It is about 48 hours straight to Guadeloupe so you do need to be able to rely on your crew to do that non-stop. I have also taken over 20 hours just to get as far as St Martin/Anguilla and during that trip, the only time I saw the inexperienced members of the crew was when they came on deck to throw up.

Forgot to ask what type/size of boat you are on? On a mono you stand a better chance of staying close to Saba, Statia and St Kitts giving you more options. I've been in to Basseterre marina on St Kitts a few times and it is a good option. I've also anchored off Bassterre which wasn't a lot of fun and in White House Bay which had good holding and was reasonably sheltered. There is a new marina near White House which wasn't there on my last visit so I don't know anything about it. If you make it as far as Nevis there are literally hundreds of moorings lined up along the west coast.

If the admiral has little experience, perhaps don't take her on the upwind bit. I never had a problem finding crew when I asked on TTOL in the old days. I'm sure some of my old crew are still lurking and would likely jump at the chance of an offshore adventure.