Road to Hana

What to See and Do in Maui, Hawaii

When the time came to choose a winter travel destination in 2014, Martin and I were stumped. Originally, we had planned to visit the Dominican Republic. However, a sudden mosquito virus outbreak around that time caused us to change plans. At the end of the day, we decided to spend our tropical holiday in Hawaii. We're no strangers to Hawaii. I grew up on Oahu and have visited not only my home island with Martin but also the Big Island in 2013. Of the Hawaiian islands, we really had only a few more to choose from when it came to discovering new areas. We decided to spend our time on Maui. This would be my fourth trip to Maui, and the very first of all for Martin.

Travel Mission: (Re)discover the Hawaiian island of Maui.

Maui Hawaii road trip map itinerary

Our Trip By the Numbers

  • 10 Days
  • 624 Miles driven
  • 69.5 Miles walked
  • 172,079 Steps Walked

Maui Hawaii travel photography

A Personal History with Maui

The second largest of the Hawaiian Islands, Maui has the third-highest population, falling behind Oahu and the Big Island. Growing up on Oahu, it was common for friends to spend weekends or summers over on Maui. We always knew who had recently gone to Maui as they would return with a box of Krispy Kreme donuts, as their only Hawaii location was in Maui. My own maternal grandmother had even been born and raised on a sugar cane plantation in the Maui town of Lahaina.

As a child, I recall making several weekend trips to Maui via family-sized Cessna airplanes flown by my dad, a former F-14 Navy jet pilot. I also visited Maui for high school cross country meets, and once with my grandmother to revisit her childhood home.

Returning to Maui in my late twenties without family definitely proved to be a different experience and a welcome change of pace. The goal of this trip was not to go slow and leisurely enjoy the island, but rather do everything we possibly could in 10 days' time.

Wailuku to Kihei

Our trip began with a red eye direct flight from Seattle to Kahului. We picked up our rental car close to 10:00 pm and jetted to a cheap hostel in Wailuku. Dinner that night was, to my delight, at a local Zippy's restaurant, the most popular local fast food chain in Hawaii. The next day, we woke up early and beelined directly to Kihei, where we would end up spending most of our time.

Staying in a simple yet conveniently located condo we'd found on Airbnb, Kihei was by far our favorite area of Maui. While rather touristy in many ways, we appreciated the calmer waters on this side of the island that allowed for stellar paddle boarding and sailing, as well as the expansive and clean-kept beach parks. We also took a couple of trips down to the famous Grand Wailea hotel.

Maui Hawaii travel photography

Whale Watching in Lahaina

After a couple of nights in Kihei, we ventured north to Lahaina, staying at Kahana Falls resort. The bulk of tourist activity in Lahaina in concentrated on the waterfront, meaning Martin and I took one quick jaunt down it before deciding it wasn't to our taste. We did, however, manage to hop aboard two marine boat tours in the area, including a sunrise whale watching cruise, and a half day snorkeling tour. Maui, I love you deeply, but the snorkeling just isn't up to par with Belize.

What was very impressive about the Lahaina side of the island was the extreme prevalence of breaching humpback whales that you could see from the shore. No matter how many times you've seen whales in the wild, it never gets old seeing these great creatures in their native habitats. The abundance of whales was at one point explained to us by a guide who said it was the result of long-time conservation efforts finally paying off.Maui Hawaii travel photography

Kula and Haleakala

Our time in Lahaina was very leisurely, despite cloudy, rainy weather. From there, we headed inland to the mountainous up-country town of Kula, where we stayed in a cute studio apartment we'd found on Airbnb. Most of Kula's residential areas are between 1,800-3,700 feet in elevation, meaning much cooler temperatures and stunning views. While small in terms of size and dining choices, Kula was the perfect base for ascending the formidable Haleakala.

A now dormant volcano, Haleakala is on the east side of Maui. It forms more than 75% of the entire island of Maui. We did the traditional routine of waking up before dawn and watching the sunrise. However, the tourist pack was quick to leave after sunrise, so we were among the few who did a hike down into the crater and back. If you want to know what Mars looks like, do this hike! It's incredibly desolate yet unique with a very photogenic terrain.

Maui Hawaii travel photography

The Road to Hana

A traditional tourist trip to vacation is not complete without attempting the road to Hana. A 64.4-mile stretch, Hana Highway is enjoyable to some and formidable to others. The road (paved, thankfully) is extremely winding and narrow through lush, wet tropical rainforest terrain. For a sense of driving difficulty, consider that the path includes passage over 59 bridges, 46 of which are only one lane wide. As a result, driving the 52-mile road can take upwards of 2 hours to complete. We were fortunate to not hit a ton of on-coming traffic and enjoyed driving this road's windy twists and turns. For us, the total drive time was in one hour, much less than expected.

One we got to Hana, we discovered it was the one town in probably the whole state of Hawaii without cell phone reception, which seems foreign in this day and age. Located on the eastern end of Maui, Hana is among the most isolated communities in Hawaii, but it is incredibly lush and green. We stayed at a dated but cute Hana Maui Bed and Breakfast we'd found via Google (alas, nothing affordable on Airbnb). Our free time was spent exploring local parks and attractions including Hana Lava Tube, Wai'anapanapa State Park, and Kōkī Beach Park.

Maui Hawaii travel photography


From Hana, we could either traverse the Hana highway in reverse to reach our next destination. Or we could drive in the opposite direction, down the dirt road to Kaupo and then back through Kula. The problem with this second option was a warning we'd heard from other travelers. This route, while faster in some ways, would require driving a stretch of poorly maintained, unpaved road. Due to the road's condition, it uncovered by our rental car agreement. Despite these warnings, we drove the road anyway without any problems, making it back to Kula; after stopping at Grandma's Maui Coffee Shop for coffee, we went to our final Maui destination: Paia.

A small, "hippie" town of sorts, Paia is known for its surfing and windsurfing spots, including those of Ko'okipa and Spreckelsville. Also located not far from Paia is the Jaws surf break, known for its bumpy, unpaved roads and enormous north shore surf in the winter.

In Paia, we stayed at a modern Airbnb house rental near the famous Mama's Fish House. Much of our time was spent lounging and boogie boarding on the nearby Baldwin Beach Park. We also made frequent trips to Mana Foods for fresh organic foods. It was the perfect chill ending to our 10-day Maui vacation.

Maui Hawaii travel photography

 Maui Travel Photo Gallery