Maui Summer Guide 2026 Experiences | Hawaii.com

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Maui Summer Guide 2026: Top Experiences

By Sarah Burchard

1 May, 2026

The Branches outdoor music venue. Courtesy of Royal Lahaina Resort & Bungalows.

If food, wine and music is your thing, summer is a great time to be on Maui. With events happening nearly every weekend, you're bound to catch at least one. Here's what's on the roster for 2026. We've incorporated events happening on the island of Lānaʻi on this list too. You can always take a ferry over from Maui.

Festivals & Events on Maui & Lānaʻi

Wailuku Film Festival

June 17-21

More than 80 films will be shown at this year's festival. The festival's mission is to celebrate and create a space for emerging and established talent. "WFF honors the depth of Indigenous knowledge and traditional art forms while embracing innovation in global storytelling across all formats and genres."

Kapalua Wine & Food Festival

June 25–28

Located in Kapalua for the past 45 years, the Kapalua Wine & Food Festival celebrates some of the world's best vintners and chefs, alongside Maui’s most beloved restaurants and local purveyors. There are intimate winemaker dinners, interactive tasting seminars and opportunities to discover exceptional wines from around the world.

June 13: Michelin-starred Andrew Yeo & Jayshree Nathoo (Chinese-Indian fusion)
July 11: James Beard Semi-Finalist Richard Sandoval (modern Latin-Asian)
August 8: Top Chef Host Kristen Kish (Soulful American innovation)
September 12: Top Chef Fan Favorite & Maui’s own Sheldon Simeon (elevated island heritage)

Kapalua Wine & Chef Series

June 13-July11

Hosted at the Banyan Tree restaurant inside The Ritz-Carlton Maui, Kapalua, this intimate dining event highlights celebrity chefs with a four-course tasting menu and wine pairing. Reservations are required via OpenTable or by calling 808-665-7089.

June 13 at 5:30 p.m. — Spence Vineyards & Chef Andrew Yeo

July 4 — Maneet Chauhan

July 11 at 5:30 p.m. — Far Niente Vineyards & Chef Richard Sandoval

Wailuku First Fridays

Every first Friday of the month

A free family-friendly event with live music, art and food in historic Wailuku town.

Kīhei Fourth Fridays

Every fourth Friday of the month

Block party at Azeka Mauka from 6 to 9 p.m. Free to attend.

Lāna‘i Pineapple Festival

July 4

This annual celebration held at Dole Park in Lāna‘i City celebrates the island's rich agricultural heritage — what was once the largest pineapple farm in the world. Come for local food booths, craft vendors, live music and fireworks.

Maui Songwriters Festival Summer Series

Grammy-winning Kristian Bush will perform at this year's Maui Songwriters Festival Summer Series. Photo courtesy of The Ritz-Carlton Maui, Kapalua.

Curated showcases featuring award-winning artists from Nashville sharing the stories behind their biggest hits in an unplugged, intimate setting. Admission is free for resort guests and $10 per non-hotel guest. Purchase tickets at the door. Hosted at at The Ritz-Carlton Maui, Kapalua.

Friday, June 19, 6-9 p.m.: Country artist Grace Tyler brings her soulful songwriting and modern country sound to Kapalua. Known for her viral hit “My Mistake” and her debut EP Everything I Didn’t Say, Tyler blends classic country roots with contemporary storytelling. Opening the evening are acclaimed Hawai‘i artists, Kala'e Parish and Kalenaku, whose dynamic performances seamlessly weave contemporary country influences with Hawaiian musical traditions.
Friday, July 17, 6-9 p.m.: Country singer‑songwriter FILMORE brings a bold, genre‑blending sound that fuses country, pop, rock, hip‑hop, and Latin influences. Known for high‑energy performances and honest storytelling, his latest album, Atypical, showcases his signature style and creative evolution. Joining the lineup is Maui-born singer-songwriter, Akoni Palomino, whose signature sound blends Hawaiian music with country storytelling and reggae soul.
Friday, August 21, 6-9 p.m.: Grammy‑winning artist Kristian Bush, best known as one‑half of Sugarland, joins rising singer‑songwriter Payton Sullivan for a compelling blend of iconic country storytelling and fresh, coastal‑inspired sound. This special night offers a rare opportunity to experience two artists whose music bridges generations and genres. Opening the evening are Hawai‘i artists Kamalani Kawa‘a and 94Tunez. Together, they showcase the evolving sound of island music through a compelling blend of contemporary Hawaiian, reggae, R&B, and soulful storytelling.

Maui Jazz & Blues Festival

August 31-September 8

The Maui Jazz & Blues Festival is a weeklong celebration with Grammy-winning legends, internationally renowned instrumentalists and soulful southern rhythms hosted at The Ritz-Carlton Maui, Kapalua. This year will include an exclusive speakeasy pop-up weekend hosted by New Orleans’ award-winning Jewel of the South, recognized as one of North America’s 50 Best Bars. 2026 artist lineup coming soon.

The resort also recently launched a weekly Maui Jazz and Blues Night at its Alaloa Lounge, featuring Maui musicians.

The Branches Music Series at Royal Lahaina Resort & Bungalows

Nightly

Set beneath a century-old banyan tree, The Branches at Royal Lahaina Resort & Bungalows for complimentary live music. Nightly lineup is generally Maui-based musicians, with special featured artists each month. This summer, The Branches will host Anuhea on May 15 and June 19, Seven Suns on July 17 and Tavana on August 21.