Witness a breathtaking sunrise or sunset from the summit of Haleakalā, Maui’s highest peak. Reservations are required for sunrise visits, so book in advance through the National Park Service. Don't forget warm layers—temperatures can drop dramatically at 10,000 feet!

Take a short, scenic hike through ʻĪao Valley, home to the iconic ʻĪao Needle, a towering green peak surrounded by misty mountains. This sacred site offers a peaceful retreat and is rich in Hawaiian history. No reservation is needed, but there is a small entrance fee.

Take a scenic drive along the legendary Road to Hana, winding through lush rainforests, waterfalls, and coastal cliffs. Stop at black sand beaches, hidden pools, and charming roadside stands for fresh banana bread. Plan for a full day and book a guided tour if you prefer to sit back and enjoy the views! Ask Jess and John for their favorite spots from their past trips!

Immerse yourself in Hawaiian culture with a traditional lū‘au featuring hula dancing, fire knife performances, and a delicious feast. One of the top options is the Drums of the Pacific Lū‘au at the Hyatt Regency Maui! (discounts may apply if staying at the resort). Reservations are highly recommended, as this popular lū‘au often sells out in advance!

Explore Maui’s crystal-clear waters by snorkeling at Molokini, a partially submerged volcanic crater teeming with marine life. Many tours also stop at Turtle Town, where you can swim alongside Hawaiian green sea turtles. Book a boat tour in advance, as spots fill up quickly!

Venture beyond the beaches and explore the rolling hills of Upcountry Maui, home to charming farms, botanical gardens, and sweeping island views.

Experience Maui from a breathtaking aerial perspective with a helicopter tour over lush rainforests, cascading waterfalls, and volcanic landscapes. Popular options include flights over Haleakalā Crater, the West Maui Mountains, and the dramatic sea cliffs of Moloka‘i.

Early May marks the tail end of Maui’s humpback whale season, offering a last chance to see these majestic creatures before they migrate north. Book a boat tour from Lāhainā or Ma‘alaea Harbor for an unforgettable experience. While sightings may be fewer than in peak months, lucky visitors might still catch glimpses from shore!

May is one of the best times for golfing in Maui, with mild temperatures and fewer crowds. Play a round at world-class courses like Kapalua’s Plantation Course, Wailea Golf Club, or the stunning Mākena Golf & Beach Club.