Charter Captain in the Caribbean - St Martin and the BVIs
- Jeff Smith
- Mar 16
- 3 min read
Updated: Apr 7
We asked Jeff if he was available to captain a charter in the Caribbean over the holidays. My husband, son, sister, nephew and I met Jeff at the boat, got aboard and unpacked and then headed to the market to provision. Jeff was excellent at recommending the right places to go, recommended meal plans and beverages for the journey. We were planning to sail across the Anegada Channel (known as the "Oh My God" Channel due to the rough wind-over-tide conditions) to the British Virgin Islands.
There is a low draw-bridge blocking the channel out of Simpson Bay Marina on St Martin. There are regularly scheduled openings so Jeff got us going in the morning so we could get to the "marina-side" of the drawbridge before it opened. It is only open for a few minutes so we motored through and then anchored for the afternoon and evening in Simpson Bay. Jeff wanted us to leave early the next morning, before the wind built and the ride became uncomfortable. My husband has sailed extensively but the rest of us had limited offshore experience.
The evening was warm and wonderful and the next morning dawned clear with a wonderful breeze out of the south. We raised anchor, navigated out of the bay and then headed across the Anegada Channel to Virgin Gorda and Tortola.

Rounding Necker and Prickly Pear Islands we sailed past the Baths and anchored close to the beach on the leeward side of Peter Island. We rowed ashore and had dinner at a beach shack with palm frond roof. Spectacular! We danced to the local band on the beach, waded in the water and had a wonderful time.
We raised anchor the next day and sailed to Norman Island and anchored again. We sailed to Road Town on Tortolla and spent the evening ashore. Our typical pattern was to have breakfast onboard, go sailing, have lunch onboard and then anchor, row ashore and have dinner. The people were incredibly friendly and welcoming and the food was wonderful. The combination of sailing, seeing the sites and having great meals was really wonderful!
We sailed over to see the Baths on Virgin Gorda - a spectacular area with enormous boulders and warm pools of water to swim in. Fantastic!
All the mooring buoys were full and the local authorities look askance if you try to anchor, so Jeff got us in the dinghy, my sister's son rowed us ashore and Jeff stayed on the boat and "hovered" - kept the boat close to shore but in deep enough water so we did not have to row too far to visit the Baths or to get back to the boat. We hiked all around, swam in the pools - sometimes inadvertently as we tried to climb around but slipped into the pools by accident. We basically laughed the entire time!
We sailed over to the Bitter End Yacht Club and anchored in a shallow, protected bay a short way from the Club. Jeff took us in the dinghy and we experienced our first thunderstorm! Jeff had his foulies on but we all had our best outfits on as we wanted to look nice at the yacht club. We all got drenched - except Jeff! - but still had a wonderful dinner and enjoyed walking around the grounds. Spectacular setting and a wonderful anchorage!
Our charter was rapping up so we headed back across the Anegada Channel the next day. This time it lived up to its name - high winds, massive lightening, tropical downpours. The boat was incredibly strong and stable but the visibility was limited so we ran the radar and kept a person on watch on each side of the catamaran for the entire trip. We got into Simpson Bay after dark, anchored and immediately fell into our berths exhausted.
Thanks to Jeff and 24 Hour Boating for an outstanding voyage around St Martin, across the Anegada Channel (both ways!) and throughout the British Virgin Islands. Jeff did an outstanding job helping us gain offshore sailing skills, plus great places to walk, hike and eat in the BVI's!
Our entire family enjoyed the experience - we all recommend you reach out to Jeff at 24 Hour Sailing if you want to build your skills day-sailing, anchoring, learning sail trim, provisioning, passage planning and navigation.
Patty
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