
moderate
9–10 hours
You should have a moderate fitness level—short hikes and steps with uneven surfaces, plus the ability to sit in a vehicle for long stretches.
Climb into a luxury Sprinter and spend a full day tracing Maui’s most famous coastal road—waterfalls, black sand, banana bread, and sea turtles. This small-group tour from Wailea balances active exploration with guided history and included admission to Waiʻanapanapa.
The Sprinter van hums to life at dawn, headlights catching the first slick breath of ocean mist. You settle into a leather seat and watch Wailea fall away as the driver tucks the van into the ribbon of highway that hugs Maui’s windward flank. The road begins as a promise—tight hairpins, a string of single-lane bridges, and green that leans in close—until the pavement peels you into a different island altogether: waterfalls that dare you to swim, black sand that looks like crushed midnight, and banana bread warm from a roadside stand.

Bring ginger or an anti-nausea medication and sit where you can see the road; the route has hundreds of tight turns and single-lane bridges.
Several stops include waterfall pools and beaches—pack a swimsuit, quick-dry towel, and waterproof bag for wet items.
Expect muddy trails, slippery lava rock, and uneven footing at coastal lookout points and caves—closed-toe shoes with traction help.
Ho'okipa is a turtle resting area; use reef-safe sunscreen and view wildlife from the shoreline to avoid disturbance.
The Hana Highway includes many bridges and concrete sections built in the early 20th century; the route threads across old taro loʻi and historic coastal communities.
Waiʻanapanapa is a protected state park with limits on beach access and cave exploration—use marked paths and pack out all trash to protect fragile coastal ecosystems.
Closed-toe shoes with grip for waterfall trails and lava-rock shores.
For swims at waterfall-fed pools and Waiʻanapanapa’s shoreline.
summer specific
Rain and mist are common along the windward coast—pack a breathable shell.
winter specific
Keep electronics and layers dry while you explore beaches and caves.