Whether you are seeking a getaway weekend or a getaway week, sailing from Miami to the Florida Keys is an ideal relaxing respite from the go-go Miami city life and action of South Beach. It’s a “back to nature” trip that can reintroduce you to the beauty of the sunset, moonrise, and canopy of stars that cover the sky every night normally hidden by ambient city lights and high rise buildings. The quiet sounds of water rippling by the boat as you sail along becomes hypnotic – quite the opposite from city traffic noise. Clean ocean air, gentle breezes, and Mother Nature provide all the entertainment you need to get in touch with that other side of life that we forget exists.

Boarding your charter sailboat in Miami and sailing on a dream vacation to the Florida Keys requires no passport, no airport pat down or scan, and no expensive parking fees for your car. No crowds to contend with prior to boarding – this is your private charter!  There is no Captain’s dress up night – it’s your vacation – wear what you want as long as its casual and comfortable!


Since the sailboat you charter will be your floating home for the duration of the trip, make certain you inspect the boat and review guest accommodations and crew quarters. Level of luxury varies widely as does level of cleanliness of yachts for charter. There are yachts for every budget – from Motel 6 to the Ritz. What you will find, however, is that the price difference between the top of the line boat and the bottom of the barrel boat is not very significant. You will be well served to charter the newest sailboat available – this will give you the best chance for a clean and modern yacht. Once a charter boat’s age exceeds 10 years, the level of comfort and quality will more closely resemble a Motel 6. That’s the very reason most worldwide sailing charter companies retire boats from their fleet before they reach this milestone.

         CHARTER TIP #1:  If you are booking a sailboat without a site inspection, always ask what year the boat was built. The age of the boat will be telling of what you can expect.   You can also request recent photos of the cockpit, deck, guest bedroom, guest bathroom (head), and galley (kitchen).  This is preferable to making a decision based upon staged website photos.  Obviously, newer boats will have more modern facilities aboard.

       CHARTER TIP #2:   Another important selection consideration is the number of heads (bathrooms) on the boat – the crew quarters should be separate from the guest quarters and each should have their own head and shower. Boats with only one head and shower generally lack the privacy you expect when planning a vacation on a private sailboat charter.


There are two sides to the Florida Keys – the ocean side (East) and the Bay side (West) – both vastly different, but each interesting in their own uniqueness.

 Ocean Side: has a narrow, defined, well marked channel from Miami to Key West (called Hawk’s Channel) to avoid the many patch reefs dotting the path southward. There are a few bridges allowing you to go from the ocean to Bay side but they are standard 65 foot maximum clearances. This is the side for snorkeling – but keep in mind that windy weather creates rough sailing conditions and poor visibility for snorkeling.

Bay side: is very shallow (5-8 feet) and provides a close up look at mangroves, bird life, and Keys culture.  There are no reefs on this side, just sand and grass bottom and hundreds of little islands to anchor next to for protection from any wind conditions.  Because of the shallow depth, you will never get rolly or rough conditions on this side of the Keys. This side also has a myriad of bars and restaurants to catch a flavor of the Parrot Head lifestyle.

        CHARTER TIP #3:   Sailboats with a keel draft of greater than 5 feet cannot go down the Bay side much past Key Largo (1st Key going south).  Boats with 5 foot draft or less can go all the way to Marathon on the Bay side (50 miles from Key West).  The ocean side is the rough side in Florida’s prevailing easterly winds – the Bay side has no waves and offers a pleasant alternative to rolly ocean conditions. Ask if your charter sailboat has greater than 5 foot draft.  Why see only half of the Keys?

        CHARTER TIP #4:  Sailboats with a mast height greater than 65 feet cannot go under the Key’s bridges and are limited to only the ocean side. If the weather turns sour on the ocean and your charter sailboat has a mast height greater than 65 feet, there is no escape from the ocean rollers. Strong NE or E winds aren’t so bad going TO the Keys but coming back from the Keys with strong head winds is never fun. Versatility is important – check that your charter sailboat has the proper mast height and draft for maximum enjoyment of the Keys no matter what the weather.

You generally won’t find captains explaining the limitations of their boat – if they are limited to the ocean side of the Keys because of mast height or keel draft, you’ll never hear about the other side of the Keys let alone see it.  And should the weather not be as cooperative as expected, your only choice may be rocking and rolling on the ocean side down to the Keys and back.  Know your limitations and the limitations of your prospective charter sailboat – you can’t choose your weather conditions for your trip but you can choose a sailboat that will deliver a smooth and comfortable sailing vacation.


You have choices as to where you eat in the Keys but it boils down to either eating aboard or eating ashore.  Eating aboard can be a gourmet experience depending upon the skills of your captain and menu planning or a dining nightmare – get references if you are having the captain (or 1st mate) do the cooking for your trip. It’s important to ask if the captain is bringing along a 1st mate on the trip – it’s preferable to limit number of people aboard to your party and the captain for trips to the Keys. Captain/chef combinations are somewhat rare, but worth seeking out. They cost no more and eliminate that extra person taking up space on your charter sailboat and introducing another personality to possibly contend with on a weeklong trip.

If you plan on dining ashore, the opportunities on the Bay side are limitless – heading down the ocean side those opportunities are more limited.  If you are doing a culinary cruise through the Keys, then the Bay side is where you want to be.  If you plan on all your meals aboard your charter sailboat, then either side of the Keys can work for your trip.


The winter season is generally the windiest season and best for sailing – however, the air and water temperature is cooler and may not be as comfortable for swimming.  It does, however, allow you to sleep each night without any generator noise or air conditioner drone. Also, the winter season has the lowest average monthly rainfall and fewest thunderstorms. If swimming is an important priority on your trip, consider scheduling your trip in the summer months.

      CHARTER TIP #5:  If you charter in the summer months, make certain your charter sailboat has sufficient air conditioning for a comfortable night’s sleep.   Some boats advertise they have air conditioning, but their BTU capacity is not capable of keeping up with the demands of South Florida’s hot summer nights and humidity.   Generally a 40-50 foot boat should have about 32,000 BTU capacity in their air conditioning systems.   These are the details that come back to haunt you when not planned and considered in advance.  And why is air conditioning so essential in the Keys on a summer night?  Because of that dirty little secret called “mosquitoes.”  Yes, the Keys do have mosquitoes and it’s hard to hide from them – don’t believe the tale of “we anchor away from shore and can avoid them” – their heat seeking sophisticated systems can find you and ruin  your otherwise tranquil vacation nights!

Here are the 3 newest charter sailboats in Miami capable of sailing down both sides of the Florida Keys:

Builder         Length         Name          Yrs in Svc      Draft     A/C BTU’s    Heads/Showers   Contact #

Island Packet   46        CAPTAIN SIR!         5                5’0”       32,000           2/3                    786-218-2454

Hunter             44        Express Mail          5                5’0”       28,000          2/3                    732-830-9285

Jenneau           46        My Chere              15               5’0”       24,000          2/3                   305-613-2049 


Doing some homework and research on your prospective charter sailboat will pay big dividends and ensure you have a memorable vacation experience in the Keys. Most often you will probably be booking a sailboat without a site inspection (unless you live in South Florida) – so insist on recent photos – don’t depend on those faraway website photos. Talk with the captain and get a level of comfort with him/her so that you understand what his/her particular boat can offer and see if that fits within your budget and expectations.  Get references--other guests who have spent extended time aboard with the captain and do some reference checking from recent guests. This will give you a second opinion or perhaps a more unbiased opinion. Newer is always going to be better in a charter sailboat. Your worst nightmare is boarding a boat for an anticipated vacation and finding that it was not acccurately represented. Also keep in mind that a plethora of internet reviews may not always be the best sole source of information for making a decision. But in the end,  go with your gut feeling and perhaps splurge a little to get that boat and captain who will go the extra mile for you.  Because in the end, what we all seek is to have not only a great vacation, but a memory that we can kick back and escape to once we return. . . an indelible mind photo of the colorful Keys water, landscape, and sunsets .. . sailing along with only the wind . . . and enjoying the peace and serenity of a unique slice of America .. . the Florida Keys.