We used Winair for first several years and certainly a good airline. Never any problems. However, last couple years we have been using St Barths Commuter...much less expensive and better planes. My wife and I will be visiting the first 3 weeks of Apiril and travel only with carry on. Keep the shoes to a minimum and it’s no problem. It’s that kind of Island. There’s nowhere quite like it in our opinion...perfect vibe for us and really nice people.
We rent a small Suzuki from Gumbs and go easy on the AC cause you’ll get sick from that if not careful. Also, be aware there is not a lot of shade on most beaches (especially not on St. Jean, Saline and Gouveneur) so be careful. We rent umbrella from Jean Michel on St Jean beach for 10e per day. He has chairs too but we bring them from the Villa.
When you’re driving around just chill out and don’t worry about the scooters...you’re not in a rush to get anywhere on St Barts