Hawaii

Hawaii has no bad month, only busy ones. April to early June and September to mid-December are the value windows, with warm water, smaller crowds and essentially the same weather. Late December to March is peak: whale season, north-shore surf and school holidays all at once, with rates to match.

Kona and Kahului both take large-cabin aircraft and Honolulu handles anything. Inter-island hops run twenty to forty minutes, which makes a two-island trip genuinely practical here in a way it is not in most archipelagos.

Among our preferred hotel partners, Four Seasons Resort Hualalai on the Kona coast of the Big Island is the one members return to most. Four Seasons Resort Maui at Wailea and the Ritz-Carlton Maui at Kapalua cover Maui from opposite ends of the island, and Four Seasons Resort Lanai is the quietest of the four by a wide margin.

Ask your advisor about humpback season between December and April, Mauna Kea summit access, and how to attach a mainland leg without losing a day to the connection.