When choosing a sailing charter there are a number of things to take into consideration.  In this blog, I will point out the five most important steps to a successful sailing charter Key West.  A person must consider the location and time of year of the sailing charter.  Other important factors are the size and style of the sail boat, your budget, whether you will need a captain, or skipper the sailing vessel yourself.  The last and most important thing to do when planning a sailing adventure is to make it safe and enjoyable.

Time of Year and Location of Sailing Charter

Trying to decide the best location and time of year for your sailing charter?  Look no further than Blue Ocean Yacht Charters in Key West, Florida.  Key West offers some of the best coral reefs in the world that helps calm ocean waters for smoother sailing. The ocean water in Key West is crystal clear with bright, beautiful, blue, colors.  The coral reefs also offer a home to millions of plants, organisms, fish, and mammals. https://www.tripshock.com/blog/visiting-key-wests-coral-reef/

Furthermore the coral reefs provide breathtaking beauty for activities such as snorkeling and scuba diving on a sailing charter.  Any time of year is great for a sailboat charter in Key West.  Spring and fall can produce some of the better winds for sailing with warm air and water temperatures.

Another factor to consider when choosing a sailing cruise is the availability of the boats to choose from.  Winter months as well as holidays can make less yachts available to choose from.  Additionally prices for the sailing charters during these busy times of the year will be bring higher prices for the charters.  If these times of the year are your desire, it is important to book your sailing charter six months to a year in advance.  This will assure you that you get the sailing yacht of your choice that will make your sailing adventure enjoyable.

Size and Style of Sailboat

Considering the size of the sailboat when choosing a sailing charter is very important.  Typically the larger the yacht, the more sea worthy the vessel will be.  Additionally the larger the yacht, the more space, cabins, and heads the sailing yacht will have.


In addition to the size of the sailing boat, one must decide on the style of the boat.  There are many different styles of a sailboat.  For the purposes of this article we will focus on the two most common styles, single-hull and multi-hull sailboats.  Single-hull or mono-hull sailboats tend to have less space than a multi hull yacht.

The most common type of Multi-hull sailboat is a catamaran.  The mono-hull sailboat will usually sail faster and sail closer to the wind than a catamaran.  Catamaran sailing yachts will be more spacious inside and out.  Additionally, catamaran boats will have a shallower draft, making navigating in shallow waters easier.  Catamaran sailing boats are becoming more popular than mono-hull sailboats for yacht charters. In Key West, Blue Ocean Yacht Charters has an abundant supply of catamaran sailboats for you to choose from.

Whether you have a restrictive budget or looking for luxury sailing yacht, Blue Ocean Yacht Charters will have the right yacht for you.  For more information on a Catamaran Charter in Key West, click here https://blueoceanyachtcharters.com/catamaran-sailing-charter-key-west/

Bareboat or Captain Sailing Charter Key West

A person must decide on a few important things in determing if a bareboat charter is right for you.  You must ask yourself, do I have the skills and experience to operate the sailboat of my choice to make a fun and safe experience for myself and my guests?  Do I want to spend my vacation relaxing or working the boat?  Do I want to spend extra money on a Captain? Do I want to assume the risk associated with skippering the vessel myself?


You must have experience sailing whichever boat that you desire to charter. In addition to experience, you should also have at least one person with you that can sail the vessel in the event you are not able to.  Sailing certifications, sailing courses, sailing endorsements, and various degrees of captain licenses are helpful when being approved by a yacht charter company for bareboat charter.  The more time you have spent on the same size and style of boat you are desiring, the more likely you will be able to take in a bareboat charter.

Vacation or Work?

Deciding on a sailing charter, you will need to decide if you want to sit back and relax or do all the work of the charter yourself.  If you decide on a bareboat sailing charter, you will not be able to kick back and relax with some of your favorite cocktails when you want.

Captain Charter

By hiring a Captain for your sailboat charter, you will not have to pay attention to many possible obstacles you may encounter.  With a captained charter, you can take in your sailing vacation with your guests more. Captains have more knowledge of the vessel as well as the geography of your sailing waters. Sailing Captains are professionals at making your charter experience better than you could.  They also know the best places and experiences to take in on a sailing charter.  Charter Captains are trained at being invisible or socially interacting.  Captain/Crew fees are typically around $400 per day plus gratuity of 20%. This extra cost is well worth peace of mind so you can have the safest and most enjoyable sailing adventure.


When deciding on a Bareboat charter you must consider the risk is all on you.  Charter companies will require a higher security deposit for a bareboat charter versus a captained sailing charter. All yachts at Blue Ocean Yacht Charters have bareboat insurance coverage that will cover you and your crew in the event of any damage caused by you or your captain.  Keep in mind that most insurance policy deductibles are around 2% of the value of the yacht. You will be required to pay the difference of your security damage deposit and the deductible if the damage caused exceeds the security deposit you paid to the charter company. For more information on a bareboat charter, please visit this article https://blueoceanyachtcharters.com/top-ten-perfect-bareboat-charter/

Budget for your Sailing Charter Key West

Most people have a budget for their yacht charter.  The budget would be the maximum you want to spend on your sailing charter.  Charters away from the marina will cost $1000 to $2000 per night depending on the supply and demand of the vessel.  Other factors contributing to the cost of the yacht charter is the size and style of the yacht as well as how long your sailboat charter is.  The shorter your boat charter, the higher the cost is per night pro-rated. The longer your charter is the lower the nightly rate.

Overnight Sailboat Rental at the Marina

Renting a sailboat that stays at the marina is the most cost effective way to take in a yacht charter in Key West.  This also allows you to enjoy the amenities of the resort as well as the city of Key West.  In addition to staying on the vessel at the marina, you can take in short sailing charters whether its 24 hours or 2hrs.  The choice is yours at Blue Ocean Yacht Charters in Key West.  Overnight boat rentals can cost $300 to $600 per night on average depending on supply and demand as well as the type of sailboat you want.  For more information on the beautiful resort where the boats at Blue Ocean Yacht Charters are kept, visit https://www.perrykeywest.com/

Itinerary for Sailing Charter Key West

After determining timing, location, size, style, and budget of your sailboat charter, you are now ready to plan your sailing vacation. The first thing you will need to do is create a plan of your sailing route and where your overnight anchorages will be.  You must pay attention to your weather forecast that may have an effect on your sailing adventure.  At Blue Ocean Yacht Charters we help all our customers plan their sailing charters for the best experience possible.  Whether it’s a day cruise or extended multi-day sailing charter, a good plan is by far the most important aspect of your preparations.  To decide on what your next sailing charter will be, visit https://blueoceanyachtcharters.com/yacht-destinations/

Have a fun sailing charter and be safe.

“Charter Booker!”

(Charter Booker, manages Blue Ocean Yacht Charters in Key West and writes many of the company’s blogs.  Having experience both on the water and off the water helping customers experience the best possible yacht charter for many years.  Charter Booker carries American Sailing Association certifications and has extensive knowledge of boat safety and regulations.  Call 305-923-4152 and ask for “Charter Booker” when booking your next yacht charter with Blue Ocean Yacht Charters in Key West, Florida.)