A Perfect Day in Kahala

Kahala may not be an area that comes to mind when you think of destination locations in Honolulu, but it’s a hidden gem just moments away from the busy streets and beaches of Waikiki where you will find pristine beaches, quiet strolls, and good eats. Kahala is also home to some of the most expensive houses in Hawai‘i, with oceanfront mansions lining the entire length of Kahala Avenue (for those with an interest in architecture or design, this is a different kind of paradise—just wandering down the avenue brings into sight designs by Vladimir Ossipoff and Roy K. Yamamoto).

For the early to rise: If you and your partner want to enjoy some of the best views on the island, then the Diamond Head hike is ideal. Beat the heat and the crowds by getting there bright and early—the trail opens at 6 a.m.—and snag an amazing rosy view. The 0.8 mile trail is suitable for all ages, but wear proper footwear and bring water. At the summit you will enjoy a 360-degree overlook, with Honolulu to the west and neighborhoods from Kahala all the way to Koko Head to the east. During the fall and winter months, you’ll even be able to catch the sunrise over the ocean and city.

Breakfast hour: If you’re in need of nourishment after the hike or just getting going and need to fuel up, Monsarrat Avenue offers a variety of options for breakfast. Diamond Head Cove Health Bar boasts fresh smoothies, juices, and acai bowls. Tip: They don’t accept credit cards or checks, so make sure you have cash. On the other hand, if you’re in the mood for a bit of a Hawaiian twist on classic breakfast, check out Diamond Head Grill. They have simple offerings of eggs, breakfast meats, fried rice, pancakes, and the classic loco moco. Diamond Head Grill is a counter-service-style restaurant with several picnic tables out front for customers.

Day cruising: Kahala is best utilized as a beach day, so next, pack your beach things and a picnic. It’s easy enough to get the perfect smorgasbord together at Kahala Mall, where Whole Foods has a large selection of organic prepared foods such as sandwiches, salads, sushi, as well as grocery goods that include a variety of fresh, locally grown fruits and vegetables to pair with their cheeses and meats. Tip: Make sure to bring plenty of water, as only one of the beaches in Kahala has drinking water. Tip no. 2: If you want to bring booze, make sure to add cups to the list, as it is technically against the law to sip an alcoholic bevy on any Hawai‘i beach.

Lei Hawaii - beach entrance

Beach, beach, and more beach: All the beaches in the area can be found off Kahala Avenue and are accessible whether you choose to walk, bike, or drive. There are several beach-access paths—denoted by blue signs—along the avenue, each offering small, white-sand beaches that are rarely crowded. If the tide is low, check out the access at Kahala Avenue and Hunakai Street for a lovely sandy spot, the perfect place to kick back and relax. When the tide is high, your safe bets are the access points between Pueo Street and Wai‘alae Beach Park. Thanks to the low traffic and typically mellow water, you are in the ideal place for paddleboarding, kayaking, and snorkeling. If you choose to snorkel, go out a few hundred feet beyond the break. Many don’t know it, but it’s bustling with sea life. Just be careful if there seems to be large waves or a strong tide, as most of these beaches do not have lifeguards. Keep in mind the Hawai‘i mentality for ocean safety: “When in doubt, don’t go out.”

A rare afternoon swim: Also tucked away in Kahala is a unique experience: swimming with dolphins at The Kahala Hotel and Resort (5000 Kahala Ave.). These exciting encounters offer “face-to-face, in-water contact” with their six dolphins and can be booked in lengths from 15 to 90 minutes. Be sure to make your reservation early, as spots are limited and in high demand.

Lei Culture - Kahala Hotel

Sundown wind-down: Head to the east end of Kahala Avenue to the Kahala Resort and Hotel (or stay put, if you just wrapped up a face-to-face moment with a dolphin), where award-winning bars and restaurants offer a wide selection of delicious cocktails and food. The Plumeria Beach House and The Veranda are the perfect settings to enjoy a drink at sunset or settle in for a full meal. Try the very tropical Royal Pine or the ever-popular Mai Tai. You also can’t go wrong with the burger.

If you’re looking for something a little different for dinner, make your way to The Olive Tree (4614 Kilauea Ave). This no-frills, counter-service restaurant serves fresh and delicious Greek fare. You really can’t go wrong with any of their main dishes, and their sides are yummy too. It’s also BYOB with a wine shop conveniently located next door. It does get crowded and seating is limited, but showing up when they open at 5 p.m. or after 8 p.m. will usually get you a spot.

After sunset: Snag some air conditioning and some more snacks by heading to Kahala 8 Theater in Kahala Mall. This theater not only screens top blockbuster hits but is also one of the few spots in the islands that features acclaimed independent, foreign, and art films. Weekend showings and openings can get crowded, but during the week you should have no problem getting tickets or seats.

Or, grab a dry towel and go back to the favorite beach you discovered during the day.  Spread the towel out over the sand and have a seat. Lean into your partner for a relaxing moment together soaking up the sound of quietly lapping waves and the twinkle of the stars. Like we said, Kahala is best enjoyed from the beach.