Amidst the fun of snorkeling, diving, kitesurfing and stand-up paddleboarding, there’s something so great about the simple pleasure of being on a boat. At the Frangipani, that often times involves heading out our power boat, Relentless, visiting off-island cays and exploring beach bars that dot the island’s perimeter. On one occasion earlier this year we headed on a boat trip that was extra special, a sunset tapas cruise on Tradition Sailing.

Operated by Laurie Gumbs (of Pumphouse fame) and Deb, his partner-in-crime, the Tradition experience has been fine-tuned to give guests an incredibly unique and memorable experience. When the sunset works in your favor, it’s bliss to the nth degree. The vessel is a traditional West Indian sloop that provides an experience markedly different from a typical powerboat. Considering the historical and cultural significance of sailing in Anguilla, a traditional sailboat is an homage to the island of yesteryear; a slow sweet sail from Sandy Ground with a cocktail in hand and the wood beneath your feet.

Tradition has a slew of offerings from a half day Little Bay sail to a custom, tailored experience in the form of a private charter (I’ve often thought this would be perfect for a small wedding party or a family trip). Along with another couple, we were fortunate enough to hop aboard the sunset tapas cruise, one of their newer offerings this year where guests not only get to sip on delicious mimosas but also get to nibble on bites from an extravagant spread while the sun sets (think decadent cheese plate, veggie platter, salmon blinis, etc).

Departing from Sandy Ground, Tradition sails east towards Little Bay, a slow breezy sail with Laurie at the helm.

Aside from being a consummate hostess – my champagne glass was never empty – Deb also hones her sailing skills, giving us a brief glimpse into the world of true sailing (which, for the record, is way more work than I ever realized). While we mellowed at Little Bay watching the sun set, we chatted with Deb, listening to the story of how she developed her love of sailing, her experiences around the Caribbean and how she ended up in Anguilla.

Below are some snapshots from our evening out. It was such a blast and the sunset was mesmerizing. We departed for our journey around 4:30PM from Sandy Ground (in front of Johnno’s) and headed back in a few hours later with only the moonlight and stars overhead. Pretty spectacular.

Even for four people that live in Anguilla – people who have seen Little Bay more than once and who’ve experienced a few memorable sunsets before – an evening out on Tradition was an incredible experience. To put it simply, it felt special. I recommend the experience to our newlyweds and anniversary couples who want a super special evening out, and I recommend it to folks getting married in Anguilla who want to do something special with their bridal party or their family.

A private charter with your friends and family, sippin’ cocktails and nibbling on tapas while cutting across the sea at sunset… how does that get better?

A huge thank you to Laurie, Deb and team for such a memorable evening at sea. A side note: for anyone interested in learning more about how sailing is weaved into the fabric of Anguillan culture, give David Carty’s documentary, Nuttin Bafflin, a watch – it’s incredibly well done and is a great way to glean a bit more insight into the significance of the ever-present boat races on the island.

Have you sailed with Tradition before? Feel free to leave us comments or questions about the experience in the comments section below.

This post appeared in its original form on The Traveling Scholar. It has been updated for Plumeria Press.