4 minute read Pack your bags -- let's go on a virtual trip together!
"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!
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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
4 minute read "This is what you do on your very first day in Paris. You get yourself, not a drizzle, but some honest-to-goodness rain, and you find yourself someone really nice and drive her through the Bois de Boulogne in a taxi. The rain's very important. That's when Paris smells its sweetest. It's the damp chestnut trees."
As I'm writing this post, I'm currently sitting in a cafe in the design district of Milan.
Coffee and espresso orders are being shouted in the most affectionate way that I think only Italians can manage, as the morning commuters hurry along outside to the nearest Metro station. Less than 12 hours ago, I wasn't entirely sure if I would be extending the last part of this jaunt through Italy before hopping over to Paris for a last minute press trip. It's a funny thing, having "unplanned" time during a trip and it's something that I think most of us dread, especially when traveling alone, as I will be for the next few days. Between social media influencing our vacation planning decisions and the seemingly endless accommodation options on AirBnB, the very thought of leaving certain decisions to chance seems reckless. Careless even? Or just plain unprepared. Why leave some decisions to the last minute when there's infinite trips being shared online all the time, with the perfect vantage points, the perfect cafes and the perfect restaurants that have essentially made the decisions for you. Takes the guess work out of traveling, so to speak.
Don't get me wrong. I don't mean for my perhaps sarcastic tone to be misinterpreted. In a lot of ways, I think social media has been an incredible gateway through which we can not only see the world but EXPERIENCE it as well -- taking the foreign and making it familiar -- encouraging us to just go OUT and GET IN IT. Heck, I owe much of my career based in traveling for a living to the democratization of travel on social media and there isn't a day or a trip that goes by that I don't feel incredibly thankful for that.
I suppose where it gets me though, is the slippery slope we find ourselves on now, myself included -- in which the very curiosity and exploration factors of travel are being homogenized. Think about it. How many times have you seen the rocky, colorful hillside of Positano this summer from the influencers you follow? Or Capri? Or Paris? Or Morocco? 4? 5? 20? And each time, I'm afraid to say, there isn't much variety in the photos shared. It's the same balcony shot, it's the same restaurant doorway, it's the same umbrella and rocky beach shot, and while I think there's beauty in sharing those gem locations, it makes me wonder what it's all for -- to experience something or just to prove something? If we don't get those exact same shots, were we even there? As someone who is certainly guilty of all of the above on previous trips and has even gone out of her way to get certain perfect vantage points all for the 'gram usually at the cost of a few grey hairs, I'm now starting to realize as a content creator and consumer, I'm exhausted and quite honestly, to put it lightly, bored.
"Trips gives influencers a chance to create unique, beautiful imagery, but it’s often the same thing over, and over, and over, and over. Same landscapes, same boat shots, same doorways. These posts gloss over the quiet in-between moments, the new things you’ve never seen before, the times you were a little scared or lost in awe. They begin to look the same and followers can’t distinguish one from the other.
You can manufacture a lot of things but in-real-life experiences should be about wonder and joy and discovery and you can’t manufacture those things."
I'm still sitting in the same cafe as before, now moving onto my afternoon espresso, killing a bit of time before my train to Florence leaves. I'm very aware that you all have seen plenty of Italy and Paris this summer on your Instagram feeds so I won't sit here and pretend that my content is somehow revolutionary -- it's not. But what I do hope to do more of, especially in the days ahead as I travel alone, is to share the sense of wonder that we all desperately look for when traveling -- the good, the frightening, the majestic -- and if I can't seem to document it in a photo, well then I certainly hope a good story will suffice.
After all, we all love a good story, right? I know I do.
Now, if you'll excuse me, I have a train to catch. Arrivederci!
OUTFIT DETAILS: Carolina Herrera ball gown skirt (picked up at their sample sale, love this current style here) // Zara halter top (similar style here) // Sergio Rossi heels // Jacquemus hat // Chanel earrings
If you've been following me for a while now, you know I'm a Broadway fanatic.
So much so, that I've gone through and marked the opening dates of most major productions as they come into town, highest on my list at the moment being Pretty Woman (but that's another post, for another day).
And while I love catching the latest openings, I'll never say no to a repeat performance, especially if that certain repeat performance happens to be a hip-hop/rap infused story about our founding fathers -- yes, I'm talking about Hamilton. If you recall, my guy and I hopped out to DC last month at the invite of The Jefferson Hotel team to celebrate their latest summer programming offer (3 nights for the price of 2, which is still running through the end of summer!). Every time I visit The Jefferson, I'm always blown away by how regal everything feels and these past few visits have been no different. This most recent weekend we ducked out of New York early on a Friday, pulling into Union Station around 10pm, just in time for a little indulgent room service and an early night cap -- had to save up our energy for the following evening! For more photos of The Jefferson (trust me, you won't want to miss their lobby!), head to this post!
On Saturday, we got up (early for my guy, late for me!) and headed straight for a slightly boozy lunch at Duke's Grocery (it came highly recommended from you guys!) to enjoy the second half of the England vs. Belgium World Cup semi-finals game. After we hung our heads ever so slightly for England (looks like it's not coming home this year, boys), we made a beeline for Georgetown Cupcakes and spent the afternoon roaming around Georgetown, as I casually picked out future homes (a girl can dream, right?).
After a brief late afternoon/early evening refresh and outfit change at The Jefferson, we made our way over to the Kennedy Center, which if you're ever in DC, you should definitely try to make one of your evenings there for a show or a performance. The architecture alone is breathtaking and if you catch if just right on a sunny, summer evening, the light is nothing short of magical as it casts shadows across the grand entrance -- quotes from JFK greeting you as you walk in -- the Potomac River just within earshot.
Of course, Hamilton left us both singing and tapping our feet -- and while it's round two for me, King George just never gets old! Every time he came on stage, I tugged my poor, bewildered boyfriend's arm in excitement, as I practically know each and every word to his musical numbers. (Perhaps you do, too?)
We then ended the evening at Le Diplomate (another spot that came highly recommended from you guys!) and it was such a treat, especially on Bastille Day! Unbeknownst to us, their evening hours turned into a drag queen show, which was the perfect ending to our day -- a lot of smiling, singing and all the french fries I could muster.
On Sunday, we spent the day recovering and getting a bit of work done at The Jefferson's library room (a must-see if you're visiting the property, such a beautiful, quiet haven if you need to get caught up on emails). And for our last few hours in town before catching the train back, we decided to walk over to the Lincoln Memorial, just a stone's throw away, and one of my all time favorite memorials to visit. I could literally sit there for hours, crowds or not, and listen to the wind pass through the trees, the birds chirping overhead and the clatter of so many different languages being spoken, all at the feet of one our most noble presidents.
Huge thanks to The Jefferson team for having us again and inviting us out to see Hamilton -- we had such an incredible time!
On that note, I've pulled a few noteworthy dresses perfect for your next evening at the theater, so keep scrolling! Are you guys seeing any performances soon? Would love to know which ones!
I like to think a Schuyler sister would love this dress -- and it was actually the first thing I packed for the weekend, because I knew I wanted to wear it to the Kennedy Center. The perfect amount of flow, this dress was a crowd favorite! I got compliments at the theater and at dinner afterward. It's currently on sale, so act fast!
My friend Courtney of Color me Courtney are currently planning our lady date for Pretty Woman (sorry to both our boyfriends -- we're leaving you out this time!). For a musical like this, I like to play homage to a character without it being too literal. You all know I love a good polka dot so I'm tipping my proverbial hat to Vivianne's polo outfit, without copying the exact color scheme.
For the classics, like My Fair Lady or Phantom of the Opera, I love wearing something a bit more refined and timeless. This Tibi dress has made the rounds in beautiful lilac and orange colors this season but I personally LOVE the white. So seasonless, yet the shape is so distinct.
Yep, another Ulla Johnson dress, but for good reason! The sheerness of this dress is just the right amount of sexy for a theater show -- but the length and flutter sleeves keep it slightly demure at the same time. All too fitting for Chicago perhaps? Yes, please and all that jazz!
So admittedly, I just want an excuse to wear something in this shade of yellow, especially if it involves Jacquemus. Best part? This dress is now on sale! For something this bright, try and snag tickets to a more lighthearted show -- perhaps Lion King or Aladdin -- or heck, maybe you'll catch The Boss' eye during his namesake show?