Packing List: 8 Days in Pebble Beach + Carmel

A love story, a packing guide. Ooh, heaven is a place on Earth!

May 22, 2022

Over a year ago, I sat at my friend Allie’s kitchen table on the verge of tears. I was frustrated. I’d recovered from yet another failed situation-ship and I felt like the dating pool was too polluted to win. I knew I was ready, I knew I felt healthy. But every time I cast the line out, I caught a throw-back. Allie was doing what good girlfriends do, offering encouragement and reassurance. But I was in a state. I dated a pro athlete in my 20s who was in town, and I was emotional enough to debate whether or not to accept his invitation to come to see him play. She was rightfully, firmly anti.

The next day, in my cute white dress on the way to see him play in my Uber, the sky opened up. It began pouring. At that moment, I came to my senses. “What am I doing?” I thought. “What am I even getting out of this? I’m going to go sit there and watch a guy I broke up with five years ago playing a sport I don’t care about in the rain in a white dress? Get a grip, Jessica.”

Redirect. I jumped into my app and told my driver I’d changed the drop-off location: Kimball House, one of my favorite restaurants in the world — a place owned by great friends with the best raw bar and cocktails in the Southeast. And I’m not the only one who thinks so: everyone from Bon Appetit to the James Beard Foundation agrees.

(If you’d like to read more about my hometown history with these guys, their restaurant, and our mutual obsession with oysters, I encourage you to read this piece I wrote for another publication.)

Kimball House is a place I never mind dining alone because I never feel lonely there. All the faces are friendly and familiar, and there is always someone to chat with at the bar. So that’s where I perched, with my half-dozen oysters and very cold martini. I figured I’d get pleasantly buzzed, take an Uber home, go to bed early and consider the night a huge win for team Me.

Except I wasn’t alone. About 15 minutes after I sat, someone else settled in a few seats down and ordered a “New Tokyo” cocktail without glancing at the menu. “A regular,” I thought. And went back to playing on my phone.

I’d been keeping an eye on my favorite corner spot at the bar, and the couple who’d been sitting there got up. I asked the host if I could move. As she walked me down there, the owner of the New Tokyo flagged me.

“Excuse me,” He said. “Are you dining alone?”

I side-eyed him. “…Yes,” I said, skeptically.

He smiled. “Would you like to dine together?”

I paused. I really did want to chill by myself that night. But he was also pretty handsome.

“….Okay,” I said, gesturing to the corner seats. “But only if you sit over there with me. That’s my spot.”

As we made our way over, the host leaned over and whispered to me protectively. “Is this okay?”

I smiled and shrugged. “I’ll let you know if it’s not.”

The man introduced himself, and we settled in to chat.

We ended up shutting the restaurant down that night.

We have been together ever since.

And that’s how I ended up spending so much time in Carmel, California — because it’s his hometown. A place I have fallen in love with as much as I have his family and him.

I just returned from another long stay, time I did not take off from work. Between remotely managing my company, spending time with his family, and running around California with him, the newsletter became my last priority. But I hope you understand now why that was: because of love! (And work.)

How’s that for an intro to a packing guide?

I try to pack light and tight for every trip and carry on whenever possible, so I bring things that I can repeat and wear in a lot of different ways. Carmel is chilly and hilly — the temps hover in the 60’s this time of year — so layers and good shoes are paramount.

This is what I actually brought and wore — no editorializing! Hopefully, the next person who Googles “What to wear in Carmel and/or Pebble Beach” will find this to be an actually useful guide. As always, I’m not telling you that you need exact items. Shop your closet and think through items you can layer, good knits, quality sportswear… and then fill in the gaps! Oh, and bring sunscreen.