McSherry said he generally opts for the lower-key side of Cabo San Lucas by eating and sleeping at local joints (such as the charming boutique hotel Los Milagros, which is where I found him shirtless and keeping cool with a bottle of Pacifico).
"The first few years I went out and partied every night and sometimes went straight on the boat still drunk," he said. "I'm a bit long in the tooth for that."
This year, he even arrived a day after Hagar's birthday party to avoid the madness.
"You know, it's not just all-you-can-eat and two-for-one down here," McSherry said. "Go 15 or 20 minutes and you're in proper Mexico."
Fine, then on to San Jose del Cabo.
San Jose del Cabo
There's a reason San Jose del Cabo is fundamentally different from its rowdier cousin: It is about 250 years older.
Modern San Jose took root with the construction of a Spanish mission in 1730. Though the town wasn't always a tourist destination, about the same time that Cabo San Lucas was fashioning itself as party central, San Jose experienced a rebirth of its own that has become art galleries, restaurants serving authentic Mexican fare and cobblestone streets.
I started my San Jose experience away from its Old World charm, in the beachfront neighborhood of La Playita, a couple miles outside the town center. For years La Playita was a quiet fishing village on the Gulf of California that went relatively unvisited by tourists. But with its miles of pristine beach, the people who build things — in this case, Grupo Questro, one of the area's largest developers — decided that made no sense.
Voila: A marina was dug into a longtime beach and soccer field. Built on its shore was Hotel El Ganzo, which opened in late 2012. El Ganzo is a hip, stylish resort that embraces both the arts (there's a recording studio in the basement) and the fact that it is not Cabo San Lucas. What you will find at El Ganzo: friendly service, a stunning rooftop infinity pool and a quiet, private beach. What you will not get at El Ganzo: waiters pouring tequila down anyone's throat.
After a couple nights in La Playita — it's worth walking through the neighborhood to see the Mexico untouched by tourism — I moved on to a couple of nights in the heart of San Jose. It had been described to me as "elegant" and "adult," but the people who swear by Cabo San Lucas say it also is more boring.
Though a sedate little town, San Jose quietly is a sensory feast. The art is much of the reason, and on Thursdays during the high season (late October through May), the galleries stay open late into the night.
But even on a Sunday and Monday it was an interesting place to be. I'd explored town all of 15 minutes before coming across a 1995 Nissan Pathfinder painted in a chaotic splatter of blue, red, yellow, black, white and pink. As I looked deeply into the pattern — clearly they were meticulous brush strokes — the man responsible for Baja's most vibrant SUV appeared before me.
"I decided to create something unusual for in front of my gallery," said Metin Bereketli, a bandanna covering his head and a faint beard on his face. "I want to help the kids with a smile."
"How long did it take to paint?" I asked.
"Eh, a few months," he said.
Bereketli, who was born in Turkey, invited me inside to look at his paintings, which were largely in the same exacting style as his truck but as city centers of the world rendered on canvas. He offered a glass of red wine and explained why he prefers San Jose del Cabo to Cabo San Lucas.
"In San Lucas, to me, everyone is trying to sell something," Bereketli said. "This is a special environment — peaceful and relaxing. Here, people choose to enjoy art and food and wine."
It's so relaxing that when I happened to walk past the small stretch of San Jose shops where merchants hawk their products as aggressively as they do Cabo San Lucas, I was caught off guard; I had settled into a peaceful groove and forgot about Cabo San Lucas' crass commercialism.
It was no surprise that I met the most interesting people of my trip in San Jose. On my last night in town, some new friends (an American, a Mexican and a Spaniard) took me to Chileno Beach, along the ocean-hugging corridor between the Cabos, where we crawled over the rocks with an eight-pack of Pacifico to reach a private sliver of sand. After 30 minutes of snorkeling above luminous blue fish darting in and out of reefs, we sat on the beach until the sun went down and Venus rose, sparkling in the quiet dusk.
We were about 10 miles from Cabo San Lucas but couldn't have felt farther.
If you go
Cabo San Lucas
Stay: A block from the beach Bahia Hotel (bahiacabo.mx) is elegant but unfussy; rates begin at about $120. Near the action but not in it is Los Milagros (losmilagros.mx), a quaint, charming escape from the Cabo madness; rates start at $85. Cabo Cush (reservations available at eurobookings.com) is a quality inexpensive option, with welcome touches such as Mexican tile floors and rooms starting at about $40 per night.
Eat: Mariscos Mazatlan (corner of Narciso Mendoza and 20 de Noviembre) is a seafood favorite of locals and for good reason; the portions are hearty and fresh. Los Tres Gallos (20 de Noviembre, near Leona Vicario) serves classic Mexican food ("No Tex-Mex," a waiter proudly informed me). Bar Esquina at the Bahia Hotel serves creative, fresh food all day long. Gordo Lele's (Mariano Matamoros, near Lazaro Cardenas) is worth a visit to see owner Javier Reynoso Ramos sing Beatles songs, but the tacos are even better than his pipes. Rumari is a brew pub with quality takes on classic beer styles offers high-end meat and fish.
San Jose del Cabo
Stay: Casa Natalia (casanatalia.com) calls itself "chic boutique" and justifiably; it hits the intersection of elegance, charm and comfort and has one of the better restaurants in town. Room rates start at $165, but cheaper deals are common on the hotel website. El Ganzo (elganzo.com) is a luxurious, artistically oriented resort with a remarkable rooftop infinity pool. Rates start at $179 per night through Dec. 20, when they climb to $315 for high season. Drift Hotel (driftsanjose.com) is a spare, contemporary and affordable hotel at $75 per night.
Eat: Run by woman who owned a coffee shop in Santa Barbara, Calif., Drunken Sailor (ohnicnic.wix.com/the-drunken-sailor) offers cheap, fresh and interesting Mexican seafood, including a wonderful shrimp-and-heart-of-palm quesadilla, fresh ceviche and shrimp-stuffed falafel. Lolita Cafe (on Manuel Doblado) is fresh and delicious three meals a day. Mi Casa (Obregon 19) caters to tourists but does it well, executing legitimate Mexican fare such as mole and chiles en nogada.