Arguably the most glamorous of Hawaii’s islands, Maui is home to some of the state’s swankiest resorts and acclaimed restaurants. It’s a favorite with visitors in search of lazy beach naps, leisurely laps in the pool and soothing spa treatments. But don’t let the island’s cushy reputation fool you into thinking it lacks history, culture, and an impressive variety of rugged outdoor adventures. Maui vacations can be as unhurried or as thrilling as you choose.

Home to the largest gay and lesbian resort in Hawaii (the Maui Sunseeker) as well as dozens of welcoming B&Bs, inns, condos and full-service resorts, Maui is often the first island visitors experience after Oahu. Although lacking Honolulu’s nightlife, this easy-going, moderately developed island is well suited to couples, families and groups of friends.

Plenty of visitors stay at one resort and visit Maui for five to seven days. But if you’re hoping to get to know the island’s diverse elements, split your time among two or three areas, and spend at least 10 days, perhaps tacking on a day or two on the quiet, underrated, and remarkable neighbor islands of Lanai and Molokai.
Maui
Geographically made up of two soaring volcanic peaks connected by a largely agricultural valley, Maui (www.gohawaii.com/maui) is the second largest of the Hawaiian islands, home to about 145,000 permanent residents. The majority of the 2.5 million visitors who arrive annual stay on the sunny and comparatively arid leeward coasts of Maui’s two halves, which include the historic fishing port of Lahaina, the modern Kaanapali and Kapalua resort areas, the ritzy Wailea resorts, and the more reasonably priced town of Kihei.
You’ll find a good mix of mid-priced to high-end resorts up around Kaanapali and Kapalua — good picks include the Hyatt Regency (maui.hyatt.com), Westin Maui (www.westinmaui.com), Outrigger Maui Eldorado (www.outrigger.com), and Ritz-Carlton Kapalua (www.ritzcarlton.com).

In Wailea, which is close to the famously gay-popular clothing-optional Little Beach at Makena, you’ll find such sumptuous accommodations as the Four Seasons Maui (www.fourseasons.com/maui), Grand Wailea (www.grandwailea.com), and Fairmont Kea Lani (www.fairmont.com/kealani). Just a few miles north, Kihei contains several gay-oriented lodging, including the aforementioned Maui Sunseeker (www.mauisunseeker.com), a stylishish boutique resort catering mostly to gay men and lesbians. Other good GLBT bets in Kihei include the elegant Pineapple Inn (www.pineappleinnmaui.com) and the affordable, whimsically furnished Two Mermaids (www.twomermaids.com).

Strike out beyond Maui’s leeward shores to discover some of the most diverse and dramatic scenery in all of Hawaii, including the Upcountry, situated along the slopes of 10,023-foot Mt. Haleakala, and home to the quirky ranching and farming towns of Kula and Makawao. Be sure to budget a few hours to drive to the peak of Haleakala’s summit, which lies within the national park of the same name

Along the breezy windward coast, you can drive the famously curvy and narrow road to Hana, which passes through verdant rainforests and beside gushing waterfalls. Return by way of the rugged Piilani Highway from Hana around West Maui’s “back side,” and the road hugs sheer sea cliffs and cuts across sweeping plains strewn with jagged lava-rock formations. If at all possible, plan for an overnight in Hana. Here you can stay at the historic, unpretentious, and wonderfully charming Travaasa Hana Hotel (www.travaasa.com/hana) — if it’s a special occasion, splurge for a room in this boutique resort’s secluded, adult-oriented Sea Cottages section. You’ll also find a handful of B&Bs in this laid-back village blessed with spectacular beaches, including the affordable, gay-owned Hana Accommodations (www.hana-maui.com).

Even Maui’s main untouristy administrative center and county seat, Wailuku, has a cool historical museum, the Bailey House; and some great little hole-in-the-wall restaurants (Tiffany’s, Tokyo Tei, Ba-Le Sandwiches); and it’s the gateway to the breathtaking Iao Valley. For an insider’s perspective on local dining, book a half-day trip through Tour da Food, whose knowledgeable guides Bonnie and Jill lead delicious culinary tours in Wailuku and Upcountry Maui.

Maui has several businesses with strong GLBT ties. You can book a massage, either in your hotel room or at a lovely on-site studio overlooking the ocean, from Relax Therapeutic Massage, whose owner Marty Guerriero is one of the most talented massage therapists on the island. Gay-owned No Ka Oi Adventures leads exceptionally fun and engaging custom half- and full-day tours around Maui — including trips around West Maui, along the road to Hana, and snorkeling off of Makena’s lava-fringed shores. Acclaimed local Chef Raja, who competed on TV’s “Extreme Chef” in 2011, is your go-to for planning a romantic meal or small dinner party. He’s especially popular with those planning gay weddings or commitment ceremonies. On that note, Hawaii’s new same-sex civil union law went into effect on January 1, 2012, and long-running Gay Hawaii Wedding can help couples plan their nuptials on Maui.

The island abounds with terrific restaurants, many of them at the big resorts, such as Ko at Fairmont Kea Lani, Spago at the Four Seasons, and Gannon’s at Grand Wailea. Locally renowned chef Peter Merriman’s hip Monkeypod Kitchen, in a shopping center at the Wailea Resort, is one of the hottest new spots on the island, as is Star Noodle, the stylish Pan-Asian eatery up in Lahaina, which is also home to the first-rate Lahaina Grill and I’o Restaurant. A few other culinary highlights on Maui include Market Fresh Bistro in Makawao, Cafe Mambo in Paia, and Izakaya Matsu in Kihei. For nightlife, the sophisticated but friendly Ambrosia lounge is popular with GLBT patrons, especially on Sunday nights.
Lanai
The gently sloping, conical island of Lanai (www.gohawaii.com/lanai) is clearly visible from the western shores of Maui, especially from Kaanapali and Lahaina — passenger ferries run regularly from the pier in Lahaina to Lanai, and the island also has regularly scheduled flights from Maui and Oahu. Just 140 square miles, this is the smallest of Hawaii’s primary islands, and historically it was known for its massive pineapple plantation industry.

Although it’s still a low-keyed, mostly undeveloped island, Lanai has become increasingly popular with jetsetters thanks to its pair of stunning Four Seasons resorts, the historic Lodge at Koele (www.fourseasons.com/koele), which is nestled beneath groves of Cook pine trees in the cool upcountry, and the seaside Manele Bay Hotel (www.fourseasons.com/manelebay), which fringes spectacular beaches and is renowned for snorkeling, golf, spa treatments, and relaxation.

Take some time to stroll around tiny Lanai City, which has a few intriguing galleries and shops and is also home to a less pricey and quite special boutique inn and restaurant, the Hotel Lanai (www.hotellanai.com).
Molokai
Although it’s significantly larger than Lanai (about a third the size of Maui), the tranquil island of Molokai (www.gohawaii.com/Molokai) receives very few visitors and is sparsely populated, with just 7,400 residents. But it’s also home to one of the most remarkable cultural attractions in the country, the colony of Kalaupapa, a peninsula physically cut off from the rest of Molokai by a wall of sheer sea cliffs, among the highest in the world. Hawaiians afflicted with Hansen’s Disease (leprosy) were tragically exiled to Kalaupapa from the 1860s through the 1960s. Although a handful of survivors still reside in this community, much of it is now a national historic site, and visitors can tour the two villages. The exciting part is getting there: you must either hike or ride mules down (and later back up) a daunting, 1,700-foot trail of muddy steps and switchbacks.

Even beyond Kalaupapa, Molokai is rich in spectacular scenery. There’s a scenic drive around the eastern half of the island, from which trails lead into the stunning Halawa Valley. And on the island’s dry, sunny western side, you’ll find some beautiful beaches. The airport in Molokai is served by several flights a day from neighbor islands. Once you get here, it’s best to rent a car, as distances are considerable.

The island has just one major hotel, the very gay-welcoming Aqua Hotel Molokai (www.hotelmolokai.com/), a fairly basic complex of ‘70s A-frame bungalows, although the rooms have been comfortably updated. The hotel is also home to one of the only full-service restaurants on the island, an open-air space overlooking the small beach. The Hotel Molokai acts as one of the island’s main social hubs, as there’s live music in the evening. The easy pace and friendly mix of locals and visitors makes for a striking contrast with hotels on the other islands.

Elsewhere, your best bets for dining are Kamuela Cookhouse, which serves up tasty grilled seafood and prime rib, and Molokai Drive-in for burgers. The Molokai Coffee Plantation serves rich and robust brews using beans grown on the island. And for breakfast or lunch, don’t miss Kanemitsu Bakery. Each evening, after the bakery has officially closed, hungry diners line up at a takeout window in the back alley to procure “hot bread.” The disturbingly enormous loaves of chewy, rich bread are doused with butter, cinnamon, jams, and other toppings. It’s the sort of offbeat tradition that captures Molokai’s quirky, small-town vibe.

Andrew Collins covers gay travel for the New York Times-owned website GayTravel.About.com and is the author of Fodor’s Gay Guide to the USA. He can be reached at OutofTown@qsyndicate.com.