Our Sailboats
If you’re an experienced sailor we invite you to use one of our own 22′ sailboats with your cottage rental at no additional charge. there’s no better way to relax and enjoy the keys.
Our 22 foot Catalina or O’Day single-masted sailboats are perfect for cruising the calm waters of Florida Bay. Just grab your cooler, walk to our dock, and point the bow into the horizon. Explore the Florida Keys in style! Leave and return when you like…after all, you don’t want to be tied to any schedule when you’re on vacation.
And if sailing isn’t for you, try our kayaks, canoes, standup paddle boards, rowboats, or even one of the floats we make available to our guests at the dock. The point is: take to the water! It’s the Florida Keys way of life!
Even relatively new sailors can enjoy the Bay on one of our easy-handling day cruisers. It’s great family fun, and a big part of the reason Key Largo Cottages remains so popular with our guests. Find out for yourself!
22′ SAILBOAT RENTALS
Rent a 22’ Catalina Sailboat and sail around the beautiful Key Largo bay area for only $300/day plus taxes. Note: We mainly rent the cottages with a free sailboat but on a case to case basis we may have an extra sailboat that we can rent out. Just call when you are in town and we will see if we can help you get your sailing needs taken care of.
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Get Away to Key West and Explore the Florida Keys by Sailboat
Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.
Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks.
While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business.
Some of the highlights to experience on a Florida Keys Sailing Charter Vacation
Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.
Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable.
Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation.
A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife.
Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers.
From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place.
If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route.
Browse our yachts for charter in Florida Keys
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We will match any discount website offer on charter boat price, and still provide our customary high level of service.
The Essential Guide to Sailing Holiday Charters
The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.
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Sailing Club
Sailing is what we’re all about.
If you’re an experienced sailor, we invite you to use one of our sailboats included in your cottage rental at no additional charge. There’s no better way to relax and enjoy the Keys.
Plus we have an onsite American Sailing Academy (ASA) Sailing School to advance your sailing, or you can just get a taste of sailing with our 2 hour Intro to Sailing .
Our sloop-rigged 22’ Catalina sailboats are perfect for cruising the calm waters of Florida Bay. Just grab your cooler, walk to our dock, and point the bow at the horizon.
We offer approximately 30 square miles of bay side water surface to sail, which includes no less than 3 specific destinations with straight runs of up to 6 nautical miles – one way. All of our sailing area is within the confines of the pristine Florida bay, Everglades National Park and parts of the Florida Keys National Marine Sanctuary . Florida Keys National Marine Sanctuary protects 2,900 square nautical miles of waters surrounding the Florida Keys, from south of Miami westward to encompass the Dry Tortugas.
A thorough brief and chart orientation is given the morning after your arrival, followed by a walk-through familiarization with the boat you will be using. You must be able to confidently handle the vessel; if you have any doubt as to your ability, please contact Cap’n G to discuss your maritime experience. We offer a variety of instruction options that can be tailored to meet your specific needs.
SAILBOAT RENTALS
The 37′ Lagoon catamaran is an ideal vessel for bay and ocean sailing. With its stable design, spacious layout with 2 queen-sized berths forward and 1 full-sized berth aft, 1 large aft cabin head with shower, plenty of room for 2, and 1 normal-sized head and shower. Its shallow draft helps you navigate the various waters with ease. Its efficient performance and comfortable amenities make it perfect for leisurely cruises or extended voyages. The Lagoon 37′ offers a luxurious “UNFORGETTABLE” and enjoyable sailing experience, combining reliability, comfort, and versatility for memorable adventures on the water.
Capacity: 6 people price: 8 hours: $750 plus taxes 24 hours: $950 plus taxes optional captain: $350 for 8 hours, $450 for 24 hours call 305-451-7057 or book online, the 35′ edel catamaran is a fast and versatile vessel perfectly suited for bay and ocean sailing weekend getaways. with its stable dual-hull design and shallow draft, it navigates diverse waters with ease and confidence. its nimble maneuverability, tight but comfortable accommodations, and modern safety features make it ideal for both short trips and extended voyages. the edel 35′ offers a seamless blend of performance, comfort, and safety, ensuring unforgettable experiences for sailors exploring various maritime environments., capacity: 6 people price : 8 hours: $750 plus taxes 24 hours: $950 plus taxes optional captain: $350 for 8 hours, $450 for 24 hours call 305-451-7057 or book online.
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