Wailea

Akamai Coffee Co. (Wailea)

Wailea

Maui-grown coffee roasted on island, the best cup between Kihei and Makena. The Wailea Gateway location is the one on the way back from Big Beach.

Monkeypod Kitchen

Wailea

Monkeypod Kitchen (Wailea, 10 Wailea Gateway Pl) — the best casual dinner in Wailea that is not a hotel restaurant. Wood-fired pizza, fresh fish, and excellent cocktails in a lively, open-air space. Arrive before 6pm or reserve; it fills quickly every evening.

Dec 15 – Apr 15, peak Feb–Mar

Humpback whale season

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

New Year's Day Virtual Run - Kahului (Maui)

A running race on Maui, Hawaiʻi, held January 1, 2026. See the linked listing for distances, start time and registration details.

2026-01-03

Quadrantid meteor shower (peak)

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

The Sentry (PGA Tour season opener)

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

2026 HSA DUKES LEGENDS of the Bay

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

World Whale Day Parade

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.