Hawaii’s Best Two-Island Combos for Every Travel Style

Hawaii may be one state, but it is home to five main islands with very different geographies, activities and vibes. Here’s how to create a two-island itinerary that best suits your interests and preferred activities.

Maui
Planning a trip to Maui? Consider adding another island to your itinerary so you can get the most of your Hawaii experience.Shutterstock

It’s a long haul to get to Hawaii—especially from the East Coast—so planning to visit more than one island while vacationing there make sense. Still, more than two demands either a serious vacation-day commitment or a crazy schedule that leaves little time for actual enjoyment of each island. Our solution: the perfect two-island combo for a week in Hawaii matched to your specific lifestyles and interests. From adventure and golf to romance and culinary pursuits, here are our picks.

Adventure and Ecotourism: Kauai + the Island of Hawaii

Does kayaking alongside coastal cliffs with Instagram-worthy views and star-gazing from the slopes of a 13,803-foot dormant volcano topped with snow sound like the coolest tropical vacation ever? Then plan to spend three nights on Kauai and four nights on the island of Hawaii.

What to do: Kauai, the oldest of the Hawaiian islands, is famous for its lush, mountainous landscape offering eco-adventure activities, plus coastal enclaves where surfing and other water sports such as stand-up paddle boarding are popular. Hike the Kalalau Trail along the Napali Coast (be sure to secure a parking pass beforehand) or trek amid inland beauty on trails in Kokee and Waimea Canyon State Parks. For aerial adventure, book a helicopter tour with Blue Hawaiian Helicopters or scream your way across Kauai's longest zipline (4,000 feet) with Outfitters Kauai

Up for a serious challenge? Outfitters Kauai also offers a 15-mile ocean kayak tour along the Napali Coast.

Eco-adventure is in the DNA of the island of Hawaii, the youngest Hawaiian island, which continues to grow thanks to eruptions from Kilauea volcano. Trek across lava fields in Volcanoes National Park or horseback ride through the rolling hills of Waimea with Hawaiian cowboys with Paniolo Adventures. Better yet, the fun doesn't end at sunset. Head up Hawaii's tallest peak for a sunset and stars experience with Hawaii Forest & Trail. You can also slip into the darkened waters of Kona Bay for a night dive with giant manta rays via Jack's Dive Locker.

Where to stay: Poipu is best for sunny weather and beaches, while the Coconut Coast is convenient for accessing activities on both the North and South shores. In the former, opt for the Sheraton Kauai Resort with its low-rise buildings and swimmable beach; in the latter, the Kauai Marriott Resort in Lihue features lush grounds and a heated, family-friendly pool. On the island of Hawaii, the Sheraton Kona Resort & Spa at Keauhou Bay is an affordable, centrally located base for exploration (there's no beach, but you can see mantas from Rays on the Bay restaurant), while the Hilton Waikoloa Village on the Kohala Coast is a 62-acre resort ideal for active families.

Food and Entertainment: Oahu + Maui

Oahu
Oahu is known for amazing surfing, but don’t sleep on the incredible cuisine options.Shutterstock

If your main desire is to dine at award-winning restaurants, try Hawaiian regional cuisine, take cooking lessons and experience local culture, Oahu and Maui offer plenty to enjoy, especially if you love seafood and fusion cuisine. Plan to spend three nights in Honolulu and four nights on Maui to taste your way through Hawaii and the entire Pacific Rim. Time your trip for mid-to-late October to enjoy events at the Hawaii Food & Wine Festival on both islands.

Must-try activities: Honolulu is home to award-winning restaurants by chefs who almost 30 years ago created Hawaiian Regional Cuisine—among them, Roy Yamaguchi of Roy's, who blends Hawaiian and Japanese flavors; Alan Wong of Alan Wong's, whose dishes are inspired by Hawaii's diverse ethnic cultures; and George Mavrothalissitis of Chef Mavro, known for his French-Hawaiian menus.

Casual local favorites abound, too: Loco Moco (a hamburger and fried egg atop white rice with a veal demi-glaze) at Barefoot Beach Café, a shave ice at Waiola Shave Ice and an Ahi Poke Bowl made with shoyu sauce at Ono Seafood. Head to the North Shore to try taro and haupia, Hawaiian staples served in the combo plate the Waiahole Poi Factory. Culture-wise, learn about Hawaiian music and dance during free shows at Royal Hawaiian Center or sip a cocktail and enjoy slack-key guitar music and hula at House Without a Key at Halekulani.

On Maui, the farm-to-fork aspect of Hawaiian Regional Cuisine is on every plate at Peter Merriman's oceanfront Merriman's Kapalua, Beverly Gannon's Haliimaile General Store in Makawao, and Mark Ellman's Mala Ocean Tavern in Lahaina.

Entertainment wise, it's hard to beat the upscale luau experience and sunset view of the Feast at Lele in Lahaina and the melodic masters of Hawaiian slack key guitar at the Slack Key Show at the Napili Kai Beach Resort. Maui is also known for several culinary festivals: the Kapalua Food & Wine Festival in June and the Four Seasons Maui Wine & Food Classic in May.

Top places to stay: On Oahu, stay in Waikiki to be in the center of action. Check into Moana Surfrider, A Westin Resort & Spa and you'll enjoy both historic architecture—it's Hawaii's first hotel, opened in 1901—and delicious seafood at Beachhouse. On Maui, the Fairmont Kea Lani is home to award-winning Ko restaurant featuring a fusion menu of Hawaiian, Japanese, Chinese, Filipino, Portuguese and Korean dishes, while the Andaz Maui at Wailea Resort focuses on farm-to-table dining.

Golf and Spa: Island of Hawaii + Lanai

Big Island
With majestic views and holes designed with each island’s natural beauty in mind, the golf courses on the island of Hawaii and Lanai should be on every golfer’s bucket list.Shutterstock

If your idea of nirvana consists of teeing off on a gorgeous fairway in the morning and cooling down with a soothing massage and hydrotherapy soak in the afternoon, a combination of the island of Hawaii and Lanai offers complementary golf and spa experiences that capture the lava-strewn wildness of Hawaii's biggest island and the quiet allure of its smallest island with resorts.

Must-try activities: Between them, the island of Hawaii and Lanai have 21 golf courses—19 of them on Hawaii, but Lanai features a course so spectacular it’s worth checking off your list. Most of the top courses on the island of Hawaii are affiliated with resorts, but are open to the public.

These include the Scottish links-style Waikoloa Kings' Course; the Mauna Lani Resort South Course , home of the Senior Skins Game from 1990 to 2000; and the classic Robert Trent Jones, Sr,-designed Mauna Kea Golf Course. The Hualalai Golf Club, on the other hand, can only be played by Hualalai residents and guests of the Four Seasons Resort, as is also the case at Manele Golf Course at the Four Seasons Resort Lanai.

As for spa-going, almost any resort spa in Hawaii is well equipped to relax your cares away with native lomilomi massage or a body scrub incorporating botanicals such as coconut, papaya and ginger.

Top places to stay: If your budget allows, book both Four Seasons properties featuring a pair of Jack Nicklaus-designed courses: Four Seasons Resort Hualalai on the island of Hawaii and Four Seasons Resort Lanai, featuring the Manele Golf Course. Can't afford such a major splurge? Spend five nights at the Westin Hapuna Beach Resort on the island of Hawaii, home to the Hapuna Course—and adjacent to the Mauna Kea course—and then hop over to Lanai for two nights to experience the Four Seasons.

Romance: Kauai + Maui

Kauai
Also known as the Garden Island, Kauai is packed with locations and views that enhance the romance.Shutterstock

This island duo is the perfect setting for an unforgettable honeymoon, destination proposal or milestone anniversary celebration. Begin with three nights on serene Kauai, where the pace is slow and the scenery is stunning, and then finish with four nights on Maui, an island that has it all when it comes to couples-oriented pampering.

Must-try activities: On Kauai, known as the Garden Island, romance is in the air (and the sea spray) as you enjoy a sunset catamaran dinner cruise along the breathtaking Napali Coast with Holo-Holo Charters, paddle a two-person kayak along to Secret Waterfall with Wailua River Guides, walk hand-in-hand along one of the North Shore's scenic beaches or enjoy a couple's lomilomi massage at your resort's spa.

On Maui, romance comes naturally, too. Drive amid the lush volcanic slopes of Upcountry, with stops at Ali'i Kula Lavender Farm, the Surfing Goat Dairy, and the historic cowboy town of Makawao.

Once at the top of 10,023-foot dormant volcano Haleakala, enjoy a scenic hike into the crater or time your visit for sunset (you'll be above the clouds!). Other magical experiences are driving the 620 twists and turns of the Road to Hana—stay a few nights in this sleepy enclave to truly relax—as well as cocktails on Kaanapali Beach near Black Rock as a lone diver performs his ritual plunge into the sea and a sunset dinner in Lahaina.

Top places to stay: On Kauai, romantic resorts come in different sizes. If you're seeking a large property with multiple on-site restaurants, a great beach and a relaxing spa, check out the Grand Hyatt Kauai Resort in Poipu; for something more intimate, book nearby boutique property Koa Kea Hotel & Resort.

Some of our favorite Maui resorts for couples are the luxurious Four Seasons Maui at Wailea, worth the splurge for a honeymoon or anniversary; the Sheraton Maui Resort with its mid-century architecture and prime Kaanapali location for sunset; and Travaasa Hana, for seaside bungalows and all-inclusive ease.