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Hawaii 101 City Trip

The beachfront setting of The Kahala Hotel & Resort

Days 1 & 2 Days 3, 4 & 5 Attractions

Hawaii for First-Timers

Have you been avoiding Hawaii because you disdain the tourist hype that often surrounds a packaged visit to The Islands? Well, it is entirely possible to visit the Land of Aloha to see what makes this place very special without feeling like a tourist. Read along and we'll give you a plan for five days starting on Oahu and ending on the Big Island. You'll see the Aloha State up close and we guarantee you'll want to come back for more.

The lure of Hawaii is such that virtually everyone around the world yearns to visit at least once. First-time tourists should make the island of Oahu their primary destination. After a few days sightseeing, playing and enjoying Oahu's natural beauty and unique charm, feel free to move on to another of Hawaii's magnificent isles. Here is our suggested five-day itinerary for your first trip to the 50th state, designed so it won't be your last.


Retreat at The Kahala

Fly into Honolulu, then rent a car. (Be sure to get an Oahu Drive Guide — it's free and full of useful maps.) Hop on to the H-1 Freeway and make your way through Honolulu to The Kahala Hotel & Resort, a beachfront oasis secluded from the crowds of Waikiki and the hotel of choice for visiting celebrities and those who appreciate privacy. The first order of business is to wander the grounds where you can check out the dolphin lagoon, order a drink from the bar and let the tradewinds whisk away all cares and concerns of the outside world. Dine this evening at Hoku's, a favorite of locals and visitors alike, and one of our Top 10 Hawaii Regional Restaurants. If you get there early enough, be sure to order the whole fried fish, a taste delight of which there are only a few available each evening. After dinner, perhaps take a moonlight stroll on the beach.

The dining room at Hoku's in Honolulu, Hawaii


Kailua Beach Park

Grab some coffee and a pastry and make your way to Kalanianaole Highway, which is just a minute or two from the hotel. Enjoy the gorgeous ocean views as you drive along the coast towards your destination, Kailua Town, and its famous beach park. Stop at Kalapawai Market (serving the community since since 1932) to stock up on provisions — you'll find absolutely everything you need for a day at the beach. Kailua Beach Park is just a block further, so park and find a shady spot to lounge away the time on one of the island's loveliest beaches. If you're feeling energetic, take a kite-sailing or windsurfing lesson from one of the vendors who set up shop on the beach every day. Otherwise, alternate between refreshing dips in the turquoise blue ocean and reading that lurid novel you've been saving.

At about 2 p.m., walk across the street and take an hour or so to hang out at Buzz's Original Steakhouse. No day trip to Kailua is complete without visiting the bar at this beachcomber-decorated hangout, where you'll definitely want to order one (only one!) of their famous Mai Tais. Getting back on the road, re-trace your route to the hotel, returning just in time to get ready for dinner in the city at Town, which is just minutes away in the neighborhood of Kaimuki. The restaurant's menu changes daily, but the focus on simple, yet perfectly prepared, dishes created from local, organic ingredients have made this spot one of the most popular restaurants in the city.

Continue to the Big Island on Day 3, 4 and 5


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