goider

I'm planning the same trip in late October, but for 5 nights.

Here's my current rough agenda. I have a $360 RT ORD-SJU and hotels currently booked (Sheraton on points, resorts on FRN). Island hop and cars are yet to be booked.

Arrive Thursday afternoon, take a cab from SJU to Old San Juan
Spend the night in Old San Juan Sheraton
Leave for Vieques Island first thing Friday morning by taking cab to SIG
Hang around the W resort on Friday
Rent a Jeep on Saturday and go to the beaches and explore the island
Leave back to main island PR on Sunday morning into SIG, cab to rental car facility, rent a car and drive to St. Regis
Hang around the St. Regis resort on Sunday
Explore PR and the rainforest on Monday by car
hang around the resort on tuesday, return car and fly back to ORD

So, in summary, 1 night at the Sheraton Old San Juan, 2 nights at the W Resort Vieques Island, 2 nights at St Regis Bahia Beach, in that order.