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Four Perfect Hawaiian Island Hopping Itineraries

There’s a chill in the air, so odds are you’re thinking of sun, or as native Hawaiians call it la. The Aloha State offers plenty of golden warmth on its four main islands, but each has its own distinct personality: bustling Oahu is home to hip-again Waikiki Beach, lush Kauai is known for its natural beauty, multifaceted Maui is celebrated for its stunning sunsets, and lava-topped Hawaii (Big Island) is home to an active volcano. All four are amazing, but difficult to see in a single visit (unless like me, you island-hop every 2-3 days), so here’s a look at four terrific two-island combos that make for a perfect week-long trip based on your preferred activities.


For Adventurers: Kauai & Big Island

If you love nature and enjoy hiking, horseback riding, or kayaking, these are the islands for you. And the best news is, nightly rates on both won’t break the bank. Start on Kauai, where the jagged green landscape means a photo-op around every corner. Activities include: hiking colorful Waimea Canyon or the scenic Napali Coast along the 11-mile Kalalau Trail; enjoying a rigorous 17-mile sea kayak paddle with Napali Kayak (or if you prefer softer adventure, a Captain Andy’s catamaran sail, during which you can snorkel with sea turtles and dolphins); and soaring above the emerald peaks on a doors-off helicopter ride with Mauna Loa Helicopters or zip-lining through them with Princeville Ranch Adventures or Outfitters Kauai. Stay at the Sheraton Kauai Resort in Poipu, which recently completed a $16 million renovation and sits on a beach with great sunset views (from $209/night); the Westin Princeville Ocean Resort Villas, a modern condo resort that has beach privileges at the St. Regis (from $280/night); or Courtyard Kauai at Coconut Beach near Kapa’a, which just underwent a $13 million renovation (from $160/night).

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As you fly into Kona Airport on the Big Island of Hawaii, you’ll be awed by the contrast. While Kauai is vibrant green, the Kona Coast is covered by a lunar-like gray-brown lava flow. And lava means adventure: On land you can horseback ride with Hawaiian paniolos (cowboys) near Waimea or ATV through Kahua Ranch, hike the volcanic desert of Hawaii Volcanoes National Park, and stargaze atop the chilly summit of 13,796-foot Mauna Kea with Hawaii Forest & Trail. In the sea, you can night dive alongside giant manta rays with Jack’s Diving Locker or watch lava flow into the Pacific by boat with Lava Ocean Adventures. Stay at the just renovated Sheraton Kona Resort & Spa, which sits atop a black lava outcropping overlooking Keauhou Bay, a favorite haunt of giant mantas (from $160/night); Waikoloa Beach Marriott Resort & Spa, located on 15 beachfront acres amid the ruins of Hawaiian fish ponds (from $182/night); or Hapuna Beach Prince Hotel, located on one of the Kohala Coast’s best beaches (from $240/night).


For Spa-Lovers: Maui & Kauai

Feeling a bit self-indulgent? Head to Maui, where the spa options range from lavish water worlds to Zen-like yoga retreats. Serious hedonists should check out the 50,000-square-foot Spa Grande at Grand Wailea, where the specialties include the couples’ Royal Niu Coconut Dream for Two (which uses coconut water, butter, milk, oil, and husk to exfoliate and moisturize) and a hydrotherapy circuit featuring five aromatic baths, a Roman hot tub and more (from $599/night). Nearby Spa Kea Lani at the Fairmont Kea Lani is petite in comparison, but the resort features spacious suites, gorgeous grounds, and a poolside massage cabana that’s a breezy spot to enjoy a lomi lomi massage (from $539/night). Over on Ka’napali Beach, the oceanfront Spa Moana at the Hyatt Regency Maui Resort & Spa offers 37 massage options and 12 facial choices amid a 40-acre setting (from $349/night). And if you want to decompress with yoga and meditation, plus delicious healthy cuisine, check out 24-room Lumeria, a new wellness retreat near Paia in a beautifully restored 1909 Craftsman-style building (from $349/night).

Next, chill out on Kauai, where the vibrant green foliage and fragrant plumeria blossoms will max out your nirvana. In sunny Poipu on the south shore, get pampered indoors or out at the 45,000-square-foot Anara Spa at the Grand Hyatt Kauai Resort & Spa, which has a lush Lokahi Garden area with thatched-roof hale treatment bungalows and a focus on traditional healing customs (from $309/night). The Spa at Koa Kea Hotel & Resort, also in Poipu, is more understated, keeping with the property’s chic boutique ambience, yet its treatment menu includes everything from a Pohaku Hot Stone Massage to an Awakening Kauai Coffee & Sugar Ritual (from $389/night). Up north, the five-star St. Regis Princeville Resort‘s Halele’a Spa is a calming oasis, and the panoramic views of Hanalei Bay from the resort’s terrace and pool area will hypnotize you into total relaxation (from $555/night).


For Foodies: Oahu & Big Island

Hawaiian Regional Cuisine is a revelation, pairing local ingredients with techniques inspired by the Japanese, Chinese, Filipino, and Portuguese cultures brought here in the 19th century. Its epicenter is Oahu, where the cuisine’s founding chefs showcase their skills: Don’t miss the chopped ahi sashimi & avocado salsa stack and the ginger-crusted onaga at Alan Wong’s, or the splurge-worthy four- or six-course degustation menus at Chef Mavro. Top-name Japanese chefs Morimoto and Nobu also have Waikiki outposts. Stay at the atmospheric Moana Surfrider, A Westin Resort & Spa, where carnivores will drool over the steak (there’s amazing fish, too) at the oceanfront Beachhouse (from $350/night); The Royal Hawaiian, the lavishly renovated 1927 "Pink Palace" that’s home to the sleek Azure restaurant (from $410/night); or Halekulani, a tranquil haven where you can enjoy AAA five-diamond French cuisine and Diamond Head views at romantic La Mer (from $500/night).

The Big Island is Hawaii’s agricultural soul, with hundreds of farms producing not only superb Kona coffee and addictive macadamia nuts, but also seasonal vegetables and sustainably raised meats. Merriman’s in Waimea, is a farm-to-table pioneer, serving a creative seasonal menu for more than 20 years and now also operating eateries on Kauai and Maui. Hawaii-grown deliciousness is showcased nightly in the new ‘ULU Ocean Grill at Four Seasons Resort Hualalai, where Chef James Babian’s "Regional, Seasonal and Artisanal" credo uses 75 percent grown-on-island ingredients to create taste sensations such as warm Keahole lobster salad with vanilla-guava sauce (from $545/night). Other not-to-miss restaurants include Brown’s Beach House at the Fairmont Orchid (from $399/night), CanoeHouse at Mauna Lani Bay Hotel & Bungalows (from $400/night), and for cocktails and pupus (appetizers) with manta ray viewing after sunset, the new Rays on the Bay at the Sheraton Kona Resort & Spa. Also be sure to try malasadas (Portuguese donuts) and on Saturday mornings browse the produce and cheeses at two farmer’s markets in Waimea—and then grab a grass-fed beef burger at Village Burger.


For Night Owls: Oahu & Maui

If vacations are for cutting loose, head to Waikiki, where revitalization efforts like Waikiki Beach Walk and the Royal Hawaiian Center have made the once-tacky Honolulu neighborhood cool again. You’ll find lively bars, like the Yard House, offering afternoon and late-night happy hours, and RumFire, a fire-pit-studded venue at the Sheraton Waikiki that’s a great spot to sip a cucumber-lavender mojito and nibble flash stir-fried edamame (from $325/night). Wine-lovers can enjoy flights and small plates at bin1901 in the Moana Surfrider, A Westin Resort & Spa, where the Old Hawaii ambience is perfect for a late-30s and up crowd. Both Outrigger Waikiki on the Beach and Outrigger Reef on the Beach are mid-action, each with "barefoot bars" and recently renovated rooms (from $299 and $269/night). Just 15 minutes by foot, The Modern Honolulu is the area’s hippest option and is home to locals’ after-work favorite The Study as well as Addiction, a subterranean nightclub (from $309/night).

Move on to Maui, where you’ll be able to recover a bit from your Oahu overindulgence since the nightlife here is more low-key. For the best mix of restaurants and bars (and surreal sunsets), stay near Ka’anapali or Lahaina. Lahaina, a former whaling town, has a smattering of convivial bars, while the strip of resorts along Ka’anapali makes it easy to hop from one resort watering hole to another, as well as to the Barefoot Bar at Hula Grill in Whalers Village. Stay at Honua Kai Resort & Spa, a three-year-old condo resort on Ka’anapali’s North Beach with a lively onsite Duke’s Beach House (from $339/night) or the Sheraton Maui Resort & Spa, with its great location next to Black Rock from which cliff divers do a ceremonial plunge nightly (from $369/night).

Getting Here and Around

It’s easier than ever to get to Hawaii—and not just from Los Angeles. Hawaiian Airlines offers daily nonstops (10.5 hours) from New York’s JFK as well as San Francisco, Seattle, Portland, Phoenix, and other cities. Once in Hawaii, Hawaiian’s numerous daily interisland flights cost $69-$139 on average. Other carriers flying to Hawaii include American, Alaska, Delta, United, and US Airways.

Photo credits: Big Island volcano crater courtesy of Hawaii Tourism Authority/Tor Johnson; Anara Spa courtesy of Grand Hyatt Kauai; Beachhouse Restaurant courtesy of Credit Moana Surfrider, A Westin Resort & Spa; RumFire lounge courtesy of Sheraton Waikiki Resort

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