This year marks the fortieth anniversary of my life as well as (much more interestingly) the lives of five of my high school girlfriends. To celebrate this coming-of-middle-age, we decided to plan a trip to Sonoma and Napa Valley, California, so we could ring in the year the right way: with wine.

One of these amazing women couldn’t make the trip because, honestly, she’s too amazing. Truth. This friend, Mary, and her husband are opening a Goddard School in Skokie, and it just so happened that the week we’d scheduled our trip was the busiest week they would have until they open their doors this August. So, please be aware that we dedicated our trip to her, and this post is dedicated to her as well. And for her actual birthday in a couple of weeks, we’ll probably kidnap her and force-feed her wine (this will not be necessary; she will drink it willingly) until we forget that we’re forty(ish).

With the tremendous planning skills of the group (minus me, because I didn’t really do anything except pack a bag and show up), we had a terrific four-day trip together. Here’s how it all went down.

Tuesday Night

I spent the night with Lisa and her husband, Matt, because our flight left early Wednesday morning and they’re just a fifteen minute taxi to the airport (at 5 a.m…). This meant that I got to witness Lisa’s spectacularly organized packing method, hang out with their dog, Cholula, and sleep in their guest Murphy Bed.

Basically, I could have gone back home the next day and still been happy.

But, no! We had…

Wednesday

Lisa and I met up with Julie at O’Hare for our flight, and then once we landed in San Francisco, we met up with Megan, who had flown in from Philadelphia.

The four of us met Amy at the rental car place, and then we hit the road to Sonoma, where we were staying on Sobre Vista Road, overlooking the Enchanted Hills. Seriously.

We stopped for provisions along the way so the kitchen would be stocked when we needed it (first on our grocery list was cheese, then more cheese, then some fruit, some bread, and then, finally, some cheese). But we had a few hours to spare until our dinner reservation, so we decided to hit up a winery, and we chose Buena Vista Winery. We chose well.

Our tasting room bartender was Dapper Don (maybe “Dapper” isn’t his given name, but, whatever) and he treated us to a one-of-a-kind experience. We walked in just an hour before closing, so when we were finished with our tasting and the winery was closing up for the day, Don took us on an unofficial tour of the Bubble Lounge (bubbles only are allowed!) and the barrel cave, where Megan may or may not have schooled him on the piano.

By this time, we were pretty hungry for dinner, so we headed to downtown Sonoma. But we were still too early for our reservation at The Girl and the Fig, so we had one more glass of wine at the Roche Winery tasting room, where we didn’t take any pictures, but it’s possible we broke a glass. It was fun.

Now, let’s talk about dinner. No, we’re not going to talk about the gorgeous mussels we ate, or the beautiful cheese plate (do you understand by now that we like cheese?), or the carrot entree I ordered and ate and am fantasizing about eating again right now because it was so good. No, let’s talk about the waiter, one Russell Sage — if that is his real name.

If you’re thinking that this distinguished gentleman was our waiter at The Girl and the Fig, you would be, unfortunately, wrong:

Our Russell Sage was a man who liked to wear cologne, who seemed to really like forty-year-old women, and who liked to lean in. He leaned in a lot.

He was also a man who felt inclined to invite himself to our house to swim in our pool, and then leave his phone number on our check, in case we were motivated to call him. Oh, Russell. You’re not going to swim in our pool.

Now, if you think that Russell provided the only strange waiter experience we had at The Girl and the Fig, you would be stone cold wrong. There was also Geoffrey, whose name I know how to spell because he said he was “like Chaucer,” as he filled up our water glasses. And Geoffrey felt inclined to follow us out after our meal and sing “Happy Birthday” to us on the sidewalk in front of the restaurant. We. Did. Not. Know. What. To. Do.

So we just let him sing, and then after he went back into the restaurant and we waited for our car to pick us up, we tried to ignore Russell Sage waving at us through the window.

Thursday

Thursday was our big Napa Valley winery day. Lisa had taken care of making us reservations at four different spots, and Amy had taken care of getting Mike the driver to take us around so none of us had to be responsible for operating a motor vehicle.

We started the morning with sparkling wine at Mumm Napa. The view was perfect, our waiter was a normal human person who didn’t sing to us or lean in at us, and, honestly, who wouldn’t want to start the day with bubbles? Probably some people, but not us. No, not us.

After Mumm, we headed to our unanimous favorite, Frog’s Leap Winery, where we did a little tasting…

…we met a dog named Abbie…

…we did some thinking…

…and a little light reading:

We didn’t want to leave Frog’s Leap, but, alas, we had to. Cakebread Cellars was waiting for us.

Our time at Cakebread was pleasant, but a bit rushed. They didn’t let us sit down for our tasting, and our guide hustled us through the wines like it was her job (I guess because it was her job). But we met two lovely young couples — one from St. Louis and another from Dallas — and we drank some good wine.

Our last stop on our wine-whirlwind was Chimney Rock, and this one was special.

At Chimney Rock, we got a guide named Donna, and Donna was the queen. She. Was. The. Queen.

Donna took us out to the vineyards to look at the crops, talk about the history of the winery and the property, and to take some pictures — with and without her finger near the lens:

Donna was an excellent guide and gave us a lot of great information about the head wine-ista (this might not be her actual title), Elizabeth, and she showed us the ins and outs of the facilities.

And then Donna gave us some wine.

We took a group picture at three of our four stops — I think we didn’t get one at Frog’s Leap because we were having such a good time there.

At the end of the day, we went home to hang around the house, chat, and drink all of the wine we’d bought that day.

Friday

Friday was our day of relaxation around the house, so we didn’t have too many adventures. Early in the day, we discovered that the owners of the house were likely watching us from their Sliver-like monitor room in some undisclosed location.

But after a bit of discomfort, we relaxed and did some swimming, some floating, some reading, and some napping. Whoever had to watch that boring video, I say, ha, sucker!

Saturday

By Saturday, we were ready to leave the house again, so we hit up a couple of wineries: Imagery Estate Winery, where we enjoyed some wine on the patio, and B.R. Cohn, where we ate some pre-lunch oysters.

And once our oysters were digested, we were hun-gree, so we headed back toward our neighborhood and to Juanita Juanita, a restaurant we’d been steered toward by our server at Frog’s Leap. And as soon as we got in, we knew we were in the best place. Kate, the owner’s daughter, helped us right away and was as friendly as could be. And when she learned that we were in California to celebrate our birthdays, she told us that it was, in fact, her actual birthday. So, of course, we loved her and joined in to help everyone sing her happy birthday, and Lisa tried to buy her a drink, but Kate told us that because her mom owns the place she’d been drinking there for free since she was fifteen. But she appreciated the gesture.

Everyone there was great, and the food was stupendous. Amy made a friend named Wyatt, who talked to her about his baseball card collection,

and we all appreciated the piñatas (although not as much as I appreciated the fish tacos).

But the best part of eating at Juanita Juanita and befriending Kate and the rest of the crew there was that when their friend Jesse, an off-duty cab driver, came in to hang out, we quickly convinced him to take us the two miles back to our house.

See, it’s not easy to get a fast Uber or a Lyft in Sonoma that fits five people, or one at all. We were looking at a wait time of at least thirty minutes, if ever, and while we loved Juanita Juanita, we were ready to head home. So we were discussing our problem when Jesse walked in and Kate told us he was a cab driver. We nearly pounced on him and the poor man tried to fend us off by telling us he had his personal car, not his cab. We didn’t care. We gave him some cash and a lot of toothy smiles, and he relented to take us.

He had to move his kid’s car seat, and Lisa had to ride in the way, way back, but Jesse was clearly the right driver for us.

He got us home quickly and with no problems, and we were left to spend the rest of the afternoon and the evening hanging around at the house, wishing we weren’t leaving the next day.

Sunday

And on Sunday, we left. We woke up and watched the sun come up over the Enchanted Hills, and then headed to the airport.

We said our goodbyes to Megan outside of our gate, and then we had an uneventful trip back to Chicago. We were subdued at baggage claim and then all went our separate ways, wine in our luggage, tired smiles on our faces.

And that was our trip! It was wonderful, we missed our friend Mary like crazy, and we are going to have to recuperate for the next five years until we’re ready to celebrate being forty-five. We’ve already decided that Key West might be our next destination, so, Florida, please start the preparations.

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