Traveling to Leeward Islands from Florida was pretty easy. Flew into Saint Martin, since direct flights to Anguilla had 19hr + layovers and multiple airlines. Little weird that we went north to go south, but the layover in Charlotte was so much less than if we had a layover in Miami. Along with arrival time earlier, it kinda became a no brainer. Being able to get in sooner, allowed us to catch a ferry that day. There were two real choices for us the public ferry out of Marigot or the semi private ferry right outside the airport. The awesome staff at Fountain Resort Residences advised us even though it was a bit more to go the semi private that it was well worth it. They even took care of booking it for us. Super quick boat ride over to Anguilla, and the car rental place (Andy's Auto) was right there at the ferry terminal on Anguilla. Which makes car pick up and drop off super easy. At Saint Martin the car rental was an easy shuttle to pick up. We had to be sure to advise that we had an early flight out, which they had another car rental place we were able to drop the car off outgoing. Princess Juliana Airport was super easy to get around and navigate thru. It's also a super cool airport because of the terrain around. A beach on the other side of the fence and mountains to in the other direction. The take off is different as the power up fully and take a steeper incline out.