Hawaii always tops travelers’ lists, and the islands have become almost mythical in many would-be visitors’ eyes. But after deciding to visit America’s 50th state (which is always a good idea), where to go in Hawaii is the second most crucial step. There are a total of eight main islands in the Hawaiian archipelago in the North Pacific, though Niihau and Kahoolawe are forbidden to visitors. Of the remaining six—Hawaii Island, Kauai, Lanai, Maui, Molokai, and Oahu—each island is unique in its ambiance and attractions, and all are perfect winter travel destinations.
Hawaii is renowned for its natural beauty, but the culture and heritage of the islands are equally enticing and waiting to be explored. We’ve categorized each island according to interests—whether you’re intrigued by tropical adventure, secluded luxury, or cultural immersion, we have something for everyone in the list below. From the legendary surf of Oahu to the breathtaking mountains of Kauai, read on for your ultimate guide to the Hawaiian islands.
Credit: Katherine Parker-Magyar
The Island of Hawaii
The Island of Hawaii is a must-visit for travelers yearning to reconnect with nature and experience what is known as the ‘old Hawaii’—as in, before the islands became as popular as they are today with tourists. The largest of the Hawaiian islands, the Island of Hawaii is nearly double the size of all the other islands combined, hence its nickname as the “Big Island.” Hawaii Island is also known as the Island of Discovery, and there’s much to explore in the island’s two distinct regions: the Kona and the Hilo areas of the island. Kona, located on the western side of the island, is sunnier and the volcanic landscape is home to coffee farms and breathtaking views of the Pacific—we recommend staying at Fairmont Orchid on the Kohala Coast, to maximize that tropical bliss. Explore the black sand coast of Punaluu Beach and visit the five-acre farm of Kona Natural Soap, located just south of Kona in the town of Holualoa, for a tour (and chocolate-tasting) with the charismatic owner, Greg Colden. King Kamehameha spent his last years in Kona, and you can get in touch with royalty yourself with a Hāloa ʻĀina Royal Hawaiian Sandalwood Tour up in the highlands.
Island of Hawai'i
Island of Hawai'i, Hawaii, USA
It rains more in Hilo, and travelers are advised to explore the waterfalls and tropical flowers that flourish on this lush part of the island. Check-in at the Hilo Hawaiian Hotel and explore the Haleolono fish pond before embarking on an ATV tour with the charismatic guides at The Umuama Experience. Afterward, head to the Temple Bar, the recently-opened craft beer & wine bar restaurant that’s a hit with visitors and locals alike. Additionally, the Hawaiʻi Volcanoes National Park, located 45 minutes to the south of Hilo, is a must-do for any traveler. Meanwhile, the Pōhāhā I Ka Lani Tour at Waipiʻo Valley Lookout is another can’t-miss activity (thanks to your fantastic hosts who share details about the island’s history and culture while you ascend to the overlook.) Finally, no matter where you are staying on the island, check out the schedule for Chef Brian Hirata’s pop-up dining experience, Na’au Hilo. The aim of the culinary project is “Ka ho’oilina malamalama,” which means enlightened through heritage. One meal will leave you with even more appreciative of the natural beauty of Hawaii Island—and how delicious its fruits can be.
From the largest of the Hawaiian islands to the smallest: Our next selection is the remote, romantic, island of Lanai. The private island, owned by Larry Ellison, is known as a secluded paradise by the jet-set crowd that frequents its luxury resort, the Four Seasons Resort Lanai at Manele Bay. Mornings are spent on a guided hike to Pu’u Pehe, otherwise known as Sweetheart Rock, at sunrise. Watch the colors change in the pink sky as day breaks above the 80-foot rock, which juts out of Manele Bay. The sight is simply magical—as is the Hawaiian legend behind the Sweetheart Rock itself: A jealous young man from Maui ordered his lover to wait for him in a sea cave beneath the rock when he was away, and she ended up swallowed in the high tide and drowned. Which goes to show that jealousy is never good —though it would be hard to succumb to petty feelings here when you’re in this environment. Visit the cat sanctuary (a truly all-ages delight) and explore the island on foot or by 4x4.
Lanai, Hawaii, USA
The Love Lanai desk will arrange sunset sailing, horseback riding and ATV rides to your heart’s content—though we wouldn’t blame you for wanting to spend the entirety of your days on the blissful property. And now, thanks to the private service offered by Lanai Air sinceApril 2018, you can hop on a 35-minute flight from Honolulu straight to the Lanai Airport (saving you the time spent on a ferry ride that was the custom in years past.) And for more good news? The plane will fly for as few as two passengers—solidifying this destination as the ultimate couples retreat. But don’t let your relationship status define your vacation plans. Lanai’s mixture of luxury and wilderness is sure to appeal to travelers of all stripes—whether on a relaxing getaway with friends or a solo trip into the rugged Hawaiian landscape, a trip to Lanai is always a good idea.
From the most remote Hawaiian island to the most metropolitan: Our next selection is Oahu, the island that is otherwise known as the “Heart of Hawaii.” The state capital of Honolulu boasts a mixture of exciting restaurants and bars, museums, and galleries, and the food and art scene in Hawaii is particularly of note for the cultured traveler. Why not stay in a location that brings the artwork to your bedroom? Book a room at Waikiki Beachcomber by Outrigger, and enjoy the local Hawaiian artists displayed throughout the property from the elevator to the hallways to your bedroom walls. The pleasing ocean-themed ambience is ideally located steps from Waikiki Beach. Book a lesson at Faith Surf School, located right on the beach across from the Outrigger Waikiki Beach Resort, and have a little faith in your natural athletic ability—the knowledgeable guides are experts at getting beginners up on their boards to catch a few waves. Afterward, order brunch at Hawaiian Aroma Caffe and grab a celebratory beverage at the Maui Brewing Company (both of which are located on the property.)
Oahu, Hawaii, USA
Honolulu’s juxtaposition of wild nature and urban metropolis seaside urban is best appreciated from the 360-degree view at the top of Waikiki’s Diamond Head Trail Hike, which offers breathtaking vistas of the Pacific Ocean. And, once you’re ready for the real gnarly waves, head up to the iconic North Shore, the place to be in the colder months when the break is excellent. The seaside scene is appealing for surfers and non-surfers alike, as the lively beach scene is perfect for spending the afternoon watching the far braver (and far more talented) athletes of Hawaii tackle the tremendous surf.
If you’re looking for luxury, then Maui is the island to visit. Nicknamed the “Beverly Hills Island,” Maui is home to an abundance of luxury resorts, particularly in the beautiful region of Wailea, along the South Shore, which is home to the Four Seasons and Waldorf Astoria, amongst other high-end properties. We recommend booking a stay at the Hotel Wailea, a Relais & Chateaux property that offers villas for rent overlooking the water, and a sophisticated adults-only ambience. Sign up for an outrigger canoe exploration down at the beach and partake in this ancient Hawaiian activity while spotting sea turtles and manta rays in the Pacific waters.
Maui, Hawaii, USA
Head over to the Maui Tropical Plantation and get a tour of the grounds for insight into the Hawaiian food scene which is quickly overtaking the rest of the nation—you can now find poke (pronounced po-kay), a diced raw fish bowl, at airports far more landlocked than JFK or LAX these days. Order a cocktail (and some delicious food) at the Mill House afterwards —the mixologist is renowned for his innovations nationwide, so you’d be remiss not to sample his version of the classic Mai Tai. Adventure-seekers can head out for some Proflyght Hawaii Paragliding in Kula, while nature-lovers should take in the calming ambience of the Ali’i Kula Lavender Farm.
Visit the Iao Valley State Park for some majestic, mountainous views at sunset, and be ready to take off the next morning for the legendary Road to Hana, which is known to be one of the most scenic routes in the country. Travelers and dawdlers should beware that they should block off an entire day for this winding, road trip journey. Maui’s gorgeous landscapes may have earned it the nickname the “Valley Isle,” but this Hawaiian island is equally renowned for its wonders out to sea, as well. Considered the whale watching capital of the archipelago, Maui is an ideal destination for humpback-sightings just off the coast. Sign up for a whale watching tour with the Pacific Whale Foundation to catch the humpback whales on their annual breeding vacation: They visit the Hawaiian islands in the wintertime, after having spent the warmer months up north, feeding in Alaska.
The oldest, northernmost island in the Hawaiian chain, Kauai is known as the “Garden Island” and is a perfect selection for nature-lovers, and travelers who want to go into the wild while on their vacation to the tropics. Though the northern part of the island of Kauai—and Hanalei Bay, specifically—are eternally popular, the southern coast of Kauai is just as magnificent (we recommend catching the sunrise at Poipu Beach to appreciate the gorgeous landscape fully). Stay at the Aqua Kauai Beach Resort in Lihue or the Grand Hyatt Kauai in Koloa and prepare to luxuriate in spectacular views of the magnificent Hawaiian coastline. Visit the beautiful (and immensely Instagram-ready) Tunnel of Trees and the dirt roads of Waimea Canyon as you cruise around the lush island, upon which 97% of the land is preserved.
Adventure travelers should sign up for a Kauai ATV Tour to off-road your way back to a land before time (or a landscape reminiscent of Jurassic Park, to be exact). Another option for adrenaline-seekers is a zip-lining course high above the treetops with Skyline Eco-Adventures—what better way to appreciate the Garden Isle than from above, after all? Finally, every visitor must embark on a catamaran cruise with Kauai Sea Tours to the Na Pali Coast; keep your eyes peeled for humpback whales on your voyage.
Only 38 miles long and 10 miles wide, the island of Molokai is home to a large percentage of native Hawaiians and remains the most authentic island experience you can have when visiting the Hawaiian archipelago. The unspoiled nature is wondrous: The sunset at Kapalua Bay is spectacular, as are the breathtaking cliffs of Molokai. Explore the Kapuiawa Coconut Grove at dusk to witness the pink sky illuminate one of the oldest royal groves in Hawaii—King Kamehameha V planted the palms in the 1860s.
Hike the highest sea cliffs in the world at Kalaupapa, which rise 3,000 feet above the ocean, and explore the Kalaupapa National Historic Park, located at the base of the cliffs, which tells the story of the isolated leper colony which once called this region home.