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The Four Seasons and Hotel Lanai are the island’s two mainstays for nightlife. Before sunset, head to Malibu Farm at the Four Seasons Resort Lanai, 1 Manele Bay Rd. (www.fourseasons.com/lanai; 808/565-2093), for cocktails; after dark, you can shoot pool in the Sports Bar & Grill. Several nights a week, local musicians get together for jams at the Lanai City Bar & Grille ★ at the Hotel Lanai, 828 Lanai Ave. (www.lanaicitybarandgrille.com; 808/565-7212). No trip to the island is complete without an evening spent here, enjoying Hawaiian harmonies under the stars alongside the locals and day-trip golfers. Bring a jacket if you plan to sit outside; the fire pits are cozy, but not quite enough to keep you warm.

Another fun option is the wonderfully renovated Lanai Theater, renamed Hale Keaka ★ (www.lanai96763.com/showtimes; 456 Seventh St., Lanai City). Built in 1926, this iconic landmark shared films, live plays, and musical performances with the community for 80 years. The $4-million renovation kept the vintage feel but added air-conditioning, digital sound, two stages and screens, cushy seats, and more. Two films—an adult and a children’s selection—change weekly. The box office opens 1 hour prior to the start of each movie. And because it’s Lanai, you’ll find furikake and shoyu among the complimentary popcorn condiments.

Celebrating with Lanai Festivals

Throughout the year, HawaiiOnTV.com and JazzAlleyTV.com bring world-class entertainers to little Lanai. These intimate annual festivals are worth planning your vacation around. The Four Seasons resorts even offer discounted room rates in conjunction with festival dates.

*       In February, the 3-day Lanai Hawaiian Culture Film & Musical Festival (www.lanaifilmfestival.com)screens fascinating shorts, features, and documentaries about the people of the Pacific that you’re not likely see anywhere else. Live music and cultural workshops round out the weekend.

*       Jazz greats from as far as Kansas City descend on the island for the Lanai Jazz Festival (www.lanaijazzfestival.com) in March. Live performances pop up throughout Lanai City: Grammy-award-winning saxophonists serenade audiences in the Lodge at Koele’s Great Hall while jazz guitars perform at the local juice bar.

*       The "jumping flea," the quintessential instrument of the Islands, is celebrated during the Lanai Ukulele Festival (www.lanaiukulelefestival.com) in June. This light-hearted musical weekend includes concerts under the stars and free clinics for beginning uke players.

*       Dole Park is the site of fireworks, a parade, and all-day entertainment during the annual Pineapple Festival, generally held on the first Saturday in July

*       The Lanai Slack Key Guitar Festival (www.lanaislackkeyfestival.com) in August is 3 days of superlative concerts and workshops led by Grammy and Na Hoku award-winning artists. Events are free and take place around Lanai City.

*       The Aloha Festival (www.alohafestivals.com) takes place in September or the first week in October, and the Christmas Festival is held on the first Saturday in December. For details on these festivals, contact the Lanai Visitors Bureau.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.