Sailing the Caribbean – the Basics

February 20, 2012  •  Caribbean, Travel

This is Part 1 in a 4-part series about my bareboat sailing adventure with three couples from St. Lucia to Grenada in the Caribbean. Enjoy the trip!
I just returned from paradise. I mean a trip to one of the most gorgeous places around – the Windward Islands of the Caribbean – to spend an incredible 2 weeks relaxing as we sailed from island to island. Curious as to how we did this? Wondering what it’s like to book a bareboat sailing adventure? Read on and I’ll fill you in on the basics.

First of all, that’s our boat above – a 46 foot catamaran rented from The Moorings in St. Lucia. Although I grew up sailing a sloop (single hull boat), a catamaran has some distinct advantages – it’s more stable and doesn’t heel over so much in high winds (which we had – 30+ knots!) and it has a wide surface, meaning more cockpit room for hanging out and dining, and more deck space for lounging and sunbathing.When you arrive at your boat, it will be provisioned as you had requested. (Note: don’t ever attempt self-provisioning, it’s just too much work.) You pick how many days worth of food you want – although we were on the boat for 11 nights, we only picked 7 days of provisioning, knowing we’d want to eat ashore at many of the islands. That food needs to all be checked off and then stowed before you can set sail.That means it’s helpful to arrive the afternoon before you want to begin your journey. It’s hard to get to St. Lucia from Denver – we left at 11am on Wednesday and arrived at 5pm on Thursday, thanks to the distance and a 3 hour time zone change. But we were able to complete the boat review and captain’s briefing and stow our provisions and unpack such that we could head out first thing on Friday morning.Alot of people assumed that we had a captain and cook – we didn’t have either, but instead each person in our group took on a role: captain, first mate, chef, cleanup, dingy duty, and music. That means that your captain must be certified to sail. I grew up sailing, but knowing how to sail is nothing compared to knowing how to handle a large boat, the mechanical considerations, etc. Learn to take orders from your captain from day one and things will go more smoothly!One of the things I should have listened to our captain about was how to avoid seasickness. The thing about motion sickness at sea is that once it sets in, and you’re out on the water sailing, there isn’t really any way to get rid of it until you stop moving. A good dip in the cool ocean helps too. There are all sorts of things you can do to prevent motion sickness – from Queasy Aids to dramamine, to transderm scop patches to homeopathic inhalers and drops – but the best way on a sailboat is to take the helm. It’s like driving in a car – rarely do you get sick when you are the driver. When you’re sailing, driving the boat makes you focus straight ahead on the fixed horizon – and not on the 10 foot swells your boat is rolling over.Although most of us enjoyed a beer while sailing, the breeze blowing through our hair, it’s best to be settled into a harbor before happy hour begins. You’ll have two options in the southern Caribbean islands – either a mooring ball in a harbor or anchoring in a protected area – and both can be tricky. Better to get that job done before the champagne starts flowing! If you are anchoring, it’s up to the captain to pick a spot, give orders, and get the anchor set.If you’re lucky, however, one of the locals will zip out in their brightly painted little boat to meet you as you’re entering a harbor. They’ll guide you to an available mooring ball and help you get tied off for the night. In return, you pay them a small fee. Make no mistake, these guys are incredibly hard working. They might work all day getting boats into and out of a harbor, then they’ll come around in the evening to take orders for the morning. Ice, croissants, homemade banana bread from their wife, baguettes, lobster – just place your order and they have you covered. They’ll also taxi you into shore if you need to clear customs or purchase something. One young guy even helped us procure a new gas can for our dingy (take note: bring the gas can for your dingy aboard your boat, don’t leave it in the dingy while you are sailing at 10 knots in 30 knot winds over 10 foot swells). We hung out having pizza and wine while he did all the work for us.As the sun sets over the Caribbean, they just might be back around, trying to incent you to come have dinner at their family’s restaurant ashore. Take them up on that – the food is really good, and it’s great to step off the boat for a bit each day.Some of my friends have asked just what did we do all day long? I could just say we relaxed, but that doesn’t seem to satisfy their curiosity. So here’s a sample daily routine. I usually awoke first, and turned on the water pumps (for sinks and showers) and the gas, then got coffee and tea going and breakfast started. Once everyone was up, we’d eat, clean up, slather up in suntan lotion, then pull up the anchor to head to our destination for the day.That might be a short 45 minute sail that landed us somewhere to go ashore for lunch, or a longer day sail with lunch on board. Either way, there was always plenty of afternoon play time. Swimming, snorkeling, chatting, reading, napping, cocktails, music – each day we managed to enjoy all of these.We always stayed in swimsuits through sunset each day – usually enjoying a glass of bubbly while watching the sunset and practicing taking silhouette photos of each other with the sun setting in the background. Once the sun was down – a little after 6pm this time of year – we’d turn on the generator to heat up the shower water, take quick showers and change for dinner. We actually ate ashore for 8 dinners, and on the boat for 4, which seemed like the right mix. You can certainly plan for more or less aboard as you want.Back on board the boat after dinner we usually hung out a bit, singing or dancing to fun music, playing cards, laughing, and having a nightcap before hitting the sack anywhere from 10pm to midnight. The next morning, I’d be up again making coffee and enjoying the early morning solitude. It’s one of the greatest ways to spend a week or two and I was really fortunate to experience bareboat sailing with such great friends!

Stay tuned for part 2, my photo journal of the Windward Islands of the Caribbean, coming Friday!


5 Comments  •  Comments Feed

  1. Lea Ann says:


  2. Barbara | Creative Culinary says:

    Love this…sounds just amazing. I’m going to close my eyes now and do some pretending…except that seasick part.

    • Michele says:

      That seasick part was ugly, let me tell you. And as I was hanging off the back of the boat on the steps leading to the water, literally a foot from falling into the sea of 10 foot swells, nobody on the boat was able to help me for fear that if they even looked at me they would get sick too! All they did was keep yelling, “Are you OK Michele?” So glad that was only one day!

  3. Karen Harris says:

    Ah, what a lovely trip. I can’t wait to see the rest.

  4. Toni @ Boulder Locavore says:

    What a wonderful start to your trip Michele. I could not even read the text for the photos my first time through; felt like being there. I love knowing all the preparations and how fortunate to have your boat stocked for you. I empathize on the sea sickness. I too get very sea sick and your story brought back the memory of a dive trip in the Channel Islands where I spent the first 24 hours hanging over the side (then felt I was rocking for 2 days after docking when the trip was over).

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