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When planning a trip to Hawaii, it can be tough to decide on which island to visit. Here, we’ll help you make your choice by matching your personality to the kind of experience you want to have. Are you a nature lover who wants to see the waterfalls on Kauai or a party goer who would love the nightlife that Oahu has to offer? Here are our recommendations of where to stay, eat and play to make the most of your time in Hawaii based on your traveler type.

RELATED: The ultimate Waikiki walking tour

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Photo: Courtesy of The Laylow

Oahu: The Party Monster

You like to party all night with a hip crowd while checking out the trendiest Oahu spots. From the pumping club scene in Honolulu, to upscale dining in Ko Olina and drinking local beer with the surf crowd on the North Shore, the island of Oahu (Hawaii’s most populated) is the perfect place to hit the scene hard and never slow down.

STAY A couple great places to stay in Waikiki-based include The Laylow, a boutique hotel located on bustling Kuhio Avenue with retro Hawaii décor and a bar lanai with fire pits surrounded by a sand-covered floor; or the Prince Waikiki, newly renovated with open-air rooms that offer expansive views of the Ilikai Marina, an exclusive club lounge, a private 27-hole golf course in ‘Ewa Plain and the Hinana Bar with its stunning infinity pool. Need to recover after a few days of South Shore partying? Head to the Turtle Bay Resort on the North Shore for some peaceful R&R in one of the oceanfront beach cottages and a relaxing treatment at the Nalu Kinetic Spa.

EAT Enjoy the rooftop restaurant and lounge and live entertainment at after-hours nightclub SKY Waikiki. Grab a Mai Tai and hit the dance floor! In the Ko Olina area, check out The Olelo Room, an upscale bar and lounge at the Aulani Resort and Spa, where the bartenders are fluent in Hawaiian.

PLAY When you’re not clubbing, rent a luxury vehicle (like a Ferrari or Bentley) for the day from Velocity Honolulu and drive to the North Shore for a thrilling zip line adventure with CLIMB Works. The longest line is 2,500 feet and will definitely get the adrenaline going.

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Photo: Courtesy Grand Hyatt Kauai

Kauai: The Nature Lover

You want to experience the lush, green, tropical side of Hawaii, swim under flowing waterfalls and hike in the rainforest, as well as visit beautiful, isolated beaches and vast colorful canyons. Kauai is the place for you. With fewer crowds and a more laid-back vibe, this island is a nature lover’s dream.

STAY The Koloa Landing Resort, located in the Poipu area on the South Shore, is a wonderful resort for those wanting to have all the amenities of a hotel and a condo. Guest rooms have full kitchens, dining rooms and washers and dryers—great for washing the mud off your clothes after hiking Na Pali Coast. Swim under a waterfall in the pool, take a dip in the island’s only Japanese Ofuro soaking tub at the spa, or sink your toes in the sand at nearby Kiahuna Beach. For a five-star experience, another South Shore gem is the luxurious beachfront Grand Hyatt Kauai Resort and Spa. Guests can enjoy elegant ocean view guest rooms, impressive outdoor treatment rooms at world-class Anara spa, scuba diving lessons in the pool or an up-close-and-personal experience with a colorful macaw parrot.

EAT RumFire Poipu Beach at Sheraton Kauai offers a top-notch dining experience with gorgeous ocean views, knowledgeable wait staff, and an extensive menu including items such as Ahi poke, coconut-lemongrass soup, Japanese pear flatbread and Hawaiian paella. It’s an ideal place to dine on locally sourced cuisine while watching the sunset. For breakfast on the North Shore, stop by Hanalei Bread Company for an unforgettable French toast and freshly brewed cup of joe. Have a sweet tooth? Don’t miss The Fresh Shave food truck in Lawai where they make handcrafted shave ice with homemade, organic syrups.

PLAY See the Garden Isle from land and air with must-do outdoor adventures that include mountain tubing and a helicopter tour. Kauai Backcountry Adventures takes groups on a wet inner tub ride through abandoned irrigation canals with long, dark tunnels (don’t worry, a head lamp is included). It’s a great way to see the hard-to-reach backcountry landscape. Next, take to the air with Blue Hawaiian Helicopters for an aerial view of the breathtaking Na Pali Coast, scenic Waimea Canyon (the Grand Canyon of the Pacific), impressive “Jurassic Park Falls” and Mt Waialeale, the wettest spot on Earth. These adventures will be stored in your memory bank for years to come.


Photo: Courtesy Sheraton Maui Resort & Spa

Maui: The Adventurer

You’re always up for an adventure and Maui won’t disappoint. The Valley Isle offers hiking through a bamboo forest and swimming under a waterfall en route to Hana to getting up at 3am to watch the sunrise and then cycle down Haleakala volcano to tackling the wind and waves while windsurfing at Ho’okipa, Maui is a destination for adrenaline junkies.

STAY If you want to snorkel with tropical fish and sea turtles, watch a Hawaiian cliff diver splash into the ocean, or hop on a catamaran for a sunset cruise, then the Sheraton Maui Resort & Spa is the place for you. Located at the end of Ka’anapali Beach, this resort features an on-property luau, an open-air relaxation lounge at the spa and ocean view suites with private lanais. For a more local, boutique hotel experience, the Paia Inn (in a historic 1920s building) offers charming accommodations in the heart of the laid-back surf town of Paia. Rooms range from petite to a three-bedroom beach house.

EAT Mama’s Fish House, located on Maui’s North Shore just past Paia, is a Hawaiian classic that has been serving locally caught fish daily since 1973. It offers an upscale dining experience with contemporary Hawaiian décor and open-air seating and a menu that includes items such as Tahitian prawns, Tristan Island lobster tails and the fish of the day. If you’re craving beef instead, grab a gourmet burger and a bourbon at Cow Pig Bun in Kihea.

PLAY Forget looking at a waterfall. Instead, how about rappelling down it instead? Rappel Maui offers a chance to “walk on the wild side” during their rappelling that takes place in the lush tropical rainforest where Jurassic Park was filmed.

ALSO: Don’t go chasing waterfalls, chase travel discounts instead. Join Orbitz Rewards and start saving!


Photo: Courtesy Hilton Waikoloa Village

Big Island (Hawaii): The Road Tripper

You like to roam the open road and take in scenery, food, and culture along the way. Circling the Big Island is the longest road trip in Hawaii —it takes about six hours. On your drive, you can explore an active volcano, ancient burial grounds, expansive lava fields, lush rain forests, black and green sand beaches, panoramic views of Waipio Valley, paniolo (cowboy) country and more.

STAY When not on the road, relax and unwind at the extraordinary Hilton Waikoloa Village spanning 62 acres—with trams and canal boats to help you get around. Although with a tropical fish-filled lagoon pool, 175-foot waterslide, Legends of Hawaii luau, dolphin experience, topnotch spa, award-winning restaurants, two championship golf courses and boutique shopping, you may never get back on the road! For more casual accommodation, Hamakua Guest House and Camping Cabanas offers screened-in cabanas with hammocks instead of beds.

EAT Fuel up for your road trip with a stop at Punalu’u Bake Shop & Visitor Center where you can pick up macadamia nut shortbread cookies, a loaf of Hawaiian Sweetbread, a cup of Ka’u coffee, fresh fruit salad or a local plate lunch. Enjoy dining in the outdoor gazebos on this lush four-acre property, or get your food to go and hit the road.

PLAY On the North Shore between Hilo and the Waipio Valley Lookout is the Hamakua Heritage Corridor, This hour-long scenic drive will take you past the Hawaii Plantation Museum, the Laupahoehoe Train Museum, several lookout points, Kalopa State Recreation Area and Hamakua Forest Reserve, Hawaii Tropical Botanical Garden and Akaka Falls State Park.


Photo: Courtesy Four Seasons Lanai

Lanai: The Romantic

You want to snuggle up with your significant other in an oceanfront hammock while sipping Mai Tais and watching the sunset, get a couple’s massage at a world-class spa and enjoy an exquisite meal under the stars. Lanai, the smallest inhabited Hawaiian island, once owned by Dole and used as a pineapple plantation, is the perfect island escape for lovers. 

STAY Perched above perch on peaceful Hulopoe Bay, the elegant Four Seasons Resort Lanai is an island sanctuary with nine restaurants, a full-service spa, botanical gardens, pool sanctuaries (a.k.a. cabanas), a large selection of posh suites, high-end boutique shopping, and access to golf, tennis, snorkeling, horseback riding and more. It’s the perfect couple’s escape. For a charming boutique hotel experience, the historic Hotel Lanai, located in Lanai City (the only city on the island), has 11 guest rooms in a garden setting and an “old Hawaii” ambiance.

EAT Recognized worldwide, Nobu Japanese restaurants are known for imaginative cuisine. Nobu Lanai at the Four Seasons Lanai, offers a fine dining experience with specialty sushi, classic dishes and teppan-yaki in a sophisticated setting.

PLAY Snorkel hand-in-hand at the Hulopoe Bay marine sanctuary where it is not uncommon to spot Hawaiian sea turtles, bottlenose dolphins and a plethora of colorful tropical fish. Four Seaons guests can check out complimentary snorkel gear. Land lovers can pack a picnic lunch and take a 20-minute hike along the southern cliffs to view Lanai landmark Puu Pehe, aka Sweetheart Rock.


Photo: Courtesy National Park Service

Molokai: The Introvert

You want to avoid the crowded beaches and resorts, and live like a local. Molokai has remained mostly untouched by throngs of tourists and offers a magical escape for those who want solitude and a rural escape—without a single stoplight.

STAY The rustic Hotel Molokai is the only hotel on the island. It is a three-star accommodation that is affordable, on the beach, and offers bungalow accommodatiosn with kitchenettes and private lanais, as well an on-site oceanfront restaurant. Situated near the island’s largest town, Kaunakakai, it allows easy access to restaurants and shopping (though you won’t find any designer boutiques or high end restaurants).

EAT While the eateries are casual, the food is “ono” (delicious). Family-owned Paddler’s Inn Restaurant and Bar offers dining on a covered lanai, live entertainment, and serves breakfast, lunch and dinner with menu items such as a variety of burgers (like the tomato jam burger and the black & blue burger), ginger scallion tofu, and furikake chicken wings (with a Hawaiian butter glaze).

PLAY Ride a mule down 1,700 feet of the world’s highest sea cliffs to the remote and once forbidden village of Kalaupapa (now the Kalaupapa National Historical Park), former home to banished lepers from the late 1800s to 1969. During the tour you’ll see stunning landscape, learn the history of the leper colony and the people who lived there, and experience several endangered flora and fauna that can only be found in Hawaii.

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Tagged: Destinations, Hawaii

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Sharael Kolberg |
​Sharael, founder of Family Travel Channel (, has been writing about travel since 1995. Her work has appeared in Sunset magazine, Outside magazine,,, and many others. Follow her on Twitter @FamTravChannel, FB and Instagram @FamilyTravelChannel. See more of her work at
Sharael Kolberg |


Where to stay, where to eat, and what to do once you arrive. Follow me on Instagram @familytravelchannel. #familytravel #travelblogger #influencer
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