One Perfect Day in Oahu

Follow our editor's itinerary for a day exploring Oahu—and spending as much time as possible outdoors

I spend every possible moment outside, especially during these early months when it’s freezing cold in my birthplace and first hometown of New York City. Weather notwithstanding, the Gathering Place and the Big Apple have more in common than you might imagine. This remote island has world-class museums, a thriving Chinatown community for shopping and dining, and it serves as both a home base and a touring destination for renowned musicians.

7 am: Paddle or Pedal

Starting with some exercise is always preferable. Take a spin class at Honolulu Holo Cycling Studio or stand-up paddle at Ala Moana Beach Park. That pau hana cocktail (see below, 6:30 p.m.) will be even more rewarding.


9 am: All Aboard

Because my two year-old daughter currently has a painful and all-consuming obsession with trains, we often make the trek out to Wahiawa, to Dole Plantation for a ride on the Pineapple Express, trying to make it back into town in time for lunch as dining in that area can be limited. On a rainy day, stay in town and visit the Honolulu Museum of Art or the Children’s Discovery Center.

12:30 pm: Lunch Break

A lunch of hand-cut pasta or fresh island fish at Town in Kaimuki or a vegan plate like the peanut-saucy Hanoi at Peace Café in Moiliili hits the spot.


3 pm: Sun & Sand

My favorite time to go to the beach is mid-afternoon (though on the Windward side of the island, at Kailua or Lanikai, morning is best as the sun goes behind the Koolau Mountains in the afternoon). You can stay all the way through sunset (in the winter months, the sun sets between 6 and 7 p.m.) without getting too much sun. Bring a book, sunscreen and a cold drink. And look for shells to create a piece of jewelry when you return home. Afterwards, take a cold outdoor shower when you’re finished and you’ll feel amazingly refreshed and ready for evening fun.

6:30 pm: Tropical Libation

I mentioned pau hana (happy hour) cocktails, didn’t I? For a mai tai, there is absolutely none better—the name “mai tai” actually means “none better”—than the Mai Tai Bar at Royal Hawaiian Hotel. 


7:30 pm: Dinner for Two

On the prowl for dinner, definitely try to find someplace with indoor/outdoor seating and, if possible, live entertainment. The Hau Tree Lanai at the Diamond Head end of Waikiki is a slam dunk for a romantic evening, but for a quality, inexpensive torch-lit oceanfront meal, live music included, Barefoot Beach Café cannot be beat. The only catch? No alcohol.