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Trip Report Trip Report: An Intoxicating Birthday Day-Trip in Napa

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For my Mom’s 49th birthday, my younger twin sisters, Ainsley and Bailey, and I decided to hire a limo and driver for a day tour to Napa. Mom is a fairly new transplant to SF, while the three of us have remained in Boston, so this was our first trip to the valley. I think there are really two ways to approach Napa Valley – either spend a long weekend and give it the time and attention it deserves, or hire a driver and make it a fun party day-trip from SF. We were strapped for time and in the mood to party, so we opted for the latter approach. In the interests of full disclosure, since we wound up getting quite intoxicated, if you’re a wine snob, you probably won’t find this report too interesting or valuable. But if you’re planning a bachelorette party or enjoy a tipsy day out, it may contain some useful pointers. Here’s hoping!

Napa Wine Tour Tip #1: Buzzed driving = drunk driving = NOT COOL. ALWAYS get a designated driver. Our driver, Amanda, was fabulous, put together a great itinerary for us, made our visit fun and worry free, and even took hilarious pictures!

Napa Wine Tour Tip #2: Always eat a big breakfast! As a group we stuck to oatmeal, yogurt and granola parfait, which wasn’t enough!

Napa Wine Tour Tip #3: Dressing nicely for a day in wine country is fun and makes for great photo memories.

Even though we grew up in Boston, Mom is a tried and true southern belle and decreed a “country club casual” dress code for the day, so that we would look our “preppy best” for her birthday wine tour. Accordingly, we set out for Napa at 8:30 a.m. that morning, tucked-in, buttoned-up and looking very crisp, colorful and blonde in our slim-fitting oxford shirts. I thought we looked like a billboard or like we were going to a regatta, but Mom seemed happy and that’s what counts! As funny as it sounds, I think dressing up was part of what made the day so fun and it made for really cute pictures.

10:30 a.m.

After reaching Napa with fairly little traffic, our first stop was at Chimney Rock off of the Silverado Trail. After Mom informed Amanda that in honor of her birthday weekend she planned to swallow the wines she liked and spit out the rest, Amanda insisted I hand over my camera to her so that she could take a “before” picture of us and photograph the day to “track our progress”. This was a good idea and produced some adorable, and later, very funny memories.

The Chimney Rock Winery itself is very pretty, but then again, I cannot think of any winery that I saw during our visit that was not super pleasant. Chimney Rock looks like a mixture of a Swiss Chalet and old adobe church of the Southwest. We made our way inside and had our first tasting of the day- the Estate White Selection, which cost $20 for 5 generous pours. We enjoyed speaking with the good-natured host at the tasting room and getting his little story about each wine and tasting for the various notes in all of them. When I closed my eyes, I actually thought I could detect the hints he was talking about, something I can never seem able to do back in Boston. Amazing things are possible in a setting like Napa.

The Sauvignon Gris was pretty good, but we all agreed that the Elevage Blanc was the best (except for Ainsley, who actually preferred the Sauvignon Gris). The wines were universally excellent and, in a harbinger of things to come, none of us spat out any of them. We thanked our host and Ainsley and Bailey, who are seniors in college, suggested we buy a bottle of Elevage Blanc to enjoy in the limo on the way to our next stop.

Napa Wine Tour Tip #4: Always spit or pour out at least some of your wine!

Napa Wine Tour Tip #5: Never try to keep up with college seniors during a day of wine tasting!

11:30 a.m.

Our next stop was the Whitehall Lane Winery. We were in a cheerful mood and uncorked the bottle of Elevage Blanc that we had bought to enjoy on our very scenic, if short, ride through the valley to Whitehall. Amanda explained the layout of the valley as we drove along. There are two main drags – Route 29 and the Silverado Trail, with wineries dotted along them and on the many turnoffs. In the fall sunlight, the changing colors made a magnificent landscape.

Napa Wine Tour Tip #6: Drink water, not wine, on the limo rides from winery to winery. The tastings at the wineries were plenty and failure to follow this rule laid the groundwork for our early bedtime!

I had never heard of Whitehall Lane and was definitely skeptical when we arrived, since, while it is pretty, it’s not one of the more magnificent tasting room buildings in Napa. We walked right in and they couldn’t have been friendlier about setting up a tasting on the spot for $15, which included pours of their recently released red wines.

Napa Wine Tour Tip #7: It’s amazing how quickly a lot of little tastes of wine can add up.

I was feeling pleasantly warm and fuzzy after the glass of wine in the limo, and my buzz continued to grow as we tasted our way down the line. We started with Cabernet Sauvignon, and followed it with a Pinot Noir, both of which met with unanimous approval from our group. Next up was Merlot. By now a very ticklish feeling had developed under my shirt collar, which made me giggle, as I freely told the tasting room attendant that the merlot “needs some work!” He took it in stride, as he poured out the fourth and final tasting, a “selection” wine, which met with a more favorable result.

It was before noon and we had finished our second tasting of the day. Judging from the amount of giggling and hair flipping that was going on, I gathered that I wasn’t the only one feeling a bit loosened up from the alcohol.

Napa Wine Tour Tip #8: Four tipsy lasses in a Napa Valley tasting room will make new friends.

“Something tells me that this is not the first stop for you ladies today”.

We collectively turned around to see who the owner of the rich baritone voice was. It turned out to belong to a handsome gentleman who I guessed to be in his middle 40s who introduced himself as Lawrence. Lawrence was accompanied by a friend of about the same age named Roger. They were both total dandies – decked out in blazers, pocket-squares and crisp white shirts. Had they been wearing tweed and ascots, they might have been out for a ride in the countryside. Ainsley and I noticed that Mom was looking them up and down from head to toe approvingly, rolled our eyes and decided it was time for a walk outside, while Bailey stayed behind to chaperone.

After about ten minutes of fresh air, Amanda found us outside and told us it was time to move on. Ainsley and I went back inside to collect Mom and Bailey. They were standing near the bar, laughing, as Mom lectured her audience about the merits of oxford shirts and how the younger generation cannot dress itself. Always smooth, Lawrence gestured at the four of us in our different colored Oxfords. “Well, I think you’re perfectly coordinated.” He then proceeded to bestow nicknames on us as follows – “Miss Preppy White Shirt” (Me), “Miss Preppy Pink Shirt” (Mom), “Miss Preppy Blue Shirt” (Ainsley), “Miss Preppy Stripey Shirt” (Bailey).

Just as I was again rolling my eyes, Amanda re-appeared and announced that it was 12:30 and we would be late for lunch. We said our goodbyes, but not before Roger and Lawrence insisted on buying Mom a bottle of Pinot Noir and a bottle of Cabernet Sauvignon as birthday presents. She accepted, with the caveat that they pose with us for some pictures.

In hindsight, judging from our glowing cheeks and twinkling green eyes in the pictures, now would have been a fine time to stop drinking.

12:30 p.m.

But we didn’t.

The laughter was flowing freely as we got back on the road to our next destination. To the delight of her rosy-cheeked passengers, Amanda put on some tunes and we bumped out to Brittany Spears, which reminded Mom of our time on the high school dance team and hearing lots of noise from the basement.

Napa Wine Tour Tip #9: If you’re tipsy and wearing a white shirt, as I was, consider sticking to white wine and under no circumstances open a bottle of red wine in a moving limo!

We were having a blast and I was somehow nominated to uncork the Pinot Noir. This proved to be a poor idea, since I was admittedly feeling very tipsy and, after a valiant wrestling match with the cork, wound up covering the right cuff of my white shirt in Pinot Noir. Luckily we were all laughing at just about anything at this point and it proved to be nothing that folding back my cuffs couldn’t cover up.

As someone who had never before engaged in morning drinking, I can tell you that it builds up an appetite! Luckily, Amanda was a driver par excellence and had gone to the trouble of buying six different kinds of sandwiches for the four of us from a deli while we were at Whitehall. I can’t recall the name of the deli, but based on my research after the fact, I believe it was called Sunshine. Anyways, good pick Amanda! (And great pickles!). We had finished the bottle of Pinot Noir we’d been drinking in the limo and the birthday girl decided that Cabernet Sauvignon would pair well with sandwiches. This time, Ainsley, who was comparatively sober, did us the courtesy of uncorking it, without incident. Although I had forgotten to take tasting notes since halfway through our tasting at Whitehall, I recall the Cabernet Sauvignon being delicious, although it did not help our collective sobriety, which was by this time in serious jeopardy.

2:30 p.m.

After another short limo ride with more singing and dancing, we made our way to the next stop on our tour – the tasting room of Castello di Amorosa. This was another beautiful winery, which, believe it or not, is life-size and modeled on an actual Italian Castello. While it admittedly felt a little Disney-like and was unbelievably crowded, it made for a very festive environment.

Napa Wine Tour Tip #10: If you’re a woman, think very carefully about wearing heels on a visit to Napa.

Thanks to our dress code for the afternoon, all four of us were wearing heels. While this would have been a bad idea in its own right, due to an abundance of soggy grass and the like, the alcohol we had consumed to that point made walking on the atmospheric cobblestones an even wobblier proposition! Even if you’re the designated driver, I wouldn’t recommend heels in Napa.

I have to pause to say that I think tasting room workers in Napa are remarkably good natured folks. Like many in the very crowded tasting room, we were clearly well past tipsy, but the staff could not have been nicer about laughing with us, offering us some complimentary cracker snacks too, and pouring appropriate tastes on the smaller side.

I can’t tell you much about the wine we tasted, except that it was clearly good because we finished all of it. Conversely, I think it’d be fair to say the wine finished us as well, as shortly afterwards I had considerable difficulty untangling my hair from my shirt collar and Mom had begun to sway quite a bit, holding on to the bar to steady herself.

Napa Wine Tour Tip #11: Research cures for the hiccups in advance.

A few minutes later, we were standing at the bar talking about god knows what, when suddenly…


I covered my mouth with embarrassment as Mom and twins looked at me. And kept talking as though nothing had happened. Until…


As loud as the tasting room was, I’m pretty sure the drunken laughter of Mom and my sisters drowned the rest out. I waited forty-five seconds and thought I was in the clear. Then…


I had no choice but to laugh with them. But, funny as it was, it was also uber uncomfortable!

Napa Wine Tour Tip #12: Most cures for the hiccups do absolutely nothing.

Nothing brings out unwelcome attempts at chivalry from strange men like a case of the hiccups. As we stood there laughing, no fewer than ten different men approached me, each with a proposed cure like suitors seeking to withdraw the fabled Arturian sword from the stone. None succeeded and I took a picture with each prospective suitor before vanishing him in a tide of laughter.

Napa Wine Tour Tip #13: Tall, blonde, German men are cute – with or without wine.

Finally, a strapping gentleman, with perfect blonde hair, in his late 30s named Oskar (from Germany) came to the rescue. He sidled up to our table and out of nowhere yelled “Boo!” loudly in my direction. I turned around with unenviable drunken precision and the hiccups stopped.

From then on Oskar was my best friend. And Mom, who had clearly emerged as the drunkest of the group, decided to interrogate him for the next twenty minutes with a series of questions, many repeated, asked in her best glossy-tongued, slurred speech. Eventually Oskar had to leave, which was very sad since he was also wearing a button-up white shirt and I enjoyed having Mom snap pictures of us together since we matched. As Mom said at least four times, “too bad he’s married”!

I’m pretty sure that by that point we were drunk enough that we would have remained in the tasting room for the rest of the afternoon (or at least until getting asked to leave), had Amanda not miraculously appeared and told us to start saying our goodbyes. Mom was very unsteady on her feet (admittedly, I wasn’t a prima ballerina at that point either), so I swung her arm around my waist and we began to stagger, Noah’s Ark style two-by-two, up from the tasting room, out of the castle, back to the limo, while Ainsley and Bailey disappeared in search of the facilities.

Napa Wine Tour Tip #14: Alcohol and modern technology are a dangerous combination!

We tottered out of the castle and began the perilous task of descending the stone stairs leading away from the entrance. About half the way down, Mom missed a step and proceeded to tumble in harmless slow motion to the ground. This, she apparently thought, was the funniest thing since creation, and she remained on the ground laughing her head off. In a misguided mixture of chivalry and over-estimated sobriety, I extended my hand to try to pull her back to her feet and wound up joining her on the ground seconds later in a matching pools of laughter. Unbeknownst to both of us, Amanda was watchfully keeping tabs on her party from the limo not fifty feet away, but decided that this footage needed to be memorialized on my camera, which she had commandeered earlier. A very funny cautionary tale it makes.

We were in a castle and a birthday fairy tale ensued.

At that precise moment, as we were on the ground giggling, a familiar baritone voice chimed in.

“I KNOW this is not the first winery of the day for you ladies!”

I looked up through my drunken fog and beheld that it was none other than Lawrence and Roger, who had also included a bit of Disney on their itinerary (perhaps, I wonder, in expectation of bumping into us again?).

He extended his hand to Mom – “Can I give you a hand, Miss Preppy Pink Shirt”?

Making sure I wouldn’t feel left out, Roger extended his to me. “You look like you could use one as well, Miss Preppy White Shirt”.

They helped us to our feet and each parked an arm behind our backs for support as they guided us toward the limo. Ainsley and Bailey had emerged from the castle, but perceiving no threat, didn’t interrupt.

Poor Mom was completely loaded by this point and with much effort, Lawrence repeatedly prevented her from again toppling over as she lavished him in slurred praise and repeatedly apologized for being “a lil’ shrunk” in response to his joking observations that her collar and her cheeks were the same shade of pastel pink. When we reached the limo, Amanda held open the door as they helped us inside, one by one. Mom planted a big kiss on Lawrence’s cheek.

And then we were off.

3:45 PM

By this point, poor, saint-like Amanda, had a car full of wine-soaked lushes on her hands. She had planned to take us next to Robert Sinsky, a winery I have heard of in day-to-day life and whose products are excellent. But keeping a watchful, motherly eye on her audience, she had cancelled it after lunch and we hit the road back to San Francisco.

You’ll have to forgive me, but at this point in the afternoon, I start to have swiss-cheese memories and what remains of this narrative is the result of the wonderful ability of i-phones to take photos and record videos. From what I can reconstruct, Mom was asleep in 10 minutes, I called two ex-boyfriends and Ainsley and Bailey laughed at both of our expenses until they also fell asleep.

We made it home from our adventure before 6 PM, all in one piece and promptly went to sleep, later to wake at 10 pm with the first evening hangover of our collective lives.


We had a great time in Napa, but there’s so much more to see, do, and yes, actually process than what we did. I look forward to returning one day soon and giving the wines, the beautifully cared for estates, and the people who tend them the time and attention that this fabulous slice of America deserves!

And for those of you wondering, Lawrence and Mom re-connected in the sober light of day and are now casually dating. They are the best-dressed couple wherever they go, but he has promised not to call her “Miss Preppy Pink Shirt” anymore.

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