Skip to main content

Maui Real Estate Resources

The Maui Real Estate Blog

May 2024 Maui Calendar of Events

The Green performing live at the Maui Arts & Cultural Center 4/19/24

The go-to guide for Valley Isle happenings, yes this is your recurring monthly map to the best things on island; welcome back to your curated Maui Calendar of Events. May 2024 on Maui is bustling with vibrant celebrations and cultural festivities. Highlights this month include a special Lei Day celebration at the historic Bailey House, an enchanting music and food festival at the Central Maui Sunflower Farm, as well as James Taylor’s outdoor concert at the MACC. You will also not want to miss the ever popular Maui Brewers Festival or the beloved Seabury Hall Craft Fair which is always Mother’s Day weekend (last minute gifts anyone?). The month finishes off with a Japanese Festival, previewing our summer’s Bon Dance season, showcasing Maui’s rich cultural diversity and one of our team’s favorite times of year!

Lei Day Heritage Festival

May 2024--May Day is Lei Day in Maui Nei

Hale Hōʻikeʻike at the Bailey House hosts its annual celebration of Lei Day, an event filled with vibrant colors, fragrant flowers, and the spirit of aloha. All in honor of the rich tradition of lei-making in Hawaiian culture. Lei Day holds a special place in the hearts of the people of Hawai’i, serving as a joyous celebration of the beauty and significance of the Hawaiian lei.

May 2024--May Day is Lei Day in Maui Nei

At the Lei Day Heritage Festival, guests of all ages will have the opportunity to immerse themselves in the art of lei-making through hands-on workshops led by skilled artisans. Learn the techniques and traditions of lei-making as you create your own beautiful flora masterpiece. In addition to lei-making workshops, the Lei Day celebration will feature live music performances by talented local musicians including Jordan Soon and Liz Morales, cultural demonstrations highlighting the beauty and significance of Hawaiian culture, and food from Tru Grindz.

May 2024--May Day Flyer

When Wednesday May 1st, 2024; 10AM – 3PM. Where: Bailey House Museum at the Maui Historical Society; 2375 A Main St, Wailuku, HI 96793. FREE ENTRY!

2024 Sunflower Farm Music Festival & Farmers Market

Get ready for a beautiful day outdoors, filled with live music, delicious food, and unique local vendors! The Sunflower Farm Music Festival is an agricultural education event featuring a Farmers’ Market, Farm Tours and incredible lineup of live entertainment. The Farmers’ market includes produce grown on Maui and items that were produced using agricultural products grown, raised, or caught in Hawaii. The number of talented names performing is a sight to behold! Musicians who’ve founded and starred in such bands like: The Beach Boys, David Bowie, Rod Stewart, Guns N’ Roses, Bad Company, Sammy Hagar, Tower of Power, Steely Dan and The Doobie Brothers, (plus so many more talented, locally based artists; just check the full lineup below)!

Sun Flower Farm Music Festival, 4th of May 2024

In between all the dancing, learn about sustainable agriculture and the circular economy while participating in a guided tour of the Maui Sunflower Farm. Admission includes all day access to the farmers’ market, a farm tour, educational opportunities to learn about sustainable agriculture from speakers and local nonprofits, and music throughout the day. 100% of the profits will benefit the following Maui-based non-profits focused on supporting local farming and helping grow Hawaii’s food security: Maui Hub, Common Ground Collective and Grow Some Good.

Pacific Biodiesel Founders and Owners of the farm, Bob and Kelly King. Photo Courtesy: Mike Sidney Photography

The VIP “Night Before Experience” is the evening of Friday, May 3rd, highlighted by a pre-festival dinner hosted by film producer Stacey Sher and Licorice Pizza Records owner Kerry Brown. Culinary masterpieces crafted by local chefs from Maui-sourced ingredients. Break bread and party with the musicians playing the festival, this will be a meal not-to forget!

When: Main festival takes place on Saturday, May 4th, 2024; from 11AM-6PM. Where: Pacific Biodiesel Technologies Sunflower Farm off of HI 380, near the corner of HI 30. Tickets are $100 (kids 12 and under free with paying adult); Night Before Experience is $250 (with a General Admission ticket included in price); both GA and VIP are available online here.

James Taylor & His All-Star Band

Music legend James Taylor and his All-Star Band are set to dazzle audiences in Maui with a special outdoor concert under the stars. Over his illustrious career, Taylor has sold more than 100 million albums, earning 40 gold, platinum, and multi-platinum awards, alongside multiple Grammy Awards. He has been honored with inductions into both the Rock & Roll Hall of Fame and the prestigious Songwriters Hall of Fame. Taylor’s iconic songs, including hits like “Fire and Rain,” “Country Road,” “Something in the Way She Moves,” and “Carolina In My Mind,” have deeply resonated with music lovers across generations. Hope to see you there!

When: Sunday May 5th, 2024; 6:30PM – 10:00PM. Where: A & B Amphitheater and Yokouchi Pavilion, Maui Arts and Cultural Center, 1 Cameron Way, Kahului 96732. Tickets: $65 (General Admission/No Seats Provided), $85, $135 (Reserved Seating) , + limited number of preferred *$195 (Gold Circle) – all plus applicable fees. Prices increase day of the show. (*All Gold Circle ticket holders receive premium seating and exclusive access to the Yokouchi Pavilion bars and restrooms.) Tickets sold online only here.

48th Annual Seabury Hall Craft Fair

The Seabury Hall Craft Fair is a vibrant celebration of art, culture, and community held annually at their picturesque campus above historic Makawao town in Olinda, Upcountry Maui. This much-anticipated event attracts local artists, artisans and crafters who display an array of unique, handmade items ranging from intricate jewelry to stunning sculptures and fine artworks. One of the more popular highlights of the fair include a robust silent auction, where attendees can bid on truly exclusive items and experiences, adding an exciting edge and anticipation of a big win to the day!

The event is further packed with entertainment, featuring live music and performances that provide a lively backdrop for fair-goers of all sizes. The Maunalei Food Court offers a variety of delicious local and international cuisines, while La Patisserie tempts with an assortment of sweet treats. For families, the fair is a paradise with numerous activities for children, including keiki games, bounce houses, the famous waterslide, and even pony rides. Additionally, the fair boasts a selection of beautiful plants, flowers, and handcrafted leis, celebrating the rich floral heritage of Hawaii.

The craft fair is the school’s largest fundraiser event and supports Seabury Hall’s financial aid programs which have a twofold purpose: to provide deserving students an opportunity for a high-quality college preparatory education that might otherwise be unobtainable for them and to provide the school with a well-qualified student body reflecting a broad social and economic mix.

When Saturday, May 11th, 2024; 9 am – 3 pm. Where: Seabury Hall, 480 Olinda Road, Makawao, Hawaiʻi 96768. Admission: Adults are $10 and under 12 is FREE!

2024 Maui Brewers Festival

MACC’s annual fundraising event extraordinaire is easily one of Maui’s top festivals and local gatherings! The event features tasty food from Maui restaurants, food trucks and caterers at no additional charge; beer tastings from island-based and mainland craft breweries; an assortment of live music, entertainment and lots of fun! Don’t like beer? Enjoy Vitalitea Kombucha, fresh made cold brew coffee, craft sodas, and plenty ono kaukau! All attendees must be 21 & over and attend with a valid photo ID.

When: Saturday, May 18th, 2024; 2PM – 7PM ‘Beer Lovers’ Happy Hour: 2PM-3:30PM; General Admission: 3:30PM-7PM. Where: A & B Amphitheater and Yokouchi Pavilion, Maui Arts and Cultural Center, 1 Cameron Way, Kahului 96732. Tickets: $85 for GA and $195 for VIP ‘Beer Lovers’; only available online here.

Maui Matsuri Japanese Festival

The Maui Matsuri Japanese Festival features Japanese entertainment, craft booths, food trucks and stands, free children’s crafts, exhibits, martial arts demos, eating contests, plus passport activity for free gifts. This is a preview of one of our favorite times to go grind on Maui, Bon Season! This festival will be highlighted by local food favorites: Maui Fresh Streatery; Only Ono BBQ; Oyako Tei; and the ever favorite Chow Fun from the Wailuku Hongwanji.

The culmination of the evening is an interfaith prayer and luminary ceremony to remember those lost in the Lahaina tragedy. A Bon Dance honoring our ancestors and all those who came before us continues until 9pm. Also don’t miss the Children’s Festival at Queen Ka’ahumanu Center on May 18th. For both gatherings, all are welcome. Let’s all get together for a day and evening that is uniquely Maui!

When: Children’s Festival will take place Saturday, May 18th, 2024; 10AM-1PM; while the main Japanese Festival will be on Saturday May 25th, 2024; 3PM-9PM. Where: The Children’s Festival is located at The Queen Ka’ahumanu Center, 275 W Kaahumanu Ave, Kahului, HI 96732; The Japanese Festival is just across the highway at University of Hawaii, Maui College Entertainment Stage, 310 W Kaahumanu Ave, Kahului, HI 96732. Admission to both events are FREE, with a $5 parking donation per vehicle to the main Japanese Festival.

Contact a Maui Real Estate Specialist

Beyond being a trusted advisor in the real estate market, your REALTOR should be a professional who recognizes their role in supporting your wealth building and wealth preservation. Helping to magnify wealth is one of the core values of The Sayles Team; a set of guiding principles for how we serve our clients at the highest level.

Pele's Paintbrush, Haleakala Crater, Maui, Hawaii

As experts in the field, we are constantly learning and providing guidance about making the wisest choices for the future. If someone you care about needs guidance or recommendations, please share our contact information and we would be honored to help them! If you would like to receive our in-depth market update or would like an evaluation of your property’s value we would love to hear from you.


Dano Sayles R(B)


Leave a Reply

Your email address will not be published. Required fields are marked *

Follow Us On Social: