There are a lot of good beaches and restaurants on St Maarten, and a cruiser might spend two weeks there, but a charterer wants to sail and see different places. So,
weather, and the prohibition against night sailing will determine your itinerary.
From Phillipsburg you will probably be able to lay
St Kitts or Nevis on one tack, and get that far in one day. You could stop at Stacia on the way, but it takes precious time to check in and out with
customs, and you will have to clear in at
St Kitts or Nevis, anyway. We think Basseterre is worth a visit, and there are nice land excursions open to you on Nevis, if you are interested in that.
From Nevis you can probably lay Montserrat in one tack. Touring the volcano-devastated area is fascinating. You need a guide for that.
From Montserrat you can lay
Antigua and Barbuda. You could spend a month in Antigua and not see everything, so you have to pick and choose.
Barbuda is spectacular. Spend a couple of days there.
Phone ashore for someone to meet you on the beach, take you to the town, and give you a tour of the frigate bird rookery.
From Barbuda the return trip to St Maarten is downwind, so bob's your uncle. If you leave at the first hint of dawn, you can probably make it during the hours of daylight. You have do do your own calculations on that. If your
boat won't go fast enough to get there with daylight to spare, then you will have to stop at Nevis or somewhere. Sounds like a great trip. We really enjoy those islands.
In really settled
weather, a trip to
Saba is a delight, but there is no protected anchorage there, so it would be an exceptional circumstance that would take you to
Saba.
There is no dishonor in motorsailing to weather. If bashing into the waves cuts your speed too much, the
diesel really makes the day go better.