In planning my next trip, I always want to feel prepared, but have room for spontaneity. For me if a trip is overplanned it feels like checking off a to-do list, instead of exploring a destination. My favorite parts of trips have become the last minute “yes’s”, the hole in the wall restaurants, and late night cannoli’s with friends we meet along the way. I want to curate a trip that makes me feel prepared enough to feel confident, but not take away the excitement.
How I pick my next destination is usually a random social media post, a comment a friend made in passing, or a deal too good to say no to. I make sure accommodations are the first thing I plan. For my flights, I always use Google Flights to begin my research for best times, prices, and airlines. Accommodations are second, being in my thirties, I do try to pick mid-range to luxury hotels if it fits into my price range. I like a nice place to be able to reset, and enjoy slow mornings. I have moved away from booking Air BnB’s and Vrbo’s due to the increased price, and for a safety aspect, I like having one door (entry/exit) only to worry about in the hotel. And who doesn’t love their rooms being cleaned and beds made for them every day?
Next I book out the main attractions I want to see and do. It is always a bummer if you get to your destination and the tickets are sold out. I will then complete a quick study of crime rates, public transportation, and local customs so I better understand where I will be. If I am able to plan ahead, it allows for more confidence in the destination.
I discussed some in my last blog, that I like to leave some time for rest to have a more enjoyable trip. Once I have selected my 2-3 non-negotiables for the trip, the things I would be devastated to miss, I create a “maybe list”. This is a list of things that if I have down time or get bored I will reference. This can be a list of attractions, food, bars, excursions that I think would be fun, but I don’t have to attend. Having your non-negotiables, and “maybe list” provides structure without constriction in your travels.
This also leaves room for my favorite part of traveling, the unexpected. Nothing in my opinion is worse than having to leave dinner, with some locals you just met, to meet your 10th scheduled activity for the day. Leaving time open allows for meaningful connections, local recommendations, popping into the hole in the wall restaurant that became a meal you still dream about, or some late night desserts with the girl who just moved to the city. This is where the memories, and connections happen that otherwise may not have.
I encourage you, if you are one that needs everything planned out to the minute, start creating space. This also allows for less stress when the unexpected happens, weather, fatigue, better recommendations can all change an itinerary, and that is not a bad thing. Feel prepared and confident enough that the unexpected becomes enjoyable in your new destination, allowing for the surprises to come your way.
Know where you’re sleeping, how to get around, and know what you absolutely can’t miss. Then leave a little room for adventuring faithfully. Do any of you have fond memories of people or places you’ve experienced due to being spontaneous, if so what are they?
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