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Top 20 things to do on Maui, Dec 28-Jan. 8: Wailea fireworks, New Year’s Eve parties, Big Mountain concert, songwriters festival, PGA tournament

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This week on Maui, thousands of people are expected to gather on the ocean, beaches and hillsides of South Maui for the spectacular fireworks show off Wailea Beach. There’s also are several other New Year’s Eve festivities around the island.

This week, there also is a concert by reggae band Big Mountain and a fundraiser for local comedian Jose Raymond, who lost his home in the Lahaina fire.

Coming up fast: The PGA kicks off its 2024 tour at The Sentry tournament, Old Dominion plays at the MACC and the Ritz Carlton is hosting the 2024 Music Songwriters Festival with Country Music Award stars.

Check out Maui Now’s Top 20 list below. And for a comprehensive list of upcoming events – concerts, shows, entertainment community activities and outdoor gift markets – for this week and beyond, click here.

No. 1 – New Year’s Eve fireworks at Wailea Beach (Dec. 31, Wailea)

The aerial fireworks was taken from a lānai in South Maui on New Year’s Eve, 2023. The dots of light are from resorts along the coastline. PC: Gary Kubota.

Thousands of people are expected to welcome the New Year by watching fireworks set off from a floating ocean platform off Wailea Beach. The fireworks permit, taken out by the Grand Wailea, is the only authorized aerial fireworks on Maui as of Dec. 22. Another aerial fireworks permit was issued for Lānaʻi.

There is a nearby public beach and parking area for oceanside viewing near the Grand Wailea, and the fireworks show is visible from the hillsides in Wailea and Maui Meadows. A number of restaurants are having entertainment on New Year’s Eve, including a second lūʻau at the Wailea Beach Resort-Marriott at 9 p.m. before the fireworks display.


Several yacht tours out of Māʻalaea will be watching the rockets great glare. The Pacific Whale Foundation and Pride of Maui were taking reservations earlier this week. For more information, call Pacific Whale Foundation at 808-249-8811 or Pride Of Maui at 808-242-0955.

No. 2 – Big Mountain performs at da Playground Maui (Jan. 3, Māʻalaea)

Big Mountain performs on Maui Jan. 3.

Acclaimed reggae band Big Mountain performs at da Playground Maui on Jan. 3 at 8 p.m. The band’s iconic love song “Baby I Love Your Way” has more than 60 million views on YouTube. The group has played at the Dallas Reggae Festival, the 50th Hawaiʻi State Fair, the Truckee Reggae Fest, Rebel Salute in Jamaica, the Houston Reggae Jam Jam, Reggae Rotterdam in Holland, the Baja Roots Festival in Mexico, and Reggae Sunsplash in Jamaica.

The Maui event also features the Hawaiʻi reggae group Nuff Seed. Doors open at 7 p.m. For ages 21 & over. There is free parking with local ID after 5 p.m. For more information including tickets, go to da Playground Maui.

No. 3 – Gretchen Rhodes performs at Mulligans for New Year’s Eve Kick-Off Party (Dec. 29, Wailea)

Gretchen Rhodes

Rock and soulful blues singer Gretchen Rhodes performs at Mulligans On The Blue on Friday at 7 p.m. Rhodes is the lead singer in Mick Fleetwood’s House of Band.

For more information including tickets, go to Gretchen Rhodes Band. Also, call Mulligans for reservations, 808-874-1131.

No. 4 – Jazz & Blues Festival at Ocean Vodka Organic Farm (Dec. 31, Kula)


A jazz & blues festival will take place at the Ocean Vodka Organic Farm & Distillery on New Yearʻs Eve from 4 to 7 p.m. The concert features Brazilian-style guitar master Dr. Nat, the duo Levi Huffman and Joie Yasha Taylor, and Fast Freddy and the Blue Lava Blues Band with Honolulu singer-harmonica player Kevin Coleman from the band Flat Five Blues.

The festival takes place at 4051 Ōmaʻopio Road on a grassy plateau overlooking the Central Valley. For more information, including tickets, call for reservations 808-877-0009.

No. 5 – Makai Jazz Group at Kuʻia Estate Chocolate Factory (Dec. 31, Lahaina)

Singer Gina Martinelli, Joie Yasha and Jeff Helmer are among performers at the early New Year’s Eve celebration in Lahaina.

The Makai Jazz Group performs on New Yearʻs Eve from 5 to 7 p.m at the Ku’ia Estate Chocolate Factory, 78 Ulupono St. It’s sunset jazz with vocalists Gina Martinelli and Abra Joy, pianist Jeff Helmer, saxophonist Bruce Boege, drummer Jimmy C, bassist Dave Graber and trumpeter Tadashi Thomas.

Hellmer has been a finalist twice in the Great American Jazz Piano Competition, and Graber has played jazz from Hawaiʻi to Hungary, including the Birdland in New York.

The performance is held on a second floor, open-air pavilion with a view. Proceeds from concert ticket sales benefit educational workshops in Maui schools through the nonprofit Jazz Maui music education programs. For more information including tickets, go to Jazz Maui or call 808-283-3576.

No. 6 – New Year’s Eve Dance Party at Mulligans On The Blue (Dec. 31, Wailea)


The dance band Island Soul will perform on New Year’s Eve at Mulligans On The Blue. Dinner seating starts at 5 p.m., with live dinner music from 7 to 9 p.m.

The dance party takes place from 10 p.m. to midnight. The party includes a champagne toast. For more information including reservations, go to Mulligans or call 808-874-1131.

No. 7 – New Year’s Eve Big Ohana Night at Taverna (Dec. 31, Kapalua)

Tempa & the Tantrums will perform at a New Year’s Eve dance celebration at Taverna’s Big Ohana Night at 2000 Village Road from 10 p.m. to 1 a.m. The music includes smart soul, rock, blues, jam and country with an upbeat for dancing.

Get ready to raise a bubbly glass while diving into Taverna’s Midnight Pizza and Dessert Bar. For more information about the music including tickets, go to Tempa.

No. 8 – New Year’s Eve at Kula Lodge & Restaurant (Dec. 31, Kula)

Sal Godinez and Joie Yasha

Dance to music by pianist Sal Godinez and saxophonist Joie Yasha this New Year’s Eve at the Kula Lodge and Restaurant.

There are two dinner seatings, including one from a pre-fix menu from 8 to 9:30 p.m., which lasts until midnight. The early seating is from 5 p.m. to 6 p.m., without live music.

No. 9 – New Year’s Eve at da Playground Maui (Dec. 31, Māʻalaea)

DJ Joe Cortez and Jamn J present a New Years’s Eve Celebration at da Playground Maui on New Yearʻs Eve at 9 p.m. The event features a red carpet entry, photo booth, a hosted champagne toast and a midnight blood drop.

Dance music includes hip-hop, Top 40, Latin, Reggaeton and Throwbacks. For ages 21 and over. There is free parking with local ID after 5 p.m. For more information including tickets, go to da Playground Maui.

No. 10 – Kaapana, Grammy winner Kahumoku at Slack Key Show (Jan. 3, Kīhei)

George Kahumoku and Ledward Kaapana

Award-winning singer and guitarist Ledward Kaapana joins multiple Grammy winner George Kahumoku in his Slack Key Show, along with ʻohana performers at an intimate concert at the Aloha Pavilion at the Napili Kai Resort on Jan. 3 from 6:30 to 7:30 p.m. Doors open at 5:45 p.m.

Kahumoku has received a 2022 Lifetime Achievement award by the Hawai’i Academy of Recording Artists.

Admission is free to Lahaina Fire Disaster survivors and emergency workers, and there is a Kama’aina rate. Tickets are available at or by calling 808-669-3858.

No. 11 – Benny Uyetake performs at Leilani’s (Dec. 28, Ka’anapali)

Benny Uyetake

Nā Hōkū Hanohano winner Benny Uyetake performs at Leilani’s On The Beach at Whalers Village on Thursday from 6 to 8 p.m. Uyetake is a slack key and ʻukulele master with a broad repertoire of music. He’s opened for a variety of musicians including Boz Skaggs and Judy Collins.

For more information including reservations and menu, go to Leilani’s call 808-661-4495.

No. 12 – Arlie-Avery Asiu at Island Fresh Café (Dec. 31, Pāʻia)

Maui musician Arlie-Avery Asiu performs at Island Fresh Café on New Yearʻs Eve from 11:30 a.m. to 1:30 p.m. Heʻs a mostly self-taught ‘ukulele virtuoso who began playing and composing music at age nine. He has produced four original ‘ukulele albums, two of which were nominated for ʻUkulele Album of the Year for the 2016 and 2017 Nā Hōkū Hanaohano Awards program.

Asiu plays his original jazz, blues, classical and rock music. For more information, go to Maui Fresh Café or call 808-446-0298.

No. 13 – Kanaka’ole, Roback perform in free Hawaiian Music Series (Dec. 28, Wailuku)

Wilson Kanakaole and Jarret Roback will perform at Hale Ho’ike’ike at the Bailey House Museum on Thursday at 6 p.m. Admission is free. Guests are invited to bring their own blankets, mats and low-back beach chairs to enjoy the music on the lawn.

Kanakaole, who grew up in Lahaina and attended the University of Hawaiʻi Maui College’s Institute of Hawaiian Music, has appeared on records by the Barefoot Natives and other island musicians. He’s from a family of talented musicians including his father Eric Kanakaole and uncle, the legend Nelson Waikiki. Roback, a firefighter, has been a singer and guitarist on Maui for more than 25 years.

The concert is made possible by the Lahaina Restoration Foundation with support from the Maui Economic Development Board. The special location for this month is provided by the Maui Historical Society.

No. 14 – Comedian Jose Raymond and Friends at da Playground Maui (Dec. 30, Māʻalaea)

Comedian Jose Raymond and Friends take to the stage at da Playground Maui on Saturday at 8 p.m. It’s a benefit fundraiser show for Raymond and his family who lost their home during the Lahaina wildfires.

Raymond has appeared on a number of comedy shows including the Apollo Theater, Hollywood Improv, NYA Comedy and the Laugh Factory. Hosting the show will be Maui comedian Chino LaForge. For ages 21 & over. There is free parking with local ID after 5 p.m. For more information including tickets, go to da Playground Maui.

No. 15 – John Cruz “Island Style” Series at ProArts Playhouse (Jan. 3, Kīhei)

John Cruz

Award-winning John Cruz performs at the intimate ProArts Playhouse Maui on Jan. 3 at 7 p.m. Cruz is a multiple Nā Hōkū Hanohano Award winner and a contributor to the Grammy award-winning album Slack Key Guitar, Vol. 2. More than 1 million listeners stream Cruz’s recordings each year, including his popular song “Island Style.”

Cruz participated in Playing For Change’s “All Along the Watchtower” video, with more than 12 million views. For more information including tickets, go to

No. 16 – Phil & Angela Benoit perform at The Empanada Lady (Dec. 31 & Jan. 3, Wailea)

Angela and Phil Benoit

Angela and Phil Benoit perform original music and jazz standards, bossa nova, pop and Hawaiian swing at Pita Paradise on Sunday and The Empanada Lady Restaurant & Lounge on Jan. 3. Both performances run from 6 to 8:30 p.m.

Angela’s vocals are smooth and rest somewhere between high alto and low mezzo-soprano while Phil provides a swinging guitar. For more information including reservations, call 808-879-7177 or go to Pita Paradise.

No. 17 – Daytime Divas Show at da Playground Maui (Dec. 31, Māʻalaea)

A Daytime Divas performance takes place at da Playground Maui on Sunday at 1 p.m. Join the LGBTQ community in bidding farewell to 2023 with Maui Daytime Divas strutting their stuff. Doors open at 12 p.m. Ages 21 & over. Free parking with local ID after 5 p.m. For more information including tickets, go to da Playground Maui.


No. 18 – Award-winning band Old Dominion performs at the MACC (Jan. 6, Kahului)

Old Dominion

Country Award Music band Old Dominion with special guest Misha will perform on Jan. 6 at 7 p.m. at the Maui Arts & Cultural Center. Gates open at 5 p.m.

The band has won six American Country Music Awards for Group of the Year. Old Dominion’s sophomore album, “Happy Endings,” debuted at #1 on the Billboard Country Albums chart and #7 on the Billboard Top 200. For more information, go to Maui Arts.

No. 19 – Ritz-Carlton Kapalua hosts 2024 Music Songwriters Festival (Jan. 6-13, Kapalua)

Chase Rice, Elle King, Emily Weisband, and Drake Milligan are among the stars appearing at the 2024 Music Songwriters Festival on Maui.

The 7th Maui Songwriters Festival will take place at the Ritz-Carlton in Kapalua from Jan. 6. to 13, bringing together some of the worlds’ best singers and songwriters.

Members of the 2023 Country Music Award group of the year Old Dominion will perform, along with a long line of other stars, including: Chase Rice, Elle King, Drake Milligan, Sonya Isaac from the Isaacs, David Lee Murphy, Emily Weisband, Chris DeStefano, Jimmy Yeary, Ryan Larkins and David Lee Murphy.

DeStefano has co-written No. 1 songs for Carrie Underwood, Dan+Shay, Jason Aldean, Billy Currington, Brett Eldredge, Luke Bryan and Miranda Lambert. Weisband has written songs for stars, including Camilla Cabello, BTS featuring Halsey, Serena Gomez and Chris Young.

For more information including tickets, go to Maui Songwriters Festival.

No. 20 – The Sentry PGA golf tournament at The Plantation Course (Jan. 4-7, Kapalua)

PGA golfers Jordan Speith and Xander Schuffele will be participating in The Sentry golf tournament at The Plantation Course at Kapalua from Jan. 4 to 7. Both have been tournament winners at The Sentry.

Jordan Spieth, Xander Schauffele, Tony Finau and Collin Morikawa are among the golfers returning to The Plantation Course at Kapalua from Jan. 4 to 7 for The Sentry tournament that kicks off the PGA Tourʻs 2024 schedule.

The Sentry features PGA Tour winners from the previous calendar year, including FedExCup Fall winners, and the top 50 players from the final 2022-23 FedExCup standings.

Since the event moved to Maui in 1999, The Sentry has generated more than $8.5 million for local community charities in West Maui. The Sentry also is providing tickets to first responders on Maui and their spouses, and to military personnel with verification of their status. To purchase tickets, visit

Editor’s Note: Send inquiries or event listings with attached photographs about Maui Entertainment, Arts and Community events to [email protected]. To add events directly to the Maui now events Calendar, click here.

Gary Kubota
Gary Kubota, an associate writer with, has worked as a staff news writer with the Honolulu Star-Advertiser and The Maui News. He lives on Maui. He’s also been an editor/business manager with the Lahaina News. He’s received national and regional journalism awards — a National Press Club Citation of Merit and Walter Cronkite Best In The West, among them.
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