I'd avoid staying in Roseau and go straight to Portsmouth. The anchorage is pretty well protected and the PAYS organization has a
security patrol so the anchorage is also quite safe. I'd recommend an earl morning Indian River tour and if you have time it is worth
renting a car and visiting the waterfalls and national parks. I like hiking, and the whole island is a wanderers paradise.
From there it is a short sail to the Iles des Saintes, part of Gaudeloupe. This is a special place and worth staying a couple of days. They used to have a morning
delivery of baguettes, croissants and other fresh bakery items directly to the
boat, but that was discontinued recently.
From the Saintes you
head north along Guadeloupe to the anchorage in Deshaies, where you can clear out. The anchorage doesn't have great holding and with my boat's deep
draft I have to
anchor way out in 40 feet or more; but if you can get in closer that will
work. Often the anchorage is backwinded in the late afternoon until close to sunset, when the
wind changes and it is interesting to watch as
boats rotate and sometimes come into contact.
From Deshaies it is a straight shot to English/Falmouth in
Antigua. I avoid
English harbor as it is crowded and the holding is only a thin layer of sand over rock, but Falmouth is better holding and very protected as well. And it is just a short walk from the
dock at Falmouth to the C&I office in
English Harbour.