Just because it’s free doesn’t mean it’s easy.

You may remember a blog post from a few months ago where Amanda and I got separated on our flight back from the Bahamas. I chose to be bumped off the flight for a credit of $800. We knew this would make our next vacation even more affordable.

But, not surprisingly, there were a few catches with the credit from JetBlue. When we looked online and planned our trip, we looked up how you use points for JetBlue. We found out that we would have to choose from one of their approved hotels or apply it to airfare. So after a first pass at looking at our options we determined that it would be easier, especially flying out of Pittsburgh, if we used the voucher to pay for the hotel and not the flight. So I came up with three scenarios of flights from Pittsburgh to various locations and the best hotels from the JetBlue list.

We sat down, ready to book. That’s when the wrench in our plans appeared. There’s a difference between JetBlue credits and points; unlike points you can only use credits for air. So I was back at the drawing board and attempt to find the fastest JetBlue flights to and from the destinations we chose and a new list of accommodations since we would now have more options.

The dates we’re considering are Monday through Friday, which can cause its own complexities. You see, planes don’t always want to go the direction you think they should go on the days you want them to go there.

We found many flights headed to our target destinations, but they had to go through places like Newark, JFK, or Boston. I hate the idea of flying north to fly south, especially in the winter when weather in the north can be a problem.

We had narrowed down our choices to return trips to St. Thomas, USVI or Playa Del Carmen in Mexico. Because we’re only getting away for four nights, we wanted to maximize the amount of time on the ground in the tropics. We are also taking a large trip in September (to Italy as we celebrate our 10-year anniversary), so we wanted to be cost-effective as well.

The minimum transit time to St. Thomas was six hours and the accommodations came to $200 a night. We settled on Mexico because the transit time is closer to four hours, although we’ll have to fly out of Washington, DC. That just means we get to drive down and spend some time with family. The accommodations were less than $100 a night.

We also compared scuba diving companies and would get more bang for our buck down in Mexico. We will be booking a room at the Hotel Kinbe which is right near the beach and we have stayed there before.

While it hasn’t radically changed our plans, a word to the wise: Before you accept a voucher when you’re getting bumped from a flight, make sure you know the rules and restrictions that may apply. In the end it was worth it. We got $800 in free travel and all it cost me was a night in Fort Lauderdale.