Hawaii is a hike, and planning a trip there can be overwhelming—so many islands, so little time. Start with a visit to Oahu, and place yourself in the capable hands of Leea Evaimalo, who runs the concierge desk at the luxurious, year-old Four Seasons Resort at Ko Olina, just afield of Waikiki’s tourist crush. Here’s where she sends her guests.
Best new restaurant: Herringbone
Herringbone opened in August in Waikiki’s International Market Place, which has become a restaurant hotspot since it was redone two years ago. Standout dishes include lemony whole-fish ceviche, caramelized Hokkaido scallops with sweet corn, and lilikoi (passion fruit) panna cotta.
Emerging neighborhood: Chinatown
Situated at the end of Honolulu’s financial district, Chinatown is a melting pot of cultures, where you’ll find lei makers, fresh-seafood vendors, dim sum restaurants, and antiques stores. Every first Friday, vendors from around the island set up shop in the middle of the street.
Cocktail spot: Bar Leather Apron
Inspired by the tiny bars in Japan, Bar Leather Apron, located in downtown Honolulu, seats 25 people, max. The whiskey selection is fantastic, as is the detail-oriented service.
Under-the-radar museum: Shangri La
Shangri La is the former estate of heiress Doris Duke. Guided tours are available of the mansion, which showcases Duke’s vast collection of Islamic art.
Day trip: North Shore
When guests want to see another part of Oahu, I send them to the North Shore. Popular local spots include Pupukea Grill’s food truck, famous for its kalua pig quesadillas, Mokuleia Beach Park, good for swimming and collecting rare seashells, and Uncle Bryan’s Sunset Suratt Surf Academy.
Island-hopping: Big Island
I recommend the Big Island, which has a little of everything: lush valleys, waterfalls, hikeable dormant volcanoes, even a green-sand beach that gets its color from olivine rocks.
Poke pick: Da Hawaiian Poke Company
When I’m craving the fish salad, I head to Da Hawaiian Poke Company, a casual joint outside Waikiki. Options range from lobster to ikura (salmon roe).
Things to avoid: Dole Plantation
Steer clear of Dole Plantation, a tourist trap, in favor of Kahumana Farm or Ma’o Organics, which offer more authentic Hawaiian farm experiences.
A version of this article appears in the Sept. 15, 2017 issue of Fortune with the headline "The Gathering Place." We’ve included affiliate links in this article. Click here to learn what those are.