Carmel-by-the-Sea proved perfect for conference and anniversary

For those who know their balance of airline miles and hotel rewards points, travel is just part of the job. There are those trips, however, that surprise even the most seasoned business traveler. A recent visit to Carmel-by-the-Sea, California, was just that for this frequent flyer, who had seen six states in the previous few weeks.

This would have been just a routine business trip were it not for a 10-year anniversary that had me looking for something special. Plus, my wife, Jamie, could not have been more deserving of a break from our young, rambunctious kids. I suggested she join me to extend a business trip to Carmel-by-the-Sea; the location definitely helped me score some big-time good husband points.

Getting down to business

You won’t find traditional hotel brands in Carmel-by-the-Sea, so for those looking to build up their points stash, you’ll need to bench that idea this time. But you’ll actually want to with all of the cool inns tucked away here.

When the standard hotel conference room is what you expect, walking into one that overlooks the ocean, where some of the greatest minds have stood to launch new initiatives, well, that was quite a thrill. We were at La Playa Carmel to prepare our team for the future as we finalized a merger.

I had the privilege of standing in the room where Steve Jobs unveiled the first Macintosh prototype to his team and board. Pro tip: Make sure you ask what else happened that weekend when you visit.

Carmel-by-the-Sea was beyond obviously a great place for an executive retreat or conference.


From sun up to sun down, Jamie and I caught glimpses of each other and shared crowded moments. From the boardroom, I’d look out the window and see her walking back from the beach with her book. While in the hotel bar, we mingled and shared conversations with others, and in the morning, grabbed coffee together at breakfast alongside others. In some ways, it was like when we had just met—always together, but never entirely alone.

During breaks, I was often with Jamie in my mind walking along Carmel Beach, feeling the sand under my feet, chatting over the susurrus of waves rolling into the beach. I pictured her stopping to meet dogs and their people, while I caught glimpses of Pebble Beach where the greatest golfers meet each year for the U.S. Open.

After our meetings, I was ready to spend some time with Jamie in full vacation mode. We power-walked to the beach at first opportunity.

Progressive dinner

Early on when we were dating, we would get together with friends and have progressive dinners—where each house would serve a successive course. We had never applied that concept to a vacation—until this trip!

We started one afternoon taking an Uber south about 30 miles from Carmel-by-the-Sea on Highway 1, a spectacular ribbon of highway that hugs the California Coast, to Nepenthe. This historic Big Sur restaurant overlooks the Pacific Ocean, from 800 feet above it. The word “Nepenthe” is derived from the Greek, meaning “no sorrow,” and with views like this—and food and wine to match—it was hard to imagine anyone feeling sorrow here.

Though, we did feel a moment of it after missing our ride home and discovering the limited Wi-Fi and cell service. The result of our poor planning, however, meant we got to enjoy a second bottle of Santa Lucia Highlands wine, and later, great conversation with a taxi driver who had lived in the area for more than 50 years. He told stories that made the drive back hugely entertaining. His family had moved to the region when his father was stationed there in the Army. As we crossed over the famous Bixby Bridge, we listened to a “spirited” story about how some of the builders of the bridge remain.

As we arrived back in Carmel-by-the-Sea, we had to pay homage to one of the most famous innkeepers in the area, Clint Eastwood. My mother-in-law, who’s a big fan of his, would not have forgiven us had we not stopped at the Mission Ranch. The Mission Ranch has a long history in Carmel, first as one of California’s earliest dairies, then as a private officer’s club during WWII, and now as a gorgeously restored property with rustic, contemporary accommodations, delicious food and wine, and relaxing views. With lovely live music, delicious wine, and crab cakes, it made it difficult to leave for our next stop.

We pried ourselves away from the heated patio and relaxing view of the mascot sheep that call the ranch home, and went to the Vino Napoli Wine Bar. The wine bar shares the kitchen with Little Napoli, so options for food are extensive. The bad-ish news is, the menu has so many choices that you have to go back again and again.

Being true to our progressive dinner approach, we ordered the truffled gnocchi appetizer at the recommendation of our server. I loved the crispness that came from the truffle oil and melted fontina cheese surrounding each piece of gnocchi. Next time, we are going to check out their Tribute to Sinatra, a plate of oven-baked ziti with spicy house-made sausage, mushrooms, and mozzarella, and Sgt. Pepe’s 1944 classic meat lasagna, which comes from an old family recipe brought back from WWII.

The star of the show was the Old Fashioned Reserve.

We chose the wine flight of seasonal reds which included two regional wines—a Pinot Noir and a Cabernet Sauvignon—and a Chianti from Italy. The star of the show, however, was from Doc Pepe’s Lab, an Old Fashioned Reserve. The rye whiskey, aged in Caribbean rum barrels for 100 days, gives it a smoky-sweet flavor. It was the best drink of the entire trip.

Heading for the main course, we needed to stretch our legs, so we strolled down Dolores Street, passing several art galleries we had seen earlier that morning. Their evening lighting made the entire street feel like it was all part of the display of Carmel-by-the-Sea—everything in its place, but with a surprise around every corner and in each window. From the fountains in the courtyards to every gallery, there was always something to spend that extra moment appreciating, both in the environment around me and in the person who has been my partner for 10 years and counting.

We crossed Ocean Avenue, making our way to Flaherty’s Seafood Grill and Oyster Bar. For drinks, we went with Ken’s Ultimate Bloody Mary, which was spicy enough to awaken the senses, and included a giant prawn that could easily double as an appetizer.

We paired the spiciness of the drink, with their clam chowder and seafood risotto, which broke our rule of only one course per location, but we both really like clam chowder! What was unique about their clam chowder was both its consistency, and it was gluten-free. The scallops in the seafood risotto were some of the best we have had. They were cooked perfectly and had a wonderful texture.

Rounding off the restaurant tour

The next step should have been dessert. Instead, we opted to head up to Vesuvio’s Starlight Rooftop Lounge, where I was able to partake in another of those Doc Pepe’s old-fashioned cocktails, while Jamie chose the Purple Margarita, two great nightcaps that capped off a once-in-a-decade day for us. It was a great evening with fantastic food, conversations about the kids, how our travel plans somehow always become adventures because we fail to plan, and just enjoying spending time together.

It’s all about the people

While this trip was special for Jamie and me, it would not have been so amazing if not for the exceptional service, and the wonderful people we met throughout our trip. People like J.C. and his brother at Nepenthe, or Vicente and Amit who we shared breakfast with at La Playa, along with Resh, Deni, and Brian—also at the La Playa—who made us feel like we were meant to be there, and taught us some of the hotel’s history. The service everywhere we went, from Flaherty’s to Vino Napoli to Starlight to the local coffee shops and art galleries, was amazing. This is a community that welcomes you, with people who seem genuinely glad you’re there. Now, we return to the kiddos and our normal schedules, knowing we’ll be welcomed back to Carmel-by-the-Sea in future visits.

We felt like celebrities flying in and out of Monterey. We took a direct flight from Phoenix into this intimate, classy airport. After landing, we discovered we could have gone from tarmac to car in 10 minutes. On the way out, we were in no hurry so, went upstairs to their restaurant. The food was impressive, and so was the view. The bay vista set the stage for the military, private, and commercial aircraft coming and going. It made for an excellent last view of a truly memorable trip.

Get a taste of Carmel-by-the-Sea.

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