Who doesn’t love summer vacation on Maui?!
June, July, and August are very popular months to visit Maui — especially for families, since children in North America are on summer break.
There are plenty of things to do on Maui in summer — from snorkeling and sunny beach days to some of the island’s most popular annual events and festivals. Planning a summertime Maui getaway? Here are a few of the many Maui events you can enjoy.
THINGS TO DO ON MAUI IN SUMMER
MAUI EVENTS IN JUNE
Waʻa Kiakahi Canoe Festival: Each year, the Hawaiian Sailing Canoe Association hosts Waʻa Kiakahi on Kaanapali Beach. This event was created to perpetuate traditional Hawaiian canoe sailing and the skills related to sailing outrigger canoes. Festivities include canoe races, demonstrations, and sailing-canoe rides. It’s beautiful to watch and a great place to learn more about Hawaiian seafaring!
2026 Date: June 13. Kaanapali (West Maui). Details & Future Dates. Places to stay on Ka’anapali Beach: The Vacation rental condos at The Whaler Resort.
Annual Kapalua Wine & Food Festival: The Kapalua Wine and Food Festival is the longest running epicurean festival in Hawaii! The event features wine tasting seminars, cooking demos, and the fabulous Grand Tasting event. Guests can rub elbows with celebrity chefs and renowned winemakers — and enjoy to-die-for food and wine pairings, of course. This is one of the most popular things to do on Maui in summer!
2026 Dates: June 25-28th. Kapalua (West Maui). Details & Future Dates (as they become available). Places to stay in Kapalua!
Wailuku Film Festival: The first annual Wailuku Film Festival is set to replace the longstanding Maui Film Festival. The new festival’s goal is to uplift local filmmakers and bolster the island’s film industry. The festival will be help over several days in June at the Iao Theater and the Maui Academy of Performing Arts building. Film themes will include students, Hawaii, Indigenous, and water sports. We don’t have much information at this point, but we’re excited to see how it goes!
2026 Dates: June 18-21st Wailuku (Central Maui). Details & Future Dates (as they become available). Stay near Wailuku.
MAUI EVENTS IN JULY
Lanai Pineapple Festival: The Annual Pineapple Festival on the island of Lanai (Maui’s sister island and part of Maui County) started in the 1970s as the kick-off for the Lanai Community Association’s annual fund drive. The Pineapple Festival is the island’s largest annual event and features delicious food, cooking competitions, entertainment, craft and volunteer booths, fireworks, and of course plenty of pineapple.
2026 Dates: TBD Dole Park on the island of Lanai. Details & Future Dates (as they become available). Ferry service is available between Lahaina and the island of Lanai.
Makawao Stampede (previously called Makawao Rodeo): Makawao Town is known for its annual Makawao Rodeo, now known as the Makawao Stampede. Now in its 67th year, the annual rodeo takes place at Oskie Rice Arena and features three days of fun events — including a Bull Bash, keiki sheep riding, country concerts, and a coveted parade through Makawao Town.
2026 Date: July 3-5th Makawao (Upcountry) Details & Dates.
Molokai 2 Oahu Paddleboard World Championships: Maui County encompasses the four islands of Maui, Molokai, Lanai, and Kaho’olawe. The Molokai 2 Oahu Paddleboard World Championships is an annual event bringing together athletes from around the world. Paddleboarders cross the Ka’iwi Channel between the islands of Molokai and Oahu, a 32-mile journey across a 2,300-foot-deep channel that has challenged athletes since the first organized outrigger race in 1952.
2026 Dates: July 26th. Details & Future Dates (as they become available).
MAUI EVENTS IN AUGUST
Cycle To The Sun: Calling all cyclists: do you have what it takes to complete one of the most challenging (but rewarding) rides in the world? The annual Cycle to the Sun is a race that travels the longest, steepest, paved road on the planet — from Paia to Haleakala’s 10,000 foot summit.
2026 Date: August 1st. North Shore/Upcountry. Details & Future Dates (as they become available). North Shore B&Bs to stay at.
MORE TIPS FOR SUMMER ACTIVITIES ON MAUI
Year-round Activities
Kihei Town Parties:
Kihei Fourth Friday: Kihei hosts a town party on the fourth Friday of every month at Azeka Shopping Center. Come for live music, vendors, keiki activities, food, and more! More Details.
Free Entertainment: When you are here, make sure you check for entertainment and events at nearby hotels and resorts, as well as island shopping centers, which often offer free hula shows, activities like lei making and ukulele lessons, and live Hawaiian entertainment. And check out my list of 25 Free Things To Do on Maui for other suggestions.
Farmers Markets: A popular stop for locals and visitors alike, peruse the delicious local produce at a nearby farmers market. Enjoy colorful and flavorful fruits and veggies, learn about the unique produce of Maui, and support the local farmers and vendors. Often local crafters and designers are also selling their unique products like jams and jellies, clothing, jewelry, and island-themed goodies. Some of our top favorites include the Upcountry Farmers Market, Napili Farmers Market, and South Maui Farmers Market. See our ultimate guide to Maui Farmers Markets.
Live Music on Maui — Mana’o Radio: Live music is happening around the island, with local musicians jamming almost every night at some of the island’s best restaurants. To find out who’s performing where, check out Mana’o Radio’s Music2Nite site for a full lineup of live music on Maui.
Mana’o Radio (KMNO 91.7 FM) is Maui’s non-commercial all-volunteer radio station. Instead of a canned, pre-programmed song list, you’ll hear local people (volunteer djs) playing an eclectic selection of the music they love best. Listen while you’re here on Maui, or live stream from their website. Tune in to a truly local radio station! Follow Mana’o Radio on Facebook for the latest word on their broadcast schedule and live events on Maui.
Grassroots Festivals and Fundraisers: Don’t be shy to buy a ticket and attend local school, church, and charity fundraisers, bazaars, and festivals. These events are a great way for visitors to experience an authentic local gathering, and the organizers will love to have you there. There is always plenty of local food (eating is a priority here on Maui!) and entertainment, and often there are fundraising auctions (silent and live) where you can snag great deals on visitor activities like luaus, golf, dining, and boat tours.
Live Webcams: When you are here planning your day on Maui, check out these webcams to view current weather conditions around the island. It’s not unusual for it to be overcast or rainy in one area but clear and sunny just a few minutes away!
Maui Arts & Cultural Center: This is another excellent resource you should check for upcoming events and performances on Maui, from world-famous celebrities and musicians to symphonies and ballet to local Hawaiian cultural programs and festivals. The Maui Arts & Cultural Center is located in Kahului.
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Aloha! Tiffany here. I've been blessed to call Maui home since 2011. With a background in the island's finest restaurants and hotels, guiding visitors to create unforgettable Maui memories is more than a skill I've mastered—it's a profound source of joy for me.
