Tales of Adventure: Sunset Sailing in Anguilla

Sailing is a sport I have much appreciation for, stemming mainly from the fact that I have absolutely no idea how to do it myself. I’m not completely inexperienced – I did have a go at it while spending 10 days sailing the Greek islands in 2011. I could tie the bumper thingies (technical term) as we pulled into port, and attempted steering at one point way out in open waters. They quickly shooed me off the helm for fear of my increasing the chances for sea sickness with my driving, ahem, style.

But I do love the idea of it. And even more, I love when someone else has the skills I utterly lack and has a boat which they are happy to share with eager landlubbers.


I was beyond excited then when I learned that as part of our #CaptureAnguilla retreat last month Tradition Sailing would be taking our group out on a luxury champagne and tapas sunset cruise to Little Bay. Umm… sunset and champagne and sailing on a classic wooden 50’ gaff rigged West Indian sloop? Yes please! And I’d say the group mirrored my enthusiasm.


The sun was still shining bright when the crew raised the sails to take off. The crew, led by Captain Laurie Gumbs and First Mate Deborah Vos, handled everything as we sipped our mimosas and snapped photos. Tradition was built in 1978 on the Caribbean island of Carriacou, and is a true classic in that she has neither winches nor windlasses. To translate, this means that everything on the sailboat has to be done by hand, making managing the sails themselves that much more of a feat. So it’s a good thing that guests aren’t expected to lend a helping hand.










The sail itself was exhilarating, and the sun was just beginning to fade in the sky as we pulled into Little Bay. We had plenty of time for a swim before dinner would be ready, and in spite of the air temperature cooling, the water proved to be too inviting. Besides, you’re only ever in Anguilla on a sunset sail to one of the most beautiful and secluded beaches on the island once in life, right? Better go ahead and jump in.


The sun was hitting the horizon as we climbed back onboard, just in time to enjoy a delicious spread set out by the crew. Deb herself prepares the dishes on land earlier in the day, and they are fantastic. We all ate to our hearts’ content, pairing it will more champagne and shots of a special Caribbean liquor that undoubtedly puts as much hair on your chest as southern moonshine.


It was well past dark when we finished our last bites of food (or shots, depending on which group member we’re referring to here). The crew had strung lights on the boat, which provided ambiance and some light, but not enough that we couldn’t see the sparkles in the water. As it turns out, bioluminescence can be found here. As if the evening could get any more magical, now we have a personal light show from Mother Nature herself.

The sail back to Sandy Ground seemed much shorter, which may or may not have been influenced by the number of champagne cocktails we enjoyed. This was also a large contributing factor, in my opinion, to the entertainment we had as we glided back – nowhere else does renditions of every classic karaoke song you can think of sound so good, sung at top volume, of course. The docks could probably hear us coming miles out.

We ended the evening by sweating it out in the most energetic fashion at The Pumphouse, a fantastically authentic local bar on The Road Salt Pond, where actual salt is harvested, just down the road. It was yet another highlight in a trip that would prove to be full of moments worth remembering.

Have you ever been on a sailing trip before? Where would your dream sailing destination be?

  • Oh wow, what an amazing experience! Champagne, sunset, swimming in gorgeous water, coasting around on a boat under sail – if the horseback pictures you posted hadn’t already made me stick Anguilla high on my travel list, this would do it!

    We’re looking into taking a sailing course here in the next couple of months. My granddad was a great sailor and just from the rush I get on any kind of boat at sea, I’m pretty sure it’s in my blood, too. Time to start working on that retirement skill and start saving up for my perfect boat 😀

    • It was the perfect ingredients for a perfect evening!! I was exhausted by the end, but in the best way possible. The kind when you fall asleep immediately and sleep solid until the smell of coffee wakes you in the morning. 🙂

      A sailing course sounds amazing!! And with your family connection, and love for active adventures, I can see it being right up your alley. There’s a really great book by an Australian girl who sailed with her then boyfriend from California, across the Pacific, around Asia. It’s called Love with a Chance of Drowning – great read! 😀

  • Mrs. Goodlife

    Sounds like so much fun! I had a similar experience in a racing yatch in Australia. Had to help with the sails and held on for dear life when the boat was going at full speed. One of my favorite memories of that trip.

    • Oooh that sounds like SO MUCH FUN!!!! I absolutely love Australia, and can only imagine how full on a yacht racing experience must have been there. Hope you had a chance to take loads of photos amidst all the helping with sails and hanging on for deal life! 😉

      • Mrs. Goodlife

        It was a lot of fun, unfortunately my computer crashed and this was before the “cloud” so we lost those awesome shots. But the memories are engraved. =)