If you’re staying over in SJU on the way to SBH then look at the first two flights of the day on Tradewind. They will be the least expensive Tradewind flights. When I take the early flights I arrive too early to get into my villa. I plan to have a long breakfast at Le Repaire, and then do an island tour to see what has changed/what’s new.
If you’re staying over in SJU on the way home, then look at the last flights of the day, which will be the least expensive. Enjoy a long, leisurely lunch, and find a place to hang out until it is time to go to the airport. I can sometimes be found reading in the park by the hospital, or sitting in the garden at Le Select watching the world go by.
Going to SBH, Tradewind’s counter is to the left of the JetBlue counter in Terminal A. Just tell the taxi driver that you’re going to JetBlue. If you get to the airport 60 minutes ahead of time then you should be fine. You’ll check in, they’ll weigh your luggage, issue boarding passes, and send you upstairs to the Tradewind lounge area, a cordoned-off comfortable seating area with snacks and beverages. Tradewind’s wi-if is available and free. A Tradewind rep will come to collect you about 20 minutes prior to flight time. (The only toilets are on the first floor, so plan accordingly.) The rep will bring you down a nearby elevator and escort you to a bus, which will take you to the plane. They will likely want to stow your carryon in the rear of the plane, so plan ahead and hand carry anything which you’ll need on the plane such as a tablet or an e-reader.
Returning from SBH, you’ll be bussed to the Immigration and Customs area in Terminal A. A Tradewind rep will bring you your checked luggage. There are a dozen or so kiosks, as well as Global Entry. Depending on the time of day, you may or may not be behind another flight, but it won’t take long to clear in. Taxis will be readily available outside. There are several hotels near the airport, some of which Tradewind has special pricing with. Lately I’ve been staying at the Embassy Suites, which does not have special pricing. The next day, plan to be at the airport at least 60 minutes before flight time. You’ll have to clear TSA security, which could take some time.
Which airline are you flying on?