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Proposalmoon

The Long Way

The road to Hana, taken slowly, in both directions

Maui, Hawaii · 4 nights · Apr · May · Sep · Oct · up to 6

The Hana road is sixty-four miles and six hundred curves, and everyone who rushes it hates it. Take a guided drive so nobody has to look at the road, and stay over rather than turning round — the far side of the island in the morning is a different place from the far side of the island once everyone else has arrived. Waiʻānapanapa is the black sand beach out there, and entry is reserved and time-slotted, so it is the one thing you book before the flights. Four nights: two in Wailea either side of two on the road.

The ending

A crescent of black volcanic sand between two lava arches, small enough to take in at once, with the surf coming through a sea cave at the north end of it.

That is Paʻiloa Black Sand Beach, Waiʻānapanapa State Park. See how private it is and when it’s open.

Do

  • Road to Hana Guided Tour
  • Snorkeling at Molokini Crater
  • Private Catamaran Sunset Sail
  • Wailea Beach Yoga Retreat

Eat

  • Mama's Fish House (Paia)
  • Lineage (Wailea)

Stay

  • Andaz Maui at Wailea Resort
  • Four Seasons Resort Maui at Wailea

Why book the beach before the flights?

Because entry is reserved and time-slotted, and that slot is the only fixed point in the trip. Everything else on Maui can move around it.

Is the road worth doing twice?

Once out and once back, and they are different drives — the waterfalls are on your side going one way and the ocean is on your side coming home.

The planner doesn’t build Maui, Hawaii yet — we can name the places here but not yet enough of them around it to fill 4 nights without repeating. Read this one, then build your own somewhere we can.

Build one in a city we cover