Key West Sailing
Book Your Florida Keys Sailing Charter
In 1513, Spanish explorer Ponce de Leon sailed the waters around Key West in search of the legendary Fountain of Youth. Nearly 500 years later, Key West sailing charters follow in his wake, offering the same promise of exploration and youthful rejuvenation. And did we mention some pretty awesome sailing charters? Yes it’s truly a Key West sailing adventure.
Call Key West Charter Boat, fill out a quote form or reserve a public sail online. Whichever you choose we’ll find the perfect vessel for you.
Few experiences stir the soul as standing on the deck of a boat under sail. Whether you’re bareboating a catamaran with friends or throwing a big group party aboard the 105-foot schooner America 2.0, set sail on the tropical breezes of the Keys and you will be transported to a whole different state of mind. Yes, sailing in The Florida Keys is truly amazing.
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Key Takeaways
- Key West is a dream destination for sailing enthusiasts. You can indulge in experiences such as the Champagne Sunset Sail, Key West sunset sail and the Snorkel & Dolphin Watching Adventure to take in breathtaking scenery and lively underwater wildlife!
- The Key West catamaran charter is a choice for sailors who appreciate its fast and comfortable sailings. Private charters can be tailored to create celebrations and intimate moments, on the water!
- Tips for making your sailing experience great involve booking by calling or filling out the quote form to get the best prices and selecting the perfect departure times.
The Florida Keys Sailing Greatness
Florida Keys sailing is some of the best in the world because of where it is in the world: latitude 24° 33’18” N, longitude 81° 46′ 53” W, between the open Atlantic and the Gulf of Mexico. A private sailing charter from here can take you wherever the mood suits. A perfect private charter day sail to uninhabited islands, exploring shallow waters, sailing snorkeling the whole way through. Sound good?
Choose a sailing excursion to the calmer turquoise waters of the north and you’re likely to get picture-perfect days of relaxed cruising, surrounded by the natural beauty of the area. Just set the auto-pilot, settle back and relax. Head south—where the continental shelf falls off a cliff—and you’re in for some true bluewater sailing. Stiffening winds push you to the horizon as saltwater spray carries the intoxicating smell and spirit of freedom in the air.
Key West Sailing Knowledge
When it comes to planning a sailing trip, there’s no substitute for local knowledge. And nobody knows more about sailing the Florida Keys than Key West Charter Boat. Whether you’re interested in custom sailing trips on a 50-foot luxury catamaran with your family for a week or overnight sailing for two on a 30-foot sloop, call us.
The Key West Historic Seaport is a vibrant and central location for sailing charters in Key West harbor, offering easy access to popular attractions and local dining options.
If you’d like a quick price quote to sunset sail Key West for an evening with your office staff, fill out a quote form. We’ll arrange everything: boat, captain and crew, and the best Key West sunset charter prices.
Key West Florida is a historic seaport with a variety of day sailors for hire, as well as the bigger Key West yacht rentals. Take a 25-footer out for a full day cruise or half-day trip around the island. Sail past Southernmost Point and see the world-famous buoy marking the point furthest south in the continental United States.
Island Sailing Destinations
Lets Circumnavigate Sunset Key, the island of the rich and famous. Who knows who you could spot sunbathing on their private beach? For a sailing adventure, you’ll long remember, cruise past Chica Boca Key, home to Naval Air Station Key West. With any luck, a squadron of navy fighter jets will take off right in front of you, heading to their carrier in the Atlantic.
You always have the option of cruising around and dropping anchor whenever the mood suits. Sailing the Florida keys is a family-friendly activity with opportunities to kayak, snorkel and explore just about anywhere. Dolphin watching is always a crowd-pleaser. Same for snorkeling North America’s only living coral reef. Designated a national marine sanctuary, the reef is teeming with colorful tropical fish, sea turtles, starfish, conch and hundreds of other aquatic creatures.
For a more adventurous experience, dive one of the many shipwrecks that dot the coastline around Key West. Several wrecks are in shallow enough water to explore with just snorkeling gear. While those lying in greater depths will require scuba diving experience. Whatever you do while Florida Keys sailing, we recommend ending the day at Mallory Square in downtown Key West for a cold drink and excellent dining as the sun sets, creating a picturesque backdrop and a truly wonderful time.
Dry Tortugas Sailing Charters
For an excellent mid-distance Key West catamaran charter, head 70 miles west of key west (112 km west of the town key west) and you’ll reach a remarkable group of islands called the Dry Tortugas. Remote and isolated, the islands are almost entirely undeveloped by man and a haven for wildlife.
Rising out of deep waters in the Gulf of Mexico, the Dry Tortugas are a migration waypoint and breeding ground for hundreds of thousands of birds. Birding enthusiasts will definitely want to bring binoculars for spotting sooty terns, masked booby, and the magnificent frigate bird, to name a few. And anglers will want to bring their rods and reels. The fish population here is also impressive, with over a dozen species to catch, including blackfin tuna, grouper, wahoo, mahi-mahi, and sailfish.
Key West Catamaran Charter Variety
Group charters are a great way to experience a Key West catamaran charter. Boat tours cater nearly any occasion, including wedding parties, holiday outings, corporate excursions, even themed events. Privately chartering a sailboat is easy.
Just tell Key West Charter Boat the size of your party, amenities you’re looking for, the desired length of cruise and any special requests you may have. We’ll put you on the perfect boat for a family reunion, Key West sunset cruise or a seagoing party for 50.
Enjoy the enchanting experience of a Key West sunset aboard a sailing catamaran, with breathtaking views, complimentary beverages, and attentive service, creating a romantic and enjoyable atmosphere.
For a swashbuckling sailing adventure, commandeer your own celebrity ship. Private charter the 1939 wooden schooner When and If. The boat belonged to World War II general George S. Patton, so it’s no surprise she’s fast and powerful. Guests are encouraged to join the crew in hoisting sails and trimming them up. You can even take the helm if you like, feeling the same exhilaration as Patton did over 80 years ago. It’s one of the most classic boats in the Keys and a highlight for those who love historic schooners.
Explore Key West’s Best Catamaran Sailing Adventures
Key West is like a paradise for sailors due to its blue waters teeming with marine life and stunning sunsets that take your breath away.The Historic Seaport in Key West is the core of sailing escapades and is filled with an array of shops restaurants bars and galleries.Whether your aim is to unwind with a glass of champagne while watching the sun set on a Key West sunset cruise sailor explore the marvel that Key West has to offer there’s something here, for everyone.
A lot of tourists often mention their sailing trips as the highlight of their holidays. The blend of indulgence,excitement and stunning scenery makes it an unforgettable experience, like no other. Whether it’s your first time visiting or a trip you plan for the future, it will feel like a true treat.
Three fantastic catamaran sailing adventures await you in Key West for an experience.
Champagne Sunset Sail
Picture yourself smoothly sailing on the waters of Key West as the sky changes into a beautiful display of vivid colors during the Champagne Sunset Sail excursion – providing a perfect view of one of the island’s most stunning natural shows! Witness the sun descending beyond the horizon while enjoying champagne and an array of beverages such as wine and chilled beers to enhance your overall experience even more delightful.
Under the guidance of an experienced captain on board during this sunset sail in Key West guarantees a pleasant and unforgettable voyage ahead of you. The sunset sail friendly crew members onboard enhance the experience by offering top notch service and sharing anecdotes about the nearby landmarks you’ll encounter on your journey.
Whether you’re marking an event or just looking to savor an enchanting evening in Key West the Champagne Sunset Sail offers an ideal way to cherish your moments there and ensure fun and memorable moments.
Snorkel & Dolphin Watching Adventure
If you’re looking for a mix of excitement and serenity you won’t want to miss out on the Snorkel & Dolphin Watching Adventure experience! This half day excursion offers the blend of snorkeling, amid lively coral reefs and observing playful wild dolphins in their own habitat. A unique way to immerse yourself in the crystal clear waters of the Florida Keys and discover the vibrant underwater realm like never before.
The adventure doesn’t stop at snorkeling! As you sail deeper into the ocean waters and explore outwards from the shorelines you might just catch a glimpse of dolphins gracefully swimming in their own world. An enchantingly mesmerizing sight that will undoubtedly captivate your senses and leave you feeling amazed by the wonders of nature.. This journey is ideal for families seeking quality time together amidst the waves, friends wanting to share moments, or even solo explorers yearning to mingle with locals and embark on a thrilling escapade full of excitement and lasting memories..
Private Charters for Special Occasions
To make your Key West trip stand out from the rest and create lasting memories that are truly one of a kind, might I suggest opting for a private charter? These exclusive excursions provide a close knit sailing adventure that’s perfect for marking special moments, in style.Whether its an event,a family reunion or a romantic escapade private charters offer ample space to host your guests with ease and elegance.
Private charters offer a deal of flexibility as you have the freedom to tailor your schedule and activities to fit your liking perfectly! Whether you’re looking to throw a daytime gathering, on the sea or have a peaceful evening cruise with your family and friends to catch the stunning sunset in Key West. Private charters deliver a unique and unforgettable experience of discovering the charm of this beautiful destination.
The Safest Sailing In Key West
As with anything on the water, safety comes first. Your sailing experience will determine what type and size boat you’re qualified to charter. Big catamarans and mono-hulls require extensive experience in similar type boats. With Florida Keys Sailing there is no shortage in boat variety.
When you arrive, expect to spend part of the first day going over the entire boat with a certified captain. All operating systems will be reviewed, including lines, setting and retrieving sails, winch and helm operation, navigation and communication equipment, and all safety procedures. It’s a great way to learn sailing, classes boost confidence, and build skills for independence on the water.
Bareboat Charters & Multiday Trips
When Florida Keys sailing you will be asked to demonstrate your docking skills as well as any other handling maneuvers your charter company may require. Trips of a certain duration or distance will require you to file a sail plan and to notify your charter company with any changes to that plan while underway.
For multiday or day trips, it is crucial to check the departure time to ensure proper planning and scheduling.
Please allow time at the end of your charter for a complete walk around with the captain or charter company member. In order to ensure a great Key West sailing experience, we only book with charter outfits that maintain their boats in constant shipshape condition. Make sure you don’t steer] your ship the wrong way, planning is key!
Exploring Unique Sailing Experiences in the Florida Keys
The Florida Keys provide a variety of sailing experiences that highlight the area’s natural charm and lively marine world. Whether it’s exploring coral reefs through snorkeling or embarking on dolphin watching cruises there’s a little something for everyone to delight in. These adventures offer a chance to discover the ecosystems and breathtaking coastal views that contribute to making the Florida Keys a prime spot, for those who love sailing.
Lots of visitors love snorkeling trips. Watching dolphins and often suggest them as top things to do while they are here, for a visit. Shall we delve deeper into these activities? Let’s begin by looking at the reef snorkeling outings.
Exploring the Vibrant Coral Reefs through Snorkeling Tours
One of the pastimes in the Florida Keys is exploring the colorful coral reefs through snorkeling adventures. These trips enable you to plunge into the crystal waters and discover the variety of marine creatures living in the reefs. The Florida Keys National Marine Sanctuary boasts the coral barrier reef, in the contiguous U.S. teeming with a multitude of animal species that create an ideal snorkeling haven.
Exploring the world with guided snorkeling tours is a wonderful opportunity to experience the marine environment in the Florida Keys while ensuring safety and enjoyment, for both beginners and experienced snorkelers alike.
Amazing Dolphins and Fascinating Wildlife
Many tourists enjoy dolphin watching excursions while visiting the Florida Keys as an experience to cherish during their trip.The Atlantic bottlenose dolphins frequently spotted around Key West often travel together and exhibit behaviors that bring joy to spectators.These clever marine beings rely upon echolocation, for navigating and hunting purposes which enhances the intrigue of the guided tours.
Catamaran Key West trips offer the chance to witness dolphins firsthand as they play in their environment—a truly memorable experience that also allows you to admire other sea creatures and appreciate the stunning landscapes of the Florida Keys. It’s another reason why our Key West’s sailing fleet remains so popular.
As Remote As You Like
Sailing the Keys is as close to nature as you can get, with the wind as your power source and aqua green water as far as the eye can see. Perhaps Ponce de Leon was right after all, only instead of a fountain, there was the sea and waves and beaches as white as the wings of a gull.
Aboard a sailing vessel of any type or size, you feel young and adventurous, as if time is standing still, or maybe even going backwards. Is that really possible? If there’s any place on earth where it could be, it’s Key West. Every summer, the waters call again, reminding us of the history and tradition of sailing.
Learn more about sailing Key West and the Florida Keys by giving us a call or filling out a quote form.
The wind in our hair, the sound of the boat cutting through the water and a drink in our hand these are moments we won’t soon forget. Five stars.
We booked a private sailing charter down to the Dry Tortugas. The experience was nothing short of amazing.
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Frequently Asked Questions
When's the optimal time for a sunset sail, in Key West?
The ideal time to go on a sunset sail in Key West is during the late fall to early spring season when the weather is just right for an unforgettable experience.
What should I anticipate on a Champagne Sunset Sail?
Get prepared for an outing, on a Champagne Sunset Sail where you’ll enjoy complimentary champagne and other delightful beverages while taking in the breathtaking sunset scenery.
Are there options for booking private charters for special events?
Private charters are fantastic for events. They provide a one of a kind and sailing adventure that will create lasting memories for your occasion!
What kind of safety precautions are implemented aboard catamarans?
Catamarans are equipped with safety equipment such as life jackets and emergency beacons. Additionally the crew undergoes training to ensure preparedness for any unforeseen events providing a sense of security during your sailing experience.
When is the best time for a sunset sail in Key West?
The best time for a sunset sail in Key West is from late fall to early spring, offering you perfect weather for a breathtaking experience! Get ready to enjoy those stunning views!
What can I expect during a Champagne Sunset Sail?
Get ready for an unforgettable experience during a Champagne Sunset Sail! You can expect to sip on complimentary champagne and other delightful drinks while soaking in the stunning sunset views!
Are private charters available for special occasions?
Absolutely, private charters are perfect for special occasions! They offer a unique and personalized sailing experience that will make your event unforgettable!
What safety measures are in place on catamarans?
Catamarans come loaded with vital safety gear like life jackets, emergency beacons, and life rafts! Plus, the crew is regularly trained to ensure they’re ready for any emergency, giving you peace of mind while sailing!
When is the best time to make a reservation for a sailing charter, in advance?
It’s a good idea to make your sailing charter reservations far ahead of time to guarantee you get the top choices and great deals. Especially during busy periods these charters can sell out fast. Don’t forget to check for a promo code.
I am allowed to bring my snacks and beverages onto the boat?
Sure thing! A lot of charter services do permit you to bring your food and beverages onboard their vessels. However it’s a good idea to reach out to the charter company in advance just to double check their specific rules and regulations regarding this matter.
What are the best clothes for a sailing charter?
Wearing the right clothes for the weather is important. Remember to bring along a hat, sunglasses and sunscreen too! It’s also smart to have a jacket or sweater on hand in case it gets chilly out on the water. Spinner white decorative clothes are also popular options.
What attractions are available at the Key West Historic Seaport?
The Key West Historic Seaport is a center of excitement with sailing excursions available and a diverse range of dining options and shops to explore in addition, to bars and galleries to visit in the area—it’s an ideal spot to kick off your Key West sailing experience and immerse yourself in the rich local heritage and traditions.
How much does it cost to charter a catamaran in Key West?
If your looking at doing a public catamaran charter, a sunset sail can start as low as $55.95 for a ticket. If you would like to charter a private sailing catamaran those begin at $645 for a smaller cat. Inquire with us today!
How long does it take to sail from Key West to Dry Tortugas?
If you want to sail to the Dry Tortugas you need to remember that it is 70 miles away from Key West and that sailing while wonderful is slow. It will take at least a full day to sail there, most it’s broken up to two days with a break in the middle in the Marquesas islands is a good stopping point.
Are the Florida Keys good for sailing?
Absolutely they are! The Florida Keys are revered by the sailing community for their clear calm sees and gentle winds. Not to mention there are 2 bodies of water to sail in both the Atlantic & Gulf of Mexico!
Can catamarans handle rough seas?
Absolutely! Catamarans are excellent at handling waves due to having two hulls, a ultra wide beam and wave piercing bows. If you are looking to go sailing in Key West but want to reduce your odds of sea sickness on an awesome platform than this is it.
What kind of sailing experience and activities can we do?
Combining multiple activities like snorkeling and kayaking with a sunset sail for a fuller day of adventure is recommended for an enriched experience.
Are Brunch Sails available in Key West?
Brunch sails are available in Key West, such as the Best of Key West Sunday Brunch.
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