Maui - Upcountry - Days 1-4

From sunrise atop a volcano to snorkeling with sea turtles, we spent 11-days (without the kiddos) in Maui. It was filled with unforgettable moments, scenic drives, delicious eats, and a whole lot of aloha. We put together a detailed day-by-day breakdown complete with tips, food finds, and favorite experiences. This section covers Day 1-4 which were spent enjoying Upcountry Maui.

Day 1: Arrival in Paradise

Our first day was filled with flights getting us to the beautiful island of Maui. We traveled approximately 16 hours from South Bend to Minneapolis, then to Seattle, and finally to Maui. We stopped to eat in four time zones.

1st Breakfast - South Bend

2nd Breakfast (apparently I’m a hobbit) - Minneapolis

Lunch - Seattle

Dinner - Maui

On our drive to our VRBO we stopped and grabbed a few groceries at the Foodland in Pukalani. For dinner, we grabbed Spam Musubi and fresh poke. Got to our VRBO just in time to see our first beautiful island sunset

Upcountry Maui

Our VRBO was located in Kula right on the slopes of Haleakalā. This made it the perfect central location to explore Upcounty. This part of the island offers a completely different vibe from the beach towns and coastline. You’ll get a unique, hands-on experience that connects you to the island’s rich agricultural heritage. You’ll find lavender farms, goat dairies, charming small towns like Makawao, and incredible sunrises/sunsets. It’s peaceful and the perfect start to our trip. We stayed in Upcountry for Days 2-4.

Day 2: Sunrise at Haleakala & Lei Workshop

If there’s a “must” when visiting Maui, it’s taking in a sunrise at Haleakalā National Park. Since we were still adjusting to the major time change, we found it really easy to wake-up and jump into the car at 3:30 AM. We cracked open our iced coffees, hit play on Shaka Guide (audio driving tour), and headed toward Haleakalā National Park. The Shaka Guide was a great addition to our trip and provide great information, recommendations, and felt like a local tour guide riding along with us.

We slowly wound our way up one of the most dramatic elevation gains in the world with only our headlights lighting the way. We took it slow because Amanda is prone to car sickness. Even with the VRBO nearby, it took about 30 minutes to get to the park entrance because of the massive elevation gain and the switch backs in the road. The stars were out in all their brilliance as we wound are way to the front entrance of the park.

Since sunrise is so popular and parking is limited, you have to have a reservation to enter the park between 3:00 am to 7:00 am. Reservations can be made online up to 60 days in advance of your sunrise visit on recreation.gov and are only valid for the day reserved. These tickets are released at 7:00 am HST. I had booked the reservation right at 60 days out (It reminded me of booking dinning reservations at Disney).

Bring layers for sunrise.

After checking in at the entrance, we continued our ascent up to the peak of Haleakalā. Two quick tips based on our experience. First, the parking lot at the summit is small and fills up quickly. We learned and recommended watching the sunrise at the Haleakalā Visitor Center. It has a large parking lot and most importantly restrooms. The best viewing is right along the railing overlooking the crater near the start of the Pā Ka‘oao Trail.

Second tip. It’s going to be chilly. You are at 9,740-foot elevation and its typically 30 degrees cooler than at sea level. This isn’t shorts and flip flop weather. We were bundled up (Jeans, boots, warms socks, hoodies, and blankets). Make sure to bundle up to enjoy this beautiful sunrise.

Slowly, the sky began to shift from an inky black to the signs of first light around 5:15. We sat in awe over the next hour as shades of orange, pink, and gold painted their way across the sky. The sun peaked above the clouds and lit up the massive volcanic crater below. Photos don’t do it justice. Honestly, these words feel cheap, too.

After sunrise, we quickly hiked Pā Ka‘oao trail (0.4 mi out & back). Offers some great views of the crater but be careful it is uneven and rocky. Once back in the parking lot, we did a very short, out and back hike on Keoneheʻeheʻe Trail (Sliding Sand Trail). We just dipped our toes into the trail. It is an 11-mile point-to-point hike into the crater. The little portion we did felt more like Mars than Maui. We jumped in the car and headed up to the Summit Observation Deck. It is the tallest point in the park and on the island of Maui at 10,023 feet and provides excellent views of the island.

Walking around the summit we got to appreciate the Haleakalā silversword. They are a rare and endangered plant that only grows on the slopes of Haleakalā. With its spiky silver leaves and alien-like appearance, it looks like something from another planet. Poetically, these rare plants can live up to 90 years but flower only once in their lifetime before dying.  

On our way down, we made scenic stops at the Kalahaku and Leleiwi overlooks, providing great views of the crater and its cinder cones. We got back to the front gate around 9:00 AM. Before leaving the park, we explored Hosmer Grove Trail. This forest feels completely different than the rest of the park. It’s lush, green, and filled with birds. Ralph Hosmer was the first Superintendent of Forestry of the Territory of Hawaii. He created this experimental forest planting a mix of native and non-native trees here in the early 1900s. After exploring this pocket of biodiversity, we spotted two Nēnē geese, Hawaii’s endangered state bird, just waddling around the nearby campsite.

After a full morning of exploring, we were ready for some food and most importantly coffee. We arrived at La Provence around 11:00 which was a little too late for a full breakfast. This charming little French bakery and café had outdoor seating with a great view, great pastries, and an excellent cappuccino. Perfect fuel for our afternoon adventures.

Next, we headed over to Makawao, a little Upcountry town with Paniolo (Hawaiian cowboy) roots and an artsy soul. The town is filled with eclectic shops, art studios, and plenty of places to grab a bite to eat. We walked around the town exploring the shops and picked up some small batch, giant sized cookies from The Maui Cookie Lady.

Next we headed to Haku Maui for a lei-making workshop that started at 1:00 PM. This was one of the highlights of our trip. Brit, our instructor and cultural guide, welcomed us into her studio with warmth. She taught us how to weave native flowers, foliage, and intention into a lei. We learned about the traditions, the meanings, and the aloha behind the process. We all sat around the table and shared stories and experiences while we crafted our lei. The 2.5 hour class flew by. The workshop was $120 per person and was absolutely worth the experience. Leaving with a beautiful, handmade lei that we wove and a better understanding of its cultural importance felt special. No surprise that Haku Maui was named the 2024 Pacific Edge Native Hawaiian Business of the Year.

Dinner that night was at Kula Bistro, an unassuming gem just a few minutes from our VRBO. The vibe was laid-back and local, and it's BYOB. There is a general store across the street where I was able to pick up Kona Longboard to have with dinner. We ordered a crab cake starter, vodka pomodoro with scallops and shrimp, and a creamy seafood risotto. Generous portions and great flavor.

Even though it was only 6:30 PM, the early start and lingering jet lag were catching up with us. We settled in on the lanai (porch) of our VRBO, watching the sunset and enjoying the evening breeze. We called it an early night.

Day 3: Goats, Pineapples & Waterfalls, Oh My!

We started the day with a quick trip back to Makawao with a visit to the legendary Komoda Store Bakery. Takezo and Shigeri Komoda started the Komoda Store and Coffee Saloon out of their home in 1916. They opened the Komoda Store Bakery in 1932. Let me tell you, it lives up to the hype, and it’s easy to see why it has stood the test of time. We grabbed some guava-filled malasadas and their famous stick donuts. They were light, delicious, and you can taste the tradition in every bite.

One of the primary reasons we wanted to stay near Kula was that its central location gave us the chance to dive deeper into Upcountry Maui’s agricultural roots, and today was all about exploring that through agro-tourism.

We arrived at Surfing Goat Dairy in time to do the 10:00 a.m. daily casual tour. We were a little early, which gave us time to enjoy a Mixed Cheese Flight while we waited. The flight featured six delicious varieties of their handmade goat cheeses, including unique offerings like the Lilikoi Quark. A quark is like a cross between cream cheese and yogurt. This quark is blended with pureed lilikoi (passionfruit) and honey. Other options included chevre with olive oil, herbs, garlic, or sun-dried tomato. The 30-min tour had us explore the dairy farm, feed the goats (they’re friendly and full of personality!), and get to hear all about the cheese-making process. And we ended on a sweet note by trying their signature goat cheese truffles. The tour was $33 per Adult, and the Cheese Flight was $27.The farm is fun, educational, and a great stop for food lovers of all ages.

Then, it was off to the Maui Pineapple Tour in Hali’imaile for our 11:45 AM tour. These famously sweet pineapples have been grown and harvested on the Slopes of Haleakalā for more than 50 years. The tour was about $90 per person. We learned all about the growing cycle, the harvesting process, and what makes Maui Gold Pineapple so uniquely sweet.

The tour is mainly in an air-conditioned shuttle bus that takes you through the pineapple fields. There were various stops where we could jump out and learn about the different growth stages of pineapples. Our tour guide shared the history, culture, and all about the hands-on process behind growing these iconic fruits. Best of all, everyone goes home with their own fresh Maui Gold pineapple. The pineapples are in approved packaging to be a carry-on if you want to take them home as a souvenir.

The shuttle bus dropped us off, and we walked over to the Hali’imaile Distilling Company for our 1:30 PM tour. The pineapples that are too small or don’t make the market cut don’t go to waste. They are either sent to MauiWine or used by Hali’imaile Distilling to produce craft spirits. We got a peek into the distillation process and learn about how each of their spirits are crafted. Most importantly, we got to sample their Pau Vodka, Paniolo Whiskey, Fid St. Gin, and Mahina Rum. It was well worth the $17 per person to have this experience. Spoiler alert: We also brought home a few bottles.

After all our amazing agro-tourism experiences, we decided to go splash around in Twin Falls at Wailele Farm. These falls are on private land, but they’re open to the public thanks to the local farm that allows visitors to enjoy the area. Parking at the Falls is $10 but they only have 55 parking spots. Luckily, since we were coming later in the day, this wasn’t an issue.

Typically, this is the first stop for folks on the Road to Hana. However, we were starting that road trip on Day 5, and that happened to be the first Saturday of the Month. On the first Saturday of the month, they have Kama’aina (local residents) exclusive days. We didn’t want to miss out on Twin Falls, so we added it in here. It’s a series of beautiful waterfalls and pools nestled in the tropical forest. It was an easy and short hike to see them. The lower falls are very close to the parking lot and relatively easy to access. The upper falls are over a mile round trip, which can be slippery as well as hazardous. We opted to explore the lower falls, which was plenty of adventure. The water was perfect for a refreshing dip, and the peaceful vibe made it the perfect spot to relax.

Afterwards we drove down the Hana Hwy about 20 mins to checkout the Ho’okipa Beach Park. Parking was crowded here in the late afternoon (around 5:30 PM). It’s a popular place for seasoned surfers because high winds tend to create dramatic waves here. It felt like everyone got off work and flocked to Ho’okipa to hit the surf. We were patient and found a parking spot near the lookout, then took a short walk down to the beach park. As we enjoyed the incredible views, dozens of sea turtles were sunbathing on the beach, completely unfazed by the crashing waves or all the onlookers.

We wrapped up the day with a spectacular dinner at Hali‘imaile General Store. This spot nails the upcountry vibes of elevated flavors in a casual, welcoming setting. We started off with crab cake and pork belly bao buns for our appetizers. Amanda got the pork shank and I got the shrimp pappardelle. We finished with a pineapple upside-down cake because the restaurant is right across the street from Maui Pineapple Tours.

Day 4: A Stroll through Upcountry Gardens

We kicked off the day with breakfast at Grandma’s Coffee House. Apparently, Grandma got started roasting coffee in 1918. Four generations later, this cozy little spot is still family-owned. Amanda really enjoyed her French toast, and I got the Loco Moco. It was a tender beef patty, rich gravy, and a runny egg all layered over rice. It was hearty, flavorful, and a perfect start for a full day in Upcountry Maui.

After breakfast, I need to walk off some of those calories. We went to the Kula Botanical Garden to stroll the garden. It was $15 per person to enter and was a self-guided tour. The 8-acre garden is tucked away on the slopes of Haleakalā at an elevation of 3,600 feet. It was initially established in the early 1970s by Helen and Warren McCord as a display garden for Warren’s landscape architecture business. We almost had the place to ourselves, so it was a peaceful oasis filled with vibrant colors. The garden had tropical orchids, king proteas, a koi pond, and rainbow eucalyptus trees. Whether you're a plant lover or just looking for a quiet stroll filled with beautiful blooms, Kula Botanical Garden is a serene stop.

Ali’i Kula Lavender Farm was our next stop, just 6 mins down the road. We got there right as they opened at 10:00 AM. We took another self-guided stroll around the 13.5 acres, hillside fields and garden. As we walked, we learned about the different lavender varieties (English, Spanish, and French). The gardens were filled with hydrangea, proteas, avocado trees, and a variety of other plants. Since the farm is on the slope of Haleakalā it offers an incredible view out toward the ocean. Before leaving, we sampled a few lavender-infused treats (the lavender lemonade was a favorite!) and picked up a few lavender souvenirs.

We made the 20 min drive down the narrow and winding Kula Hwy to get to our lunch destination. Ulupalakua Ranch Store & Grill, a rustic spot with an unbeatable lunch. I went for the Kalbi ribs, which were packed with flavor. Amanda had a juicy burger, grilled to perfection. You could taste how fresh everything was, I assume straight from the ranch. The ranch has a rich history dating back to 1856 and it is one of Hawaii’s largest working cattle ranches.

After lunch we walked across the road to MauiWine. Amanda opted for the Pineapple Flight, which included a blanc and sparkling wines made with Maui Gold pineapples. I went for the Estate Flight, which featured a Syrah, Grenache, and a smooth GSM blend. We toasted to a perfect Upcountry afternoon and went back to take a nap.

About 5:30 we made the drive back up to the summit of Haleakalā, this time for sunset. No reservations are required for sunset but you want to get their early because sunset happens fast. Watching the sky turn brilliant shades of orange, pink, and purple as the sun slipped below the clouds was breathtaking. The sky faded into dark shade of blue and eventually completely black.

We stayed a while after dark for some impromptu stargazing, on the pristine dark sky. At 10,000 feet above sea level, there is no city lights impacting the sky. We spotted constellations, planets, and even the Milky Way stretching overhead. We only stayed until about 8:00 PM but it was enough time to slow down and get lost in the stars.

Upcountry was the perfect start to our Maui adventure. Next, we head out on an epic road trip taking on the legendary Road to Hana.