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Key West, FL
boating guide
In addition to the best offers we have for boat and yacht charters in Key West, FL, see also options available for rent in these nearby locations:
- 10 boat rentals in Key West, FL
- 10 boat rentals in Stock Island, FL
- 10 boat rentals in Key Haven, FL
- 10 boat rentals in East Rockland Key, FL
- 10 boat rentals in Cudjoe Key, FL
- 10 boat rentals in Summerland Key, FL
- 10 boat rentals in Little Torch Key, FL
- 10 boat rentals in Big Pine Key, FL
Discover Key West, FL with Sailo - a gorgeous boating playground for you to enjoy!
Ready to see your options for renting a sailboat in key west, fl, learn how to find the perfect yacht for you, how much is it to charter a key west, fl yacht for a day, what is sailo’s cancellation policy, sustainable yachting tips.
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- Key Largo, FL
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Welcome to our unique little hideaway. Secluded, serene, and perfectly located, our self-contained cottages have everything you need for a relaxing waterfront vacation.
There are no hidden charges – your stay includes:.
- Unlimited private sailboat use
- Snorkeling equipment
- Stand-up paddle boards
- Fishing gear
- Use of BBQ grills
- Onsite parking
In the evening, just walk or paddle around to local dining and dancing. Or stay on site and enjoy Key Largo’s incredible sunsets from one of the area’s most intimate settings… the Key Lime Sailing Club & Cottages. Easy to reach, hard to forget!
This was my 10th year of staying at KLSC in early March – it continues to be my vacation site of choice – and I’m already in the book or 2016. Great location, amenities and staff. It doesn’t get any better than this.
We had the most wonderful vacation. I want to thank you and your staff. It felt like everyone went out of their way to see our vacation was more then we expected. And it was. If anyone ask me where to go on vacation I only have one answer, “The Key Lime Sailing Club!”
Totally enjoyed our trip,staff was great, my wife had never sailed. She is hooked now, will be back soon, thank you for a great vacation.
Can’t say enough about the staff, perfect! Enjoyed all the watercraft available for use, kids loved the place:) Really enjoyed our stay, Talofa was great, the people and staff really made the trip awesome!
We had an amazing vacation at the Key Lime Club and so much fun sailing in the Keys! The staff were MORE than helpful and so fun to talk with. Loved the relaxed atmosphere, the family feeling at the tiki, and being able to use the water toys was a big plus. Give our love to Captain G, Irene, James and CJ! And thanks again for the sunset sail and the hospitality! We’ll surely recommend the Key Lime Club to others:)
We had a fantastic time. All of the water equipment was awesome! It was so nice not to have to worry about bringing all of that stuff with us. Our home was also equipped with tons of movies and games. What an excellent option for a family to have. Thank you KLSC!
We had a great time at KLSC. The staff was especially wonderful and attentive! We loved it there.
Sailing was great and your staff was very accommodating and top notch.Hello to Capt. G, Irene and Jeff
Perfect for our family vacation. Not over commercialized and a great place to get outside and discover things! Out boys loved it.
We were so pleasantly surprised at Key Lime North! Breathtaking, beautiful, and very hard to leave! Sandra, Nick, and Heather were wonderful, helpful, and will be our lifetime friends. Paulie made everything special including remembering birthdays and beyond! Captain Sheldon was a fantastic sailing instructor. Nothing beats this vacation!
We LOVED our stay and your hospitality. Everyone went above and beyond to make the stay enjoyable, including John from Michigan who took us out in his sailboat one afternoon. That was definitely our treasure of the week, spending time visiting with him while sailing. Diamond in the rough, so glad we stayed! Definitely would book here again if the Keys were our destination.
We Still Have Cottages Available, Request to Book!
Private & Shared Sailing Charters
Sunset sail key west.
Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.
Get inspired with our most popular trips!
Private sunset sail.
Chillout Lilypad Sail
Key West Daysail
Sunset Sail on When & If
Privates Charters
Discover your perfect private charter.
Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.
Shared Trips
Come together on a shared charter.
Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.
Three Classic Boats
View our fleet.
We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.
Real. Fun. Sailing.
When And If is back at beautiful Stock Island Marina!
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Sail the Florida Keys
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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.
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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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Key West & Marathon, Florida
We specialize in private luxury yacht & sailing charters at affordable prices. we offer day charters as well as multi-day charters., why blue ocean yacht charters.
Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing. We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys. Just looking for a day charter? Look no further. We offer four hour, eight hour, and 24 hour charters as well multi-day charters.
All our yachts come fully equipped to make your private boat charter experience what you’re looking for. We offer motor and sailing yachts that provide the best boat rental experience.
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