Back in February of 2025, we announced St. Martin and the Leeward Islands as the location of the 2025 Club Flotilla. Just 48 hours later, all 10 boat reservations were claimed, setting a record for the fastest sell-out in 10 years of club flotillas! Fast forward to a November 25’ when 50 sailors converged on Fort Louis Marina in St. Martin, where our fleet of boats awaited us for the week. Over eight days, we visited three islands across three overseas territories of the Dutch, French, and British: St. Martin (St. Maarten), St. Barts, and Anguilla. This cruising ground is truly unique as Caribbean ease meets European elegance, and bathing suits mingle with cocktail dresses. By trip’s end, we had logged 100 miles in conditions ranging from 5 to 25 knots, with everything in between. We sailed, swam, savored excellent food, shared cocktails, and had an unforgettable time.
Day 1: Our 11 a.m. skippers’ meeting marked the official start, complete with a welcome cocktail and a weather/chart briefing courtesy of The Moorings and Sunsail (from whom we charter from). After loading the boats, completing checkouts with dock staff, and provisioning, it was time to cast off and head to Grand Case just a few miles away on St. Martin.
The last boats left the dock at 3 p.m., so we made quick work to reach the anchorage before sunset and a building breeze that would challenge us over the next few days. With 20 knots of steady wind and 120 feet of anchor chain deployed, skippers felt confident in their holding and went ashore to enjoy the French restaurants and BBQ joints lining the shore of Grand Case.
Night one on the anchor in conditions not seen much in San Diego…it’s fair to say some skippers slept better than others, but all the boats held!
Day 2: The fleet awoke to the same 20-knot breeze and faced a long, uphill sail to St. Barts, a tough first full day to say the least. Beating upwind in big breeze and the occasional 8-foot wave was hard work and not the gentle welcome we’d hoped for, but you can’t control the weather! Some boats broke off to Île Fourchue for shelter in its small anchorage about six miles short of St. Barts, while others pressed on. Little did we know, those at Île Fourchue enjoyed a far calmer night.
Ashore in Gustavia, we completed customs and immigration paperwork and soaked in the high-end luxury of mega-yachts, designer shops, and fine dining—a stark contrast to St. Martin. On the dinghy ride back to our boats, the rolly anchorage was impossible to ignore; masts were swinging 40 degrees side to side in the confused swell. We braced for a rough night.
Day 3: Earlier than ever, anchors were up shortly after 7 a.m. as the fleet motored just a couple of miles to the protected bay of Colombier and the welcoming sight of mooring balls. This was what we signed up for with dead-calm seas, turquoise water, white sand beach, and excellent snorkeling. We spent the day relaxing and planned a 5 p.m. sunset happy hour on the beach. There, we adjusted the float plan to spend another night here thus avoiding one final day of strong breeze and big waves… no one was interested in that again!
Post happy hour, we went our separate ways, enjoyed an epic sunset, and fired up the BBQs for dinner (Colombier has no onshore services).
Day 4: Our float plan change required updating customs paperwork back in Gustavia. Some skippers hitched rides on one of catamarans while others hiked the Colombier trail catching amazing ariel views of the anchorage and then took a short taxi into town. Back in Gustavia, we again indulged in French luxury before returning to the serene anchorage of Colombier. The rest of the day was more swimming, snorkeling, and pure relaxation. With the revised plan, tomorrow’s sail would be a big one of 30+ miles. We placed wagers on the “race” and turned in early.
Day 5: The last boat departed just after 9 a.m. into much kinder conditions. Wind started at 12 knots, dipped to 8, rebuilt to 17, and dropped to 10 again. Given the mileage, no one hesitated to fire up the “Iron Whomper” (as one boat dubbed it over group text) during the light patches.
30 miles later, we arrived in Road Bay, Anguilla and back to Caribbean vibes. Perfectly placed right outside the customs office and a couple paces up from the water was a beer shack that happily took our American bills. As 10 boats (plus a few others) filled the anchorage, beach bars and restaurants sprang to life, thrilled to kick off their busy season. Many of us chose Roy’s for dinner and trivia night, an understatement; it felt like the Jeopardy World Championships. We licked our wounds, returned to our boats, and slept soundly thankful to once again be in a calm anchorage.
Day 6: Anguilla is famed for its beaches, most accessible only by small boat or car. This was a dedicated exploration day so there was no need to move the boats. Some took go-fast boats to Sandy Island or Prickly Pear; others rented cars (remembering to drive on the left) to visit postcard-perfect beaches: Little Bay, Shoal Bay, Meads Bay, and Rendezvous Bay. The relaxation was well-earned and deeply enjoyed.
For happy hour, all 50 of us converged on Elvis’ Beach Bar—voted the #2 beach bar in the Caribbean (second only to Soggy Dollar Bar in the BVIs). One skipper, unaware of the rivalry, had his Soggy Dollar hat swiftly swapped for an Elvis’ hat free of charge and without request.
Day 7: Another 30-mile passage from Anguilla back to St. Martin. The original plan was lunch at Tintamarre marine park and overnight in Orient Bay. But after Day 2’s lesson, we stayed flexible.
The sail from Anguilla was the trip’s best with a close reach in 14 knots and flat seas over the tip of Anguilla, transitioning to a beam reach with following seas down the coast. Hull speeds for nearly the whole fleet and a memory that will last a long time!
After a quick lunch and swim at Tintamarre, we headed for Orient Bay but reports of rough conditions and visual confirmation prompted an audible. We diverted to Grand Case a day early.
Watching the sunset with cocktails in the cockpit, we were glad we pivoted. Dead calm. Just seven days earlier, this same anchorage had tested our nerves; now it was as flat as Mission Bay.
Day 8: With Grand Case secured a day early, we had a full day to explore missed St. Martin gems including a morning snorkel at Creole Rock. In the afternoon some hitched to Maho Beach (where planes skim feet above sunbathers…you’ve seen the videos), others taxied to Orient Beach, and some lounged on the floating bar anchored nearby.
That evening, we went ashore for a final French meal, reflected on an extraordinary week, talked about our favorite and least favorite parts, and began planning our return in a couple more years!