5 Tips for a Vacation That Doesn’t Result in the Need for Another Vacation

2 Mar

Our Oahu Google Map

I haven’t posted in awhile because I’ve been doing Very Important Things like parasailing and swimming with dolphins. I joined my family on the island of Oahu for our second quinquennial Hawaiian vacation. Despite having skin that burns easily, I have always loved Hawaii – first the idea of it, and then the real place when I went for the first time in 2004. In fact, my family’s very first theme party was an Aloha-themed surprise 18th birthday party for yours truly. We had bacon-wrapped pineapple, fresh leis, and fruity drinks with little umbrellas. I’ll post an Aloha DIY video soon!

In the meantime, I thought I’d share my top five vacation planning tips, based on this most recent trip that I planned with my sister.

  1. Use technology, and not just an airplane and digital camera. Google basically co-sponsored our trip in that we used lots of their products to plan our vacation. My sister and I used Google documents and spreadsheets to keep track of activity ideas and booking details, flight information, and our budget. This was useful since my sister and I live 3,000 miles apart and we were able to work collaboratively from afar. One of the smartest things we did was plot all of our key places (airport, lodging, good snorkeling sites) on a customized Google map, so that we could familiarize ourselves with the driving directions in advance. By the time we landed in Honolulu, we were able to drive anywhere without a map!
  2. Just like in the stock market…diversify your portfolio. We made sure to plan some early morning activities (to make sure we’d get out of bed by 9 on at least a few days and not sleep our vacation away), some active stuff, some laidback stuff, and a lot of downtime. Having a mix of things to do made every day exciting, and planning for downtime kept the trip from becoming too stressful.
  3. Pay as you go. We booked our flights well before the stock market took a nosedive, but the costs of planning a trip can be stressful no matter what the economic climate. My philosophy is to spread out the costs over a long period of time so it’s not so painful all at once. Book flights, hotels, car rentals, and activities early, so by the time you arrive your costs are limited to food and incidentals. Vacation travel is definitely a luxury, but I’ve always found it worth it to prioritize it above things like new clothes and haircuts. I may wear the same thing most days and have split ends, but I sure have gone whale watching in Mozambique!
  4. Be flexible. If you’re a planner like me, you’ll have some ideas about how to spend your days before you go because you’ll have done your research, and maybe even made some reservations. But I think the best strategy is to do a bunch of research and prep work, but then throw out your itinerary once you actually arrive. You want to be flexible enough to change plans, be spontaneous, and respond to what’s in front of you! The planning just prepares you to take advantage of more stuff because you know what you’re doing.
  5. Find a local. Fortunately, I have a cousin-by-marriage in Oahu, so we were able to get a guided boat tour from his 12-year-old son, as well as the inside scoop on some good restaurants and swimming spots. I’ve found that people are often excited to play tour guide and show you around their hometown, so call up that second cousin twice removed and get the lowdown from someone who knows best. Having said that, if you visit me in New York City, please know that I am not interested in taking you to Times Square or to the top of the Empire State Building.

Happy travels!


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