I’ve just returned to New York City after nearly a month on the west coast for my annual California visit featuring palm trees, a boys golf trip, some work, and lots of family time in Palm Desert. Highlights included a bunch of birdies, catching up with the parents, daily jogs through the desert, and endless hours of fun in the pool with Finn.
The difference with 2025’s visit was a side-trip to Northern California with Lynn to visit wine country. This was my first time to Napa Valley, while Lynn was visiting for her ~8th time, so it was super fun to have someone who knows the area so well show me around. Although we’ve talked about visiting Napa for years, the catalyst for this trip was Lynn getting back on her run game and aiming to complete the Napa Valley Half Marathon - a race that’s famous for featuring stunning scenery, and a predominantly downhill course.
We flew from PSP to SFO on Friday after work, and drove our rental car 2 hours through traffic, over the Golden Gate Bride, and into wine country. We were armed with a jam-packed schedule for the next five days including the 13.1 miles, exciting restaurants, and many winery reservations. For those readers who have been to Napa, you’ll know what I mean, but it can be very overwhelming. It’s so cool how the entire region is centered around one industry. Once I saw how every acre of the land is covered with vineyards, I was even more thankful I had Lynn’s experience and passion for wine and planning to help guide us through the beautiful area.
The Race
The Napa Half Marathon runs south down the famous Silverado Trail, the eastern highway barrier of the valley. The first ten miles are on this road before diverting through some more residential areas towards the finish line.
Lynn crushed it. We woke up at 4:30am to catch our shuttle bus up to the start line. The gun went off at 7am and we were off in pretty much perfect weather, around 10 Celsius. I ran alongside Lynn the whole time, who expertly executed her game plan just like we practiced: run one mile, walk one minute, and repeat. After weaving our way through the beautiful countryside and talking about each winery that we passed, we crossed the finish line in 2:14:39, injury-free and smiles on our faces.
After a quick snack and shuttle back to the hotel, we took a 30-minute nap then had to promptly get ready for our first wine tasting of the day, scheduled for 12:45. I would definitely recommend this race to people looking for a fun race-cation. It’s in a beautiful spot, well organized, not too big, and a very comfortable course.









Our Hotel
After staying in the generic Marriott race hotel in the city of Napa for convenience, we moved up to Yountville, a super quaint town with essentially one main street filled with luxurious boutique hotels and Michelin-starred restaurants. We stayed at the Napa Valley Lodge, and would do so a hundred times over. Great service, good breakfast, a beautiful location, and fantastic pool/hot tub area with fire pits for a late night glass of Malbec.


The Wineries
Before the cabernet fogginess causes me to blend all NINE wineries that we visited together, I wanted to document the various spots based on experience (including the customer service), property (including the tasting room, vineyards, views, etc.), and wine.
Ram’s Gate
Experience: 9/10; Property: 9/10; Wine: 9/10
Ram’s Gate is the house wine in our Upper West Side apartment, which we’re forever grateful for. Lynn has been a member since one of her first trips to Napa, in 2015, so we get quarterly shipments, and it was such a fun experience for me to see where the magic happens. We headed there the day before the race so we could take our time. Their property is stunning, like the nicest golf clubhouse you’ve ever stepped into. The tasting occurred at a beautiful big bar that sits in the middle of a rustic building with a fireplace and plenty of tables and natural light. Afterwards, we took a walk through the property, down to their natural pond, and near the vines.
Laird Family Estate
Experience: 8/10; Property: 6/10; Wine: 8/10
We scheduled a tasting at Laird because it was started by a Georgia Tech grad (Lynn’s alma mater). Beautiful property and great location with fantastic wine and a very casual atmosphere. We just got one tasting between us, The Big Reds, sampling 5 of their popular reds. Excellent service from a guy who grew up in the valley and it was at this point that I realized they weren’t just pouring little tasters; it was a good 3 oz per glass. I’d definitely recommend Laird, and we left with 3 delightful bottles, a Merlot for Lynn’s parents, and a Malbec and Cab for us.
Alpha Omega
Experience: 8.5/10; Property: 8.5/10; Wine: 8.5/10
Although the name sounds fancy and the wine is expensive, the property was very approachable. They have a beautiful indoor wood bar for tastings, but because it was a delightfully sunny day, we sat outside on a comfy couch admiring the fountains and vineyards. Lisa, a retired local, was our host and gave us some fun restaurant suggestions in Yountville. We took our time here, surprisingly enjoyed their whites, and left with two bottles (one for us, one for Lynn’s parents).
Laird and Alpha Omega
Frog’s Leap
Experience: 7/10; Property: 8/10; Wine: N/A
Day two began with a quick stop at Frog’s Leap, specifically to grab one of their bottles of Petit Syrah that is only available on property. It gave me a chance to check out the vines up close, and after the lady at the front was a curmudgeon, her coworker came through, offered us a tasting of their crisp zinfandel and told us to stroll the property. They have a beautiful deck and are very environmentally friendly.
Quintessa
Experience: 9.5/10; Property: 10/10; Wine: 10/10
The winery that Lynn built up the most, did not disappoint. Driving up to Quintessa is like approaching an ultra exclusive golf club, mixed with a high-end spa. Gates from the road require you to buzz in, and the winding road takes you through the property up to the massive building that could be either the HQ of a well-funded tech company, or a Bond villain’s hideout. The tour took us on a 5-minute walk up the mountain to overlook the entire property. That was followed by a hike down to our own private tasting inside the most zen room of all time (think waterfalls and calming music). Quintessa makes one red wine each year. One. It’s $260 per bottle, and while that’s too much, it’s an absolute treat to taste. Would highly recommend, they know what they’re doing.
Gott's Roadside Grill, Frog's Leap, Quintessa
The Terraces
Experience: 7/10; Property: 6/10; Wine: 6/10
The Terraces was a roll of the dice, in pursuit of a family-owned winery, somewhere close to Quintessa, that Lynn had never been to. We were greeted by one of the owners who took us on a gator cart for a tour of the property, including the vines on crazy hills, the wedding venue they have maintained from the 1800s, and the balsamic vinegar barrel room. She then took us up to the tasting room, which was super casual (basically a living room with a kitchen), where we sat on a couch and she poured us wine. The husband (and co owner) popped in for a bit and we traded stories about NYC and the wine business. Lynn knew more about wine than they did, but they were super friendly, and we talked a lot about the grind of running a winery, and the alcohol industry in general. A great, homey experience, which I won’t soon forget. We bought one bottle.
Storybook
Experience: 9/10; Property: 7/10; Wine: 8.5/10
Storybook kicked off our Tuesday, with a long drive up highway 29, to the top of the valley in Calistoga. During the summer, it can be up to 10 degrees Fahrenheit warmer in Calistoga compared with the city of Napa. However, as we learned from the most in-depth tour we experienced, because Storybook is only 40 miles from the Pacific ocean, they get the benefit of the cooler, moist winds which create a perfect climate for Zinfandel grapes. In the sea of cabernets that the valley is famous for, this family-owned property has carved out world-leading Zinfandel that is far from the traditional fruit bombs that you think of. It’s got deep flavor and lower alochol than your standard Christmas zins. Our tour guide, Rick, had married into the family, and worked there since 2003. He took our group around the property and shared secrets of their agricultural process, regaled us with stories of the Napa fire in 2017 and the owner’s passion (who is now 87 and still picks every grape), and then finished with a tour of the cave, where he also hosted the tasting. Lynn loved all the facts about this place, and we left with four delicious bottles.
Oakville Grocery and Storybook
Girard
Experience: 5/10; Property: 6/10; Wine: 5/10
Easily the worst experience and wine we encountered on our escapades. If you’re heading to Napa, don’t worry about this place. Pretty lame customer service in a so-so setting, and the wines were forgettable.
O’Brien Estate
Experience: 10/10; Property: 9/10; Wine: 9/10
Before driving back to San Francisco to catch our flight back to Southern California, we stopped in at O’Brien for a private tour of their property, including their own bottling process - they do everything on-site, from grape to glass. One of the coolest parts about this place was the sustainability practices they have in place, including a bunch of animals from roosters to dogs to lambs to goats. Our guide, Logan, took us around the vineyard, then set us up in the family’s backyard (their house is right on the land) for a lovely tasting. The owner, a former tech entrepreneur, Bart, came out to say hi, and we left with a brand new membership, committing to 12 bottles per year, shipped right to New York. I highly recommend O’Brien if you find yourself in wine country.
Aside from the wineries, we had some lovely meals at Oakville Grocery, Gott’s Roadside, and Ciccio’s. Oakville Grocery became a daily stop for us as they sling out some incredible sandwiches and salads, perfect for refueling while on the go between tastings. Gott’s is a famous burger drive-in where you can enjoy your meal on some picnic tables on their roadside lawn. Ciccio’s was a highlight dinner for us, flavorful Italian cuisine, hosted in a quaint little storefront on Yountville’s main street.
If you haven’t been to Napa, hopefully this paints a picture of what wine country is like in Northern California. If you’re going (like I will be again), maybe this can serve as a bit of a map to simplify the journey. Overall, I was totally impressed. It wasn’t too commercialized like I thought it would be, it wasn’t too pretentious, and the people were all fantastic. If I were to offer a couple additional tips: plan ahead - you need reservations at restaurants and at wineries; don’t over-extend - two wineries per day seemed like the perfect balance; pack food - most tastings don’t include food, so plan accordingly and take food on the go. As an aside, we now have way too many (80) bottles of wine for our tiny NYC apartment, so if you’re thirsty, please swing by.
Cheers,
Mike