Here's the worst way to begin a trip to the Caribbean: on Spirit Airlines. The video below, one of many, has 147K views.
Here's the best way: on Tradewind Aviation.
Tradewind is one of a new breed of small-plane brands catering to the customer who, say, doesn't hate themselves enough to fly a nickle-and-dimer like Spirit. (See also: Surf Air.) It's not private charter per se, in that you'll share your cabin with other people — but it's certainly an elevated experience.
Some things to look forward to on Tradewind: leather seats, free Champagne, lounge wifi, a meet-and-greet escort (for an additional fee). Most notably: none of the no-changes nonsense we've gotten used to with major carriers — Tradewind's shuttle tickets are transferable and changeable.
How's it work? Buy your ticket — the interface is slightly wonky, but OK. Then, show up at the airport — ideally in St. Barts or Anguilla, or San Juan, where Tradewind maintains its flagship lounge. Tradewind's other Caribbean destinations include Antigua, Nevis, and St. Thomas. From there, you'll be escorted onboard a Pilatus PC-12 jet-prop aircraft.
You'll land. You'll go about your day in your destination of choice, without wanting to make an angry YouTube video about upcharges for luggage.