I’m back from a well deserved (or at least I like to believe) vacation. Even though the vacation went almost as well as could be expected, I definitely came away with some insights that could’ve easily chopped as much as 1/5 of the total cost. I had never been to the U.S. Virgin Islands, and because of that lack of experience I made more than a few rookie mistakes.

As measured in overnight stays, I was gone for a total of 9 nights. I could’ve easily reduced this to 7 nights without losing anything in terms of experience.  I needlessly bookended my vacation on St. John with two nights on St. Thomas. I did this for two reasons.

  1. I thought I would want to spend time on St. Thomas - I didn’t
  2. I thought traveling to and from St. John and St. Thomas would be more difficult - It wasn’t.

However beyond just the two extra nights, I didn’t do a very good job of researching and making plans.  I made one huge blunder of booking a $125 windsurfing lesson at Cinnamon Bay when I could’ve had a lesson at Caneel for $25. This was my fault because I didn’t realize all the watersports equipment at Caneel would be free.  While true that some watersports are always free to play, I had assumed that there would be a fee for something like a Windsurfing board.  Never assume anything.

Experience is often the key to being financially savvy.  Vacations however are often engaged for the sake of new experiences.  You can’t bring experience to something that is a completely new experience.  For example I rented a car for the entire week I was in St. John.  In hindsight, I only really needed or wanted to have a car for 3 days.  However, I wouldn’t really have known that I only needed a car for 3 days if I hadn’t actually had the car for the entire week.  I had to use the car for 5 days to know that I wanted only 3 days. Experience is the catch-22 of life.  Clearly here is where the saying, “the truly wise man learns from other people’s mistake” applies. I should’ve done more research even though I went on Vacation thinking that I had.  This lack of research is partially my own fault, I’m not a planner. I don’t want any vacation completely planned out.  Yes, I want to know where I’ll be sleeping, but that’s about it.  Having too much of plan  takes the fun out of vacationing for me.  At the same time I should’ve been more prepared.  My lack of preparation was evident in not asking enough questions before I left, and therefore not knowing all my options.

In the next couple weeks I will have follow-up posts reviewing much of my vacation. St. John is a wonderful island that is eminently enjoyable on a limited budget even though it can be one of the most expensive island destinations out there in terms of lodging and food.