Photo of a plane's wing flying over the water with clouds in the background.

Planning for Paradise

There’s a fine line between not enough vacation planning and too much. You don’t want to waste precious time at your destination getting lost, but you don’t want to be tied down to a rigid schedule, either.

On a recent trip to Key West, Florida, I created itineraries for several “days” that didn’t have to be used in any particular order and could be selected depending on what kind of mood the weather and I were in.  I didn’t assign any particular start or end times to each stop, but I grouped them together based on location so I didn’t end up retracing my steps more than necessary. This allowed me flexibility while still keeping efficiency in mind.

Did I stick to these itineraries? Sort of. Sometimes I’d do the morning from one list and the afternoon from another list. A few places were unexpectedly closed for remodeling. One restaurant was too crowded when I planned to have lunch there, but the sports bar across the street had great food and fantastic live music. It all worked out in the end, and I had a wonderful time.

I created a custom map in Google Maps and marked which restaurants, shops, museums, and other points of interest I wanted to visit. That way all the operating hours, admission costs, and other details were there at my fingertips (as long as my phone battery lasted.) There’s an option to write your own notes for each map pin, too.

If you’re the kind of person whose travel souvenirs consist mostly of photographs and memories, you don’t need to worry about leaving room in your luggage for the return trip, but for those like me who load up on T-shirts, postcards, books, and tchotchkes, here’s another tip: let the postal service do the heavy lifting for you. It’s cheaper to send yourself a box via priority mail than it is to pay the airline for an extra suitcase, and there’s the added advantage of not needing to lug the additional weight through airports. I ended up sending two packages home from Key West, and it was worth every penny. I wrapped my breakable souvenirs in the T-shirts I had bought, and everything arrived home in one piece. Thanks to my advance planning, the post office was only two blocks from one of the stops on my itinerary, so it was no trouble to drop off my treasures there.

Key West is only four miles long and less than two miles wide, and not much of that precious space is devoted to parking. A rental car is often a waste of time and money, and many tourists rely on other modes of transportation. My hotel had an hourly shuttle bus to and from the main tourist area. Bicycle and moped rentals do brisk business. There are trolley tours that allow you to hop on and off throughout the day. A free, air-conditioned bus runs up and down the famous, frenetic Duval Street. Your next travel destination may not have quite as many options as this, but your wallet and the environment will thank you for looking into alternatives.

Photo by author depicts a street trolley passing in front of the Key West Lighthouse in Florida.

Trolley tour passing the Key West Lighthouse. Photo by author.

Be sure to check the weather for your destination and plan your wardrobe and activity level accordingly. I thought my research had given me a good idea of what to expect in south Florida in November, but I underestimated how oppressive the heat and humidity would be. I had to scale back some of my plans, especially ones that involved a lot of walking.

Perhaps the most important vacation tip I can give is this: remember that not everything will go according to plan, and that’s okay! The best adventures always have an element of the unexpected, after all. What matters is getting away from it all, having fun, seeing someplace new, and coming home safely afterward. Bon voyage!


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