start From $240.00
 
 

Catamaran and Snorkel in Isla Mujeres

(3 of 4 reviews)

Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will snorkel (depends on weather) and spend time in the exclusive beach club where you will have a delicious buffet.... More

Free Cancellation
Private Tour
Start From $65.00
 
Catamaran and Snorkel in Isla Mujeres Likely to Sell Out

Catamaran and Snorkel in Isla Mujeres

  • North America

Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will s....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Private Sunset Sail on San Diego Bay with Champagne

(3 of 4 reviews)

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully crafted French yacht, designed for comfort, performance, and elegan... More

Free Cancellation
Private Tour
Start From $975.00
 
Private Sunset Sail on San Diego Bay with Champagne Likely to Sell Out

Private Sunset Sail on San Diego Bay with Champagne

  • North America

What makes this experience truly unique is the combination of refined European luxury and a relaxed,....

    Free Cancellation
    Private Tour
    Start From $975.00
 
 

Whale Shark Experience Lifetime Memory in Cancun (snack included)

(3.9 of 17 reviews)

Join one of the most wonderful wildlife experiences in Cancun during the whale shark season! Explore the Caribbean Sea aboard a small-group boat for a more exclusive adventure. Experience a memorable whale shark encounter featuri... More

Free Cancellation
Private Tour
Start From $159.00
 
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

Join one of the most wonderful wildlife experiences in Cancun during the whale shark season! Explor....

    Free Cancellation
    Private Tour
    Start From $159.00
 
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