Making a Vacation To-Do List.

As you read this, I have probably started my world-wind 72-hour trip to New Orleans, stock full of things that I am super super excited about. I get a lot of comments on my travel-fu, so I thought it was only time to share my process.

First, if you know nothing about your location, look it up on Wikipedia or other basic knowledge-providers. It’s weirdly helpful to know the basics of what you should be excited for. It’s even helpful if you think you’re in the know; anyone trying to plan a trip to Chicago based on reading The Jungle will be severely disappointed.

After that, there’s a few websites I like to hit: Atlas Obscura, Roadside America, the Lonely Planet, weirdly Yelp, and even Pinterest. At that point I’m just brainstorming ideas and places to explore more thoroughly.   This is a great time to also Google for things you’re generally obsessed with; for me that’s vending machines, which lead me to the Musée Mécanique in San Francisco.

There’s also knowing what you like. I, for example, am not a huge fan of tours, but some people really love them. Meanwhile, I love window-shopping weird stores – it feels almost like a free art gallery – but a lot of my friends do not (until they end up in the store full of fossils or a candy store demonstration using 100 year old molds).

There’s also asking people you know or even asking people you don’t know. One of my best travel suggestions was given by the owners of an Irish knitwear booth at the Kriskrindlemart (a German Christmas market in Chicago). You may get a lot of suggestions that are eye-roll-worthy, but it’s a good way to find new things to do. I also like taking out travel guides out of the library for the same reason.

Urban Bourbon Trail Passport from Louisville, KY Tourist BoardDon’t automatically rule out the super touristy. Sometimes things are popular for a reason – the Art Institute in Chicago – other times they can be fun in a kitschy way. When we went to Louisville last summer we did the tourism board’s Urban Bourbon Trail. Go to five bourbon heavy bars, get the world’s most elaborate “passport” stamped at each, get a free t-shirt and certificate, and get to keep the overly fancy passport. On the other hand, do not just do the tourist. No one will be impressed with your trip, it will be overpriced, crowded no-matter the time of year, and it’ll weirdly feel just like being a tourist anywhere else.

Now that you have your list, it’s time to prioritize. It can be as simple as jotting a few things on a post-it or as complicated as… well… this:

spreadsheet(in my defense, my travel buddy did the color coding).

It helps to know what’s near what else and to make sure you don’t forget that one thing or two that you really really want to do. However, don’t over plan either. I’ve gone that route and it almost never works out. There’s always a random street that needs walking down, an emergency coffee or beer stop to make, or, sadly, transit problems.

My goals for New Orleans? Bars like the Carousel and Lafitte’s Blacksmith Shop; beignets, proto-tiki (?) and Cajun food; the ‘tit Rex and Chewbaccus parades; the Pharmacy museum, architecture, and cemeteries; and plenty of wandering around enjoying the 40+ temperature bounce I’m about to enjoy.

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