I did a lot of research for this trip, so I thought I’d share my itinerary. My number one source for researching this trip was the book Maui Revealed. I highly recommend it. I also set up a map of all the locations mentioned here.
Where to Stay
Two of the most popular areas on Maui are the South (near Wailea/Kihei) and West regions. Kihei is easier to get to from the airport, although it may not look like it on the map. To get to the west region, you have to either go all the way around the south side of the western half of the island or take the very narrow Kahekili Highway on the north side.
Day 1
Start out with a cheap breakfast at 808 Grindz. Be sure to try the macadamia nut pancakes. Pick up any rental gear if you have time (snorkeling, boogie boards, etc.) After that, I recommend the biggest splurge on the trip - zip-lining with Flyin Hawaiian down the West Maui mountains. There are a total of 8 ziplines, and it can last up to 4 hours depending on the group size. Finish up the day with local beer and great food at Maui Brewing Co. Their Ahi tuna salad was one of the best salads I’ve had. The imperial porter was also great on tap.
Day 2 - West Maui
If you don’t get the macadamia nut pancakes at 808 Grindz, try them at Gazebo. They’re just as good. This place can get crowded, but one tip is to order takeout and eat at the tables by the pool if it isn’t too hot. After breakfast, continue north to Dragon’s Teeth. The rock formations that look like teeth are not that impressive, but the scenery surrounding is.
Finish the day by exploring Lahaina. Pick up some shave ice at Local Boys and enjoy it while walking through Banyan Tree Park. I also highly recommend a splurge for dinner at Lahaina Grill. There’s no view, so I would recommend going after sunset.
Day 3 - Hana
If you’re staying in West Maui, this might be the day to brave the Kahekili Highway on the way to Hana. Otherwise, take the same route back to the airport to get started on the clockwise route around East Maui. I recommend leaving as early as sunrise to avoid a lot of traffic. Be sure to pick up some banana bread from one of the stands along the route. Must-sees include Waianapanapa Beach (Black Sand Beach):
A tiny hike to Kaihalulu Red Sand Beach:
and Braddah Hutts BBQ
If I had to do the trip over again, I would make it a point to stay in Hana for a day, so we could explore the surrounding areas more. If you’re coming from West Maui, the total Hana loop can be around 6 hours depending on traffic and how quickly you can handle the windy roads.
On the way back, be sure to check out the Pools at Ohe'o. We also did the PipiWai Trail to Waimoku Falls, but depending on what kinds of hikes you’re used to, it may not be that impressive. The sound and calmness of the bamboo forest was my favorite part of the hike.
Day 4 - West Maui
After a day full of driving, I would recommend a relaxing day around your resort/hotel/local beaches. A massage at the Westin Maui Resort in Ka'anapali is a great break, but I would recommend avoiding the Cabana massage. The cabana is right next to a very busy walkway, and it is not as relaxing as it should be.
Day 5 - Kihei
The best snorkeling I found was on Po‘olenalena Beach. We considered taking a boat out to Molokini where the snorkeling is supposed to be the best around Maui, but we opted out to save money. I also recommend Big Beach for swimming or boogie boarding.
Day 6 - Haleakala
The sunrise at Haleakala was probably the most overrated part of the trip from all of my research. We woke up at 3:00 AM to make sure we didn’t miss it. Haleakala peaks at 10,023 ft. and the temperature was in the lower 40s (in winter), so bring a lot of water, blankets, and flashlights if you decide to go.
I did find the hike on the nearby Sliding Sands Trail very impressive. It felt as though we were hiking on Mars (and the thin air helped add to that illusion). I would definitely recommend this trail over the Pipiwai Trail.