Hawaii

Hawaii is six very different islands wearing one name, and the biggest mistake travelers make is treating them as interchangeable. Our coverage concentrates on the two we believe reward luxury travelers most. Maui is the classic: golden resort beaches, the Road to Hana, Haleakala at sunrise, and two distinct luxury coasts to choose between. The Big Island is the connoisseur's pick — younger, stranger, and more dramatic, where black lava fields run down to white-sand coves and the state's most exclusive resorts sit along a single sunny coast. Nothing here is sponsored, and no stay was comped.

Where we cover in Hawaii:

Maui — Maui's luxury story is a tale of two coasts. Wailea, on the island's sunny southwestern shore, is the polished resort strip — a string of beaches fronted by the Four Seasons Maui, Andaz, and Grand Wailea, with golf, shopping, and the island's most reliable weather. Kapalua and Kaanapali, in West Maui, trade some of that polish for drama: pineapple-field highlands, championship golf, winter whale watching from your lanai, and Montage Kapalua Bay anchoring the quietest corner of the coast. Choosing between them shapes the whole trip, and our guide to the best hotels on Maui breaks down both coasts, the flagship properties on each, and which fits the trip you're planning.

The Big Island — The Big Island's Kona-Kohala Coast is the most concentrated stretch of luxury resorts in Hawaii, and possibly in America: Four Seasons Hualalai, the resort many consider the single best in the state; Mauna Lani, Auberge Collection, reborn after a $200 million renovation; and Kona Village, A Rosewood Resort, the storied hideaway rebuilt from the ground up into one of the most exclusive addresses in the Pacific. Beyond the resorts, this is the island of superlatives — an active volcano, snow-capped Mauna Kea, manta ray night snorkels, and Kona coffee farms in the hills above the coast. Our guide to the best hotels on the Big Island covers the full flagship tier and how to choose among them.

Which island should you choose? — For first trips, families, and travelers who want beaches, dining variety, and iconic sights in one itinerary, Maui is the answer. For return visitors, resort connoisseurs, and anyone drawn to landscapes that feel genuinely otherworldly, the Big Island rewards the choice — and its flagship resorts outclass nearly everything on the other islands. With a week or more, the inter-island flight is thirty minutes, and pairing the two makes one of the great American luxury trips.

Best time to visit Hawaii — Hawaii is genuinely a year-round destination, but the calendar still matters. Mid-April through early June and September through mid-December are the sweet spots — warm, drier, and meaningfully less expensive than peak season, with resort availability that actually exists. Winter (mid-December through March) brings peak rates and peak crowds, but also humpback whale season, when the channel off Maui and the Kohala Coast fills with breaching whales — for many travelers, worth every premium. Summer is family high season: reliable weather, calm leeward waters, and the busiest pools of the year.

FAQ

Which Hawaiian island is best for luxury travel? The Big Island's Kona-Kohala Coast has the strongest collection of flagship resorts in the state, led by Four Seasons Hualalai, Mauna Lani, and Kona Village. Maui offers the best combination of luxury resorts, beaches, and things to do, split between the Wailea and Kapalua coasts.

Is Maui or the Big Island better for families? Both work well. Maui offers more variety — beaches, the Road to Hana, casual dining — while the Big Island's top resorts (Mauna Lani and Four Seasons Hualalai in particular) run some of the best kids' programming in Hawaii.

When is the cheapest time to visit Hawaii at the luxury tier? Late April through early June and September through early December bring the softest rates of the year at the flagship resorts, with spring and fall shoulder seasons offering the best weather-to-value ratio.

When is whale season in Hawaii? Humpback whales are present roughly December through April, peaking January through March. West Maui and the Kohala Coast of the Big Island offer the best shore and resort viewing.

Do you need a car in Hawaii? On both Maui and the Big Island, yes. Distances are real — the Big Island especially — and the best of both islands (Hana, Haleakala, Volcanoes National Park, Waipio Valley) lies well beyond the resort gates.