how we plan our trips

by Krystal Bick
April 15, 2019

“How exactly do you plan your trips?”

The above is perhaps one of most frequently asked questions I get — a close second is something usually to do with Elvis, meaning, you guys are my kinds of people. Travel and corgi lovers, in equal measure.

Admittedly, as much as I wish I had a succinct answer to the above question, I’m probably the most organic traveler around (within reason). I like a good amount of structure with healthy room for flexibility, because it’s always those moments that you don’t plan for that end up being the most memorable (like that one time we rented a car in Austria to head to a last minute music festival only to find out the car had been towed during the show but that’s another story for another day).

Today, I wanted to break down how I go about planning my trips, from deciding where to ultimately go, where to visit, what to do, how we coordinate our photoshoots and I’ll be tackling a lot of the specific questions you guys sent in via Instagram DM! Before I dive in, I just want to be the first to say, planning trips still stresses me out to a degree (I probably put too much pressure on myself to get things just right) but I’ve realized over the years how much I need to embrace the serendipity of it all — to travel (especially at the rate I do) is an extreme privilege, one I don’t take for granted and if you’re in the midst of planning an excursion yourself (near or very far), I hope you can take a step back and really appreciate the moment.

That said, let’s dive in!

First things first, where to go?!

Perhaps the most obvious starting point, where to even go? Each year, I make long wish lists of places I’ve been dying to visit. And each year, I check some of the spots off the list (certainly not all!) and I consider the year well traveled! The idea isn’t to feel like you need to see everything all at once (you’ll always be disappointed if you harbor that feeling) — but rather, pick one or two big trips (and big is a subjective word here), and really gear up for them. Of course, when I worked in a more corporate environment, a lot of my travel was dependent on my available vacation time but generally speaking, I found the further in advance I planned a trip, the more appreciative my boss was for the early notice (and usually would let a few days slide here and there if I was ‘working remotely’).

Picking destinations can be nerve wracking but it really comes down to gut for me. Sometimes seeing a certain editorial spread in a favorite magazine will spark it, sometimes reading a new favorite book that’s set somewhere specific gets me going, sometimes a location in a movie (Harry Potter and Lord of the Rings have to name a few). Of course, it’s worth mentioning how much of travel these days tends to be a cyclical pattern of what’s trending on Instagram — the aptly dubbed Positano Effect that I wrote about here over the summer — and we only need California’s recent #SuperBloom to see how much travel can impact an area for better and sometimes unfortunately for worse. My main goal, whether I’m visiting somewhere on the main path or off the beaten one, is to find elements of it that I find uniquely interesting and distinct (we’ll dive into what this means below). If you’re stumped for locations, my personal favorite sites to check for international and domestic inspiration include: goop, Conde Nast Traveler, National Geographic, Anthony Bourdain’s Parts Unknown and the New York Times 36 Hours series.

Where to stay?

What I’m about to say next may be controversial: I don’t necessarily need a fancy hotel. Don’t get me wrong, I love indulging when the moment and the price is right, but I’m generally of the belief that if you’re traveling right, you won’t be spending much time in the hotel anyway, so I don’t understand allocating most of the budget that way. Instead, if I’m truly left to my own devices when planning the trip, I much prefer to either book a spot on AirBnB for a more local experience or perhaps a hotel that earns me bonus points for my next trip (like a Hyatt property, which are pretty much available in every city imaginable!).

AirBnB launched their Plus section earlier last year (an assortment of high quality homes from power hosts) — sometimes, when I need trip inspiration, I’ll browse through different spots in certain cities just to see what’s available and if anything pulls at the heart strings.

Tips for pulling the trigger on flights?

I try my hardest to book the largest portions of our trips (hotels and flights) early on, but sometimes it just can’t be helped. Generally, I usually know the time frame, so I’ll set up a Google Flight alert for several different dates, just to monitor when they might drop a bit (they send email recaps when they do). I also love their Date Grid feature which helps you glance at a calendar to see the price estimates from day to day. Set a price range you feel comfortable with and get ready to book once prices drop close to it.

How to plan an itinerary? That doesn’t involve all the touristy spots?

This is where things really come down to preference and I don’t always follow the same plan of attack for each trip. Generally speaking, I’ll map out the main touristy spots — places I’ve seen lots of photos of, spots that are highly recommended on travel blogs — and research the surrounding areas to see what else might be around it, in order to line up a few different spots of interest, some well known, others not so much. My go-to resources for this step are both Pinterest and Conde Nast Traveler — both their site and their IG are chock full of inspiration (not to mention, it’ll give you a good idea of what time of day might be best photographically speaking to visit). I’m a very visual person so I love being able to picture an environment before slotting it into the schedule and I’ll generally start a mood board specifically for the trip on Pinterest. A good rule of thumb is to also check out the tourism site for your destination, to see what areas and historical points of interest they recommend to see how you’d like to sprinkle those in (or not).

Once you have a general idea of what’s on deck for each day (I’ve been organizing mine in Hit Pause — more on that below), start researching details about each spot — how to get to each one, do you have to buy tickets, do you need to arrange a tour ahead of time? Are there certain days it’s closed? Is there required attire? Sorting out these specific details beforehand will save you a lot of headache (and heartache) in the long run as there’s nothing worse than realizing the only day you reserved to visit a certain museum is the one day of the week they’re closed.

Of course, you should also always ask your immediate friends and coworkers for any tips they might be able to provide if they’ve been to the area you’re visiting — that’s how Heather and I planned a lot of our trip to Japan, as one of her coworkers shared a very detailed Google Doc with all the bars, cafes and restaurants they had been to — plus their thoughts on each spot!

In a few weeks, I’ll be heading to Marrakech and I’ve been using the recently launched Hit Pause travel site, which I mentioned above. It’s a well-curated boutique travel planning site that makes organizing, saving and booking your next big trip extremely easy. Every activity is vetted by their team, with a lot of great local recommendations and tips.

I also love my friend Kat’s travel app — she has great cafe, bar and restaurant recommendations, which brings me to one big time-saving tip: Take care of your lowest hanging fruit first if you can. Dinner reservations tend to fill up fast, especially if you’re aiming to check out spots that are trending or are very popular. A few weeks before traveling, try to reserve as many dinners as you can, usually aiming for a late enough slot so it’s easy to sneak in a nap before hand — I like 8 or 9pm.

Coordinating photo shoots — deciding on where and when?

As much as I try to plan for our photoshoots, usually the best ones happen when we lease expect it. Either we stumble upon something while exploring or the light just happens to do something really magical after we think we’re done shooting for the day — and we just start all over again. Whenever possible, we try to spend our first full day in town exploring around — since we’re usually jet-lagged at this point, I don’t expect to shoot much on the first day, instead, I’m taking notes for unexpected spots to return to the following day: a cute old book store, a quaint cafe with outdoor patio seating, a tucked away cobblestone street. These spots make for great easy little shoots to return to either at the beginning of your day or at the end of the day, when you’re heading back to your hotel so take note of them so you can pop back in when the timing makes sense.

For each subsequent day of the trip, I usually have 1 or 2 spots of interest that I think will make for a great shoot location (I’ll plan my outfit — or outfits — for the day accordingly) and we’ll try to have these spots bookend the day, meaning first thing in the morning (to avoid crowds) or at sunset (for golden hour). As I mentioned before, you can’t always plan when you might stumble upon a great spot to start shooting, so allow for some serendipitous moments to happen along the way as well — that’s more than half the magic of traveling.

To rent a car or not to rent a car?

If possible, I always want to rent a car, especially if I’m staying in a country for a week or more, with a few different cities in mind. Of course, if trains are accessible, they’re a great option too, but I really love being able to explore a new place by car because you can detour where you want to detour, stop where you want to stop and take the longer way around if the sunset calls for it. Depending on the country, I generally try to reserve a car a head of time, mainly because automatic vehicles usually are the most highly requested, and therefore, they go fast. Yours truly doesn’t drive stick and I’ve almost gotten into a few binds because of this.

How to find local photographers?

If I’m not traveling with a photographer, my boyfriend or a friend who’s willing to indulge me from time to time with photos, I always post on social media a few weeks before hand asking for recommendations for photographers based in the destination city. I’ll also look on Instagram filtered by geotags, to see what images pop up with a photographer credited. Moral of the story: a little detective work goes a long way — you can usually find a ton of local photographers this way, and depending on your budget, you may be able to work out a deal that works for everyone, whether’s that trade based or rate based.

A note about working with local photographers: they truly are a blessing. They generally know the best spots, the ideal times to shoot at them and where to avoid crowds. Pick their brains if you can, they usually have great local restaurant and sight-seeing recommendations.

How to balance content creation and being present while traveling?

This was a repeated question from you guys and I have to say: I wish I knew the answer! This is something I still struggle with pretty often when traveling. My best tip I can share: while I do snap a lot with my phone throughout the day, I don’t post on Instagram or Insta Stories until much later in the day, usually after dinner. I find that this helps me stay much more present during the day without getting lost in my phone.

Do you guys have any tips for staying present while traveling? Would love to hear. I feel like this could be a much longer post for another day.

How to budget for a trip?

Everyone has a different way of approaching how to budget for a trip — but I truly believe the key is setting a limit for yourself with a daily budget and sticking to it. Easier said than done, of course, but I find once I have my general itinerary sorted, I’ll list out my initial upfront costs (flights and accommodations) and estimate a fair amount per day to cover ticket admissions, transportation, meals and any other miscellaneous shopping you might want to do along the way. Be realistic with this number — you need to be comfortable with it and if you need to trim some activities, make those decisions before you get there. You’ll avoid impulse decisions that you may otherwise regret.

How to get sponsorships with hotels?

This question was also popular amongst you guys — working with hotels. Admittedly, while I prefer staying at an apartment through AirBnB, I do also love a good boutique hotel moment and exchange partnerships with hotels can be really beneficial for both parties involved. If you’re an influencer and looking to work with more hotels, you need to always remember, you’re bringing an element of work to your trip and you need to treat it as such. Any agreement you land on with their marketing team, make sure you’re comfortable with the deliverables and the timelines — and keep communication very open. Make sure to follow up with any relevant analytics that you can share afterward.

The best way to broker these deals? Research their Instagram accounts (to get a feel for what kind of content they’re used to posting) and send a proposal to their marketing/PR team (usually listed on their website). Sometimes this means a comped stay, sometimes a discounted media rate, sometimes a mix and sometimes, they might say no. Send a solid proposal through with a detailed content and posting plan and you’ll stand a good chance to discuss further with their team, if they’re open to it.

How to account for magical moments?

As I stated at the beginning of this very longwinded post, I like my trips to be structured, but not too structured. Sometimes when planning a trip, it’s easy to veer into “over planned” territory and I generally try to avoid this at all costs. Have a few activities lined up for the day and give yourself extra time to wander and roam between them. Take the longer route there, pop into interesting stores along the way, sit longer at that cafe to enjoy an extra glass of wine. Relish in the moments you’ve already picture for yourself and embrace the moments that land in your lap just the same.

And that’s it! Would love to hear from you guys though — how do you plan your trips?!

OUTFIT DETAILS: Zimmermann dress (similar style here) // LOCATION: Wave Rock in Western Australia

Photos by Ty Johnson

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