Marathon Sailboat Rides

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    • Home
    • Day Sail
    • Sunset Sail
    • Private Sail
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    • Blog

Marathon Sailboat Rides

Marathon Sailboat RidesMarathon Sailboat RidesMarathon Sailboat Rides
  • Home
  • Day Sail
  • Sunset Sail
  • Private Sail
  • Our Boat
  • Location
  • Blog
Several sailboats navigate the calm waters of Marathon FL, perfect for a day sailing adventure.

Welcome

Marathon Sailboat Rides

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Reserve your Sailboat Ride today!

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Looking for unforgettable things to do in Marathon, Florida?

Marathon Sailboat Rides is the premier boat tour company in Marathon, Fl offering the best in Day Sails, Sunset Sails, and Private Sailboat Rides. We're located in Yacht Haven Marina at 5 Sombrero Blvd. Dock 6B.  


We offer daily sailing charters that take you through the stunning waters of Boot Key Harbor, Hawk Channel, and the Florida Keys Marine Sanctuary. Along the way, you’ll have the chance to spot dolphins, manatees, and other fascinating marine life. 


Our tours are limited to only six people at a time, so sign up early to assure your spot before the next sailboat ride fills up. Marathon Sailboat Rides promises a unique way to enjoy your visit to the Florida Keys.  

Reviews

Marathon Sailing Options

Chose Your Perfect Sailing Adventure

Sailboat under full sail. Click here to be taken to the Day Sailing web page on this site.

Day Sailing

$89

A three-hour boat tour through the breathtaking waters of  the Florida  Keys Marine Sanctuary.  This guided sailboat tour combines relaxation and exploration, making it the perfect daytime activity.  

Sunset captured from the deck of Chao Lay

Sunset Sail

$500

 Witness the magic of  a Private Marathon sunset sail overlooking the iconic Seven Mile Bridge. This 3-hour sunset sail is a romantic and serene way to end your day in paradise.  

Husband & wife sitting in the cockpit of a sailboat in Marathon FL . Click for sailing tour info

Private Sail

$500

Enjoy a three-hour private sail that includes the  breathtaking sights and serene beauty of the Florida Keys Marine Sanctuary. From one to six guests

Sailing with dolphins !

If you're lucky, you may witness a pod of dolphins gracefully swimming alongside our boat,Chao Lay. DOLPHIN SIGHTINGS ARE NOT GUARANTEED.

Why Choose Marathon Sailboat Rides?

  • Our Special Boat : Our yacht, “Chao Lay,” has crossed the Atlantic, Pacific, and Indian Oceans and is now available for you to experience right here in Marathon, Fl. With its luxurious design and spacious layout, it’s perfect for both intimate and group settings.
  • Our Special Captain:  Captain Mike is a seasoned mariner with over 50 years of boating experience, including a voyage around the world. He holds a U.S. Coast Guard 50-ton Master's Near Coastal License with a Sailing Endorsement, ensuring you're in expert hands. Aboard "Chao Lay", comfort and safety come first. Designed for ease, not speed, she sails only in calm conditions—so you can relax and enjoy the journey. Join Capt Mike for a smooth, enjoyable charter and hear firsthand tales from a life at sea.
  • Eco-Friendly Sailing Excursions: Explore the pristine waters of the Florida Keys while treading lightly on the environment. 

Marathon Sailboat Rides - Manatee Sighting!

If you're lucky, you may see  Manatees swimming alongside Chao Lay. These intelligent and playful creatures are known to frequent the area, and encountering them in their natural habitat is a magical experience. We frequently see them next to the boat before we even  leave the dock!

Plan Your Sailing Charter Today

 Make the most of your visit to Marathon, Florida, by adding a sailing charter to your itinerary. Whether you’re looking for a relaxing boat tour, an adventurous day at sea, or a romantic sunset sail, Marathon Sailboat Rides has you covered. Book your sailboat ride now and discover why we’re one of the top things to do in Marathon, Florida.

Book Now

Sailing The Keys

WELCOME ABOARD!

Husband and wife seated in cockpit of Chao Lay enjoying a Day Sail with the sea in the background.
Young couple seated in the cockpit of Chao Lay during a Day Sail with turquoise sea in background.
Four lovely ladies enjoying a private sailing charter to celebrate a birthday with Boot Key behind.
Husband and Wife enjoying a day of sailing in the cockpit of Chao Lay. Blue seas in the background.
Couple are sitting and relaxing on a sailboat charter in Marathon, FL, enjoying the gentle sway.
Girls are enjoying a sailboat charter in the clear blue waters of Marathon, FL, under a sunny sky.
A couple enjoying a delightful day sail in Marathon FL, sitting on a sailboat under sunny skies,
Three people complete a day sailing adventure and are seated in the cockpit upon returning to dock.
Two people stand on a moored sailboat in Yacht Haven Marina, getting ready for a sailboat tour.
  • Home
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Marathon Sailboat Rides

5 Sombrero Blvd, Marathon, FL 33050

(305) 307-9816

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