Tips and Tricks: How to Travel Like a Pro and a Local
Do you love to travel, but wish you could refine your process both before and while you travel? We’ve got some tips that’ll improve your experience traveling and maximize your time.
A shot I took in Charleston Harbor while on the top deck of the USS Yorktown (CV-10), an aircraft carrier that saw significant history in WWII’s Pacific Threater and which has been turned into an excellent museum. Highly recommend a visit for the views, history, and an appreciation of how cramped those ships can get.
We’re all tired of the “Top 20 things you can do in X City…” articles, so let’s dive right into this with the appropriate amount of context. You’re going to need to start off by doing some general planning and research - I’m not saying you need to write a thesis on the location or be an expert, but it helps to set up expectations and a framework for everything that follows - we love being efficient with our time both before and during our travels, right?
1) Thinking / Devising a Plan
Here are some things I want you to think about: Are you traveling solo or with a group (maybe family)? If solo, this is easier in some sense, although a little introspection into what you enjoy doing and some balance of “wing it - I’ll see what happens” vs. “I want a planned group event at the location” may be useful. I’ve done solo trips, and I admit that they are nerve-wracking at first, but I had some of the best experiences talking and learning from people I wouldn’t have spent time with if I were in a group. We’ll do our best to always consider solo travelers in these articles and to include some specific articles for solo travelers.
Now, what if you have multiple people in your travel group? This may cause some of our “planner types” a lot of consternation and anxiety, and to be fair, sometimes that’s justified. Let’s try to mitigate that on the front end. Do a survey of your group into what types of things they generally like to do or might specifically want to do in the location you’re visiting or considering. Sometimes it’s difficult when people don’t offer up easy answers, but maybe ask a few questions of what types of vacations they’ve enjoyed the most in the past and what do they remember about them?
The mind is a great indicator of preference, so this usually works quite well. Once you have those ideas in mind, I’d recommend doing two things: 1) Either ask or figure out on your own whether your group likes to “wing it” or have everything pre-planned. I generally don’t recommend either of those absolutes when in a group, but it’s useful knowledge of your companions and will make your life so much easier in the long run; 2) Tell your group that you’re trying to accommodate different peoples’ interests and that everyone needs to buy in so that everyone wins and has fun. There are, no doubt, people who complain when they get to the location that they can’t do everything they want, but that’s the trade-off when traveling with a group; when you are open and honest about that beforehand, it helps. Plus, there’s something gratifying about seeing someone truly enjoy something that you might not even care about, and that only happens when everyone is fair on the front end.
Taken during a trip to Maui, Hawaii, almost a decade ago. The beaches and forestry are a sight to behold, especially on Maui.
2) On the Ground
As far as planning, also make sure you maintain flexibility in your end plan. Things will come up that you never expected (not always, but like a war plan, I always bank on it). Maybe you see something that you’d never heard of or a local tells you about a hidden gem that it perfect for the group. Being able to pivot is a huge skill (and sometimes a learned one). When I plan trips for groups, I’ll have general, conservative estimates of what I think certain items / places might take to visit, and then I’ll also block out small- to medium-sized time ranges in which we have full flexibility to do what ever people want. Maybe someone in your group finds a great store, restaurant, or other venue that they just have to visit… You’re golden. Just use the flexible time for that and make sure you maintain your general timelines so that everyone benefits in the long run.
I’ve also known people (some very good friends) who loved to request changes at the last second once you were on the ground. I’d strongly recommend that you hold strong and try to push those requests (if reasonable) into the flexible timeslots. Not everyone is great about that, but it does seem like certain people just love chaos when they travel and to test the person running the show. Stick to your research and prior discussions and do your best to work in their request, if possible. If you haven’t traveled with this group before, they’ll appreciate the combination of structure and flexibility, and they’ll respect you for having arranged it. In the end, we’re all traveling just to have fun and have a good time, right? Collective experiences are the best, after all.
3) Keep Notes and Be Flexible (If Possible) During Your Trip
I won’t harp too much on this point, but I do think it’s useful for a few, useful reasons: Ask locals where they like to go (and try to match it up with certain things that you and/or your group like to do). Locals are usually one of the best resources. I also ask my Lyft / Uber driver when I get into an airport what he or she recommends or has heard is fun. If the correct situation is appropriate, random people you chat with in establishments or on the street are also great resources for things like this. People love to tell others about their city, and most will be great resources. At worst, they’ll redirect you to a better area of town or the city. The beauty of this strategy is that it might not even be applicable to your current trip - maybe you’ve done such an outstanding job planning this first round. In that case, it may be fantastic for a return trip if you enjoy the city. I highly recommend keeping a pen in your pocket or at least writing things down in your phone’s notepad. You’d be amazed how often this comes in handy!
This is a just a brief snapshot of how you can jumpstart your planning and overall procedure to improve your traveling. We’ll have numerous other articles over the coming weeks and months with more tips, as well as city-specific suggestions. Stay Tuned.