Three-hour sails aboard the 50-foot Bavaria sloop S/V Chao Lay — private charters and intimate day sails departing the Marathon area.
Private Sunset Sail, Day Sail, and Private Sail — choose the intimate three-hour trip that fits your group.
boat-charters · Marathon
Discover a private sunset sailing experience in Marathon, Florida Keys aboard a luxurious 50-foot Bavaria sloop. Perfect for intimate groups seeking unforgettable views near Sombrero Lighthouse.
Marathon Sailboat Rides offers guided small-group and private sailing experiences in the Florida Keys. Operating from a base in Miami, Florida, the company runs three-hour sails aboard the 50-foot Bavaria sloop S/V Chao Lay, carrying up to six guests on public trips and up to five guests on private charters. Trips depart from Yacht Haven Marina in Marathon, Florida, and navigate picturesque Boot Key Harbor with close views of the iconic Sombrero Lighthouse.
Available experiences include the Private Sunset Sail, a three-hour exclusive cruise for up to five guests that emphasizes sunset views near Sombrero Lighthouse; the Day Sail, an intimate three-hour shared voyage limited to six guests with a friendly crew guiding the route; and the Private Sail, a private three-hour charter for up to five guests focused on marine life and coastal scenery. Each trip highlights quiet sailing, coastal photography opportunities, and hands-on time aboard a comfortable, well-maintained sloop.
Marathon Sailboat Rides emphasizes safety and a personalized sailing experience. The crew provides local knowledge of the Florida Keys, navigational expertise in Boot Key Harbor, and attentive service suited to families, couples, and small groups. The 50-foot Bavaria sloop offers stable sailing and covered deck space for comfort.
Bookings are ideal for visitors seeking a relaxed, private way to experience Marathon and the surrounding Keys. The business's clear guest limits and specific vessel details make it easy for customers to choose the right sailing option. Reservations are available year-round subject to local weather and daylight conditions and capacity limits.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Official business location listed
50-foot Bavaria sloop
Small groups for private trips
Day Sails depart from Marathon marina
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Marathon Sailboat Rides listing.
Marathon Sailboat Rides offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Secure a Private Sunset Sail, Day Sail, or Private Sail aboard the S/V Chao Lay — small groups and defined guest limits.
water-activities · Marathon
Set sail from Marathon, Florida, on a peaceful 3-hour Day Sail through Boot Key Harbor and past the iconic Sombrero Lighthouse. Experience an exclusive, small-group voyage that captures the best of Florida Keys’ coastal beauty.
boat-charters · Marathon
Embark on a private three-hour sail in Marathon, Florida, aboard the S/V Chao Lay. Experience crystal-clear waters, vibrant marine life, and iconic sights like Sombrero Lighthouse in a serene, exclusive setting perfect for families and small groups.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.