My roommate and I just snapped up a couple tickets to Puerto Rico for $253. It's half-mileage run, half let's-spend-some-time-on-the-beach. I'll rack up over 15,000 miles for the journey and get my tan on while we're at it. Having never been to the Caribbean before, I'm looking forward to the tropical beauty and the balmy weather. It's also my first time traveling with Andrew -- that's an adventure in and of itself.