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 questions!

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 sail!  I took a liveaboard sailing class from Offshore Sailing School in 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!