Outbound Collective logo

How to Plan a Trip for People Who Aren't Good at "Winging It"

We all know them- the adventurers who throw some gear in a car and set out to a destination with no plans other to just "figure it out." We're not those people.

By: Jess Fischer + Save to a List

"Just wing it." Ahh that wonderful phrase I've been told a time or two but has always fallen on deaf ears. My whole life I've read trip recaps by my favorite travelers who pick a destination and don't have any plans other to just go there and "figure it out." I've never been one of those people. I scribble down every thought and plan every detail of my trips. I map out exactly where I want to go, what I want to see and where I want to hike. Sifting through Outbound Adventures, personal blogs and hiking webpages is a genuine hobby of mine. When I decide I want to go somewhere I spend hours researching campgrounds, where gas stations are and what weather patterns are like for whatever time of year I'm visiting. My itineraries don't always go according to plan but before I leave my little apartment I have a darn good idea of what adventure I'm about to get myself into. Creating structured, planned-out trips gives me peace of mind because, well, that's just who I am. Additionally I have a job so when I do travel I tend to only have a long weekend or 10 mere days to explore another country- in the grand scheme of things these are very short periods of time so I like to utilize my time efficiently. So for those of you who are like me and love nitpicking little details and building itineraries that make people question your sanity (or for those of you who need a little bit more of that in your planning), here are a few random tips for planning the perfect-not-winging-it-trip:

1. Map Everything

Seriously, map everything. All the research you've done thus far gets to be applied in this simple step. Download Google Earth or use Google Maps to save every point of interest you want to hit during your trip. As you map waterfalls, hikes, campgrounds, etc. you'll begin to see where "hotspots" are and where there are outliers (things you might not have time for). If you're feeling fancy make each point of interest group a different color. Ex. campgrounds can be red, waterfalls are blue, hikes are green, etc.

2. Figure out Lodging

You gotta sleep somewhere right? From all your little points you have plotted try to find lodging that's close to "hotspots" or close clusters of points on your map. When I plan trips I figure out where everything we want to see is, then pick a town or campground close to areas with a lot to do. This ensures that we're never too far away from where we want to hike or explore. I don't like going on vacation and spending 50% of my time in the car when I could be spending it exploring. For me, figuring out a central location to set up a "home base" is one of the most important parts of planning.

3. Sweat The Small Stuff

People always tell me "don't sweat the small stuff." I do the exact opposite, I sweat allll the small stuff. I brainstorm like a lunatic during my planning stages. Where are the closest gas stations? What are we doing for food? What gear do we need? What are we going to do if it rains? Have we made a pack list? One thing I always do no matter what is pull out all my gear and check it. Make sure the rainfly and footprint are with the tent, that still have matches in my waterproof case, that my credit card is in my wallet (all things that I have had happen because I didn't check beforehand), you get the picture. Brainstorming all the small stuff helps when plans don't go accordingly and personally it helps me keep the stress levels low in the event that plans do go awry.

4. Excel is Your Best Friend

My itineraries are slightly insane. Seriously, every single day is planned out. I use excel because it's an easy way to organize all your information. I start by mapping out each day of the trip which includes the date and day of the week (ex. September 21, Wednesday). In the columns under the day I list where we're staying, when our transition days are (moving from one lodging location to another), what town we're in and/or what town we're going to next, what our reservation is for (camping, AirBnB, etc.) and what attractions we want to hit for that day (I even color code waterfalls blue and hikes green). I make notes of what has been paid for already with confirmation numbers, how long of a drive it is from Point A to B to C, check out and check in times, when we plan to eat out and when we plan to eat in. On days we're flying I have all details for our flights, departure times and arrival times for the appropriate time zone we're flying into... I organize everything. By putting it all "down on paper" I have a better idea of what things I'm missing, if I've planned too much or if I have extra time to fit something else in! However I love packing trips to the brim so I rarely find that I have extra time to fit more activities in.

5. Add Up Everything

One of the worst things is being mid-vacation and realizing you need to dish out an extra $50 that you didn't plan to spend. Before you go anywhere make another column in your excel sheet that lists out all the costs of your trip. AirBnb/campground fees, estimated gas costs, food cost, etc. If you know you'll need to buy or rent some gear before you trip, add that in too. If you have planned activities, like kayaking, look up the rental prices. Make sure any parks you visit don't have daily fees or parking costs. I always also bring an extra $100 just incase something happens and I need backup money. If you plan well you won't over-spend or get hit with unforeseen fees. 

6. Relax

Yes, here I am telling you how to organize everything and be a crazy planner but that doesn't mean you cant "go with the flow" if something happens. In all seriousness just remind yourself that things can, and will, go wrong. Even after having every detail planned out for a trip there are still things that can't be prevented... popped tires, rain, ripping a tent... As long as you thoroughly plan for your trip you know when something goes wrong it probably isn't your fault. Even if it is, you're already on your trip so might as well relax and take it step by step. 

Do I sound uptight? I must sound like the least easy going person in the world! I promise that's not the case and I'm actually really easy going but there's something in my brain that needs structure when I travel. I know there are so many of you that can easily just throw gear in the back of a car and take off for the weekend and I hope one day I might be a little bit more like you, but for now I am the crazy-planner-girl-who-doesn't-"wing-things." But that's not to say I'm not also the girl who can go with the flow when she recognizes her plans got flipped upside down. 

We want to acknowledge and thank the past, present, and future generations of all Native Nations and Indigenous Peoples whose ancestral lands we travel, explore, and play on. Always practice Leave No Trace ethics on your adventures and follow local regulations. Please explore responsibly!

Do you love the outdoors?

Yep, us too. That's why we send you the best local adventures, stories, and expert advice, right to your inbox.


10 Things you need to do in Baja

wyld honeys

Journey to Wyoming’s premier snowmobiling destination: Togwotee Mountain Lodge

Samuel Brockway

Hiking in comfort: a review of Danner Mountain 600 Evo boots

Meghan White

A peek through God's window

Heather Arnold