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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.
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.
Book with Marathon Sailboat Rides
Verified experiences and guided adventures in the surrounding area.
Operated by Marathon Sailboat Rides · Marathon, Florida
Set sail on the tranquil waters of the Florida Keys with the Private Sunset Sail, an uplifting three-hour escape aboard the impressive 50-foot Bavaria sloop Chao Lay. Based in Marathon, Florida, this experience offers an intimate charter for up to six guests, blending luxury, comfort, and the vibrant natural charm of Boot Key Harbor and beyond. If you’re looking to unwind while soaking in some of the best marine views the Florida Keys have to offer, this is the perfect outing.
Marathon sits roughly midway along the Florida Keys archipelago, a string of coral islands renowned for their crystal-clear waters, vibrant coral reefs, and historic maritime landmarks. The Private Sunset Sail stands out here by providing a personalized and peaceful setting on the water, far from the busy shorelines and crowded tours common in the region. The Chao Lay yacht is meticulously maintained to combine classic sailing elegance with modern comfort, making the experience both accessible and luxurious.
Your journey begins with a welcome aboard from Captain Mike, who brings rich local knowledge and careful navigation skills. Departing from the heart of Marathon at 5 Sombrero Boulevard, you glide quietly through Boot Key Harbor, home to one of the largest mooring fields in the Keys. This harbor is a panoramic showcase of varied boats and maritime life, giving a glimpse into local boating culture.
As the sail progresses, you cruise toward Sombrero Reef and the historic Sombrero Lighthouse, built in the late 1800s and standing sentinel over the vibrant coral reef below. This lighthouse is a defining feature of Marathon’s coastline and provides a stunning backdrop for photos as the sun begins its descent.
The highlight comes as the yacht positions itself under the vast open sky just off the reef, where the horizon bursts into rich hues of flaming orange, pink, and purple. With a chilled drink in hand, you’ll find no better spot to watch the sun slip below the Gulf of Mexico. The crew ensures the environment remains serene and inviting, fully supporting guests’ comfort and enjoyment.
Unique to this trip is the exclusive nature of the charter—you won’t share it with strangers, allowing for a private, relaxed vibe perfect for couples, families, or close friends. Lifesaving equipment, bottled water, and soft drinks are included. Bring your camera, sunscreen, and perhaps a light snack or your favorite beverage to make the most of this memorable outing.
Perfect for all ages and skill levels, this sunset sail fuses natural beauty, leisure, and top-tier service to create an unforgettable evening on the water. Whether you’re a returning Keys visitor or discovering Marathon for the first time, this private sail offers a refreshing vantage point on one of Florida’s most celebrated coastal destinations.
easy.
3 hours.
Suitable for all fitness levels; minimal physical exertion required as you relax on the sailboat.
The Private Sunset Sail accommodates up to six guests, making it ideal for family or small groups.
No sailing experience is required; the captain handles all navigation and sailing.
Bottled water and soft drinks are included; guests may also bring their own food and beverages.
The sail departs daily, with start times adjusted to coincide with the local sunset and tides.
Yes, sailing is subject to weather conditions to ensure safety; trips may be rescheduled in adverse weather.
Departures are from 5 Sombrero Boulevard in Marathon, Florida.
Sombrero Lighthouse, constructed in 1890, guided ships safely through Marathon's reefs and remains an iconic landmark today.
The Florida Keys Marine Sanctuary protects coral reefs and marine life; the charter operates sustainably with no impact on local habitats.
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.
Book with Marathon Sailboat Rides