I recently had to fly out of STI on jetblue at 1:40 am. I was in santo domingo with a friend. She is from santiago and doesn't get to SDQ often, so I was shoing her around a bit. She was dying to see the jardin botanico so we got there about 1pm and had a great time.
We got to caribe tours about 5 but all buses were sold out till 7pm. After arriving at about 9:30 to caribe tours, I said my goodbyes and headed to rancho tipico las colinas, and sat at the bar. There was a cardinals baseball game on, and when that ended the Mets game came on, apparently starting late because of a rain delay.
I told the taxi guy to pick me up at 11:30 and had a blast watching pedro pitch with all the guys at the bar. The bartender was high fiving me. I was explaining to some guys that vic diaz played for the Aguilas in the winter league etc. After 3-4 grandes, my taxi showed up.
Not bad at all. Having to get to the airport at 4:30 would be a bit tougher. What night of the week are you leaving? I assume it may be harder to find a place to hang out till 4:00 am. Wonder what time the bar at the airport closes?