Wailea
The name Wailea translates to "water of Lea" — Lea being the Hawaiian goddess of canoe-builders — and there's something fitting about that origin for a coast so shaped by the sea. Five crescent beaches curve along South Maui's leeward shore here, each one sheltered enough that the water sits unusually calm, and a 1.5-mile paved path stitches them together for anyone willing to walk.
What exists today is the product of deliberate invention: 1,500 acres of post-war scrubland that Matson Navigation Company bought in 1957, later passed to Alexander & Baldwin, and by the early 1970s committed to becoming a resort community from scratch. The result is planned, yes — but the beaches and the dry, clear light are entirely real.
💛 What travellers fall for
People who return tend to time their mornings around the Wailea Coastal Walk before the sun gets high — the path is free, public, and connects Polo Beach all the way to Keawakapu. November through May, they scan the water from that path for North Pacific humpback whales, which pass close enough that binoculars feel almost unnecessary.
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Book directly at the providerHow Wailea came to be
Before the hotels arrived, Wailea's shoreline was a fishing settlement, and the slopes above it shifted to cattle ranching after the Great Mahele land redistribution of 1848 under King Kamehameha III — eventually becoming part of Ulupalakua Ranch. During World War II, Marines trained for amphibious landings along these same shores; Ulua Beach was called Little Tarawa by the men rehearsing for the assault on that Pacific island.
The transformation into a resort began in 1957 when Matson Navigation purchased the land, and accelerated after Alexander & Baldwin took full ownership in 1969. In 1971, A&B partnered with Northwestern Mutual Life Insurance to form the Wailea Development Company. The first condominiums — Wailea Ekahi Village and Wailea Ekolu Village — went up in 1978 and 1979. The Grand Wailea opened in 1991, built by Japanese developer Takeshi Sekiguchi on nearly 40 acres.
Who and what shaped it
People who shaped it
Landmark buildings
Plan your visit
On the map
When to go
Wailea's position on Maui's leeward side keeps it drier than almost anywhere else on the island — about 15 inches of rain a year and 276 sunny days, with January highs around 82°F and July around 88°F. Even in the nominal wet season (November through March), you're unlikely to lose a beach day.
Right now
Background & history adapted from Wikipedia (CC BY-SA) · specs from Wikidata (CC0) · weather from Open-Meteo · map data © OpenStreetMap contributors · photos from Wikimedia Commons / Unsplash with per-image credit. No third-party reviews or social posts reproduced.