It'll likely be a long day of beating closehauled into the Trades to get to Antigua
, so if you're determined to do it, I'd suggest leaving from St Barth to get the best possible angle on the wind
. The passage
from St Barth to Jolly Harbour, Antigua, where you can clear in, is a little over 70 nm. Leaving from St Barth means you can take advantage of dennisjay's suggested stops as you come east from St Maarten: Ile Forchue and Anse de Colombier. Antigua to Guadeloupe
should be a nice sail, as well as the broad reach back to St Maarten. Nevis
could be nice stops on the return, if you have time.
Where do you plan to go in Guadeloupe? It's a big island!