When it comes to catamaran and sailing charters in the Florida Keys, Calypso Sailing is your first mate. Given our diverse fleet of vessels and time spent on Key West waters, there’s no better ally when it comes to exploring Southern Florida, whether at sea, or on land.  The team here at Calypso Charters prides itself on decades of experience in expertly guiding families, commercial parties, and couples through their Florida Keys sailboat charter adventure. 

From Key Largo, Islamorada, Marathon to Big Pine and the Bahamas, Calypso Sailing can offer you the experience, vessel, equipment, and luxuries you need to make your Florida Keys sailing vacation a lifelong memory. One of our most popular sailing charter destination is Marathon, Florida, a world-renowned tropical destination that’s bound to become one of the most interesting cities you’ve ever visited. 

The city of Marathon is located in Monroe County, across thirteen islands in the Florida Keys, among them Knight's Key, Boot Key, Key Vaca, Fat Deer Key, Long Point Key, Crawl Key and Grassy Key islands, each located at the center of the Florida Keys island chain. When you set off on your Calypso Sailing catamaran or sailing charter adventure with Marathon in your sights, there’s no telling what kind of family adventures you’ll embark on. Here, you’ll find a list of just a few of greater-Marathon’s incredible sites, nearly each of which is easily accessible by your vessel. Remember, a Florida sailing charter vacation with Calypso Sailing is always about more than being at sea —it’s about uncovering the amazing culture, food, fishing, wildlife and arts the Florida Keys has to offer. 

Eat, Drink & Be Merry

When you dock your Florida sailing charter at Marathon for a day, a night, or even a weekend, you'll find there's no shortage of delicious cuisine. Dozens of seafood restaurants offer delights that are caught fresh in the waters just outside the city limits. From lobster to sushi, tuna to octopus, there's no sea-borne cuisine you won't find amid Marathon's thriving restaurant culture. In fact, the restaurant scene in Marathon is as diverse as the ocean life in the Florida Keys. Those who have had their fill of seafood can also enjoy the city's Cuban, Caribbean and Italian options. No matter which menu you choose, you'll be able to enjoy your meal on any number of outside dining areas and eat while you enjoy a sunset or the lapping sounds of the warm Atlantic waters. Visitors can even take a quiet seaside stroll before returning to the welcoming comfort of their sleeping cabin aboard their Calypso Charters vessel. 

Swim With the Dolphins

Want to you parlay your Florida catamaran rental experience into a date with dolphins? When you visit Marathon, Florida, you can. Founded in 1984, the Marathon Dolphin Research Center is a non-profit marine mammal education and research facility that is also known across the Florida Keys for it's exciting, education, and immersive wildlife programs. The Dolphin Research Center offers a wide variety of programs ranging from dolphin research experiences, paint with dolphins and a family dolphin swim that will provide you and your family with many happy memories while you explore and learn about one of the world's most fascinating animals. 

Take to the Air

If your relaxing sailing vacation through the Florida Keys has you yearning for a better view, Marathon’s array of helicopter tour operators can help you get it. From quick five-minute jaunts to hour-long sessions, a helicopter tour out of Marathon, Florida is an excellent way to enrich your relaxing sailing charter vacation. Soar high above the teal waters of the Florida Keys and get a once-in-a-lifetime view of the verdant vegetation and colorful architecture. You can even book a tour that cruises over the Sombrero Lighthouse and the coral reef that lies just outside of the archipelago where it sits.

Make Friends With a Turtle

Dolphins aren’t the only marine friends you can explore when your Florida catamaran sailing charter docks at one of Marathon’s islands. The Turtle Hospital is another popular destination where visitors can learn about one of the Florida Keys most precious species: sea turtles. Opened in 1986, The Turtle Hospital rehabs injured sea turtles and returns them to their natural habitat while spreading knowledge about this fascinating species through an annual calendar of community and public education programs. Guests to the facility can take a 90-minute guided educational tour of the hospital facilities and the sea turtle rehabilitation area. It's an excellent destination —particularly if you see a sea turtle in your travels throughout the waters of Key West.

Florida’s Sailing Charter Experts

When you set sail with Calypso Sailing Charters, the waters in and around the city of Marathon are yours to visit as you like. That’s why Florida Keys visitors who set sail with us return season after season. Why be encumbered by crowded tours or stuck in line at overpopulated theme parks? Whether you jump into the crisp, warm waters for a swim, go fishing for your favorite sport fish, or take in the underwater sights and ocean life, Calypso Sailing charters gives you and your family a fully-immersive, educational, and environmentally friendly way to explore the planet in ways you never thought possible. Contact our friendly team today to learn about how you can book an unforgettable Florida Keys sailing vacation and create a lifetime worth of memories.