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Oahu for dudes
Making the most of Oahu as a single guy
The Hawaiian Island of Oahu is a great place for a man to get out and explore. Whether you’re flying solo or you’re just dropping your lady off at a shopping mall (or the salon) for the day, there’s plenty for a guy to do to get in touch with his machismo and unbridled masculinity.
One of the last times I was on Oahu, Tawny and I were staying downtown at a local hotspot, the Hotel Renew. It was the ideal location because it offered easy access to the main strip of downtown Oahu and a quick escape out of the city when we needed it. Tawny had been planning a spa day complete with hair and shopping, which more or less sounded to me like being water-boarded. It was up to me to make alternate plans.
I set to work immediately. One of the great ambitions of my life at the time was to get a straight-razor shave in a barbershop. This type of manly treatment is a dying art, but Mojo Barber Shop & Social Club, in Honolulu’s Chinatown, is one of the last bastions of gentlemanly style left in the world. The place is a swanky hole-in-the-wall, smack in the middle of the arts district. The folks at Mojo offer the works: haircuts, beers, and all of the most in-demand games on TV. Not to mention that Mojo employs a number of beautiful woman who gladly will remove your morning beard with a lethal weapon. To be completely honest, the experience was almost too many dreams coming true at once.
With my cheeks as smooth as a baby’s bottom, I headed for Route 72 and high-tailed it in my rented Mustang out of town, toward Hanama Bay. A lot of my favorite hiking spots studded the journey along the coast. No. 1 on the list, of course, is Diamond Head, with its classic hike to an old WWII-era bunker that offers flawless views of downtown Oahu and the sapphire waters that hug the entire island. Another of my faves: the Koko Head Trail, an old rail car trail that climbs hundreds of steps to a summit with a (nother) panoramic view.
I wasn’t stopping for hikes today, though; I had 200 some horses to push along the serpentine highway that courts the coastline and is robed in sea spray on blustery days. Not only is this the most stunning length of roadway on Oahu but it is also a treasure trail that leads straight to Kailua—or more importantly, to Cinnamon’s Restaurant. Cinnamon’s is famous for being one of Oahu’s best spots for breakfast. On the morning I visited, I had a stack of guava chiffon pancakes. Don’t let the guava part fool you; this stack of pancakes was huge. Devouring it tested my manhood and I aced the test with flying colors.
Viewfinder Tip: Consider spending a little extra for a convertible. The highway that follows the edge of Oahu is often mere feet from the sea.
After Cinammon’s, I took Route 72 back up through the mountains, and felt the weather change around me almost instantaneously. Next, from the Pali Lookout, in Nuuanu, I marveled at the cliff where King Kamehameha had his decisive battle that united the Hawaiian Islands. Driving up to this site proved to be too much of a temptation not to stop. An added bonus: gale-force winds that rip through the narrow cut in the mountain provided a fun challenge to see if I could fight them and stand up straight and tall. To be honest, walking to the viewing rail was, surprisingly, one of the more exhilarating experiences of my life.
That night I sought to go out where the locals go, and ended up in Honolulu at a restaurant/lounge named Town. The eatery has a rotating menu of dishes that are just as much art as they are haute cuisine. For me though, the biggest sell was the bar; bartenders keep a huge selection of artisan liquors and know how to use these tools to manifest your dreams into cocktail form. I thought I was a staunch bourbon man until my mixologist converted me to the wonderful world of Mezcal (a pure agave cousin of tequila.) By the time I met Tawny for dinner that night I had been reborn into a new man. Aloha, indeed.
How do you like to spend a guys’ day in a new place?
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Chris and Tawny have had articles and videos published on USA TODAY TRAVEL, BBC Travel, Matador Network, as well as appeared as guest stars on TLC Asia's Fun Taiwan television series. When not on the road, you can find Chris and Tawny nestled in their home in Tacoma, Washington fueling up on coffee and cat cuddles while planning their future adventures. You can follow their travels on their blog, Instagram, and YouTube