Maui is two volcanoes joined by a valley, and the weather on either side of them is not comparable. Haleakala rises to 3,055 metres on the eastern half and catches the trade winds coming in from the northeast. Hana, on the windward side, receives several metres of rain a year. Kihei, in the rain shadow forty kilometres away, gets around 250 millimetres.
That is why every resort on the island is on the leeward coast, and why the drive to Hana is a famous day trip rather than a place people stay.
The two leeward coasts
The dry side splits into two resort strips about forty minutes apart, and they are genuinely different.
Wailea, on the south shore, is the newer and more manicured of the two: a run of crescent beaches with resorts spaced along a coastal path, a golf course behind, and the most consistently calm swimming on the island. It is the safer choice for a first visit and it is where most of the top-tier hotels are.
Kaanapali and Kapalua, on the west shore, are older, greener and set against the West Maui mountains, with better snorkelling at Black Rock and Kapalua Bay and a livelier stretch of beach.
Upcountry and the north shore at Paia are a different Maui again: cooler, agricultural, and where the island's own life happens, with almost no hotels.
The twelve below are grouped by coast.
Wailea, the south shore
Calm water, spaced-out resorts and a coastal path linking them.
Four Seasons Resort Maui at Wailea sits on Wailea Beach with terraces stepping down to the sand, three pools including an adults-only one, and the deepest service bench in Hawaii. It is the best hotel on the island.
Four Seasons Resort Maui at Wailea
Wailea Beach · 5★ · $$$$
Terraces to the sand with the island's best service
Check availabilityGrand Wailea Resort Hotel & Spa, A Waldorf Astoria Resort occupies a very large site next door with a water complex that includes a river pool and a rope swing, a serious art collection and a chapel. It is the family answer on Maui and it is enormous.
Grand Wailea Resort Hotel & Spa, A Waldorf Astoria Resort
Wailea Beach · 5★ · $$$$
River pool, rope swing and a serious art collection
Check availabilityFairmont Kea Lani, Maui sits on Polo Beach in a low white building with an all-suite layout, kitchens in most rooms and the best food of the Wailea group.
Andaz Maui at Wailea Resort - A Concept by Hyatt occupies a hillside above Mokapu Beach with cascading pools, a design-led interior and the most contemporary rooms on the coast.
Andaz Maui at Wailea Resort - A Concept by Hyatt
Mokapu Beach · 5★ · $$$$
Cascading pools and the most contemporary rooms
Check availabilityWailea Beach Resort - Marriott, Maui sits on Ulua Beach with a large pool complex, several restaurants and reliable rooms below the rates above.
Wailea Beach Resort - Marriott, Maui
Ulua Beach · 4★ · $$$
Large pool complex below neighbouring rates
Check availabilityHotel Wailea, Relais & Châteaux - Adults Only occupies a hillside site inland from the beach, adults-only, small and quiet, with a shuttle to the sand. It is the value pick in Wailea and the trade is that you are not on the water.
Hotel Wailea, Relais & Châteaux - Adults Only
Above Wailea · 5★ · $$$
Adults-only and quiet, with a shuttle to the sand
Check availabilityKapalua and Napili, the northwest
Set against the mountains, with the best snorkelling and a cooler feel.
The Ritz-Carlton Maui, Kapalua sits above Kapalua Bay, which is consistently rated the best swimming beach on the island, with two golf courses and a spa. It is the most complete resort on the west side.
The Ritz-Carlton Maui, Kapalua
Kapalua · 5★ · $$$$
Above the island's best swimming bay, two golf courses
Check availabilityKBM Resorts: Palapala at Montage Kapalua Bay Ocean Front Resort Includes Rental Car occupies the bay itself in an all-suite property with kitchens, a pool over the water and the shortest walk to the snorkelling.
KBM Resorts: Palapala at Montage Kapalua Bay Ocean Front Resort Includes Rental Car
Kapalua Bay · 5★ · $$$$
All-suite with the shortest walk to the snorkelling
Check availabilityKaanapali, the west shore
The original resort strip, with a beach path, Black Rock and the most life.
Sheraton Maui Resort & Spa sits at Black Rock with the best snorkelling on the strip directly offshore, a cliff-diving ceremony at sunset and a large pool complex.
Sheraton Maui Resort & Spa
Black Rock, Kaanapali · 4★ · $$$
Best snorkelling on the strip directly offshore
Check availabilityHyatt Regency Maui Resort & Spa occupies a long stretch of Kaanapali Beach with a water complex, a garden of wildlife and full family facilities.
Hyatt Regency Maui Resort & Spa
Kaanapali Beach · 4★ · $$$
Water complex and a wildlife garden for families
Check availabilityThe Westin Maui Resort & Spa, Ka'anapali sits on the same beach with a large recent renovation, several pools and reliable rooms.
The Westin Maui Resort & Spa, Ka'anapali
Kaanapali Beach · 4★ · $$$
Recently rebuilt with several pools
Check availabilityRoyal Lahaina Resort & Bungalows occupies the northern end of Kaanapali with lower-rise buildings, mature grounds and the best value on the strip.
Royal Lahaina Resort & Bungalows
North Kaanapali · 4★ · $$
Mature grounds and the best value on the strip
Check availabilityWhat we have left off
The condominium resorts at Kihei and along the Kaanapali beach path are excluded, and they are how a great many families do Maui: kitchens, space and a fraction of the price. They are apartments with a rental desk rather than hotels.
What to do
Drive the road to Hana once, early, with a full tank. It is 100 kilometres, 600 curves and 50 one-lane bridges, and it takes most of a day. Many people find the drive better than the destination.
Watch sunrise from the Haleakala summit, which requires a pre-booked reservation and a very early start at 3,000 metres in near-freezing conditions. Bring more clothing than seems plausible.
Snorkel Molokini crater, a submerged volcanic rim off the south coast, on the first boat out.
In winter, humpback whales calve in the Auau channel between Maui, Lanai and Molokai, and they are visible from the shore.
Go upcountry to Makawao and Kula for the cooler air, and to Paia on the north shore for the surf town and the best eating on the island.
Practical notes
Kahului airport is central: 30 minutes to Wailea, 45 to Kaanapali, an hour to Kapalua.
The leeward coasts are dry year round. December to April is peak and whale season. September and October are the quietest and warmest.
A car is essential.
On Lahaina. The town of Lahaina was destroyed by wildfire in August 2023 with significant loss of life, and its recovery is ongoing. The Kaanapali and Kapalua resorts north of the town reopened and West Maui welcomes visitors, but Lahaina itself is a community rebuilding rather than a sightseeing stop. Check current guidance before travelling, respect closures and access restrictions, and spend money locally where you can.
Explore 4 & 5 Star Maui Hotels
Questions people actually ask
Wailea or Kaanapali?
Wailea for calm water, newer resorts and space. Kaanapali for snorkelling at Black Rock, a livelier beach path and slightly lower rates.
Is the road to Hana worth it?
Once, if you enjoy driving. Start early, do not rush it, and do not attempt it as a half day.
When are the whales there?
Roughly December to April, and they are visible from the leeward shore without a boat.
How many nights?
Seven. The distances and the day trips need the time.