How to plan a sailing vacation

  Ever looked at a magazine cover of a beautiful white
sailboat surrounded by gorgeous turquoise water and wondered how in the world
do people plan a vacation like that?  Well, I’ve been dreaming about
sailing lately, and since I’m not planning on taking my three month old sailing
any time soon (they won’t let me start him in swim lessons until he’s six
months!), I thought I’d share how I planned my sailing vacations and live
vicariously though those that might decide to go.  Feel free to send me

First you have to decide what type of sailing vacation you want.  In part
it will depend on how much sailing experience you have and in part it will
depend on how comfortable your traveling companions are with sailing.

There are five basic ways you can take a sailing vacation:

  1. Bareboat Charters. In a bareboat charter you rent a
    sailboat, usually between 30-50′ and it’s yours for your vacation.  It will come full of water and gas and you can
    usually choose to have it provisioned (stocked with food) in a number of
    different ways from just the basics like cereal and sandwich meat to all the
    fixings for gourmet meals. In order to
    bareboat you will need to provide the charter company with a sailing resume. You will need some experience with sailing
    larger boats and navigating via a coast line.  If you are afraid you won’t be able to handle
    a particular boat or if you are a bit rusty, you can usually have a skipper
    join you for the first afternoon for about a $100.  Sometimes the charter company will require you
    to take a skipper for a test run. Several
    of the charter companies like Moorings and Footloose Sailing have online tools that will give you estimates based on the size boat, time of
    year and number of days and people.
  2. Crewed Charters.  You can get the same
    boat but if you are willing to pay for it, you can have a captain and a chef.  Or one or the other. It’ll run about $2000 extra for the week and
    you’ll also have to make sure your boat is big enough to have cabin space for
    all the adults including your crew.  Another
    alternative to this is to rent just a cabin on a crewed sailboat.  My friend Gilbert and I did this and we were
    the only ones that showed up.  We ended
    up with a 50’ boat with a captain and a chef all to ourselves!  Talk about a luxury vacation. They took us where ever we wanted, made us
    four meals a day (happy hour counted as a meal) and even cleaned up after us! Everyone we ran into was extremely envious of
    our 50’ boat with only four people.   (This
    ran us $1000/each including all food and drinks. I think it’s closer to $1500/each now.)
  3. Flotillas. This is like bareboat
    chartering but the charter company sets up a group of boats that all want to
    travel together.  They plan the itinerary
    for you and they always have a lead boat with a couple of experienced crew
    members that are available to help if anything should go wrong.  Not only do you have a safety net but you also
    get to meet lots of people.
  4. Passage on a bigger boat. Maybe
    somebody in your group isn’t thrilled about the idea of spending a week in very
    small quarters or maybe somebody in your group would have a hard time getting
    in and out of the cabin not to mention the bunk.  In that case Windjammers, such as this company offers, might work
    for you. They are old sailing ships,
    usually over a 100 feet long that take passengers on cruises. You won’t get to do much sailing and you won’t
    have any control of your itinerary as it will be more like a traditional
    cruise, but you will still be out on the water sailing!
  5. Learn to
      I took a liveaboard sailing class
    from Offshore Sailing School
    the British Virgin Islands and it was a great
    vacation!  I didn’t have as much time for
    snorkeling as I would normally have liked, but I got lots of sailing time in,
    learned a lot, ate well, made some new friends and even saw a turtle or two.

After you decide what type of sailing vacation you want, you
have to decide which company you are going to work with and where you are
going.  Depending on what type of sailing
vacation you picked, one might dictate the other.  For example, if you decided to take a class,
you should pick your school based on recommendations and reviews and that might
dictate your location.  Offshore Sailing School was terrific – I’ll write about
them in another post. 

If you decided to bareboat charter, you will have lots of
charter companies to choose from. It
probably makes sense to pick your location first and then your charter company.
(A good website to start with for
picking charter companies is SAILONLINE.COM.) When picking
a location be sure to review what type of sailing, i.e. what type of winds and hazards,
you might encounter.  I wouldn’t
recommend that a beginner charter in the Whitsunday Islands because the winds are tough,
but I think most people would be comfortable in the British
Virgin Islands.  Also, the
time of year will make a difference. In
the British Virgin Islands, the winds are strongest
around Christmas time which makes sailing more difficult (and more fun) and
much lighter in September.  (If you
enjoy the island nightlife, don’t go in September – all the beach bars are
closed for the month!)

If you want a crewed charter, you will have to stick with
charter companies that offer them. I
know that the Moorings does and many companies will let you
add a skipper or chef as an option.

I haven’t even touched on which boat to pick … Have you ever
been to an RV or boat show and crawled all around the inside of about 50 of
them?  Did you enjoy it? If so, then you will enjoy picking out a
sailboat.  Your choices vary from catamaran
vs monohull (a highly debated topic!) to how long to what layout to how many
cabins to … If you are ever near a marina with a charter company take the
opportunity to ask if you can look around.  After my sailing class last summer we spent a
couple of hours crawling in and out of every boat there and I wrote down which
ones I liked and didn’t like with hopes that I’d be back soon!

So now you know the basics about where to start looking … you
too can start dreaming about that turquoise water. 

Let me know if you have any questions!