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Magical and Charming, Maui in May Will Make You Swoon

Beach surrounded by trees

When you need a place to ring in summer a little early, visiting Maui in May is the answer! It’s less crowded, the weather is lovely, and the island still radiates its captivating charm. On Maui, you will find awe-inspiring sights, unique cultural art, and lively local happenings on every corner. Ready to plan your journey? Access our free Vacation Guide to unlock the best things to do in Maui.

5 Unique Ways to Spend a Day on Maui in May

Take a Stroll on a Black Sand Beach

Ever dreamed of spending the day in a beautiful, private cove? Then Pa’iloa Beach is the perfect place for you! The black pebble field, glistening blue water, and lush tropical greenery will make you want to stay all day. This unique beach has much to offer as beach-goers can also explore sea caves, lava tubes, and hiking trails that promise even more glorious views.

Hike a Beautiful Trail

For a short hike and jaw-dropping views, follow the Ohai Loop Trail along a stretch of rugged coastline. This trail extends for 1.2 miles and gets its name from the Ohai plant, an endangered plant species that you might encounter along the trail. As you wander through the rocky path, try to spot Kahakuloa Head in the distance and take a moment to appreciate Mother Nature’s creation.

Local tip: Although this trial is for all skill levels, it’s rocky and rough, so wear sturdy shoes.

Attend one of Maui’s Top Festivals

Spend an afternoon at the Maui Brewers Festival and show your support for the Maui Arts and Cultural Center. The Brewers Festival takes place once a year and promises to delight attendees with delicious local foods, live music, and, of course, world-class craft beers.

Party Like a Local

Events on Maui are always special, but the island’s Friday Town Parties are like no other celebration. The weekly parties highlight each of Maui’s historic towns, and the authentic atmosphere is a local favorite. Each Friday Party has live music, local vendors, and free entertainment for everyone.

Maui Friday Town Parties:

  • 1st Friday – Wailuku, Central Maui
  • 2nd Friday – Lahaina, West Maui
  • 3rd Friday – Makawao, Upcountry Maui
  • 4th Friday – Kihei, South Maui
  • 5th Friday – Lana’i, Lana’i City

Don’t miss these unique, culture-filled celebrations!

Find a Maui Memento

Don’t forget to take home something special to remind you of Maui’s magic! Lahaina is a historic town located in West Maui and is the best place to witness Maui’s thriving art scene. It’s home to dozens of art galleries and showcases the work of hundreds of local artists. While you are here, you don’t want to miss Friday Art Nights when you will have the opportunity to chat with artists, discover unique art, and pick out a special souvenir.

Other activities

  • Enjoy whale watching in May.
  • Cruise down the Road to Hana.
  • Discover the bamboo forest on the Pipiwai Trail.
  • Explore Maui’s most beautiful waterfalls.
  • Admire the beauty of Maui’s Sacred Garden.

Unwind at The Historic Wailuku Inn

Continue your authentic Hawaiian experience at the Old Wailuku Inn at Ulupono. Our bed and breakfast is the best option for your stay on Maui. When you stay in any of our island-inspired rooms, you’ll have access to our homemade breakfasts and our charming backyard garden.

Our innkeepers, Tom and Janice, grew up in Hawaii and know Maui like the back of their hands! Together, they are dedicated to making you feel right at home during your stay at the Old Wailuku Inn at Ulupono. Check our availability and book your stay now!

Check our availability and reserve your room today! We can’t wait to host you soon.

The Historic Wailuku Inn

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  • 808-244-5897
  • 2199 Kaho'okele Street Wailuku
    Maui, Hawaii 96793