Wandering 101

a trip planning guide from wbh co-founder dakota

Phase 1: The Birth of A Trip

Organizing a group and making travel arrangements

“I need a vacation,” I text my friends on a whim one morning.

They love getting this text from me.

“Where to?”


Brooke, my travel buddy, is the first one to say she’s down, then our friends Jon and Chris.

I swear it isn’t usually this easy to coordinate a group vacation-but it worked out beautifully.

We would also be meeting up with a bunch of friends who live in CO once we got to Denver.


The crew is set, our flights are booked and we grab a celebratory black-and-white cookie latte from our fav local coffee shop, Coffee Booths, to start our planning.

Seven days and we want to see it all. Hiking. Riding. Climbing. No time allotted for sleeping.

We will fly into Denver, rent a vehicle and proceed to drive a total of 1,300 miles over the week of our trip.

When I put a trip together, I’m always very careful and conscious of who I invite—the dynamic of your group is important, so remember you will be shoved in a car/room with these people for days. Flexibility, the ability to be decisive but not overly opinionated or pushy, easy going, willing and able to contribute, and obviously having a shared interest in the planned activities of the trip are all key qualities to keep in mind when you’re extending a trip invite.

Also, remember a trip is not official until the plane ticket is booked!!! People can always insist they are down and then bail, so make sure you are not reliant on anyone else and always be prepared for plans to change.

Phase 2: The Obvious and the Not-So-Obvious

This is where you ask yourself things like:

Do I need to rent a car and if so, what kind of car?

Stay with friends? Hotels? AirBnbs? Camping?

Will I have a “home base” or will I have different sleeping arrangements every night? and How many people need to fit?

How many miles is it from Denver to Breckenridge? And Breckenridge to Moab?

What are the crowds like on different days of the week at the places I want to go? Are there any special events held at these places on the dates I’m planning that might mess up my plans?

and so on…


Don’t get me wrong—I love to be spontaneous.

But I will be prepared, there will be an itinerary, and any opportunities for spontaneity will be scheduled and color coded for your convenience.

Pulling out my Nat Geo map collection (yes, REAL maps, kids) I’ve accumulated in the five-six-seven (?) previous trips I’ve taken out west to CO/UT, we start to list off our favorite spots that will become the stops on our trip:

Visit friends in Denver.

Sleep in Denver.

Hit ‘The Spot’ climbing gym in Boulder.

Garden of the Gods in CO Springs.

Sand Dunes National Park.

Hot Springs in Moffat.

Ride at Breckenridge.

Moab is only a few hours from Breck?! Done.

Arches and Canyonlands National Parks and climbing in Moab.

Rocky Mountain National Park in Estes.

Back to Denver to fly home.

First things first: With all the driving planned, we need a car.

My experience with Colorado in winter time tells me that 4WD is a must, and since we are traveling with 5 plus luggage AND snowboards, we definitely need a truck.

We decide to stay the first night in Denver at a friend’s house, and then do each night in a different AirBnb. Denver is pretty central, so where we go from there is really just a matter of preference. I’ve gone North first to Estes, West first to Breck, and it doesn’t matter—all trips to Colorado are equally wondrous. Sometimes weather is a good deciding factor, like for a camping trip—but in instances where lodging needs to be booked weeks/months in advance, this is not something we take into consideration. This time we chose to head South first, for no other reason than I have this rule where I totally REFUSE to visit any of the ski resorts on weekends, so the way we arranged it had us at Breckenridge on a Tuesday and we based the rest around that aspect. Practicality differs between individuals so do whatever makes sense for your group! This is something that gets easier to gauge the more you travel.

Travel experience has helped me realize the importance of things like:

-Knowing the typical weather for the time of year in the region you are visiting - this not only helps you to pack appropriately, but to account for things like road closures, and the necessity of a 4WD vehicle/snow chains. There are various websites that list weather related closures like blizzards and rockslides, but there are also some seasonal closures, for example Trail Ridge Road in RMNP.

-Having a gauge on traffic patterns/busy times/special events at tourist hot spots and how to avoid them. For example, during the ski season a lot of people head West on I-70 out of Denver on weekends so we try to avoid travel during those peak times (Friday-Sunday) and holidays.

-A collaborative playlist that everyone can contribute to! (When you’re in the car for hours with spotty cell service, having plenty of quality, pre-dowloaded music matters!)

Phase 3: Sh*t Gets Real

Here your life is spent endlessly searching

for the perfect AirBnb…the perfect rental car…researching the best restaurants, bars, hikes, climbs, the secluded-enough-to-feel-lost-in-nature-and-not-be-totally-surrounded-by-tourists but equally not-quite-secluded-enough-to-be-creepy-or-dirty hot springs. And then you get to spend all your money making them yours for a night.

I am a wanderess.

But I am also a businesswoman.

When your friends agree to a trip, one of the first things you should do is figure out how much needs to be spent as a group, and for yourself personally, then get on the same page with financing the bookings: Who is able and willing to book the car? Will the AirBnb’s fall on one person or will they be split?

We used Turo (click here to save $25) to rent a Toyota Tacoma with 4WD, chains, snowboard racks and a locking cap over the bed.

We got so lucky in finding the most unique, dreamy but still somehow cost friendly AirBnb’s (to save $40 click here). We like to use the map feature of AirBnb to find the perfect digs, searching outside of the main, more expensive areas.

The best way to select the right AirBnb is, after planning, to pin your destinations on a map and search for places somewhere between each destination. We always want to do the bulk of the driving at night, so we mostly try to select places with close proximity to the next morning’s plan, but this is a matter of preference (and your first preference may not always be possible). Make sure you read each listing’s rules and features carefully, as they differ per host! You can filter specific amenities like A/C, fireplaces, washer/dryer, hot tubs, etc.

Our plan, if you recall from Phase 2, is: Visit friends in Denver. Sleep in Denver. Hit ‘The Spot’ climbing gym in Boulder. Drive South. Sunset hike at Garden of the Gods in CO Springs. Sleep in Crestone. Morning hike at Sand Dunes National Park. Sunset soak at Valley View Hot Springs in Moffat. Sleep in Salida. Early Drive to Breckenridge. Ride at Breckenridge. Sleep in Breckenridge. Arches and Canyonlands National Parks and climbing, two nights in Moab. More climbing. Drive to Lyons. Sleep in Lyons. Sunrise Snowshoeing at Rocky Mountain National Park in Estes. Back to Denver to fly home.

Here are the ones we chose:

Crestone, CO

Salida, CO

Alma, CO (Breckenridge)

Moab, UT

Moab, UT (2) (this one has a hot tub!)

Lyons, CO (Estes)

We all have equal money invested and therefore equal input. Together we select each arrangement and then designate the financial responsibilities amongst the group. Immediately, I create a payment table, showing each of our output and how much we were owed in return. Having this be explicit and straightforward from the get-go is a huge help, especially with a big group.

The second most asked question is “wow, where is this? how the hell do you find these places???” (the first is “do you ever work?” to which I wish the answer was NO!!!)

Experience and people skills are the two most helpful things for finding good adventure spots.

Get out there. Be nice. Talk to locals, spend hours looking at maps, terrain maps, and google maps. Read hiking books and blogs, even something as simple following like-minded people on social media has lead me to what have become some of my favorite hidden gems (like Valley View Hot Springs, some absolutely batshit crazy bartender in a dive bar in Boulder told me and my girlfriend about its magical squirrels on one of our vacations, and clearly this man’s advice needed to be taken…write it down, catch a sunset from the waterfall or top pool, get naked—you’re welcome in advance).

Phase 4: The Art of Packing Appropriately

don't over do it

It’s all booked. You’re ready. You’re going. You’re packed right?


A week before the trip and your suitcase should be ready to be loaded up… It’s about this time when I begin to regret every piece of clothing and gear I wanted and needed but for some stupid reason didn’t buy, and looking down upon my pitiful collection that takes up about half of my huge, walk in closet, I call Jon begging him to go to REI. This is a no no.

This is something I’m still learning.

The Art of Packing Appropriately.

First things first, always bring a bathing suit and towel.

Now. Listen to me…seriously. Put down the eight base layers, six pairs of shoes, and about half of the options of cute clothing you were planning on brining “just in case.”

Shed the societal holdbacks of so-called “good hygiene.” You’re exploring the earth!!

You don’t need to be hygienic (just kidding please shower or I won’t invite you next time)..

But, you ARE gonna end up wearing the same LL Bean merino mid-weight base-layer, under your Solomon wind-stopper leggings, Prana flannel shirt, Smart Wool down vest and Ahnu boots.

Every. Damn. Day.

You will be too tired to shower, let alone get cute for an evening drink. And you will like it.

You may not like the idea, but the convenience and ease is unsurpassed. Fun fact: If you invest in good wool base layers (and, ya know, deodorant) you won’t be stinky! Wool is LIFE!! Basically anything from REI is reliable. Farm to feet is my favorite brand for wool socks. My other go-to’s are listed above!

aaaaand..you still almost forgot your bathing suit didn’t you?

Obviously this whole packing deal will differ with your destination/weather, but the bottom line is that in hiking you don’t need much, clothing wise.

Gear-wise my anytime essentials are: Osprey daypack and packable backpack, Sea-to-Summit waterproof stuff-sac, NiteCore headlamp & charger/batteries, always a few yards of brightly colored paracord/rope, Lifestraw/Platypus refillable water bottle or Camelbak (and plenty of water), hiking snacks, first aid kit, windbreaker/waterproof shell, sunglasses, relevant maps, compass, notebook and pen, chapstick. (In Bear/Cougar Country: Bear spray is always good to have (not just for bears but cats and murderers!), and a knife—all just in case and not to be used irresponsibly—the boys usually bring this stuff, go figure).

For fun I like to bring: my climbing shoes/chalk/crash pads, binoculars, my hammock, camera.

Seasonally: crampons, mittens, hand warmers, snow gear, trucker hat, beanie, sunblock.

With the intensity of the hike, the amount of gear (and water intake) increases. For this trip, we were exclusively doing day hikes, so only the most basic items were needed. My daypack for a morning hike weighs about 2 lbs at most, where my frame pack for a week-long backpacking trip usually weighs about 25 lbs.

Get a hold on what you consider your personal basics, take note of what you use and don’t use on your trips, and every time you say to yourself “I wish I brought _______”—write down that item.

If you forget something, it is what it is, don’t let it ruin anything, you can get it there or you might just realize that you can go on without it just fine.

Also, get yourself an REI membership, its $20 and you’re in for life—and the dividends are SWEET!

Phase 5: The Trip

So all the planning has lead to this

Two words, one thing, will help you now: Time Management.

Give yourself extra time to get to the airport. Starting the trip off with a missed flight and stress is no good! The most important thing is being happy!

Agreeing on a plan as a group is helpful, but things can sometimes be unpredictable and out of your control, so if not everything goes according to plan—go with the flow!

The planning is perfect, the flight left on time with you and all your bags on it.

You’re here.

Now, try to execute all of your trip goals but always keep an open mind — sometimes better things find you. Again, talk to the people you meet, locals, travelers. Tell them your plans, ask for suggestions, utilize their knowledge!

Always be respectful of nature, your friends, travel companions, and anyone that crosses your path. Be a good guest, to the earth and the people—this is just good karma, especially when traveling.

Your trip should be..a trip. It should be fast paced. It should be crazy. Hectic. Exhausting.

All of that.

But it should not ever be stressful. This is where the importance of those qualities like flexibility come in. Be easy. Keep an open mind. If things go wrong, accept that it is for a reason, make the best of it or better yet, use it as an opportunity to make your new plan even better. Sometimes spontaneity is forced. Follow the path you’re led to. It is exactly what you decide it will be.

Our days start before dawn, most meals consist of peanut butter cliff bars, shitty gas station coffee and whatever is presumed to have the most nutrition in the air filled foil packages of the snack aisle. Home for the night is wherever the maps lead, bags are unpacked and then right away packed up again, late-check-in, heads to the pillow and by the time the neighbors open their eyes, we’re gone. We push ourselves to our limits physically, mentally. Things go wrong. We go with it. We motivate each other, we face our fears. Run along the edges of cliff-sides making the palms of onlookers sweat, climb anything that looks remotely send-able, and end it all dirty and squished into a stinky, cramped car for hours. Oh and the shower runs out of hot water fast with five people, so you better call next, quick!

The way we do vacation is not relaxing and we may get to know our travel companions WAY better than we intended to, but the memories and bonds created on trips like these just can’t be beat.

Phase 6: The Aftermath

Ugh, home. No longer a tumbleweed blowing in the wind. That first day back is rough, when you’re like “how do I even start being a normal person in REALITY, not surrounded by my friends and nature all the time? I have to go to work?!?! All I want to do is sleep!”

They call it jet lag but it’s really post-travel depression.

This is when you book the next one.


this post was originally written for our friends and readers at pen and trail


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