“Rich people like crystal meth, too."

"Yeah, just ask Bushwick."

We were sitting in a van on our way from the airport to the hotel in Waikiki, Oahu. Five writers from New York had been invited to Hawaii to pay tribute to the late Norman Collins, also known as Sailor Jerry. It was his birthday, and he had founded his small tattoo shop here 50 years ago in Chinatown where his famous flash art became hugely popular among servicemen. According to my guide, Paul Monahan, the area is as seedy as it was when Collins came back after a tour in the Navy during WWII. Crack, crystal meth, prostitution, tramps. "There's a lot of poverty,” he said. “No gambling, though. Gambling's illegal." Noted.

After going to the original location of Collins’ shop, which is still a tattoo parlor, I was eager to visit one of these famous brothels. I didn’t want this to be an ordinary (read: boring) press trip. Paul assured me that the brothels in Honolulu are similar to what you see in an old James Bond movie. He said he’d consider taking me to one and I believed him. I thought, underneath the dick jokes and copious amounts of spiced rum, this man has a heart of gold. Of course, Paul didn’t take me to a brothel, but he did take us to some of the seediest bars in Honolulu, including the Alley Cat, a place so weird it’s hard to describe, but if you’re curious I highly recommend this Yelp review. (For the record, Paul does have a heart of gold.)

Some magazines and websites are famously strict when it comes to writers accepting gifts from publicists or brands—something about conflicts of interests and journalistic ethics. Times writers, for example, can't accept a cocktail from a publicist, much less go on press trips like this one. Whatever. What does the Times know about trying to make a living writing on the Internet?! I was determined to have fun in warm Hawaii during the middle of winter. As it happened, it wasn’t that hard.

The best part of this trip and the Sailor Jerry brand is that, in addition to making clothes that I actually want to wear and spiced rum that I actually want to drink, its reps are people you legit want to spend time with. They are true reflections of a brand that prides itself on keeping the spirit of the original sailor in tact. OG Jerry had a massive influence on modern-day tattoo culture; he’s a cult figure with a legion of dedicated fans who ride or die for his flash art. (I considered getting a tattoo while in Hawaii—one featuring a blonde in thigh highs who seems to be touching herself—but I hadn’t had enough rum at that point to justify getting my first tattoo on a press trip.)

Back in New York, even though I didn’t go to a brothel or try any crystal meth or get that tattoo, I do feel closer to Mr. Collins and the legacy that has made him a household name among the hipster set. I’m not sure if that was the point of this trip, but I’ll take it.