Sailboat cruising at sunset on open ocean, deck view

Private Florida Keys Sails — Small-Group Sunsets & Day Trips

Three-hour sails aboard the 50-foot Bavaria sloop S/V Chao Lay — private charters and intimate day sails departing the Marathon area.

Featured Sailing Experiences

Private Sunset Sail, Day Sail, and Private Sail — choose the intimate three-hour trip that fits your group.

Marathon

Private Sunset Sail in Marathon: Experience Florida Keys’ Best Views Aboard a Luxury Bavaria Sloop

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.

Private Sunset Sail in Marathon: Experience Florida Keys’ Best Views Aboard a Luxury Bavaria Sloop

Intimate Day Sail Adventure in Marathon, Florida: Explore Boot Key Harbor & Sombrero Lighthouse

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.

Marathon

Explore Florida Keys on a Private 3-Hour Sailing Adventure Aboard S/V Chao Lay

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.

About Marathon Sailboat Rides

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.

Couple relaxing on sailboat cockpit in turquoise waters, leisure trip

Marathon Sailboat Rides — Florida Keys Sailing Experiences

Marathon Sailboat Rides operates small-group and private sailboat trips while the business is based in Miami, Florida. The company runs three-hour sails aboard the 50-foot Bavaria sloop S/V Chao Lay, offering intimate outings that showcase Boot Key Harbor and views of the Sombrero Lighthouse.

Popular Trips and What to Expect

The offered experiences are consistent in duration and focus:

Private Sunset Sail — a three-hour private cruise for up to five guests, timed to capture sunset near Sombrero Lighthouse.
Day Sail — a three-hour shared sail from Yacht Haven Marina in Marathon, Florida, limited to six guests with a friendly crew guiding the route.
Private Sail — a private three-hour charter for up to five guests focused on marine life and coastal scenery.

Each three-hour trip emphasizes relaxed sailing, opportunities for coastal photography, and hands-on time aboard a well-maintained sloop. The small guest limits make these trips suitable for couples, families, and groups seeking a private maritime experience in the Florida Keys.

Vessel, Crew, and Safety

Marathon Sailboat Rides uses the 50-foot Bavaria sloop S/V Chao Lay, a vessel described in trip details that provides stable sailing and covered deck space. The crew provides local navigational knowledge in Boot Key Harbor and attentive service during each voyage. Day Sail departures are listed from Yacht Haven Marina in Marathon, Florida, with routes that typically include views of the Sombrero Lighthouse.

Why Choose These Sailboat Rides

Travelers searching for Marathon sailboat rides, sailboat rides Miami, Florida Keys sailing, private sunset sail, day sail, or private sail will find specific, factual trip descriptions to compare. Key practical advantages include:

Defined guest limits for more personal experiences
Specific vessel information (50-foot Bavaria, S/V Chao Lay)
Departures listed from Yacht Haven Marina in Marathon, Florida
Scenic passages through Boot Key Harbor and past Sombrero Lighthouse

Booking and Practical Tips

Trips are three hours long and list guest limits: six guests for the Day Sail and up to five guests for private charters. Travelers should consider daylight and local weather when selecting times; the crew manages safety and timing for the best on-water experience. Reservations are recommended to secure preferred dates.

Local SEO and Search Terms

This content supports searches for Marathon sailboat rides, sailboat rides Miami, Florida Keys sailing, private sunset sail, day sail, and private sail by providing clear, factual information about trip types, vessel specifications, departure location, and typical highlights like Boot Key Harbor and Sombrero Lighthouse. Prospective guests can use these details to pick the right three-hour experience aboard S/V Chao Lay.

Sailboats racing off coast under clear blue sky, regatta scene

Reserve a Marathon Sailboat Ride Today

Secure a Private Sunset Sail, Day Sail, or Private Sail aboard the S/V Chao Lay — small groups and defined guest limits.