9 curated experiences
Kahului
The only way to truly see Haleakala's massive crater from above, fly the Road to Hana without driving it, and see the interior waterfalls that have no land access. The West Maui Mountains — also only accessible by air — are as dramatic as Kauai's Na Pali Coast and almost no one has seen them. Blue Hawaiian has the best safety record and narration; Air Maui offers doors-off tours for photographers. The Na Moku 45-minute route covers the most essential sights; the Circle Island route adds the Kaupo Gap and Hana coast and is worth the extra cost.
Wailuku
A stone house built in 1833 at the mouth of ʻĪao Valley, later the Wailuku Female Seminary run by Caroline and Edward Bailey. A museum since 1957: pre-contact Hawaiian artifacts and Edward Bailey's paintings of ʻĪao. Open Tuesday to Friday, 10 AM–2 PM.
Wailuku
A short paved loop of the plants early Hawaiians brought and grew in ʻĪao Valley.
Wailuku
Queen Kaʻahumanu visited in 1832 and asked that the permanent church bear her name. The present building, the fourth on the site, dates from the 1870s; services and hymns are still in Hawaiian.
Wailuku
The name means "damming of the waters", for the 1790 Battle of Kepaniwai, when Kamehameha I's forces defeated Maui's army here. The county park honors Maui's peoples with Hawaiian, Chinese, Japanese, Filipino, Portuguese, Korean and New England pavilions. Open 7 AM–7 PM, free.
Wailuku
Kūkaʻemoku, the ʻĪao Needle, is an erosional ridge rising 1,200 ft from the valley floor that looks like a spire seen end-on; it is sacred in Hawaiian tradition.
2 trails
Wailuku
Sacred valley with a striking 1,200-foot green needle (Iao Needle) rising from the valley floor. Site of the 1790 Battle of Kepaniwai. The valley receives 400 inches of rain annually — impossibly lush.
Central Maui
The best mountain hike on Maui that is not Haleakala — 6.4km round trip through the lush West Maui Mountains with 500m elevation gain. The upper ridge delivers sweeping views of the north coast on one side and Ma'alaea Bay on the other, with deep green valley walls on either flank. After rain, waterfalls appear on the ridges and the vegetation turns impossibly vivid. Far less crowded than Iao Valley 15 minutes away. Pairs naturally with Iao Valley for a full West Maui day: do Waihe'e Ridge in the early morning while it's clear, then Iao Valley after.
1 place our scouts eat
53 on the calendar
Dec 15 – Apr 15, peak Feb–Mar
Leeward coast (ʻAuʻau Channel)
Every winter, thousands of North Pacific humpback whales migrate roughly 3,000 miles from Alaska to the warm, shallow waters around Maui to mate, calve and nurse their young. The ʻAuʻau Channel between Maui, Lānaʻi and Molokaʻi becomes one of the best whale-watching areas on Earth, with sightings of breaches, tail slaps and mother-calf pairs. You can watch for free from Maui's leeward coast — the Papawai Scenic Lookout (Māʻalaea Pali), McGregor Point, and the beaches of Kāʻanapali and Wailea are reliable vantage points — or take a naturalist-led boat tour out of Lāhainā or Māʻalaea harbors. Morning trips generally have the calmest water. Peak season is February and March, though whales arrive as early as December and linger into April. Federal law requires staying at least 100 yards from a whale.
2026-01-01
A running race on Maui, Hawaiʻi, held January 1, 2026. See the linked listing for distances, start time and registration details.
2026-01-03
The Quadrantids are one of the year's strongest meteor showers, with a brief, sharp peak in early January that can produce 40 or more meteors per hour under dark skies. Because Hawaiʻi has some of the clearest, darkest skies in the U.S., the islands are a superb place to watch. Look in the hours before dawn, away from town lights — a high-elevation spot or a dark leeward beach is ideal. No telescope needed; just let your eyes adjust for 20 minutes.
2026-01-05 – 2026-01-11
Kapalua Plantation Course
The Sentry is the PGA Tour's season-opening event, a winners-only tournament that gathers the previous season's Tour champions to tee off the new year. It is played on the dramatic Plantation Course at Kapalua Resort on Maui's northwest coast, famous for its sweeping downhill fairways, trade-wind-swept greens and Pacific-and-Molokaʻi backdrop — including the par-5 18th, one of the most photographed finishing holes in golf. Held in early January in Kapalua, West Maui, it draws the world's top players and pairs perfectly with the start of humpback whale season just offshore. Grounds tickets and hospitality packages are sold each year; the West Maui resorts book up early around the event.
2026-02-04
An amateur surf contest on Maui, Hawaiʻi, held February 4, 2026. See the linked listing for distances, start time and registration details.
2026-02-15
Kīhei · Kalama Park
World Whale Day is the centerpiece of the Maui Whale Festival — a whale-themed parade followed by an all-day festival at Kalama Park in Kīhei. The free celebration features live Hawaiian and contemporary music, food trucks, local craft and nonprofit booths, and keiki (children's) activities, all honoring the humpback whales that winter in Maui's waters. Held in February; come early for parking along South Kīhei Road.
1 narrated route
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