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Which Hawaiian island is the best for your next vacation?

Which Hawaiian island is the best for your next vacation?

Kahala neighborhood with Leahi in the backgroundKahala neighborhood with Leahi in the background — Photo courtesy of Hawaii Tourism Authority (HTA) / Tor Johnson

The idyllic islands of Hawaii are a year-round paradise and the lingering days of summer are one of the busiest times to visit. While all of the islands are equally beautiful, they each have a unique charm that appeals to different travelers depending on the type of vacation you’re looking to have.

For starters, if you’re planning on renting a car to drive around the islands, it would be wise to book your car first as inventory is extremely limited and tends to book weeks and even months in advance.

Or skip the traditional car rental services and check out the San Francisco-based startup Turo, a peer-to-peer car sharing marketplace where locals rent out their personal vehicles on the platform. The entire booking process is seamless and all communication is done through the app (or desktop). The platform inventory ranges from the popular Jeep Wrangler to the ultra-luxury Bentley Continental GT Convertible.

Before you book your car, start planning your trip. This guide to Hawaii will break down some of the islands, what to expect on each island and the best things to do while you’re there.


Maui may be the island that most travelers think of when planning a tranquil beach vacation in Hawaii, but fancy resorts are not all that the island has to offer. From the sparkling coastline of West Maui to the lush vegetation of the east, there is something on the island for everyone.

Wailea is most famous for the cluster of upscale resorts that dot the glistening stretch of Wailea Beach. Well-appointed resorts offer a wide selection of amenities and experiences that give guests no reason to leave the property. Among those is Four Seasons Resort Maui at Wailea, which delivers luxury accommodations and exceptional service in an airy oceanfront setting.

Four Seasons Resort Maui at WaileaFour Seasons Resort Maui at Wailea — Photo courtesy of Rich Stapleton

Restaurant standouts at the resort include Spago from renowned chef Wolfgang Puck and the Italian-inspired Ferraro’s Bar E Ristorante, which features seafood, pasta and wood-fired pizzas.

Families traveling with kids should consider Grand Wailea Maui, A Waldorf Astoria Resort, which boasts a Lava Tube water slide and several other kid-friendly amenities including lawn games and an interactive luau.

Lava Tube water slideLava Tube water slide — Photo courtesy of Grand Wailea, A Waldorf Astoria Resort

Turn your Maui memories into a magical keepsake with a fun family affair and book a private sunset photo session with local lifestyle and wedding photographer, Matias Ezcurra.

Photo shoot of couple in MauiPhoto shoot of couple in Maui — Photo courtesy of Matias Ezcurra of @matiasezcurraphotography

On the west side of the island, check into The Ritz-Carlton, Kapalua, a quaint, oceanside oasis which is also home to the Honokahua Preservation Site. Cozy up in front of the outdoor fire pits at Banyan Tree, the hotel’s signature restaurant, and enjoy a farm-to-table menu that celebrates Hawaiian flavors.

Aerial shot of The Ritz-Carlton, KapaluaAerial shot of The Ritz-Carlton, Kapalua — Photo courtesy of The Ritz-Carlton, Kapalua

Hawaii has been practicing farm-to-table cuisine far before it became a worldwide culinary trend. The Maui Tropical Plantation will take you on a tram ride through the fields to learn how sugarcane, pineapples and coffee are grown.

In the Lahaina Getaway shopping center, the female duo behind Moku Roots founded a popular casual vegan eatery that is nearly 100% sustainable. You won’t find any single-use plastic here – even the sandwiches and burritos are wrapped in ti leaves in lieu of to-go containers.

View of West Maui mountains from a farmView of West Maui mountains from a farm — Photo courtesy of Hawaii Tourism Authority (HTA) / Dana Edmunds

Walk around the former whaling village of Lahaina, where cute boutiques and notable restaurants line the street, including Fleetwood’s on Front Street, owned by rock legend Mick Fleetwood. Reservations are hard to come by and typically book a month out, but the best time to dine here is during sunset hour. Make sure to request a table on the open-air rooftop to get the best views and enjoy live music everyday at 7:30 pm.

Fleetwood's on Front StreetFleetwood’s on Front Street — Photo courtesy of Brendan Smith

Traveling to Maui without driving the Road to Hana is like visiting Paris without seeing the Eiffel Tower. The 64-mile road trip consists of narrow roads and hairpin turns, but you’ll be rewarded with some of the most scenic views in Maui.

When you get to the northern coast, you’ll pass through a small town called Paia where you’ll find Mama’s Fish House tucked away on the sand. It’s one of the most sought-after seafood restaurants in Maui, with stunning sunset views and delicious food and cocktails to match.

Jeep driving on the road to Hana with beautiful ocean viewJeep driving on the road to Hana with beautiful ocean view — Photo courtesy of Hawaii Tourism Authority/Tor Johnson

Maui beaches are just as beautiful above water as they are underwater with an abundance of tropical marine life on display. Maui Kayak Adventures will take you on a kayak and snorkel tour in Olowalu, depending on the weather, to spot colorful creatures – and if you’re lucky, you might even find a few sea turtles.


The island of Oahu is oozing with culture, natural beauty and a vibrant nightlife ideal for travelers who love the beach but also like to get lost in a bustling city. The Ritz-Carlton Residences in the heart of Waikiki Beach is a convenient lodging option after a long day of adventures. The property boasts 552 residential-style suites that are all ocean-facing and operate similar to a hotel.

Guests can enjoy facilities like the rooftop infinity pool overlooking the city’s skyscrapers, the 24/7 fitness center and daily housekeeping services, all while enjoying the conveniences of a home including an in-unit washer and dryer and a full kitchen.

Rooftop poolRooftop pool — Photo courtesy of The Ritz-Carlton Residences, Waikiki Beach

If you’re lucky to snag a reservation at the 16-seat omakase-style restaurant on property, Sushi Sho, you won’t be disappointed. Quiora, the other restaurant on property, serves delicious homemade pastas and steak in an open-air setting with nightly live music. Try the porcini pappardelle for a hearty vegetarian dish.

For a more traditional Hawaiian-themed resort, check out The Kahala Resort, a seaside property nestled in the quiet residential neighborhood of Kahala where high-profile guests such as Princess Diana and President Obama have once visited. Get pampered with one of their signature spa treatments held in private treatment rooms furnished with a glass-enclosed shower and separate deep-soaking tub.

Aerial view of The Kahala Hotel & ResortAerial view of The Kahala Hotel & Resort — Photo courtesy of The Kahala Hotel & Resort

Swimming with dolphins in their natural habitat is a once-in-a-lifetime experience that you can do at Waianae Harbor. Unlike other dolphin tours where the marine mammals are held captive in lagoons, guests on the Dolphins and You tour are able to swim in the ocean just a few feet away from large pods of Hawaiian spinner dolphins playfully swimming and slapping the water. Book the early morning tour for a better chance of dolphin sightings.

Spinner dolphinsSpinner dolphins — Photo courtesy of Island of Hawaii Visitors Bureau (IHVB) / Emily Dickey

In downtown Honolulu, chef Peter Merriman is no stranger to Hawaiian cuisine with a number of acclaimed Hawaii restaurants under his belt. Like the other outposts spread across the islands, Merriman’s in Honolulu follows suit, serving elevated comfort food with a nod to local farmers and seasonal ingredients.

No trip to Hawaii would be complete without watching a sunset and it’s even better when you’re on a boat. Set sail from Kewalo Basin Harbor with Hawaii Nautical for a 1.5 hour group cruise toward Diamond Head and then watch the sun as it sets over Waikiki.

Catamaran cruise during sunsetCatamaran cruise during sunset — Photo courtesy of Hawaii Tourism Authority (HTA) / Kuni Nakai


Arguably one of the more underrated Hawaiian islands, Lanai is the state’s smallest inhabited island and is just nine miles away from Maui. Back in the day, Lanai City was a plantation town and the island was responsible for 75% of the world’s pineapple production. Today, Lanai blends luxury accommodations with the rugged outdoors to create an untamed haven for travelers that seek both adventure and tranquility all in one.

Four Seasons Resort LanaiFour Seasons Resort Lanai — Photo courtesy of Barbara Kraft

The main attraction and one of only two hotels on the island is the Four Seasons Resort Lanai, a luxurious oceanfront property that overlooks Hulopoe Bay. Southern California guests will feel right at home with two of the city’s hot spots located on-site: Malibu Farm and Nobu. Take a guided tour of the island in an open-air Jeep or saddle up for horseback riding through the mountains.

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