The Leeward Islands provide a fantastic cruising opportunity. 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. 
In '92 and again in '93 four of us chartered a Jeanneau 442 from ATM, more recently aka Stardust. The first time we sailed for a week out of St. Martin, looped through St. Barts, Nevis, Statia and returned to Snt. Maartin/St. Martin. 

The second trip, two weeks in duration, we sailed out of Guadeloupe and visited Iles des Saintes, Dominica, Antigua, Nevis and Snt. Maartin, dropping the boat off, as the first time, in Anse Marcel, 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. 

We would spend one day sailing between islands, and the next one or two exploring the island. 

The islands are (in origin) British, French and Dutch. This provides a challenging mixture of languages, culture, food and currency. Also the adventure of locating and dealing with customs and immigration at every landfall. 

Dominica is wet, with waterfalls and lush foliage. Although we never saw much of the inside of Antigua, the number of harbors is amazing, with English Harbor incredible for its facilities, character and terrain. Nevis is quiet and beautiful. St. Barts is an upper-class tourist trap with bad $5.00 burgers at Le Select. But worth seeing. I could go on and on; contact me if you want to hear more. 

Only caveat to mention is theft: we had possessions taken from the boat on both trips; once in St. Martin and once in Dominica. 

We made our arrangements through Ed Hamilton, who has a web site at . 


Four of us have twice cruised the Leeward Islands on a Jeaneau 44 in 1992 and 93. We found them to be a varied and interesting group of islands and cultures. It is an ambitious vacation you have planned, but if you like sailing, it offers great trade winds sails, interspersed with intriguing stop-overs. 

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. 

Our first itinerary was: 	St. Martin, Anse Marcel;
				St. Barts, Gustavia;
				St. Barts, Gustavia;
				St. Kitts, Basseterre;
				Nevis, Charlestown;
				Statia, Oranjestad;
				Sint. Maarten, Philipsburg;
				St. Martin, Grande Case.

The second itinerary was:	Gualdaloupe, Pointe 'a Pitre;
				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;
				St. Martin, Anse Marcel

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 interesting fort and hiked around the small island opposite the main island. Poor stores for provisioning. 
Get a copy of Chris Doyle's Cruising Guide to the Leeward Islands, if you haven't already. Excellent and accurate information and charts good enough to navigate by, even if he says you shouldn't.