No doubt one reason is that a sailing cruise hints at more excitement and perhaps tall sails adventure like ocean travel was a couple hundred years ago, whereas the floating hotels just don’t do it for me. I mean the big cruise ships are nice enough, but I want something I can feel working in sync with the ocean.

One of my all-time favorite movies is “Master and Commander” at the very beginning when it opens with a nighttime, below decks scene where all you hear is the water and the creaking of the wooden hull working against it. Makes you feel like you’re really there.

And no, my preference to participate in working the ship as part of the crew doesn’t help win anyone over to my side either. Some folks don’t think that sounds like much of a vacation, whereas I see it as a super way to clear my head and unwind.

Anyway, the dilemma will likely continue with the end result being the compromise of taking turns so each gets their preference. The good news is I do believe we’ve at least agreed on smaller ships as opposed to the mega-carriers.

If fact, as long as you’re in reasonably good shape and willing to learn, there are any number of boats you’ll be welcome on. And if you’ve got some good skills and experience, so much the better. That gives you even more choices.

My first experience joining a crew happened after talking with a friend and hearing he was heading off to race sailing yachts for a week in the Caribbean. Of course my immediate response was envy, followed quickly by a question – does the skipper need an extra hand?

Now the boat in question was a fairly new 42’ Dufour, and my experience up til that time was just small stuff like Hobie’s, plus it had been a while. Anyway my friend said he’d check to see if a grunt was needed and lucky for me, they were short one man.

All I had to do was get myself to the island and the rest was covered. During the week when not racing, was diving, sightseeing and fun. Most of the crew slept on board and I had one of the four cabins. Food was also provided and the only money I spent that week was the odd drink or meal ashore. Admittedly, not sharing in the cost of food is unusual, but there was a sponsor involved.

Anyway, that’s what got me hooked on sailing bigger boats. Point is, anyone can. Even if you don’t have friends that sail, there are ways to get on. If close to the marinas and anchorages you wish to sail from, post your availability. Otherwise, the internet can be useful – just do a search on “crew wanted for sailing” and start investigating. A couple useful sites are floatplan.com and cruiser.co.za.

You’re going to find boats and skippers looking for a willing crew for anywhere from a few days to several months. One key to getting chosen is being ready to go when the boat is. Often it’s a last minute need, because someone pulled out.

When making a decision on joining a crew, take the time to ensure you understand all arrangements and that you and the captain have the same understanding. The above sites also have info on what to expect in terms of “free cruising”.

The cost should be no more than your share of food and personal expenses. Anything beyond that like fuel, moorings, etc, means it’s a commercial enterprise. Also be aware that there are folks out there looking not so much for help on their boat as help supporting their cruising lifestyle. A good deal for them and maybe for others, but not what we’re looking for.  

That being said, what’s stopping you?

Known as one of the islands most popular events, the festival, which was first held in January 1994, attracts sailing enthusiasts from all over the world. It features several days of races and regattas, as well as a day-long craft market and street festival. Over the years, the event has helped put Grenada on the world map for international sailing in the Caribbean.

The Grenada Sailing Festival is run in association with the Grenada Board of Tourism and supported by many sponsors. It lasts for four days and each year organizers report seeing ever stronger and more competitive fleets and record numbers of yachts and participants.

The yachts race in several different classes including J24s, racing, cruising, charter and multihull, and the challenging ocean racing is overseen by a team of internationally accredited judges and officials. The sight is spectacular each morning as the yachts maneuver for positions at the starting line, and even more so during the races themselves.

Along with Grenada’s own home-grown talent and local crews, the festival attracts some of the best names in Caribbean racing from neighbouring Trinidad, as well as Barbados and Antigua. You’ll also see a great mix of other nationalities, including skippers and crews from the UK, Ireland, USA, France, Netherlands, Holland, New Zealand, South Africa and more.