Hello Kitrob,
your itinerary depends a bit on what sort of cruising you enjoy doing. First of all, don't forget the
anchorages and beaches of Antigua since there are some true gems there.
Barbuda, if not red-lined by the charter company, is a wonderful out of the way
destination with somewhat difficult shallow approaches and not much in the way of nightlife - but lots of birds.
St. Kitts and
Nevis are interesting but somehow I've never found them to be charming as I do other islands. Taking a day to visit Brimstone Fort on St. Kitts is a must, I like to rent a car for the day and drive all the way around the island on my own time rather than as part of a tour.
I really like Statia. I rented a moped with some other cruisers and we explored the island and taking a day to hike around (and up) the volcano is wonderful.
Saba is a
destination that should be visited in calmer seas, as the anchorage is exposed and can be rolly and uncomfortable.
St. Barths is one of my favorites, but not the town and anchorage at Gustavia - I like Anse Colombier and Ile Fourchue, both with no facilities on shore.
Don't forget that only a short sail south of Antigua brings you to
France, the little port of Deshaies on
Guadeloupe makes a nice anchorage and starting point to look at
Guadeloupe.
Three weeks is quite a long time for that trip. My personal preference would be to go (depending on your
draft and winds)
Antigua :
English, Falmouth, Green Island, Deep Bay, Five Island, Willoughby and perhaps Barbuda
Downwind to Montserrat - clear in and
anchor, take a tour of the island and of the exclusion zone around the ash-covered city of Plymouth.
Beam reach to Nevis,
anchor and clear in at Charlestown / Pinney's beach. Lots of mandatory
mooring balls and the anchorage is protected despite looking open to the sea. Perhaps a day tour of the island and the cloudforest.
Across the Narrows to St. Kitts. I always anchor at White House Bay, but there's nothing ashore there. Basseterre has an anchorage, but it is always rolly and I only stay there for clearing in/out at the
cruise ship terminal and while I explore the island by car. I'd do a day tour while the
boat rolls around there and then return to White House Bay for a calm anchorage.
Reach to Sint Eustatius - clear in and anchor off Oranjestad and don't let all those tankers in the distance put you off. The city of Oranjestad is full of signs and plaques and other informational material about the
history of the island, and the fort is worth a visit.
Next would be Saba, if the conditions are right, or St. Barths if the waves are too high for comfortable
anchoring.
St. Barths - clear in at Gustavia and don't miss the short walk to the top of the hill overlooking the
airport and see some impressive final approaches and remember to duck as the twin Otters fly by overhead! Anchor in Colombier and take the walk along the shoreline. After clearing out, spend a night or three at Ile Fourchue (uninhabited island, but beautiful) before continuing to St. Martin where such
anchorages as Grand Case and Ile Tintamarre await you.
I've got some pictures and stories of those places on my blog, if you are interested.