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Palm trees on the lawn in front of the Grand Wailea.
The Grand Wailea

Maui

Maui, Hawaii

Three nights at the Grand Wailea, and a raft trip along the South Maui coast.

September 8 through 11, 2025. Three nights at the Grand Wailea, a Terrace View king. I booked it as a Hilton Standard Room Reward, 110,000 points a night, 330,000 for the stay. I bought the points on a sale, about 2:1. The longer version is Buying points for the Grand Wailea.

I flew Alaska via San Diego, and I had a rental car. On September 10 I did a Redline Rafting trip out of Kihei, around Molokini Crater and along the South Maui coast. The flight home was a red-eye on September 11, OGG to San Diego, and it upgraded to First.

Stops

  1. September 8–11

    Grand Wailea

    Three nights, a Terrace View king. Hilton Standard Room Reward, 110,000 points a night, 330,000 total. I bought the points on a sale, about 2:1.

  2. September 8

    Alaska, via San Diego

    Flew in. I had a rental car.

  3. September 10

    Redline Rafting

    Molokini Crater and the South Maui coast, from Kihei.

  4. September 11

    OGG to San Diego

    Alaska red-eye home. Upgraded to First.

Photos

Grand Wailea

The Grand Wailea lobby, a long reflecting pool between columns, with a large flower arrangement at the far end.
An indoor hall at the Grand Wailea, with a shallow pool down the center and white statues along the wall.
A balcony looking over the Grand Wailea pools toward the ocean and the mountains.
The pool entrance at the Grand Wailea, under a blue-and-white striped arch. The sign reads Pool.
The Grand Wailea infinity pool, with the ocean and a small island beyond the far edge.
A white chapel with a blue roof on the lawn at the Grand Wailea, with the ocean behind it.
The Grand Wailea towers across a lawn and a row of palm trees.
Palm trees on the lawn in front of the Grand Wailea.
A beach chair and a palm on the sand, facing the ocean, with the resort behind.

South Maui

A coast road in Maui, dry brush on the hill above and the ocean below.
Open ocean off Maui, photographed from a boat, with the wake in the foreground.
Dark rock along the water, with a small sandy cove and green hills behind it.
The South Maui coast at sunset, steep green hills along the water.