That is a big trip, and very exciting. Are you thinking one-way or out and back?
You definitely want to start upwind, in Antigua.

We will typically do the following:
Falmouth Harbour, Antigua
Barbuda
Nevis
St Barth
Anguilla
St. Martin
St Maarten

These are big sails, so be sure all are interested in that. 3-6 hours depending on the day and the boat.
Provisioning in Antigua is okay, but you have to drive up past St. Johns to the Epicurean. 35-40 minutes each way. Big store with everything you need, but prices are typically 20% higher than Grand Marche in St. Maarten.

That time of year, winds are typically east, with some north. Christmas Winds are common, in the 20's. Otherwise, trades are more easterly, in the mid to high teens.

Clearing in and out of Antigua and Barbuda is straightforward but detailed. Same with St. Kitts & Nevis

St. Barth and French St. Martin are simple and can be done on line.