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Top 10 Best North America Sailing Trips

Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 29
 

Private Sailboat Charter from San Pedro: Port of Los Angeles

(5 of 1 review)

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a sunset sailing adventure on a Beneteau Oceanis (39ft) sailing yacht, perfect for couples or small groups looking for a memorable out... More

Free Cancellation
Private Tour
Start From $380.00
 
Private Sailboat Charter from San Pedro: Port of Los Angeles

Private Sailboat Charter from San Pedro: Port of Los Angeles

  • North America
  • Superb1 review5

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a su....

    Free Cancellation
    Private Tour
    Start From $380.00
 
 

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

(5 of 2 reviews)

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on board sound system with Tiki-Oki, and the friendliest most fun captains around. You'll be sure to have... More

Free Cancellation
Private Tour
Start From $349.00
 
Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise Likely to Sell Out

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

  • North America
  • Superb2 reviews5

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, b....

    Free Cancellation
    Private Tour
    Start From $349.00
 
 

Private Dolphin Sightseeing Sail Aboard Daydreams Sailboat

(5 of 2 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! Your 90 minute Dolphin Sightseeing Sail on our Daydreams sailboat will inclu... More

Free Cancellation
Private Tour
Start From $499.00
 
Private Dolphin Sightseeing Sail Aboard Daydreams Sailboat Likely to Sell Out

Private Dolphin Sightseeing Sail Aboard Daydreams Sailboat

  • North America
  • Superb2 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 $499.00
 
 

Private - Bacalar sailing across the mesmerizing waters

(4.9 of 10 reviews)

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence of colonial history & pirates. We embark upon a sailing boat to navigate our way across the mesmerizing waters of 7 different shad... More

Free Cancellation
Private Tour
Start From $499.00
 
Private - Bacalar sailing across the mesmerizing waters Likely to Sell Out

Private - Bacalar sailing across the mesmerizing waters

  • North America
  • Superb10 reviews4.9

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence o....

    Free Cancellation
    Private Tour
    Start From $499.00
 
 

Key West Nighttime Full Moon Sail

(5 of 10 reviews)

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moo... More

Free Cancellation
Private Tour
Start From $83.85
 
Key West Nighttime Full Moon Sail Likely to Sell Out

Key West Nighttime Full Moon Sail

  • North America
  • Superb10 reviews5

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1....

    Free Cancellation
    Private Tour
    Start From $83.85
 
 

6 Hour Private Fishing Charter in the Riviera Maya

(4.9 of 16 reviews)

Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully private experience, not a shared tour. The itinerary is flexible ... More

Free Cancellation
Private Tour
Start From $1,050.00
 
6 Hour Private Fishing Charter in the Riviera Maya Likely to Sell Out

6 Hour Private Fishing Charter in the Riviera Maya

  • North America
  • Superb16 reviews4.9

Unlike many destinations, your fishing time starts within minutes of departure—no long boat ridesâ....

    Free Cancellation
    Private Tour
    Start From $1,050.00
 
 

Introduction to Sailing in Saint John, NB

(5 of 9 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 $72.83
 
Introduction to Sailing in Saint John, NB Likely to Sell Out

Introduction to Sailing in Saint John, NB

  • North America
  • Superb9 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 $72.83
 
 

Full-Day Sailing Isla Mujeres with complimentary Transportation

(3.5 of 4 reviews)

Set sail on a fun-filled 7-hour adventure along the beautiful Cancun coast, perfect for the whole family! Your exciting day starts with complimentary transportation from your hotel right to the marina in Cancun's Hotel Zone ( only... More

Free Cancellation
Private Tour
Start From $89.99
 
Full-Day Sailing Isla Mujeres with complimentary Transportation Likely to Sell Out

Full-Day Sailing Isla Mujeres with complimentary Transportation

  • North America
  • Good4 reviews3.5

Set sail on a fun-filled 7-hour adventure along the beautiful Cancun coast, perfect for the whole fa....

    Free Cancellation
    Private Tour
    Start From $89.99
 
 

Honolulu Sailing and Snorkeling Activity

(3.5 of 4 reviews)

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine creatures that call the Hawaiian islands home.... More

Free Cancellation
Private Tour
Start From $105.00
 
Honolulu Sailing and Snorkeling Activity Likely to Sell Out

Honolulu Sailing and Snorkeling Activity

  • North America
  • Good4 reviews3.5

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine c....

    Free Cancellation
    Private Tour
    Start From $105.00
 
 

Dolphin Sightseeing Sail Aboard Daydreams Sailboat

(5 of 3 reviews)

Your 90 minute Dolphin Sightseeing Sail on our Daydreams sailboat will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way... More

Free Cancellation
Private Tour
Start From $75.00
 
Dolphin Sightseeing Sail Aboard Daydreams Sailboat Likely to Sell Out

Dolphin Sightseeing Sail Aboard Daydreams Sailboat

  • North America
  • Superb3 reviews5

Your 90 minute Dolphin Sightseeing Sail on our Daydreams sailboat will include a scenic trip through....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Private Tour Isla Mujeres excursion in Transparent Boat

(3.3 of 3 reviews)

We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our 100% transparent boat. It will be a unique activity for you, where you will be given a guided tour of different reefs to apprecia... More

Free Cancellation
Private Tour
Start From $373.14
 
Private Tour Isla Mujeres excursion in Transparent Boat Likely to Sell Out

Private Tour Isla Mujeres excursion in Transparent Boat

  • North America
  • Good3 reviews3.3

We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our ....

    Free Cancellation
    Private Tour
    Start From $373.14
 
 

Holbox Island Boat Tour Punta Mosquito Yalahau and Isla Pasion

(3.3 of 3 reviews)

This Holbox experience is more than just a boat tour — it’s a carefully curated full-day adventure designed to showcase the very best of the northern Caribbean coast in one seamless journey. Unlike basic transfers to the isla... More

Free Cancellation
Private Tour
Start From $159.00
 
Holbox Island Boat Tour Punta Mosquito Yalahau and Isla Pasion Likely to Sell Out

Holbox Island Boat Tour Punta Mosquito Yalahau and Isla Pasion

  • North America
  • Good3 reviews3.3

This Holbox experience is more than just a boat tour — it’s a carefully curated full-day adventu....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Two Fantastic Islands To Discover: Tour To Contoy & Isla Mujeres

(3.3 of 3 reviews)

Begin your adventure with hotel pickup and a light breakfast at our private marina in Punta Sam. From there, set sail to the charming Isla Mujeres, a Pueblo Mágico (Magical Town), where you’ll have an hour to explore its vibran... More

Free Cancellation
Private Tour
Start From $198.30
 
Two Fantastic Islands To Discover: Tour To Contoy & Isla Mujeres Likely to Sell Out

Two Fantastic Islands To Discover: Tour To Contoy & Isla Mujeres

  • North America
  • Good3 reviews3.3

Begin your adventure with hotel pickup and a light breakfast at our private marina in Punta Sam. Fro....

    Free Cancellation
    Private Tour
    Start From $198.30
 
 

Paddle at Dawn with visit to Cenotes and Islands

(5 of 103 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 $23.07
 
Paddle at Dawn with visit to Cenotes and Islands Likely to Sell Out

Paddle at Dawn with visit to Cenotes and Islands

  • North America
  • Superb103 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 $23.07
 
 

Original Cruisin Tikis Snorkeling Safari

(5 of 1 review)

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart of Destin Harbor while you soak in the scenery and the good vibes... More

Free Cancellation
Private Tour
Start From $89.00
 
Original Cruisin Tikis Snorkeling Safari Likely to Sell Out

Original Cruisin Tikis Snorkeling Safari

  • North America
  • Superb1 review5

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Miami: Ultimate Boat Party with Open Bar, DJ & After-Party

(5 of 1 review)

Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience. This 3-hour Miami booze cruise offers a unique nightclub atmosphere on the water, complete with a FREE open bar serving unlimited... More

Free Cancellation
Private Tour
Start From $139.00
 
Miami: Ultimate Boat Party with Open Bar, DJ & After-Party Likely to Sell Out

Miami: Ultimate Boat Party with Open Bar, DJ & After-Party

  • North America
  • Superb1 review5

Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience.....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Sunset Cruise Tequila Tasting

(5 of 4 reviews)

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the history of one of Mexico's most iconic drinks, brought to you by Tequila Cabo Único and Sunrider. You'll get to know the iconic Cabo S... More

Free Cancellation
Private Tour
Start From $115.00
 
Sunset Cruise Tequila Tasting Likely to Sell Out

Sunset Cruise Tequila Tasting

  • North America
  • Superb4 reviews5

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the histo....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Moana’s Luxury semi-private Sunset Cruise on Nalu

(4.8 of 22 reviews)

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback Whale watching at no additional cost. Dolphins, Sea turtle... More

Free Cancellation
Private Tour
Start From $149.99
 
Moana’s Luxury semi-private Sunset Cruise on Nalu Likely to Sell Out

Moana’s Luxury semi-private Sunset Cruise on Nalu

  • North America
  • Superb22 reviews4.8

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....

    Free Cancellation
    Private Tour
    Start From $149.99
 
 

Isla Mujeres Catamaran Tour with Snorkeling Spinnaker and Lunch

(4.8 of 22 reviews)

Discover the beauty of Isla Mujeres on this 7-hour catamaran adventure from Cancun. Sail the vibrant Caribbean waters while snorkeling in a stunning reef, then take to the skies with a thrilling spinnaker ride. Once you reach Isla... More

Free Cancellation
Private Tour
Start From $18.00
 
Isla Mujeres Catamaran Tour with Snorkeling Spinnaker and Lunch Likely to Sell Out

Isla Mujeres Catamaran Tour with Snorkeling Spinnaker and Lunch

  • North America
  • Superb22 reviews4.8

Discover the beauty of Isla Mujeres on this 7-hour catamaran adventure from Cancun. Sail the vibrant....

    Free Cancellation
    Private Tour
    Start From $18.00
 
 

Intrepid SpeedBoat Tour in Cancun with Snorkel Experience

(4.8 of 22 reviews)

This is the best experience in Cancun and one of the most wanted, here you will feel 100% free, take a break and relax in this amazing activity. Enjoy and have fun driving your own speedboat across the Nichupte lagoon that is one ... More

Free Cancellation
Private Tour
Start From $70.00
 
Intrepid SpeedBoat Tour in Cancun with Snorkel Experience Likely to Sell Out

Intrepid SpeedBoat Tour in Cancun with Snorkel Experience

  • North America
  • Superb22 reviews4.8

This is the best experience in Cancun and one of the most wanted, here you will feel 100% free, take....

    Free Cancellation
    Private Tour
    Start From $70.00
 
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Booking.com
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