@Matt - i just put in a very long answer on the other forum you posted your question in, some of what I wrote is identical to @Jeannius. I think that the Îles des Saintes, which also rank among my favorites, is too far. It is a whole day of sailing/motoring from Deshaies to the Saintes, and another day to get back north to Deshaies. Here's a copy:

I would keep a list of potential destinations and then, a day or two before you start, finalize the itinerary. The weather can play a big role, and there's nothing worse than beating to weather because you have a fixed plan. I've done deliveries where you are on a schedule and have to go, despite knowing that if you waited a day or two, you'd have a better trip.

From Antigua (I'll assume you are chartering from English Harbour):
If you love sailing, then the relatively short run south to Deshaies is a blast. Note that holding in the anchorage can be difficult, and the wind conditions in Deshaies can be gnarly. But it is nice ashore and a particular treat for fans of the TV Series "Death in Paradise". You can now clear in and out of the French islands electronically without having to go ashore to an office - that simplifies things greatly.

From Deshaies, you can either head back to Antigua - perhaps clearing in at Jolly Harbour, spending the night there or just around the corner at Deep Bay (if you want to stay aboard). Then north to Barbuda. I believe you can now clear out of Antigua & Barbuda there, sparing you the return trip.

Or head west from Deshaies to either Montserrat or Nevis. I've sailed past the exclusion zone but haven't stayed in Montserrat, so I can't help there.

Nevis you can clear in at Charleston and anchor off Pinney's Beach, and you only need one day to explore that island, then sail past the Narrows to St. Kitts. There's a lot there - I like anchoring in White House Bay but there are other options. The UNESCO World Heritage Site at Fort Brimstone is impressive, as are other sights on the island. I like renting a car, and with only one road going around the island, it is hard to get lost.

From Nevis you can either do a short sail to Statia (St. Eustatius), which is a great off-the-beaten-path place for a day; or head up to Saba or sail to St. Barths. Saba is only recommended if the conditions are very, very settled. You would be mooring in an open anchorage subject waves and swells.

St. Barths is a nice place, but somewhat pricey. Clearing in at Gustavia means you have to find an anchoring spot in one of the three anchoring areas. That can be a bit challenging. If you have a dinghy that can plane, I like to anchor in Anse Colombier and dinghy in - plus Anse Colombier is among my favorite anchorages. You shouldn't miss the airport approach and "Le Select(Cheeseburger in Paradise)", the latter being the only really affordable restaurant I've found on the island. Shell beach is worth a walk as well.

St. Martin has 2 parts - the French and the Dutch. You can dinghy and drive from one side to the other, but you need to clear in and out with a yacht. So it would be best to clear in on the French side since Sunsail is in Marigot. I like clearing in at Anse Marcel, but with the new French online system you don't need to go ashore anymore. I recommend spending one night at Ile Fourchue, then sailing on to Tintamarre for a day on a wonderful beach. Then head to Grand Case for 1-2 or more nights, perhaps a day sail to Anse a Pere.

I would suggest skipping Anguilla - there's not much in the main anchorage, and cruising the island is a bit pricey.

Last edited by Zanshin; 09/23/2025 04:38 AM.
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