key west sailing academy & yacht charter

Guide to Key West Yacht Charters —What Are They, Where Do You Go, WhatDo You Do, and How to Book One

I'm on a boat, I'm on a boat Everybody look at me, 'Cause I'm sailing on a boat I'm on a boat, I'm on a boat Take a good hard look at the motherf*ing boat (boat, yeah) — The Lonely Island, "I'm on a Boat" Tweet

Grab your nautical-themed Pashminas, everyone; we’re going to charter a yacht in Key West! What the what? That’s right, with a high enough credit limit, you too could be ‘on a boat like Leo.’ 

Here’s a look at the types of yachts you can charter in Key West and what’s involved in getting one. 

What Is a Yacht Charter?

Did you know you can just pick up the phone and rent a yacht? As the saying goes, all it takes is money! That’s a saying, right?

While the price of a yacht charter might look shocking at first, it’s important to remember everything you get. By staying aboard, you won’t have to worry about hotel rooms or resort costs. You will probably still eat and drink ashore, but you will have access to the boat’s galley to cook food. On a crewed yacht charter, the cook might prepare delicious food for you! You also won’t have to worry about booking snorkel trips or other excursions since you’re living an adventure every day on a yacht charter.

You can charter a yacht anywhere from a few hours to a few weeks. For an overnight trip, you can explore more of the Keys by visiting other marinas or anchoring for the night in secluded coves. Every day, you can pick from a variety of activities like snorkeling, scuba diving, fishing, lobstering, sandbar hopping, or just taking relaxing sails along the island chain.

There are two types of yacht charters you’ll find in Key West: crewed and bareboat. 

Crewed Charters

Crewed yacht charters typically provide a captain, but sometimes, you also get a cook. It depends on the yacht size and how long you’re going out. Crewed charters usually include food and some beverages, but policies differ depending on your company. The overall goal is always for the trip to be all-inclusive — just step off the plane and onto your own private yacht for an island getaway.

In Key West, a popular crewed charter option is to rent the yacht for a few days but only have the captain aboard for day trips. Each evening, you’ll return to the marina and use the boat like your hotel room. If you’ve ever dreamed of watching the sunset from your own yacht, this provides a glorious little taste of the yachting lifestyle. 

Bareboat Charters

A bareboat charter does not come with a crew or provisions — you’re just renting a ‘bare’ boat. That means you’ll be responsible for all the things a boat owner would be, like navigating safely, planning for the tides, not running aground, avoiding bad weather, and not getting lost. It also means you’ve got to dock the boat when you get back without crashing into anything!

If you think it sounds shady to hand someone your credit card and be given the keys to a yacht in return, know that it’s not quite that easy. Charter companies require that you have some documented experience in similar-sized boats before they’ll let you take theirs out. Even if you’re a seasoned boater, the company may make you go out for a few hours with their captain to check you out in the boat. If you don’t have quite enough experience, they may be able to get you a captain to spend the first day or two of your trip getting you up to snuff.

Regardless of your experience, most companies will spend time with you going over the boat and its systems. They’ll also review your itinerary to make sure you know everything you need to. Remember, on a bareboat trip, you’ll be responsible for buying all your food and beverages. Be sure to review our five killer cocktails to make on the boat.

Training Charters

If you are new to boating but dream of the bareboat yacht charter lifestyle, you could choose to combine your vacation with some training. 

There are several different training programs out there for power and sail. If you dream of sailing yachts, ASA (American Sailing Association) has a course curriculum designed to prepare you to take bareboat charters anywhere in the world. You can take these classes at any sailing school or find a school that combines the vacation with the training. Over the course of a seven-day sailing vacation, you’ll go through the courses necessary to become a bareboat captain. 

Sail Away Key West and Offshore Sailing School are two such providers on the island. 

Key West Boat Rentals

Generally, when you’re looking for a “boat rental,” you’re looking for something for day trips — not for overnights. Boat rentals in Key West are usually center console or pontoon boats between 20 to 25 feet long, and they’re usually rented by the half or full day .

There are a ton of boat rental places on the island, and generally, you don’t need very much boating experience to rent one. You are, however, required to have taken the Florida safe boater course (or your state’s equivalent) if you were born after 1988. 

Types of Boats You Can Charter in Key West

Both powerboats and sailboats are available for charter. Charter company fleets vary considerably from company to company and location to location. Some places specialize in renting the newest, sleekest charter boats, while others find good ol’ boats that can be offered at lower prices. 

Monohulls vs. Catamarans as Charter Boats

Catamarans make up the overwhelming majority of the Key West charter fleet — and most other charter fleets, actually. Catamarans, both sail and power, are popular because of the amount of space and accommodations that they have. The interior of a 45-foot catamaran is about the same as a 60 or 70-foot monohull. A catamaran this size will have four separate staterooms, each with a private bathroom, meaning you could comfortably divide the cost of your charter among four couples. Plus, cats have huge windows, large patio tables, and lots of outdoor living space. They also have the added benefit of having a much shallower draft, which is great for exploring the Keys.

Catamarans are bigger and more expensive than monohulls, however. If you’re looking for a cheaper ride during your stay, you might do well to find a company that charters a monohull. 

Key West Yacht Charter Destinations

Where you go on a yacht charter in Key West depends on how long you’ve booked your charter for. If you’re only going for one or two nights, you’ll have to stick close to the island to ensure you can get the boat back on time. Never fear; there are plenty of incredible sandbars and reefs for exploring.

Three or four-day charters can explore more of the Lower Florida Keys. You might check out places like Little Palm Island Resort, Looe Key, and Bahia Honda State Park.

Five or six-day trips can get you to the Middle or Upper Keys. Places like Marathon, Islamorada, and Key Largo are possible options. For the entire 100-plus-mile stretch of the Keys, there are tons of reefs, sandbars, and little towns to check out and explore.

The longer you’re on the water, the more likely weather will play a major factor in your trip. Strong winds may be unfavorable for travel, or they may limit you to one side of the islands. The seas that can be kicked up on the ocean side can make for very long and uncomfortable travel days, so every captain must pick their destinations with a close eye on the weather.

The most asked-about yacht charter destination in the Keys is probably the Dry Tortugas. Dry Tortugas National Park is about 70 miles west of Key West, far out in the Gulf of Mexico. It’s a beautiful place, but there aren’t many places to stop and very little protection from the weather. Most companies recommend you have a five or six-night charter booked if you intend to call on the Dry Tortugas. 

Another option for longer charters is a one-way trip from Key West to Miami or vice versa. 

Florida Yacht Charters has a great list describing the various activities and destinations you can see on a Key West yacht charter.

Booking a Yacht Charter in Key West

Here are some companies to check out, whether you’re looking for crewed or bareboat yacht charters in Key West. Some of the major charter companies operate here seasonally, so you can also check with The Moorings and Sunsail to see if they are operating out of Key West for your desired itinerary.

https://www.moorings.com

https://www.sunsail.com

Florida Yacht Charters https://floridayachtscharters.com

Blue Ocean Yacht Charters https://blueoceanyachtcharters.com  

Luxury Yacht Charters https://luxuryyachtcharters.com  

Key West Yacht Rental (90′ motor yacht) https://keywestyachtrental.com

Calypso Sailing https://calypsosailing.com/charters

Or, You Could Save a Few Thousand...

Truth is, you don’t need to charter a yacht to have a great time on the water in Key West. Every day, I take visitors out on Key West sandbar charters and private cruises. We see dolphins doing flips and all sorts of…stuff. So grab your swim trunks and flippie-floppies, and spend the day exploring Key West by water with Casual Monday Charters. 

Plus, we’ll be back by dark, so you can spend the night on terra firma, safe from the Kraken and wonky boat toilets.

Call Captain Zak today and book a private charter to see what all the commotion is about.

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Come Enjoy our smooth riding ocean going 25 ft Hydrasports center console upgraded with twin 200 EFI engines. Whether you’re looking to jump in the water at the sandbar and turn up the JL Audio system while you enjoy a cold one or make a quick and comfortable ride out to the reef our boat is just right for the occasion.

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207 Simonton St

Key West, FL 33040

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EXPERIENCE THE FLORIDA KEYS LIKE A LOCAL

Live, learn, and explore the best of the yachting lifestyle with Bluesail.

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Immerse yourself in the tranquil beauty of the Florida Keys and experience the vacation of a lifetime with TripAdvisor's 3-time Traveler's Choice Award Winner, Bluesail Yachting. A 5-star rated charter company, established in 2018, is your go-to destination for all things sailing and has been recognized by Fatherly  and Maxim as a top charter experience in Key West, Florida.

For those seeking to expand their sailing expertise, Bluesail Yachting is a accredited sailing academy offering 3, 5, or 7 day education aboard a 38' sailing monohull or 40' sailing catamaran for building confidence on the water. Bluesail can also assist in selling or buying the yacht of your dreams with knowledge of the entire boating lifecycle and partnerships with world renown manufacturers.

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Explore the hidden gems of Key West with one-of-a-kind charter experiences including 6-10 hour day and sunset sails, plus, multi-day custom charters to unforgettable destinations like The Marquesas Keys and The Dry Tortugas.

Knowledgeable, highly experienced, and licensed Captains will provide a true local experience, sailing to secluded islands where you can paddle through mangrove tunnels, rest and relax on natural beaches, snorkel at the Florida Reef, and cook your catch right on the boat. Your luxury yacht features 3 cabins, 2 heads, a salon with near 360 degree views, large back deck, and trampoline for soaking up the sun, sipping champagne, and spotting dolphins and turtles throughout your journey.

Looking for the ultimate VIP experience? Add a First Mate who will assist with all your activities, special requests, and a custom curated menu for you and your group.

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~ william, november 2021, 75 miles away from 500 years of north american history, accredited sailing academy.

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Bluesail's award-winning private training clinics are perfect for everyone from new sailors who want to develop foundational skills to experienced mariners looking to earn a license. Once we know your level of experience, we'll craft a plan tailored to your specific goals and timeline.

Utilizing NauticEd's internationally renowned online curriculum, our sailing programs provide a structured approach to help you reach your objectives. Our 1-7 day monohull and catamaran clinics, along with a customizable 30-day insurance sign-off course, are designed to help you become an educated and capable mariner. That way, you, your friends, and family can feel safe when exploring the waters of the world.

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Unlike any other program offered in the market today, Bluesail takes a "best of breed" approach to all the most effective sailing education tools.

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The Bluesail Catamaran clinic offers training options from 1-7 days and is a perfect fit for both the beginner or intermediate sailor.

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New boat owners: this course is for you! We ensure you have all the foundational elements for becoming responsible and competent mariners.

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Whether you are selling a boat, buying a new or pre-owned yacht, or simply learning about the yachting lifestyle, the Bluesail team of licensed experts is here to help.

We pledge to take the time to walk each client through the entire buying or selling process.

From listing your boat for sale to conducting market searches to handling offers, trial runs, and surveys, we’ll be transparent about what to expect while ensuring the buying or selling process aligns with your timeline and objectives.

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44' SAILING CATAMARAN

Our flagship sailing catamaran cruiser sits at the intersection of luxury and adventure sailing.

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With nearly 360 ° salon views, this sailing catamaran will become your own private island oasis.

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Her performance design and balanced hull make this sailboat a perfect fit for adventure & training.

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“This company made our trip simple to plan. They went out of their way to ensure we had a great time. We plan to return to the keys just because of this one experience.” 

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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.

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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.

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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.

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Key West Sailing Charters

Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you the offshore beauty offered only in the Florida Keys. Our native Floridian staff knows how to find the best activities on land or at sea, to guide you as you plan a unique and customized getaway.

Our Key West Sailing Charter Fleet

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Southern Cross

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Ever Summer

Fountaine pajot my44, key west attractions.

Historic Duval Street

One of the most popular destinations on the island of Key West is Duval Street. Visit the Ernest Hemingway Home and Museum where you can take in some history about the writer and meet a legendary six toed cat. If you feel like taking in some nature, visit the Key West Butterfly and Nature Conservatory where there are 50 - 60 different species of live butterflies from around the world. On Duval Street, you can simply take a stroll and hear live music, see art galleries, enjoy coffee shops and great restaurants, or find unique souvenirs at one of the many boutiques.

Romantic Sunsets

Beautiful sunsets are what Key West is all about. Enjoy the soothing ocean breeze, a glass of wine, and relax to the backdrop of the setting sun on your own private catamaran cruise. Watching the sunset has become an integral part of everyday life in paradise. This is one tradition you don’t want to miss!

Crystal Clear Snorkeling

Key West offers many beaches and reefs where you can experience snorkeling in warm crystal-clear water. At Cottrell Key, see the unique sponge garden and large coral reefs. It is also an excellent place to see dolphins, sharks, stingrays, and Goliath groupers. Fort Zachary Taylor is considered one of the best offshore snorkeling spots in Key West where there are a variety of tropical fish species and living coral to see. A favorite among snorkeling enthusiasts is Sand Key Lighthouse Reef. With a remote location and strict no-take policy, the Sand Key Lighthouse Reef is one of the healthiest coral gardens in Florida.

Pristine Sandy Beaches

Craving a drink in your hand and your toes in the sand? Check out the turquoise waters at Smathers Beach. Rental shops are available with beach chairs, shade umbrellas, kayaks, jet skis and much more. Try South Beach for calm, shallow waters that are excellent for swimming and great for families. Higgs Beach is unique for its historical significance. Take a wander around, and you'll find monuments dedicated to the 19th-century slave cemetery located on the site. There is also a pier at Higgs Beach, where visitors can often spot stingrays and other marine species.

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Three heads are better than one…

Three friends met in a coffee shop on a rainy day, quit their boring corporate jobs and moved to a tropical island to live the dream. Well OK, the real story is we didn’t meet until we were already well ensconced in our Island lifestyles, and it might have been more like a tiki bar as it is Key West after all. But we really are three professional friends with perfectly aligned skills, who through a series of fortunate events ended up working together in an industry we’re passionate about. We share that passion with a team of consummate maritime professionals & land-based staff, who together endeavor to deliver a truly fine experience to our clients, and share what a special place the Florida Keys are with the yachting world at large.

Kimber Tracy

Owner, operations & sales.

Kimber was born & raised on Oahu, Hawaii. The daughter of passionate lifelong sailors, Kimber started sailing at age seven, was an avid surfer through her teens, got into scuba diving early on & worked at the Waikiki Aquarium in Dolphin & Monk Seal volunteer research programs for many years. Her first study expedition was to ID humpback whales in Alaska aboard a 65 ft. Ketch, sailing the magnificent inside passage in 1981. She has since sailed aboard every type of vessel imaginable, from a 3 masted schooner through the Seychelles, Dhows off the coast of Kenya and down the Nile, to the historic Swedish tall ship Tre Kronor over the Baltic. A lifelong love of adventure and exploration has driven her to the four corners of the world and both Polar regions, traveling thus far through over 50 countries mostly solo. She enjoyed a career as a successful entrepreneur and corporate executive in the US and Europe before a stint as a consultant for a well-established charter company ignited an interest to enter the yachting industry as a second career. Kimber enjoys the opportunity to combine her endearing love of the ocean, passion for adventure, international experience of five-star hospitality, with a genuine enthusiasm for helping people fulfill their dream of “sailing off into the sunset” in one of the most beautiful sailing grounds in the United States. Her attention to detail and desire to ensure clients have a first-class time aboard is readily apparent from beginning to end of every charter.

Captain Jon Skiffington

Owner, fleet manager.

Following in his family’s maritime footsteps, Jon came into sailing as a bucket list “must do” 16 years ago. He fostered a dream to leave the white snow behind for white sand and pursue a career in the maritime industry. He managed to cram a good deal of experience into ten years of working with boats and adventuring in and around the North East’s waters before striking out aboard his Pearson sailboat Coyote on a grand three-month adventure from Annapolis to Key West. He joined forces with Kimber in 2016 to oversee fleet management for Key West Sailing Academy and the business partnership continued growing from there. He holds a USCG 50-ton master license, is an ASA sailing instructor and brings to bear a broad experience of vessel management, along with all manner of repair & maintenance. Jon has also enjoyed a busy 35-year career as a professional musician, singer, songwriter, music educator, and toured with several acclaimed musicians in North America & Europe. He enjoys discussing the finer points of sailing with guests and when he’s not playing music with several popular Key West bands, you’ll find him sailing Coyote, enjoying another perfect tropical breeze as often as he can.

Partner, Marketing & Sales

Emily is passionate about all things coastal, beached as it were in her summers spent at the Jersey Shore, sailing and cruising with dad, her grandparents, aunts and uncles in Toms River and running around the Raritan Yacht Club in Perth Amboy catching sailing regattas. Sometimes life comes full circle. Armed with a degree in hospitality management, substantial experience in visual communications, marketing and a burning desire to live a tropical coastal lifestyle, she and her fiancé relocated to Key West where she and Kimber first teamed up in 2013. Before joining forces to master the charter industry, she had a successful career here in Key West as an events/hospitality manager & marketing coordinator for an international hotel chain and several notable Key West operations including the Botanical Gardens. In her down time, you’ll find her with her family on their boat at a sandbar, snorkeling the reef, offshore fishing or catching another famous Florida Keys sunset, all the while documenting every moment with photos. With her passion for photography and the island life be prepared to fall in love with the Florida Keys through her eyes and wanting to see it for yourself.

[email protected] 305-934-5295

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