vacation, travel, sea, sailing and people concept - close up of friends legs sitting on yacht deck


My man has many amazing attributes; my favorite one being that he has his captain’s license. For 12 years we have been planning sailing vacations with friends all over the world. Why sail? Because there is nothing more spectacular than traveling over intoxicating crystal blue waters to far off places with the people whose company you enjoy the most. It’s an unforgettable experience …promise! No captains license? No problemo! Here’s how to plan an exhilarating and memorable sailing vacation with your friends.

Choose Your Destination

Sometimes I have a very clear idea of where I want to travel to on a seagoing vessel and sometimes I have 2 or 3 destinations in mind. If it’s the latter, I let my crew decide. Personally, I always recommend the Caribbean to nautical newbies for a number of reasons -.crystal 80-degree water and white sugar sand beaches being just two of them. However, one of the more practical reasons is the number of island chains in the Caribbean. The British Virgin Islands (BVI) for example, are relatively close together. This means shorter crossings and typically smoother waters.

Although most people usually know whether or not they are prone to seasickness before they leave shore, I’ve encountered a few that don’t realize it until they are traveling over rocky waters. Take it from me; the middle of a boating vacation on a 55 foot catamaran is not the best time or place to discover you are likely to get seasick! Unless you are a seasoned sailor, sticking to shorter crossings is advisable. Also, remember to consider the season when booking your sailing vacation to avoid inclement weather.

Select Your Crew

When you pitch your dream sailing adventure to your peeps, prepare for them to get excited, like just got picked to be on “Price is Right” excited.  I mean, how could they not? Of course, there are a number of logistics to consider before one can commit, so it’s best to decide which candidates to pitch to first. Choose friends that love adventure and can go with the flow. High maintenance individuals can be a disaster on a boat and the last thing you want to do is share a small space with someone that ends up driving you nuts. Bottom line…choose carefully!

Choose Your Type of Boat Charter

If someone in your crew has a captain’s license, easy peasy…you can bareboat charter. If not, you can go one of two ways depending on your budget. The first, and also cheapest, option is a skippered bareboat. In this case, you are still using a bareboat charter but you are adding a freelance skipper. In total, a skippered bareboat will cost you and your crew somewhere between $100 and $140 per day depending on the location of your charter. Add in a little extra for the skipper’s meals; you will be expected to feed him. 

The second option is a fully crewed charter. More expensive and luxurious than bareboats, this option includes a 24/7 live onboard captain and chef. Keep in mind, selecting the right crew can make or break your vacation. Be sure to find an experienced broker that will help guarantee that you get a knowledgeable crew and the best experience possible.

How to Use A Charter Broker to Help You Find Your Boat

When it comes to finding a boat, a charter broker can be the deciding factor on whether your vacay sinks or swims. Charter brokers are like travel agents. They do the legwork for you in terms of researching local companies, comparing prices and providing user reviews.

Over the years, we have had numerous issues with our yachts, which is why I cannot stress the importance of using a broker who can help you avoid potential problems from the get-go. Here are three reasons why you should use a broker.

1.    A charter broker ’s knowledge of available and reputable charters and crews in the area will guide you in making the right choices and finding the best deals.

2.    Charter brokers are unbiased. Yacht owners and captains have a vested interest in their services and tend to give information to turn you in their favor.

3.     Charter brokers can help you charter your course, select hotels near the marina where you will board your boat, and give valuable information regarding sight-seeing and must-do activities along the way.

Have Loads of Fun

Now that you have your logistics in place, it’s time to get excited about your trip and have some fun with it! One thing we like to do to get all our peeps “on board” is to have everyone pick an island to research and report it to the rest of the crew. We use this valuable information to gauge our itinerary.  BTW: Creating a crew name and putting it on matching hats or t-shirts can be great for photo ops.

Now you are ready to pack your bags and enjoy an adventure of a lifetime. Bon Voyage!

Planned a sailing trip of your own? Would love to hear your tips in the comment below.

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