Planning Serendipity

Spontaneity is my new luxury

I’ve always felt that travel planning is like cooking—you hope to get to the point in the kitchen where you can be creative, spontaneous, and work with the ingredients on hand! (This is part of my friend Cinda’s recipe collection!)

On New Year’s Day afternoon I—like many of you—spent probably too much time scrolling through Instagram. There’s something about a shared moment in time that just makes me happy to see how everyone in my feed celebrated (or didn’t).

One friend’s experience really stood out to me. My friend Bruce Pask had the downright audacity to think he could leave his apartment in NYC with no reservation, on New Year’s Eve, and find a place on the fly. I mean, I love anyone who has this fearlessness, but I was really on the edge of the Instagram-caption seat to see what happened. Okay, so he didn’t succeed at Le Rock, Via Carota, or I Sodi, but he did find a lovely table at The Commerce Inn. And then during dinner, a friend of his called for some style advice, which then resulted in an impromptu NYE party invite, which of course he said yes to, and it ended up being a completely dreamy night.

After spending several very scheduled weeks in New York over the holidays, I—who am not usually prone to making such declarations—found myself saying that spontaneity is the new luxury. Planning ahead for every single thing—putting a credit card down for a reservation you’re not even excited about but is better than no plan, waiting forever for a table, or hoping that your Resy Notify pulls through—just feels like work. Ever since restaurant bars stopped being a safe place where you can just roll up and grab a drink and maybe share a small plate, the need to plan ahead has escalated to a level that just isn’t fun anymore. Also, you can no longer call up places and ask if you can grow a table! Nobody picks up a phone in a restaurant anymore—it’s all via apps.

On a similar winging-it note, right before Christmas I was at my dermatologist’s (who’s an avid traveler) and he told me how he and his wife like to build in some “no plan days” whenever they travel. They’d recently been to Japan and had left the last three days wide open—they didn’t even book a hotel in advance—and he said that having the freedom to be carefree really made the trip. There’s something about setting out with the mindset of anything can happen, rather than the lists upon lists and too many Google pins most of us travel with, that’s a beautiful thing. Maybe that sounds really off for someone who makes a living from telling people where to go?! I really hope not. I’d love it if all the stuff we put out for you to read, skim, save and cherry-pick from is a foundation to help you feel confident to just go out there, to believe it’s going to work out—and then maybe storing the lists in the back of your mind as a backup plan.

Serendipity is a word I’ve always loved—not only does it sound like it’s from a Disney princess movie, it kind of makes you feel that way, too. I looked up its origin story and learned that its root is the word Serendip, Arabic for Sri Lanka. The English writer Horace Walpole first introduced the word “serendipity” in his fairy tale, The Three Princes of Serendip, in which the heroes made a series of unplanned, fortunate discoveries. I didn’t even know that the word “serendipitist” existed until I started to write this—someone who has a lot of serendipity, or luck. I think we all know people who just seem to know everyone, and have real confidence, and are fine to just wing it, knowing that the right thing will fall into their lap—even if that “right thing” might not be on anyone’s list. Back when I was in high school with nothing to do on a weekend, my best friend and I had no problem setting out on an adventure, even if we had no plan. Just saying we were going to have an adventure meant that it became one, no matter what we did. Without veering too much into Carrie Bradshaw territory trying to come up with a thesis for an idea that really isn’t heavy—here’s to more travel confidence this year. Whether that’s exploring a neighborhood near yours that you haven’t gone deep on, or going somewhere for the twentieth time where you don’t make any plans, you just live your days—I hope you have enough swagger to just leave yourself open to… whatever!

Happy New Year! —Yolanda

P.S. We have a full schedule for you this month at Club Yolo! Upcoming posts include our travel dreamscapes for the year (the places we can’t get out of our heads and Google flight alerts we keep checking), a Q&A with our friend Tyler Dillon, a travel advisor from TrufflePig who has ideas for less-touristed places that satisfy some of whatever it is you keep looking for in Spain and Italy, and a long YAFI (You Asked For It!) post about how I navigated taking my dog, Prune, to Europe!

P.S.S. Want to keep on planning?! Did you see Our Giant Paris Black Book that we published just before the holidays?!