What to Do in Hawai‘i in May

Surf lessons, tanning on the sand, and snorkeling above Pacific reefs are sure bets in Hawai‘i. Once you’ve gotten your fill, these community events, performances, and parties are perfect outings for the socialite or curious traveler.

The Barefoot Beach Café | 2699 Kalakaua Ave., Honolulu (O‘ahu)  | Every Saturday, 5:30 to 8:30 p.m.

Chris Salvador plays live music every Saturday night from 5:30-8:30 p.m. Order a simple plate lunch, gaze out at Queens Beach, and listen to live tunes. What’s more blissful than that? (If your Saturday is booked, there is also live music every day but Monday at the same time).

88th Annual Lei Day Celebration | Queen Kapiolani Park and Bandstand (O‘ahu) | May 1, 9 a.m. – 4:30 p.m.
Lei, those beautiful circlets and necklaces of fragrant flowers, are both a symbol of aloha and a true practice on the islands. At this event marking Lei Day, observe some of the most exquisite lei and enjoy local food and music.

Upcountry Farmers Market | Kulamalu Town Center (Maui) | Saturdays, 7 to 11 a.m.
Drive out to this eclectic market complete with crafters, farmers, and bakers. If you want to get a taste of local produce, this is for you! Expect fun treats ranging from the classic to the innovative, including Maui Cones (We recommend the mochiko chicken.). If you can’t make it, don’t stress—there are markets all around the islands on various days.

Brothers Cazimero Lei Day Concert | Maui Arts & Cultural Center (Maui) | May 1, 7:30 p.m. | $12 – $55
This annual concert is always a celebratory event! Enjoy contemporary Hawaiian music and hula performances, as well as local arts and crafts.

Cinco de Mayo Block Party | Restaurant Row (O‘ahu) | May 2, 5 p.m. | Free – $15
If you were worried you weren’t going to be able to celebrate Mexico’s 1892 victory over the French since you were on an island amidst the Pacific Ocean, toss those cares out the window now. This block party features food vendors, live music, and Hawaii nightlife fun. (Heads up, this one may be a bit of a bro-y scene.)

Slack Key Guitar and Ukulele Concert | Hanalei Community Center (Kaua‘i) | May 3, 3 – 5 p.m. | $20 (prices may vary)
Experience the unique style of slack key guitar. This concert will provide local products for sale along with live entertainment and music.

World Fireknife Championship & We Are Samoan Cultural Arts Festival | Polynesian Cultural Center (O‘ahu) | May 7 – May 9
The world’s most talented fireknife dancers come together at the Polynesian Cultural Center to compete in three nights of literally heated competition.

Kickoff Event for Maui Matsuri | Queen Kaahumanu Center (Maui) | May 8, 6:30 p.m.
This event will feature taiko performances, karate demonstrations, and more! The event will conclude with obon odori (bon dance) practice around the stage.

Big Island Chocolate Festival | Fairmont Orchid (Big Island) | May 8, 5:30 – 9 p.m. | $75 – $100
Indulge in the rich taste of chocolate while participating in delicious, chocolate-themed activities. The event includes a cacao farm tour, a student culinary competition, and more.

Maui GLBT & Friends Hiking Group | Waihee Ridge Trail Hike (Maui) | May 9, 8:30 a.m. – 1 p.m.
This month the hiking group is heading to one of Maui’s best hikes. With views ranging from the Waihee Gorge to the Kahakuloa slopes, this scenic hike will keep you on your toes.

The Lava Soiree | Wailea Beach Marriot Resort and Spa (Maui) | May 9, 5:30 – 10 p.m. | $125
This lavish event is so worth it: It raises funds for a scholarship for an amazing Maui student headed to college. Join others at sunset for a rooftop shindig with a full luau dinner and live entertainment by the Deborah Vial Band. This is Maui Pride’s most glamorous evening affair.

Maui Brewers Festival | A & B Amphitheater (Maui) | May 16, 4 – 7 p.m. | $60+
Definitely not a buzz kill. This festival showcases the best craft brews in Hawai‘i and the U.S. Mainland. Tickets include eight samples, a commemorative glass, and island-style dishes.

32nd Annual Universal ShowQueen Pageant | Hawaii Convention Center, Honolulu (O‘ahu) | May 16
This fabulous pageant, which kicked off in 1984, celebrates the “ultimate in boy beautiful.” Such a good time.

Honokaa Western Week Parade and Block Party | Honokaa Town (Big Island) | May 18 – 25
Big Island is known for its ranches and paniolo (Hawaiian for cowboy). Experience this yourself in Honokaa with different paniolo themed activities every night of festivities. The block party will take place on May 22, and a rodeo will take place May 23–25.

Cabaret IV: Jack Clone’s Mardi Gras Follies | Hawaii Theatre (O‘ahu) | May 23, 7 p.m. | $30
Ah, who doesn’t love a good ballroom dancing fix? The Hawaii Ballroom Dance Association (HBDA) takes the stage for this show, highlighting everything from jazz to the tango scene. They will be joined by hip hop dancers and local entertainers.

Hibiscus Half Marathon | Kapiolani Regional Park (O‘ahu) | May 24, 5:30 – 9:30 a.m.
This 15k and 5 miler is fun for all ages! The course will start and end at Kapiolani park.

Splendors of Ikebana | Honolulu Museum of Art School (O‘ahu) | May 22- May 25, 10 a.m. – 4 p.m.
Take a break from all the hustle and bustle of the city to see the wonderful art of Ikebana, a Japanese form of flower arrangement. Complete with demonstrations, workshops, and public exhibitions, this exhibition will make you feel at peace.

Lantern Floating Hawaii | Ala Moana Beach Park (O‘ahu)| May 25, 6 – 7:30 p.m.
Take part in one of the most famous Memorial Day ceremonies on the island. Write on your own lantern and set it out to sea in a touching ceremony. First come, first serve basis (AKA get there extra early, since this is an incredibly popular event).