The Four Seasons resorts and the Hotel Lanai are the island’s mainstays for nightlife. Nightly, in the Great Hall atthe Lodge at Koele, in Four Seasons Resort Lanai, 1 Keomoku Hwy. (www.fourseasons.com/koele; tel. 808/565-4580), various local musicians perform from 7 to 9pm. Sink into a plush chair by one of the manorial fireplaces and let them serenade you with lovely contemporary Hawaiian music. Uncle Kimo tickles the ivories of the grand piano and throws in a few show tunes for fun.
At Kailani, the poolside restaurantoverlooking Manele Bay, atFour Seasons Resort Lanai at Manele Bay, 1 Manele Bay Rd. (www.fourseasons.com/manelebay; tel. 808/565-2093), nightly live music enhances the already romantic atmosphere. On Friday night, local musicians get together for jams at the Lanai City Grille at the Hotel Lanai, 828 Lanai Ave. (www.hotellanai.com; tel. 800/795-7211 or 808/565-7211).
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.