Ryan Shepard
About Author
April 10, 2025
 in 
Life

Our Weekend in Napa Valley: Scenic Drives, Wine Tastings & A Dash of Chaos

This past weekend, Shep and I took a quick getaway to Napa Valley, and even with a few unexpected hiccups (literally), it ended up being such a fun and memorable trip. We flew into SFO, rented a car, and instead of beelining it to wine country, we opted for the scenic route over the Golden Gate Bridge. It added about 30 minutes to the drive—making the total around 90 minutes—but it was 100% worth it. That view? Instant mood booster.

Before checking into our hotel, we made a pit stop at Rutherford Grill for lunch. If you’ve ever been to a Houston’s, it’ll feel like home—same vibe, same delicious, no-fuss menu. It hit the spot.

We then checked into the Alila Napa Valley, and let me just say… I’m already mentally rebooking. The rooms were stunning, the view was all rolling vineyards and tall trees, and the heated toilet seats? Game changer. Never felt more pampered.

After settling in, we drove up into the mountains for a tasting at Stony Hill Vineyard. The drive alone was beautiful, and once we got there, I was floored by the view—we could see so much of the valley. The tasting room was unlike anything I’ve ever experienced. It’s set inside a converted family home with mid-century modern design touches everywhere. I could have moved in.

Unfortunately, that’s when the drama started. I randomly got sick during the tasting (and no, I’m not pregnant—just wildly unlucky). I spent a good chunk of the tasting in their bathrooms, which, silver lining, were clean, peaceful, and oddly comforting. If you have to vomit somewhere, this was not a bad setup. lol.

That night, we had reservations at Kenzo, and I was so looking forward to it. It’s a high-end Japanese restaurant with a serious reputation, and Shep came back absolutely raving about it. He said it was one of the best meals of his life, with hospitality that blew him away. I didn’t get to try the food, but I can personally vouch for the staff: the general manager literally brought me a plastic bag and a cold bottle of Pellegrino while I was—yet again—vomiting in the back seat of our rental car. Talk about luxury service.

Day one was a wash, but I was determined to make up for it.

We ordered breakfast in bed the next morning (nothing to write home about), then got dressed for our first tasting of the day at The Prisoner Wine Company. The tasting room was super stylish, and the hospitality was top-notch, but the wines were just okay, in my opinion. Shep loved them though, and we ended up with a membership because the fee for the tasting goes toward joining—which is a pretty smart little marketing trick.

From there, we headed to Bouchon for lunch. I briefly (and I mean like 2 weeks) worked there, so going back felt nostalgic and indulgent in the best way. We split a few rounds of their iconic bread, some oysters, French onion soup, beef tartar, and a croque madame. After lunch, I needed a nap—because I'm older and I was full af.

Dinner was supposed to be at Scala Osteria in downtown Napa, but I made a rookie mistake and booked the reservation for the wrong night. We ended up waiting about two hours to be seated. While we waited, we found Hog Island Oyster Bar and downed a round of oysters. Then we wandered next door to a bar called ArBARetum—which had a really cool vibe from the outside. I ordered the hibiscus gimlet thingy, and it blew my mind. Of course, the moment we got our drinks, we got a text that our table was ready. I downed mine and sprinted over.

Honestly, I kinda wish I hadn't. Scala was... mid. It looked beautiful, and the crowd was buzzing, but the service was so slow. Our chopped salad was fine but totally forgettable—flavorless and lacking balance. It had no acidity or brightness of any kind, which made it feel like a sad afterthought. The spaghetti con gamberi & vongole (clams, shrimp, garlic, chili, white wine) was better, but there is still nothing I need to have again.

We ended the night back in the room, binging The Pitt on Max (highly recommend).

The next morning, Shep hit the gym (because he's weird), and I took a long, hot bath. We packed up, grabbed some breakfast sandwiches, and squeezed in one last tasting at Cakebread Cellars. If you’re into Chardonnay, Sauvignon Blanc, or Cabernet Sauvignon, run here. It was my favorite tasting of the whole trip (likely because I wasn't off somewhere puking)—ten out of ten—and the grounds were absolutely stunning.

I wish we had time to do more tastings (so many places, so little time), but that just gives us a reason to plan another trip back. Despite the rough start, our Napa weekend was equal parts relaxing, hilarious, and luxurious—and I already can’t wait to return...maybe with my besties next time, though.

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