Maui | Hawaii Itinerary
where we stayed
Hotel Wailea, Relais & Châteaux—
We stayed at Hotel Wailea during our entire stay in Maui, and it was so nice to retreat to this private oasis each day after being out and about on various excursions around the island.
We assumed the hotel concierge was exaggerating when he said we’d need sunglasses to watch the sunset from the hotel lounge. He was not.
Sunrise at Haleakala—
Just a few tips: Wear many layers (warm jacket, scarf, gloves, etc), pack a flashlight, and bring water and snacks. Temperature can drop to around 40 degrees even in the middle of summer. I was wearing about four layers but was still freezing. Take a moment to turn away from the sun rising to watch the moon setting. If you plan on visiting at sunrise, make sure you purchase a ticket for the day you’re going. Without a reservation, you will not be permitted entry, no exceptions. If you are planning on going at another time, you do not need a ticket.
We arrived at the top of the crater about two hours before sunrise to stake out a spot and enjoy stargaze sans light pollution. It was my first time shooting in extremely low light conditions, so I didn’t do the best job of capturing just how saturated the sky was with stars.
Once the sun began its ascent, the sky was changing colors every second.
Upcountry Farmers Market—
Sip Me, Makawao—
Maui Tropical Plantation—
A working sugarcane and tropical plantation. The in-house restaurant and coffee shop are definitely worth checking out.
Road to Hana—
A few tips: Fill up your gas tank. Pa’ia is first and last place to fill up along Road to Hana. Pack lunch, snacks, and water. Bring swim gear, mosquito repellent, rain gear, and full change of clothes. Not the best cell phone reception, so don’t rely on it! Pull over to let local drivers pass.
Stop One: Wainapanapa State Park (Black Sand Beach)—
Waimoku Falls & Pipiwai Trail—
A moderate hike that takes you through banyan trees and a bamboo forest and ends at Waimoku Falls, Maui’s tallest waterfall.
Some tips: Spray yourself down with mosquito repellent. The ground is uneven for most of the hike— you will be walking over roots and loose rocks, so choose your shoes appropriately. You’re hiking in a rainforest, so it will be at minimum very humid. It will most likely rain at some point during your hike, so plan accordingly.
It took us about 3-4 hours round trip to complete the hike.
Da Fish Shack—
Kaihalulu Beach aka Red Sand Beach—
Aunty Sandy's Banana Bread & Ke‘anae Point—
Grab some banana bread and take it to the beach. Soak in the views and ASMR as massive waves crash into lava rock at Ke’anae Point.
I ended up having to get some work done on day four, so we took full advantage of the cabanas by the pool and treated ourselves to pool service. Not a bad office for the day. We took the rest of the day easy, spending most of our time at the resort.
Ate here twice during our stay! Owned by Top Chef alumnus Chef Sheldon Simeon, this super casual eatery (no seating, just pick up and go) serves up creative and flavorful Hawaiian comfort fare.