3 Tips For Planning Trips


If there’s one thing in life I would consider myself legitimately skilled in, it’s planning. Despite the fact that I love to visit new places I honestly don’t travel well (so much could go wrong!), but having a plan is honestly the best way I’ve found to keep worry at bay.

In my last post I mentioned that I’ve almost forgotten how to plan a trip and I was only half joking — it’s a lot of work. Typically I’d source family/friends for recommendations and fill in from there, but because not many people I know have been to Portland I’m having to nearly start from scratch. It’s a bit reminiscent of exploring San Francisco for the first few weekends we were here; there are endless options but it’s almost too overwhelming to choose!

I know I can’t be the only person who feels this way. Growing up your parents plan the vacations and most college breaks are focused on drinking on the beach, so planning a real getaway that’s only semi-focused on finding the best beer is a challenge of the mid-twenties I didn’t know about until now! Here are the top 3 tips for how to not pull your hair out when planning:

Avoid Over/Under Scheduling: When you’re on vacay or even a day trip, no one wants to feel like they’re following an itinerary. On the flipside, my worst nightmare is being somewhere new and spending countless amounts of time scrolling through Yelp for the next thing to do. For this trip, I’m trying to outline some “must-sees”, setting up a natural flow around that, and letting the rest fall into place. This way we’ll have a good mixture of activity and time to just see what happens without feeling like there’s a million places we have to go.

Become BFFs With Street View: The Google Maps street view function is a game changer. Even when we were finding an apartment from across the country, I would go on “walks” around potential neighborhoods to get a feel for what was around. Something looking close on a map is a totally different scenario than something actually being close enough to walk, so taking a virtual stroll can be the difference between trip-ruining blisters or a $6 Lyft.

Take Reviews With A Grain Of Salt: This is true for anything, but especially when you’re looking up places you have no basis to go off of — i.e. restaurants in a new city. Depending on where you’re getting your travel intel, recommendations and reviews can be extremely biased. In my experience, I’ve noticed that Yelp tends to skew negative (people complain about ANYTHING), TripAdvisor tends to skew towards middle age/family-friendly preferences, and Google Reviews is a little all over the place. As is in my nature, I tend to read most reviews from all 3 to form a composite image, but that’s a lot of work and I don’t recommend it. Just remember — a well-balanced 3 star review carries far more weight than a ranting 1-star in most situations. 😉

p.s. I am SO scared about leaving the pets, so if anyone has any tips about how to not worry about them or just general Portland recs, hmu!

Amanda McDowellComment