Eat, Beach, Repeat: A Sisters’ Getaway to O'ahu

When you arrive at HNL airport, pick up your rental car and head to your Waikīkī hotel to check in after your long travel day. Dinner at Side Street Inn caps the night—platters of garlic fried chicken and local-style pork chops, shared family style, setting the tone for a trip centered around comfort, laughter, and discovery. If there are only two of you, you’ll likely have leftovers, so staying at a hotel with a kitchenette or full kitchen will be key to enjoying those leftovers later.

Insider tip: The Kapahulu location of Side Street Inn has happy hour each day of the week with discounted small plates.

Jet lag works in your favor here—you’ll be up early, which is perfect for a morning hike to Manoa Falls. The rainforest trail is lush and shaded, ending with a dramatic 150-foot waterfall. Refuel with brunch at Moena Café (the banana chantilly pancakes are legendary and big enough to share). Spend the afternoon at Waimanalo Beach, a long stretch of sand framed by dramatic mountains, with fewer crowds than Waikīkī. Pick up a plate lunch from Rainbow Drive-In for an easy, casual dinner.

Insider tip: Bring water shoes as the Manoa Falls trail can get quite muddy.

This day is all about a mix of art, culture, and relaxation. Pick up fresh Leonard’s malasadas (Portuguese donuts) for breakfast on your way out of Waikīkī. These can be a messy, but oh so delicious, breakfast to eat on the go, so make sure you have plenty of napkins. Start with a morning tour of the Shangri La Museum of Islamic Art, Culture & Design (make sure to make online reservations in advance). The oceanfront estate and the art collection are absolutely stunning and are one of O'ahu’s most unique experiences. After the tour, head to Lanikai Beach, known for its calm waters and postcard-perfect turquoise hues. In the evening, explore Kailua Town and grab dinner at the Thursday night farmers’ market, where local vendors serve everything from poke bowls to freshly made pasta.

Insider tip: Parking in the residential neighborhood near Lanikai Beach is limited and not allowed on weekends or holidays, so weekdays are best.

Your itinerary for today is focused on exploring the famous North Shore. Drive to the North Shore and stop for an açaí bowl from Haleiwa Bowls on your way to Waimea Bay Beach Park. Get there early (before 10 am) so that you can be sure to get a parking spot in the beach park’s small parking lot. Note that depending on the season, the waves are either massive and thrilling to watch or calm enough to snorkel. No matter the season, Waimea beach is always lovely. On your way back, pick up cream pies from Ted’s Bakery and garlic shrimp from Giovanni’s Shrimp Truck, two North Shore institutions you shouldn’t miss.

Insider tip: On the North Shore in winter, the waves are massive and thrilling to watch; in summer, the water is calm enough for swimming.

If it’s Saturday, spend the morning browsing KCC Farmers’ Market or Kakaʻako Farmers’ Market, where stalls overflow with tropical fruit, local crafts, and island snacks. Graze your way through breakfast and lunch before returning to Waikīkī Beach for a relaxed afternoon of swimming and people-watching. Dinner can be as simple as enjoying leftovers or snacking on your farmers’ market finds.

Insider tip: Bring cash and reusable bags to reduce litter and make carrying your farmers’ market haul much easier.

Spend the morning floating in the calm waters of the Ko Olina lagoons, a series of man-made coves perfect for a leisurely swim. For lunch, stop at Tanioka’s for fresh poke and plate lunches. Leave the afternoon flexible, whether that means shopping, revisiting a favorite beach, or simply slowing down. For your final evening, visit House Without a Key in Waikīkī for happy hour. Sip their signature mai tai, savor a slice of coconut cake, and watch the sun set to the sounds of live Hawaiian music and graceful hula.

Insider tip: Arrive before sunset to snag a prime spot with an ocean view.

On your way to the airport, swing by Nico’s Pier 38 for one last fresh seafood fix. Grab cream puffs from Liliha Bakery to snack on mid-flight. If you’re a Costco member, fill up your rental car nearby for the best gas prices before returning it.

Insider tip: If you’re traveling with lots of luggage, save yourself some hassle by dropping your bags, and your travel companion, at the departures curb before returning the rental car. It makes the process much smoother, especially at busy times.