Hello!
The ferry to Mayaguez leaves Santo Domingo at 8pm and arrives the next day at 8am, the same coming back, so you wouldn't actually lose any sightseeing/relaxing time, and depending on where you are going in Puerto Rico, you could actually save time.
Air Caraibes doesn't fly to San Juan. LIAT does, but you would have to fly to Antigua, transfer, and then fly back to San Juan, which doesn't make any sense. So much so that it is not even an option on their website
If you just want to get off the island, rather than going to Puerto Rico in particular, I've found the cheapest prices are either Turks and Caicos from Santiago or Puerto Plata, as Adrian mentioned, or Curacao from Santo Domingo on Aeropostal, followed by New York, then Miami, then San Juan, strangely enough.
For AA tickets, I either buy on the website or go to their booth in Bella Vista Mall. It once worked out $10 cheaper to buy from the booth than on the website, but sometimes there are special offers you can only buy online.
Kiboko
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