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  • Allyson Rychlak

The Complete Guide to Maui, Hawaii's Valley Isle

On Friday, my family and I returned from our annual vacation, this time visiting Maui and Oahu, where we spent ten days. We began our trip in Oahu to see Pearl Harbor, and then spent the majority of the time exploring the beautiful island of Maui. My parents have been to Hawaii twice without me and my brother, first on their honeymoon thirty years ago and then for a second time a few years later, and have raved about the islands for years. We were so excited to experience it with them and truly had the best trip.

The beachfront view from The Mauian in Napili Bay, our first stop in Maui

Day 1: Tuesday (Honolulu, Oahu)

Our original flight left Philadelphia around six a.m., which got us into Oahu in the early afternoon, but American unfortunately shifted both flights a a few hours later. After a five hour flight to LAX and another five hour flight to Honolulu, we arrived in Oahu around seven p.m. Because of this delay, we didn't have a lot of time to explore Waikiki Beach or the area where we were staying. We took a taxi from the airport to The Modern Honolulu, which was an adorable boutique hotel on the left end of Waikiki Beach, but I think the taxi system here is a bit of scam. I looked up Uber prices when we first landed, which ran about $20-25; the taxi meter was about $40 without tip (we were having trouble finding the ride share spot in the airport exit, and the taxi stand was right in front of us).

The Modern Honolulu's poolside restaurant at night, where we ate our first meal in Hawaii after checking in

That night, we had a reservation at Herringbone Waikiki, but ultimately decided to eat at the hotel's poolside restaurant and bar, which had beautiful ambience and tasty quick bites. Tired from travel, we went to bed early before our first full day in Hawaii.

Day 2: Wednesday (Pearl Harbor)

Jetlagged, we woke up before 5 a.m. on Wednesday morning and walked to Waikiki to see the sunrise over Diamond Head. I would have loved to hike Diamond Head if we had more time on Oahu, but there's always future trips! We had coffee and breakfast at Big Wave Dave right off Waikiki - I highly recommend their honey lavender iced coffee and an açaí bowls.

Sunrise over Diamond Head on Waikiki Beach, Oahu

By 7:30 a.m., we were picked up at a hotel down the street from The Modern for our Salute to Pearl Harbor tour, which I found on Viator after scouring many reviews of the countless tours offered to the memorial. We sat in a double-decker, open air bus and toured through Waikiki to pick up other guests before traveling from Honolulu to Pearl Harbor, listening to fun facts and trivia from the driver along the way. This was considered a half-day tour, which my family and I all believed was a perfect amount of at the museum and memorial, since many exhibits are not included. The tour covered our entry and ticket to the USS Arizona Memorial, which is a highlight of the trip with reservations required if you were to visit on your own without a tour. Ticket-holders to the USS Arizona are not guaranteed entry on the day of the tour, since the US Navy has final say in weather conditions for trips out via boat each day. We were lucky to see the memorial and pay our respects to the soldiers who lost their lives there on December 7th, 1941. The museums on site are informative and beautifully done.

The USS Arizona submerged from the Memorial with the USS Missouri in the background

After our tour dropped us back off near our hotel at 12:30 p.m., we headed back to the same street as Big Wave Dave's at Nalu Health Bar & Cafe for a quick lunch, devouring ahi tuna wraps, salads, and chicken sandwiches. We then returned to The Modern's pool to have a drink at the poolside bar and lounge before leaving for the airport for our flight to Maui. In the afternoon, we took an Uber from Waikiki to the airport once again, concluding our very short stay in Oahu, and flew Hawaiian Airlines to Maui on what was the quickest flight of my life!

Once the rental car was picked up - a Jeep Wrangler for our adventures - we drove from Kahului to Napili Bay, above popular towns Lahaina and Kaanapali on Maui's west end. We stopped at the Ono Tacos truck outside Lahaina, which was recommended to us by my cousin Ashley from her previous trips to Maui, and had delicious tacos before heading to our hotel at Napili Bay, The Mauian. After a quick check in, heads hit the pillows, as we still were fighting jet lag!

Day 3: Thursday (Napili Bay, Maui)

It was dark when we arrived the night before to The Mauian, so we loved waking up to our beautiful beach at Napili Bay, complete with a full rainbow after sunrise. We walked several yards down our beach to the Sea House, part of the neighboring Napili Kai Beach Resort, and tried their famous sweet potato frittata, fried rice, and house-made macadamia nut cinnamon rolls to start. My mouth is watering just thinking about the menu!

The Mauian's beachfront on Napili Bay, Maui's west end

That morning, we hung out at the beach in front of the hotel with provided beach chairs and towels, and headed to Kaanapali Beach, once named America's Best Beach, to check it off the bucket list. Although Kaanapali is a beautiful beach area with luxurious resorts like the Hyatt, where we parked and visited the craft fair in front of their pool (the fair runs every Thursday from 9:30am to 3pm), we favored Napili Bay for its smaller feel and less crowds. My brother and I got hand-poured candles from one vendor, which smell amazing - "Aloha Maui" and "Coco Lime" - and I recommend checking out a beautiful jewelry vendor called Ilihia Maui for handcrafted earrings, necklaces, and bracelets from the island.

For dinner, we ate at The Plantation House on the Kapalua Golf Course, which stunned us with a vast view of the course, ocean below, and surrounding grounds kept pristine. We tried ahi tuna ceviche, shrimp scampi, and mahi mahi along with tropical drinks and a Hawaiian blonde ale, all while people-watching a wedding that was happening beneath us on the golf course. After dinner, we watched sunset over Moloka'i, the island that Napili Bay faces, and celebrated a lovely first day in Maui.

The Plantation Course at Kapalua Golf, the grounds the Plantation House Restaurant overlooks

Day 4: Friday (West End, Maui)

To start the morning, my mom and I walked the Kapalua Coastal Trail along The Mauian and other neighboring resorts. As a family, we then walked to The Gazebo, a famous Maui restaurant hidden on the Napili Shores condo complex. We got in the already robust line at 7 a.m. - they open at 7:30 a.m. - and still waited about forty minutes. The wait was worth it for their pork fried rice and macadamia nut pancakes with banana and coconut syrup. We may have over-ordered the fried rice - the portions are huge, and we ended up taking it home to eat for breakfast the next day before we left this side of the island. While there may always be a wait at this restaurant, the staff hustles, and we were in and out in no time.

Breakfast of banana + macadamia nut pancakes and fried rice at The Gazebo

After breakfast, we headed north of Napili Bay to visit the Nakalele Blowhole, a natural geyser where trapped seawater spurts out when large waves come in. This is a quick hike down from the road, but beyond this point, the Kahekili Highway to the Waihe'e Ridge Trail turns into a almost completely one-way, narrow path through the mountains, with plenty of switchback turns and steep inclines. We did not know it at the time, but the Kahekili Highway is nicknamed the "death road of Maui" and widely known for being the most dangerous road on the island, even above the Road to Hana (continue reading below for our Road to Hana excursion). Although we were not as prepared, my brother was calm as a cucumber driving the Jeep around hairpin turns, and thus we saw beautiful, sweeping ocean views along the Highway.

My family at a lookout point on Kahekili Highway, Maui's most treacherous road

Once we made it through our treacherous drive, we hiked the Waihe'e Ridge Trail, a four mile out-and-back hike through the mountain ridges. It is pretty steep, and we did it in the heat of the day, but I do recommend this hike for its beautiful views of lush greenery and the ocean below. There are two parking lots for this hike; the first is nearby the Mendes Ranch, in case you miss the parking lot turn like we did, and the second is up the mountain much closer to the trail head. However, since this is a popular hike, it can fill up, thus the second parking lot with a bit of a hike up the mountain through farmland to get to the trailhead.

One of the many views from the Waihe'e Ridge Trail on the west side of Maui

We drove back through Kahului, not the Kahekili Highway for the sake of my dad's blood pressure, to Napili Bay, stopping for smoothies and refreshments at the Olowalu Juice Stand, where there is an open air food market as well. Sweaty from our hike, we showered and headed to Lahaina for dinner at Pacific'o on the Beach, a farm-to-table restaurant with oceanfront views and a carefully curated dinner and drink menu. The service and food here was incredible, so I highly recommend. We also got to see sunset from this restaurant before heading into Lahaina for some shopping at the many stores.

Day 5: Saturday (Haleakalā National Park)

We were sad to leave Napili Bay and The Mauian behind, but excited to see other parts of the island during the rest of our time on Maui. With plenty of leftovers from The Gazebo, we got coffee at Napili Coffee Store (which we all agree was the best coffee we had throughout our entire time in Maui; you must try the iced coconut cold brew) and had breakfast on our deck at The Mauian before heading to the east end of the island.

The view of Haleakalā's crater at the visitor center's viewpoint, approximately 9,000 feet above seal level

Before climbing the Haleakalā Highway up the volcano, we made pit stops upcountry at the famous Hali’imaile General Store (which was closed, so look up their limited hours before trying to stop by) and Maui Bees, a bee farm with an adorable farm stand and gift shop. The bee farm has tours and farm-to-table dinners, and this was a surprising highlight of our day. We then traveled on to Haleakalā National Park, which is hard to describe in words, to view the summit at 10,023 feet above sea level. Our hike on the Sliding Sands Trail into the crater, where cinder cones are visible on a day not quite as foggy as the one we visited, felt like it was out of a movie. The suggestion to dress warmly is no joke - when we arrived at the summit, I changed into leggings and wore a sweatshirt and a rain jacket. Be sure to see the volcano's famous Silversword, a silvery-haired plant that grows low to the ground only near the summit of Haleakalā, and nowhere else in the world.

The famous Sliding Sands Trail is an 11.5 mile out-and-back trek, but we made it several miles since it began to rain

We descended the mountain and had a late lunch / early dinner at Kula Bistro about fifty minutes from the summit. Their desserts are fabulous - we left with a chocolate peanut butter pie and a coconut cream pie for later on. After a long day of hiking, we were eager to settle into our BnB in Paia, a small surf town on the northern coast of Maui within distance to Haleakalā Highway and the Road to Hana. Originally, I planned for us to spend this day traveling the Hana Highway and spending Saturday night in Hana, but then I realized that our Haleakalā sunrise reservation for Sunday morning would involve driving over two hours in the dark to the summit of the volcano, so plans had to change!

One more summit photo for good measure; the elusive Silversword, which only grow on the volcano's terrain

Day 6: Sunday (Haleakalā and Hana)

My family and I all agreed that the sunrise at Haleakalā was one of the highlights of our whole trip. I logged onto to reserve a ticket for our car sixty days in advance. Haleakalā means "house of the sun" in Hawaiian, and it certainly did not disappoint. We parked at the visitor's center at the summit and gathered with many others to watch the sun rise over the clouds. Local guides from a tour group sung a beautiful Hawaiian chant welcoming the sun. Dress warmly for this as well - I was in the same outfit (leggings, sweatshirt, rain jacket) as the day before, and was shaking as we waited for the sunrise for about twenty minutes.

Photos do not do the sunrise justice! Views of the crater as the sun finally rose around 5:45am

After the sunrise, the drive down the mountain to start our trek to Hana was equally as stunning, with sweeping views over west Maui and a beautiful, colorful sky as the day started. For our Road to Hana adventure, I downloaded the GyPSy Guide, also recommended by my cousin Ashley, for an audio tour of our drive that worked even as my phone lost service, which was most of the time. The app is $15, but worth every penny. We would've been driving blindly without the audio guide in terms of stops, and the narrator shares essential pullovers, what to skip, and parking tips, as well as fun facts and trivia as you drive through. Many travelers say that the Road to Hana is treacherous - and it is, with narrow turns and mostly one-way bridges - but after our drive on Kahekili Highway two days before, we were barely phased.

Jagged beachfront near the village of Ke'anae off the Road to Hana

We briefly hiked a one-mile loop in the jungle at Waikamioi Ridge Trail, but I wouldn't consider this an essential stop. Along the way, we parked at Kaumahina State Wayside Park for a bathroom break and a beautiful vista, and then continued past the Ke’anae Arboretum, even though I would have stopped if we had more time. The village of Ke‘anae was a beautiful stop right after the Arboretum, where the famous Aunty Sandy's Banana Bread is located; she was closed, as it was a Sunday, but I've heard many raving reviews! We saw many waterfalls on the Road to Hana, including the Upper Waikani Falls (also known as the Three Bears) where people were swimming, as well as Hanawi Falls. The Nahiku Marketplace is known for famous pork tacos if you're in the area for lunch, but we stopped at the cafe located in the same parking lot for banana bread and coffee. There is a beautiful craft store next door to the cafe for local Maui jewelry, art, and other gifts.

We skipped the Kahanu Garden, where the National Tropical Botanical Garden is located, as well as the lava tube near mile marker #31. Since we wanted to complete the drive past Hana at the Haleakalā end of the tour to make it back to Waiʻānapanapa State Park for our reserved timeslot on the drive back, we had to be picky with our stops. Once past Hana, the cute but sleepy town that gives the drive its name, a stop at Koki Beach Park gave us gorgeous views of red sand. We then swam at the beautiful Hamoa Beach to cool off during a very hot day! To finish our Road to Hana adventure, we checked back in at Haleakalā National Park (park passes required) to hike the bamboo-lined Pipiwai Trail and see the ʻOheʻo Gulch, often called the Seven Sacred Pools.

Koki Beach Park, a much less traveled spot on the Road to Hana

On our drive back, we continued to listen to the narration from the app to learn more about the Road to Hana and the towns along the way. We made it to the black sand beach at Waiʻānapanapa State Park in time for our reservation, which I made thirty days in advance. While this is a staple Road to Hana spot, I think I would prefer it at sunrise or sunset, when the crowds are less. It was packed with people, and since we were at the tail end of our journey that day, we were both tired and hungry. It was stunning, but other spots topped it, in my opinion. Eager to stop before the two hour drive to our condo in Kihei, we stopped for delicious pizza at The Bamboo Hale at Hana Farms.

Waiʻānapanapa State Park, famous for its black sand beach

Sunday was a packed day, but so worth it! We checked into our condo from VRBO in South Kihei, just above Wailea, for the last leg of our trip and went to bed. For recommendations about our VRBO and why we chose this location, feel free to message me.

Day 7: Monday (ʻĪao Valley and Wailea)

We started the day with breakfast and coffee, a staple for our family, at Kihei Caffe just down the road from our condo. Before we spent the afternoon lounging at the beach, we headed twenty minutes back towards west Maui to hike the ʻĪao Valley State Monument, a short climb into the mountains that make you feel as though you're right in the original Jurassic Park movies. Cue John Williams. Although the Needle is spectacular, explore the park for other trails, especially along the water.

Mountain in ʻĪao Valley, which also requires reservations through Hawaii's state park system 30 days in advance

Sore from a few days of hiking, we grabbed our beach chairs, umbrellas, and towels and headed to Wailea Beach, where several of Maui's most luxurious hotels are located. Public parking is available, and we snagged a spot on the beach in between the Grand Wailea and the Four Seasons, where season one of The White Lotus was filmed. Thanks to its proximity, we grabbed lunch from the Four Seasons' beachfront cafe along with an aptly named Wailea Spritz, which was definitely overpriced but quite refreshing.

Fans of HBO's The White Lotus will recognize this famous hotel on Maui's Wailea Beach

Originally, I had booked us for Monkeypod's Happy Hour at their Kihei / Wailea location, but we decided to eat at the Fairmont Kea Lani's signature restaurant, Kō, which ended up being one of our favorite meals. The mahi mahi here was by far the best we had on Maui, with coconut jasmine rice, kale pesto sauce, and roasted veggies. I had fabulous sushi as well, so you really cannot go wrong with this menu. The restaurant is located alongside the adults-only pool at the resort, and after dinner, we walked along the Wailea Beach Path from the Fairmont, where my parents stayed for their honeymoon in 1993, to the Four Seasons as the sun was setting.

A moment for the sushi from Kō; I wanted to take these chopsticks and the holder with me!

Day 8: Tuesday (Lahaina and Wailea)

Ahead of our snorkeling adventure to Lana'i, leaving from Lahaina, we stopped for a quick breakfast at Java Cafe in Kihei for breakfast sandwiches, coffee, and peanut butter, banana, and honey toast. Yum! From 8:30 a.m. to 12:30 p.m., we snorkeled in two spots and saw a massive pod of dolphins in a small group tour booked on Viator. There were 3 guides and only 5 other guests with my family of 4, and it was a perfect amount of time on the water.

A pod of dolphins off the coast of Lana'i, one of the smaller islands in the Maui Valley Isle

After our snorkel adventure, we headed back to Kihei and got ready for another beach day at Wailea. We also walked around the Shops at Wailea, an open air shopping mall, where the Tommy Bahama Restaurant and Bar is located. I originally had us booked for Happy Hour here as well, but wanted to enjoy the beach longer, and I thought the restaurant seemed a little touristy when we walked by it in the shopping center that day. Instead, we ate at a casual spot within walking distance of our condo called Three's Bar & Grill, also recommended by my cousin Ashley, and had delicious sushi and a coconut-crusted fish sandwich.

Day 9: Wednesday (Upcountry Maui)

Wednesday was dubbed our "eating from the earth" day, as we started with breakfast at Grandma's Coffee House with yummy food and coffee on the slopes of Haleakalā before a morning tour at the Maui Tea Farm. Our tea farm tour was such a highlight of our trip, and we really enjoyed our guide, learning about the tea process and plants, the land, and so much more. The staff here was so kind and we tried many teas that they make on the property.

Don't miss the Maui Tea Farm on an adventure through upcountry Maui

After the tea farm, we headed to MauiWine at ʻUlupalakua Ranch for a wine tasting with beautiful, sweeping views of neighboring islands Lanai, Kaho‘olawe, Molokini crater, and the West Maui Mountains. We had a tasting booked at the King's Cottage, where we tried sparkling, red, and white blends. Our favorite was the Maui Blanc, a pineapple wine that was incredibly unique. Looking to ship wines home, since pineapple wine isn't quite the same in Pennsylvania, my parents ended up signing up for the wine club through the vineyard, which will ship 6 bottles twice a year.

The Rose Ranch tasting at MauiWine, offering a sparkling, white, and red blend of Hawaiian wine

After our tasting, we headed back down the mountain to visit Wailea Beach one final time before saying goodbye to Maui the following day. For dinner, we visited Cafe O'Lei at The Mill House, a locally farm-owned and operated restaurant on the Maui Tropical Plantation. The views of the surrounding mountains were stunning, and the food and service, as well as the mai-tais, were also exceptional.

Family photo and views of the surrounding mountains and golf course at Cafe O'Lei, one of my favorite dinners

Day 10: Thursday (Kihei and Kahului)

With checkout by 11 a.m. from our condo and an 11 p.m. flight, we choose to use ResortPass for the first time (which I learned about via an Instagram ad) to spend our last day poolside and beachside. We originally aimed for day passes at the Fairmont Kea Lani to stay in the Wailea area, but we waited too long to book. Instead, we landed on the Maui Seaside Hotel, the only available spot on ResortPass for a day room. We checked in after 9 a.m. like a normal hotel, and had access to the pool, a full-service hotel room to shower or nap if needed, and the beach until checkout at 6 p.m. We also were given a discount at the neighboring restaurant, which we used for lunch. This was the first time I've ever used ResortPass, and I think it is a phenomenal idea when travelers are stuck with late flights and nowhere to go. Also, it was so nice to shower and get changed before our big travel night and following day home to Pennsylvania.

The rental car was due back at 6 p.m., so we left the hotel around 5:30 p.m. with a short drive to OGG to complete our journey.

While we spent only a short amount of time on Oahu, seeing Pearl Harbor was truly moving and I highly recommend it. Our nine days on Maui were incredible, and this family trip certainly was one for the books. If you're planning a trip to Maui, feel free to reach out for any and all tips and tricks, including those recommended to me that were not checked off by my family on this latest trip. If you've read this far, mahalo! I hope you enjoyed hearing about our adventures in Maui.

Sunset at the Fairmont Kea Lani's beach, just steps from Wailea Beach


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