A Journey Through Maui: From City Vibes to Untamed Wonders

Maui: A Small Island with Big Personality

Aloha! Welcome to Maui, Hawaii’s second-largest island, where rugged coastlines, volcanic landscapes, and vibrant towns create a paradise that’s equal parts adventure and relaxation.

As a part of a larger trip to Japan, we will use Hawaii as a place to explore before and after to get acclimated to the time change. We’ve never been to Hawaii before and in fact, since we have been to all 49 other US states, this marks our 50th state and means we have officially traveled to all 50 states!

Let’s dive into this island odyssey, starting in Kahului.

Maui Driving Tour

DAY 1: Arriving in Hawaii – our 50th state

Kahului: Maui’s Gateway

Kahului, the island’s commercial hub, greets us with a laid-back vibe and practical charm. Just minutes from the airport, we decide to kick off our Maui adventure by staying here 2 nights. It’s not flashy, but it’s the perfect launchpad for what’s ahead. We leave our home for the airport in Virginia at 5:00am and land in Maui and get to the airport shortly before sunset. We take the airport shuttle over to our hotel for a couple days to just chill out and get acclimated to the time shift.

Kahului

Maui Beach Hotel

We get checked into to the Maui Beach Hotel just steps from Kahului Bay. The big selling point for us was the free airport shuttle and the rooftop swimming pool. Additionally, there are several restaurants within easy walking distance. The rooms are outdated but spacious and the lush grounds are ideal for unwinding.

Maui Beach Hotel

Kahului Ale House

We had done some research before we landed to find a place to catch part of the Division 1 NCAA football championship game. The Kahului Ale House turns out to be a local gem with its casual atmosphere, craft brews, and hearty pub grub (burgers and fish tacos). We order a sampler that turns out to be more than enough food as we watch the game.

Kahului Ale House

Day 2: A Day to Settle In and Relax

We spend most of the second day just hanging around the pool at the hotel before heading out to dinner at a great local place.

Maui Beach Hotel

Dinner at Bistro Casanova

Not far from our hotel is the Bistro Casanova which turns out to have something we had never eaten before: a “Salmon Marscapone Pizzette” – unbelievably good! In general, the items on the menu are all unique and incredibly flavorful (we know because the place is packed and we talk with several regulars that frequent the place). This is a must-eat-at restaurant if you are ever in the area.

Dinner at Bistro Casanova

Salmon Marscapone Pizzette

Day 3: Bucket List – Driving the Road To Hana

The Drive from Kahului to Hana

Early in the morning we take the shuttle back to the airport and pick up our rental car for the next 7 days. We buckle up for the Road to Hana, a 64-mile ribbon of Highway 36 that twists from Kahului to Hana. This legendary route has 620 curves and 59 bridge (many are one-lane) and offers waterfalls, black sand beaches and jungle vistas. The speed limit is 15mph along the majority of it so it takes about three hours without stops. Since this is a bucket list item, we take time to explore some of its treasures along the way. It’s not just about the drive, or the scenery, it about the combined experience we share with hundreds (if not thousands) of other tourists. It’s a slow scenic drive with waiting on one-lane bridges but we finally reach Hana in the early afternoon after making a number of stops along the way.

In all honesty, it wasn’t quite the “wow” we anticipated. We’ve done so much extensive travel that it didn’t live up to the hype for us.

Road to Hana

Hana Lava Tubes

In Hana, the Hana Lava Tubes (Ka’eleku Caverns) beckon us. Formed by molten lava thousands of years ago, these underground tunnels offered a cool, eerie detour. The Self-guided tour with a flashlight took us about 1/2 mile into the earth.

Hana Lava Tubes

Hana

Hana itself is a sleepy hamlet on Maui’s eastern edge and is rural and untouched for the most part. Since it’s a long way down this windy road there isn’t much development here with the exception of a few small lodging options and a couple of restaurants. Most of the food options are a handful of food trucks parked together in a central location in the town.

Hana

Day 4: Exploring the Hana area

The Drive from Hana to Haleakalā National Park Waterfall Area

Unlike the drive to Hana the previous day, as we push on to Haleakalā National Park Waterfall area the road is mostly deserted as it winds through a beautiful rural area.

Hana to Haleakalā

Haleakalā National Park Waterfall Area

Within Haleakalā National Park’s Kipahulu district, near Hana, the waterfall area along the Pipiwai Trail stuns. Before departing on the 4-mile round-trip hike, someone just completing the hike offers Nancy a walking stick – which proves invaluable. It’s a bit uphill and a little rough in some parts but it’s a must-do for nature lovers. The hike leads us past bamboo forests to Waimoku Falls, a 400-foot cascading waterfall that plunges into a misty pool. After the hike, Nancy hands off the walking stick to another person about to begin and we head to the ranger station to get our “We drove entire 64 mile adventure road” certificate.

Haleakalā NP Waterfall Area

We drove the whole road length!

Haleakalā NP back to Hana

After completing our hiking and snacking on our packed lunch, we head back towards Hana. We veer off the way we came to head down to one of the black sand beach areas to explore the shoreline.

Haleakalā back to Hana

Waianapanapa State Park Maui

As we return to Hana, we head towards Waianapanapa State Park only a short distance from the town. It is known for its black sand beach, sea arches, and blowholes. The Pa’iloa Beach contrasts jet-black pebbles with turquoise waves, while trails wind through coastal cliffs. It’s a postcard-worthy stop on the Hana Highway. We spend a few hours hiking around the area and even dipped into the ocean for a bit although it was a little rough to really swim. NOTE: The park requires a timed entry pre-purchased pass.

Waianapanpana State Park

Food Trucks

After we finish up at Waianapanapa, we decide to grab take-out dinner at one of the food trucks. We decide on Thai and head back to the Bamboo Inn, a 3-room bed and breakfast where we’re staying. We enjoy our dinner from our balcony as the sun sets and then enjoy the outdoor hot tub for a while. It was a great ending to a great day.

Food Trucks

Day 5: Transitioning from Hana to Kihei

The Drive from Hana to Kahului

The road AFTER Hana used to continue hugging the southern coast and you could drive a complete circle back to Kaluhui. In May of 2023, a rockfall blocked the road, destabilized the cliffside and damaged a vehicle. They originally estimated it would re-open in 1 month, but it remains closed, and drivers cannot travel between Hana and Kaupo areas. This means we have to drive the “Road to Hana” in reverse.

We get up early as we want to try and beat the tourist traffic we experienced on the way down. As luck would have it, traffic is light early in the morning and for one of the only times in our life we are glad we got behind a school bus. This guy must drive this road every day as he was hauling down the road. We followed closely to scoot along through a large section of the road. The view going back, as is often the case when you travel in the opposite direction, has more than its share of scenic moments.

Scool bus in the lead

A different view point on the return

via Pi’ilani Highway

In Haiku-Pauwela, we take the Piilani Highway (Route 31), a rugged, less-traveled loop that takes us down to Kaupo, around Maui’s northeast coast. This narrow, bumpy stretch offers raw ocean views and a wilder return to Kahului. It’s not for the faint-hearted—potholes and cliffs abound—but the solitude is sublime. It is still early afternoon, so we decide to drive to Kaupo and back before going to our VRBO rental. As previously mentioned, Kaupo used to be just a 7-mile drive from Hana, but with the road closure, this is now the “left” part of the old circular drive. This stretch of road is magnificent and should not be missed!

Pi’ilani Highway

Sun Yet-Sen Park

Midway through our drive we stop at Sun Yat-Sen Memorial Park, a small roadside park in Keokea between mile markers 18 and 19. It is about 2,400 feet above the south Maui coast and scenic views here are excellent. Sun Yat Sen (1866-1925) was the first president and the founding father of the Republic of China. He beat the Qing Dynasty to establish the first Chinese republic in 1912. He was also a physician. He lived at his brother’s home in Kula, Maui, off and on from 1879 to 1910.

Sun Yet-Sen Park

Maui Vista Condos in Kihei

In Kihei, a sunny coastal town, the Maui Vista Condos offer a comfy, low-key stay. Our VRBO rental is everything advertised and we’re delighted to be in a central, walkable area of Kihei. Across from Kamaole Beach Park, it’s a perfect place for beach bums and sunset chasers. Kihei itself hums with shops, eateries, and a laid-back surf vibe—a great base for Maui explorations.

Maui Vista Condos

Dog and Duck Pub

We walk north along the main Kihei drag to seek out a place for dinner. There’s a cluster of restaurants about a 1/2 mile up the road. We choose the Dog and Duck Pub, an Irish pub with tropic vibes. With cold pints, fish and chips, and a friendly, welcoming atmosphere, it’s a cozy spot to unwind after a day of adventure.

Dog and Duck Pub

Day 6: Exploring the Summit District of Haleakalā National Park

Haleakalā National Park

Beyond its waterfalls, Haleakala National Park spans Maui’s volcanic soul. The summit—10,023 feet above sea level—delivers sunrise views over a crater that feels otherworldly where temperatures are 20 degrees colder than at sea level. Reservations are needed to come early to enjoy a sunrise. We aren’t able to snag one, so we just go to enjoy it for the day. It takes all of 1.5 hours to drive from Kihui to the summit and it’s just beautiful. Trails are strenuous in the Summit Area because the high-elevation causes a lower concentration of oxygen in each breath. Altitude sickness is a concern. Signs remind us that when beginning your hike on a downward slope, allow for twice the time hiking to get out, e.g. 15 minutes hiking down + 30 minutes up = 45 minute hike. We opt for part of the 11-mile Keonehe‘ehe‘e (Sliding Sands) Trail that starts at the Visitor Center. It is a soft cinder trail into the caldera of this dormant volcano. The crater floor is 3.9 miles one-way, so we just hike about half of that.

Haleakalā National Park

Moose McGillycuddy’s Pub

After a full day at the park, we return to our condo and then walk south to see what restaurants are in this direction. After walking 1/2 mile south along the main drag, we find Moose McGillycuddy’s, a lively haunt with ocean views from its upstairs perch. The menu is primarily pub classics, offers numerous Hawaiian tropical cocktails, and definitely boasts a party atmosphere—perfect for a night out with a Maui twist. And with tons of TVs, we think we’ll return here tomorrow to watch the NFL Championship game (between our home team, the Washington Commanders) and our division rivals, the Philadelphia Eagle. The winner will go to the Super Bowl in 2 weeks.

Moose McGillicuddy’s

Day 7: A Day of Rest and Watching Football

One thing we’ve learned over the years, is for long-term trips, you have to build in “down days”. Our entire trip is 31 days and since we’ve already been on-the-go for 6 days, we will rest on day 7. It helps that it is a Sunday and today is the NFL Championship games that will determine which two teams will go to the Super Bowl.

Since there’s a 5-hour time difference between Hawaii and home, the first game starts at 10:00am here! We head back to Moose McGillicuddy’s which is surprisingly filled with Washington Commanders’ fans. We meet a lot of awesome people during a very tense and close game. We are disappointed when our favorite team loses, but they did far better this season than anyone expected. We also watch the 2nd game between the Buffalo Bills and last year’s Super Bowl champions, the Kansas City Chiefs. It was another close game.

Three’s Bar and Grill Maui

After some pool time, we head north again for dinner, this time choosing Three’s Bar and Grill. Slightly upscale, this place blends surf culture with gourmet flair. From poke bowls to kalua pork sliders, the menu shines, paired with craft beers or mai tais. It’s a local favorite with a patio vibe that screams island life. The kalua pork quesadilla’s – with asian peanut slaw, cilantro aioli, pineapple chutney – are to die for.

Three’s Bar & Grill

Day 8: Exploring Northern Maui

We’ve definitely explored the southern region of Maui and now it’s time to head north. There is essentially one road that hugs the island shore, a circular loop around Pu’u Kukui, the 5788-foot-tall lush mountain on Maui. Our car rental company told us only the left side of the circle (to Nakalele Blowhole) is open and the right side (from Nakalele Blowhole to Wailuku) is on private land, so we won’t be able to drive on it.

Route 30 to Nakalele Blowhole

Route 30 (Honoapiilani Highway) from Kihei to Nakalele Blowhole first hugs Maui’s west coast before rounding out around the north coast. This scenic jaunt offers ocean panoramas and a glimpse of rugged cliffs. About 30-minutes into the drive, we pass by the outskirts of Lahaina where a massive wildfire in August 2023 devastated the town. Other than missing trees and foliage, there isn’t much evidence of damage from the fire from the road. After Lahaina, there’s Kaanapali, another popular town where tourists stay.

Rt 30 to Nakalele Blowhole

Rt 30 to Mokolea Point

Rt 30 to Nakalele Blowhole

Nakalele Blowhole

Thirty minutes later, we arrive at the Nakalele Blowhole, a unique geological formation where the ocean blasts air and water through a hole as it crashes against the shore. The sound is eerie but the sight of the water rising into the air is magnificent. You can see it from a distance after a short 1/4-mile hike from the parking lot. Some people venture another 1/4-mile to get an up close and personal view.

Nakalele Blowhole

Drive on “Death Road” Route 340

We aren’t sure where the route turns into the private area (as told by our car rental company), so we decide to just drive as far as we can. As long as the road is paved, it is legal to drive our rental car on the road. The road has changed names from Rt 30 to Route 340 and this portion is dubbed “Death Road” or Kahekili Highway. We never see any “private” signs and it remains paved (or tar-n-chipped), so we continue on. The road snakes along northwest Maui’s cliffs. Narrow and winding, it’s a thrill ride from to Wailuku. We reach our first one-lane stretch that begins at a blind curve – only to be met by a string of 3 vehicles traveling in the opposite direction. We all stop and when we chat with the lead driver to negotiate this section, we learn this is THE toughest part of the entire road and we have nothing big to fear after this section. We carefully back up about 30 feet to let the vehicles pass and decide to press forward. We are rewarded with stunning views. Be warned—this one’s not for novices. You will have white knuckle moments and remember to drive slowly.

Death Road

Wailuku

Wailuku, Maui’s county seat, blends old-town charm with history. Near the Iao Valley, it’s a quieter stop with mom-and-pop shops and a glimpse of pre-tourist Hawaii. It is NOT a tourist town and in fact, is a bit “worn” and uninviting. It doesn’t help that it drizzles rain while we drive through the town, making it drearier than it probably is when the sun is shining.

Wailuko

Kepaniwai Heritage Gardens Park

Just outside of Wailuku, Kepaniwai Heritage Gardens Park honors Maui’s multicultural heritage with gardens, pavilions, and a peaceful stream. Tucked in the Iao Valley, it’s a serene spot for a picnic or a history lesson amid nature. There are sections with architecture, gardens, and statues, portraying the Chinese, Japanese, New England, Portuguese, Native Hawaiian, Korean, Puerto Rican and Filipino people.

Kepaniwai Heritage Gardens Park

Iao Valley Road

The drive up Iao Valley Road from Wailuku leads to Iao Needle, a 1,200-foot volcanic spire shrouded in mist. This sacred site, surrounded by lush cliffs, offers short hikes and a haunting beauty that echoes Maui’s past. From here, we head back to Kihei, a mere 20-minute drive.

Ion Valley Road

Day 9: Last Day to Explore Maui

The Drive from Kihei to Lahaina

Having talked to several local folks about Lahaina, we realize the route we took the other day past the town was not INTO the area still battling the destruction. The wind-driven fires prompted evacuations, caused widespread damage, killing at least 102 people and leaving four persons missing. It is the deadliest US wildfire in more than a century. More than 250 structures were damaged or destroyed as entire blocks of Lahaina went up in smoke. Nearly 1200 families were displaced. They determined the cause was broken power lines. While over 320,000 tons of fire debris have been cleared, only 50 building permits have been issued as of the one-year anniversary of the fire. The rebuilding process in Lahaina is complicated by regulatory challenges and emphasis on the use of fire-resistant construction materials.

We take Route 30 from Kihei to Lahaina, then veer off into the town.

Road Trip to Lahaina

Lahaina

We drive both directions of the main drag. The southern portion is still closed and we see that 18 months after the fire, crews are still clearing out fire debris. With so many buildings gone, it is eerily flat and quiet. There are some sections of the town that look untouched.

Lahaina

Diamonds Bar and Grill

We didn’t find anywhere for lunch while driving around Lahaina, so we head back to Kihei to one place we’d read about before our trip. Diamonds Bar and Grill claims to be the best sports bar in Kihei, but it wasn’t close enough to our condo to check out earlier in our visit. The restaurant serves up ice-cold beers and comfort food—think wings and burgers—in a fabulous sports-bar setting. The place is really hopping mid-day, filled with locals just hanging out together. They welcome us and we enjoy lots of interesting conversations. It’s a chill hangout to cap off a day of more Maui exploration.

We spend our last afternoon in Maui at our condo swimming pool. We have a crack of dawn flight in the morning, so we keep our evening mellow.

Diamonds Bar and Grill

Summary

Maui is a tapestry of wild roads, hidden gems, and laid-back haunts. From the Hana Highway’s waterfalls to Kihei’s pubs, every mile tells a story.

What’s your must-see spot in Maui? Drop it in the comments—I’d love to hear your Maui tale!

We visited four of Hawaii’s Islands. Which is your favorite Hawaiian Island? Drop it below—we’d love to hear your take!

Here are links to our other Hawaiian Adventures:

Oahu

Kauai

The Big Island of Hawaii

A Journey Through Maui: From City Vibes to Untamed Wonders

Maui: A Small Island with Big Personality

DAY 1: Arriving in Hawaii – our 50th state

Kahului: Maui’s Gateway

Maui Beach Hotel

Kahului Ale House

Day 2: A Day to Settle In and Relax

Dinner at Bistro Casanova

Day 3: Bucket List – Driving the Road To Hana

The Drive from Kahului to Hana

Hana Lava Tubes

Hana

Day 4: Exploring the Hana area

The Drive from Hana to Haleakalā National Park Waterfall Area

Haleakalā National Park Waterfall Area

Haleakalā NP back to Hana

Waianapanapa State Park Maui

Food Trucks

Day 5: Transitioning from Hana to Kihei

The Drive from Hana to Kahului

via Pi’ilani Highway

Sun Yet-Sen Park

Maui Vista Condos in Kihei

Dog and Duck Pub

Day 6: Exploring the Summit District of Haleakalā National Park

Haleakalā National Park

Moose McGillycuddy’s Pub

Day 7: A Day of Rest and Watching Football

Three’s Bar and Grill Maui

Day 8: Exploring Northern Maui

Route 30 to Nakalele Blowhole

Nakalele Blowhole

Drive on “Death Road” Route 340

Wailuku

Kepaniwai Heritage Gardens Park

Iao Valley Road

Day 9: Last Day to Explore Maui

The Drive from Kihei to Lahaina

Lahaina

Diamonds Bar and Grill

Summary

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