I'd use Moorings/Sunsail from Oyster Pond
Because of filghts/times/lenghts/distance from airport i would seriously consider having a night before and after in Simpson Bay at Mary's Boon. Its $100 per night, beach front. At that price its NOT TOP LINE RESORT! But it is in the cruising hub and you can walk to the Yacht Club and see the boats go through the bridge, see the supermegahugybigyachts at Isle de Sol (you can go for a drink there leaving id at the gate), say hi to 'real' cruisers etc.
Then next morning refreshed (hung over) taxi to Oyster Pond and be the first people in line for their boat.
Same with the last charter day. Its so manic its nice to have a relax night in Simpson bay.
Best time to go December throu March. Thats peak season. Its exciting.
Other times of the year its much quieter, all the mega yachts are back in the Med, most of the cruisers are down south.
I get off on the excitement of the Season. Sharing a bay with a 200 foot boat whose tender is bigger than my boat, window shopping in St Barts where you ask the price just to go 'wowwwwwwww' pretending you can afford it.
The sailing is good. Its grown up sailing... Not 5 miles mooring ball to mooring ball but 15 miles in full tradewinds where you have to navigate, have to double headlands, have to use tactics, have to anchor, have to clear in and out.
Marys Boon. https://www.tripadvisor.com/Hotel_Re...St_Martin.html