In 1992 and 1993, four of us cruised the Leeward Islands in Minstrel, a Jeanneau 442. We found them to be a varied and interesting group of islands and cultures. It can be an ambitious vacation, but if you like sailing, it offers great trade winds sails, interspersed with intriguing stopovers.

The islands offer a great variety in culture and geography. And because they are very close together, when you sail you get to really sail.

None of the passages between islands should take more than a daylight trip, although you might want to start early for the longer ones. We tended to sail for a day, then spend one or two days exploring the island.
The first time we made a seven-day loop from and to St. Martin; the second we spent two weeks wandering from Guadeloupe to St. Martin.

Both charters were in the late winter. The weather was great and the Trade Winds almost always blew as expected. Winds was often 15-20 kts, with one day of 35; seas usually were 6-10 feet.

Our first itinerary was:

St. Barts, Gustavia;
St. Barts, Gustavia;
St. Kitts, Basseterre;
Nevis, Charlestown;
Statia, Oranjestad;
Sint. Maarten, Philipsburg;
St. Martin, Grande Case.

The second itinerary was:

Iles des Saintes, Bourge;
Iles des Saintes, Bourge;
Dominica, Rousseau;
Dominica, Rousseau;
Dominica, Portsmouth;
Gualdaloupe, Anse a la Barque;
Antigua, English Harbor;
Antigua, English Harbor;
Antigua, Green Island;
Nevis, Charlestown;
Nevis, Charlestown;
Nevis, Charlestown;
Sint. Maarten, Philipsburg;
St. Martin, Grande Casse

Some thoughts on the islands (which may or may not be true two decades later):

Barts is overcrowded and overpriced. But a still beautiful island for all that. And excellent provisioning.

St. Kitts has a grubby harbor, but the rest of the island seems like it would be a nice place to tour. We didn’t.

Statia has a fairly unprotected anchorage, subject to a surge making it uncomfortable on the boat and almost impossible to dingy ashore. Saw not a lot on the island, but then were there lass than 24 hours. We climbed the volcano in the morning and then sailed to Snt. Maartin that afternoon.

As you can see, we liked Nevis. Nevis is less known, not crowded and a delight. An open but beautiful anchorage off Pinney’s Beach. Interesting old sugar plantation ruins and a quiet town. Good market, if a long walk in the direction of the police (immigration) station.

Antigua, at least where we were, is a great place. English Harbor is remarkable, and Nelson’s Dockyard offers most everything from food to customs to showers and laundry. A small shop easily put right the hinges of our anchor locker cover which had been attacked by the CQR in high winds. Good provisioning.

On Sint/St. Maarten/Martin, Philipsburg is a great place to shop, or at least provision. Grande Case is restaurant heaven and a quite anchorage. Marigot, the French capitol, is a nice town; we were robbed there but also taken good care of in the hospital (both at the same time, unfortunately). Excellent provisioning.

Dominica is a lush, beautiful place that should not be missed. That said, it is the other place we were burgled, this time while sleeping. The islanders have not learned quite how to deal with tourists; since we look affluent (and probably are by comparison) we are fair game on and off the water. But good markets, restaurants, waterfalls and the usual great views. Good provisioning.

Iles des Saintes are (were, anyway) not crowded (were no hotels) and with interesting climbs. We walked up to the cactus-studded fort and hiked around the small island opposite the main island. Poor stores for provisioning.

Our bible was Chris Doyle’s Cruising Guide to the Leeward Islands. Excellent and accurate information and charts good enough to navigate by, even if he says you shouldn’t. (Hey, that’s what Garmin says, too!)

We booked the cruises through Ed Hamilton and chartered from ATM, now Stardust.