Maui, Hawaii {May 22-June 1, 2021}

Day 1: Arrival & Exploring Oakland and San Francisco (May 22, 2021)

This trip took place while COVID restrictions were still in effect. To enter Maui, we needed a negative COVID test from an authorized facility taken within 72 hours of arrival, and we had to upload the results to a database. Since we live in a rural area with no nearby testing sites that met the requirements, we made a 1.5-hour drive to get tested a couple of days before departure. Thankfully, all our results came back negative, and we were all set for our trip!

We took an early flight out of St. Louis to Oakland, CA, where we planned to stay for the day before heading to our final destination—Maui—the next morning. After landing, we took an Uber to the Oakland Marriott City Center, checked in, and dropped off our bags. Then, we set out to explore.

It took us a moment to get the hang of the Bay Area’s BART (Bay Area Rapid Transit) system, but we figured it out! Fortunately, there was a BART station on 12th Street, just a 5-minute walk from our hotel. We hopped on the train to Powell Street and then walked to our first destination—Chinatown. It was a lively and interesting part of the city, and we enjoyed strolling through the streets, taking in the sights, and exploring at our own pace.

Next, we took a long 30ish-minute scenic walk to Pier 39 to catch a ferry and tour around Alcatraz Island. While waiting to load the ferry, we bought a snack from a food cart and watched the sea lions sunbathing out on the docks. The ferry ride was incredible, though we weren't prepared for the chilly breeze on the water and definitely could have used jackets! We saw parts of the Golden Gate Bridge, though much of it was hidden by fog, and we were able to hear the history of Alcatraz Island as we circled it. Despite the cool weather, the views were stunning, and it was definitely one of the highlights of the day.

Afterward, I couldn't help but admire the picturesque streets lined with trees and the outdoor cafes where people were dining with their dogs resting by their feet. Such a cozy feeling. For dinner, we stopped at an Italian restaurant. While the food wasn't particularly amazing, it was a warm spot to take a break from the cold and enjoy some time together. We headed back to the hotel the way we came and rested up for the next day's adventures.

Day 2: A Rocky Start to Our Maui Adventure (May 23, 2021)

We arrived at the airport with plenty of time to spare, so we decided to treat ourselves to breakfast at Peet’s. Everything seemed to be going smoothly until we boarded our flight—only to be told we had to deboard due to a mechanical issue. As I already mentioned, this trip was during the height of the COVID pandemic, so we had to get a negative COVID test within 72 hours of our arrival in Hawaii. With the flight delay, our timing was starting to feel a bit tight. But luck was on our side. While wandering around the airport, we discovered that we could take a COVID test right outside the airport—phew! Even better, we got precheck bands, which would help streamline our process when we finally landed later that day.

The delay turned out to be a bit of a blessing in disguise. Southwest Airlines offered us travel vouchers for the inconvenience, which we ended up using for another trip later in the year. So, although the day was a bit stressful, it ended up working out in the long run. When we finally landed in Maui, it was late, but our rental car was ready and waiting for us at the airport. We made a quick stop at Safeway to grab some groceries we had pre-ordered before hitting the road to Hana.

The drive to Hana is notorious for its winding roads—narrow, curvy, and often just one lane. It was late when we were on the road, so traffic was almost nonexistent, and we took our time driving to our VRBO. Just before we reached our rental house, we had to slow down for a cow in the road (yes, really!). It was the perfect introduction to Maui. We finally arrived at our Hana house, tired but excited to settle in and begin the next chapter of our Maui adventure in the morning.

Day 3: Exploring Hana – A Perfect Blend of Adventure and Relaxation (May 24, 2021)

We woke up to a picture-perfect morning—our two girls were peacefully lounging in the hammock on the outside deck, the sun was shining, and the weather was absolutely perfect. The view was breathtaking: towering palm trees and a sparkling ocean on one side, majestic mountains on the other. It was paradise.

We kicked off the day with a delicious breakfast of pancakes and fresh fruit, the perfect sweet treat before a day of adventure. Excited to explore the famous Road to Hana, we used the Shaka Guide app to navigate the journey, and it made all the difference! The app provided fascinating facts and helpful tips along the way, making the drive even more enjoyable.

Marked by mile markers, the Road to Hana is packed with must-see stops, and we made sure to hit some of the best ones. Our first stop was Wailua Falls, a stunning waterfall with a small swimming area. We couldn’t resist a quick dip and, of course, snapping a few photos before continuing on.

Next up was the Pipiwai Trail, an unforgettable hike through a dense bamboo forest. Walking beneath the towering bamboo stalks felt like stepping into another world. Along the way, we admired (and maybe even hugged) the massive banyan trees before reaching the grand finale—Waimoku Falls. Standing at the base of this breathtaking waterfall made the already incredible hike even more rewarding.

After our adventure on the trail, we spent the afternoon unwinding at Hamoa Beach—a hidden gem. The beach was peaceful, with surfers dotting the waves in the distance, and the sand and water were absolutely perfect. We spent hours body surfing, playing in the ocean, and soaking in the sun.

Day 4: More Hana Adventures – Black Sand Beaches, Lava Tubes, and Delicious Roadside Snacks (May 25, 2021)

We had reserved time to visit the stunning Wai'anapanapa State Park, home to the famous black sand beach. The sight of the jet-black sand against the turquoise water was nothing short of mesmerizing. We spent some time walking along the beach, soaking in the beauty of the area. Then, we ventured into the lava tubes, which were a cool (literally and figuratively) and fun experience. It was incredible to be inside these natural formations, a reminder of the island’s volcanic history.

On our way back, we couldn’t resist stopping at a few roadside stands for some delicious local snacks. We picked up peanut brittle, banana bread from Hana Lima Baked Goods, and coconut macaroons—a little taste of paradise.

After indulging in our snacks and getting lunch back out the house, we decided to head back to Hamoa Beach to hang out for the day. The beauty of this beach was simply too good to pass up, and we were ready to take in a few more hours of sun and sand. Another redundancy was Coconut Glens. This time we also drank coconut milk from a coconut--not a fan, but glad I did it. ha! I will stick with the ice cream!

Day 5: Scenic Views, Local Fun, and a Jurassic Park Vibes (May 26, 2021)

Our morning started with a delicious breakfast of fluffy biscuits paired with strawberry guava jelly and fresh fruit. It was the perfect way to fuel up before heading to our next adventure.

Our first stop was the Garden of Eden Arboretum, a more touristy attraction with breathtaking views. As soon as we arrived, we were struck by the incredible jungle scenery, which felt like something straight out of Jurassic Park. In fact, the rock that appears in the opening scene of the movie is located here in the arboretum—so, naturally, we had to snap a photo of it! I LOVE plants, and this was like paradise inside of a paradise. We took lots of little hikes and read about the plant life in the area...and hugged a rainbow eucalyptus.

Next, we made our way to Ching’s Pond, a local swimming spot known for its quiet beauty. I had read on a few blogs that non-locals could sometimes feel unwelcome, but that wasn’t the vibe we got at all. Everyone was friendly, and we were respectful of the space. We spent the afternoon swimming, and the highlight was watching my family jump off some of the bluffs into the water. While we were there, a local set out a tip jar and entertained everyone by jumping off the bridge a few times--kind of scary, but he made it seem like no big deal. We enjoyed the show so much that we tipped him on our way out. Hope he’s doing well and still bringing smiles to visitors.

Back at the house, we decided to make our own version of a poke bowl with fresh ingredients we picked up at Safeway. We ate while watching Jurassic Park, enjoying the ocean breeze with the windows open—it was the perfect way to end a day and our last night at the Hana house.

Day 6- Adventurous Jungle Zipline and an Evening Oceanview (May 27, 2021)

We had to say aloha to our Hana house, but we were moving on to the west coast for the other half of our trip. The road to Hana lived up to the hype, and I am so grateful we were able to experience it in all its beauty. My husband was a natural driving it's curvy, narrow, windy roads by the time we were leaving. It really it is all about common courtesy when passing, and after a while, you get the hang of it. Before we were completely off the road to Hana we stopped to do a jungle zip line tour. This was a first for us, and I think it was enjoyable for everyone. We walked between various platforms and took turns gliding through the tropical trees with some of the ziplines having ocean views. Between the platforms our knowledgeable guide taught us about plants native to the area. Learning about the local flora was just as exciting as the ziplining itself--or at least it was for me.

After a beautiful morning, we headed to the charming town of Paia to take a look around. It was a bit crowded this day, and we decided to keep going and pick up lunch along the way. We stumbled upon a food truck and were pleased to get delicious French toast topped with bananas, savory burritos, and crispy potato wedges—great find, although I can't remember the name.

Finally, we checked into our condo in Maalaea Harbor area. For dinner we did simple take-out and enjoyed the ocean view and sunset from our balcony.

Day 7-Morning Surprises, Surfing Thrills, and Delicious Seafood (May 28, 2021)

While we saw plenty of free-range cows on the east coast, the west coast had a plethora of free-range chickens--including roosters that served as an alarm clock. Excited to start the day, we got ready and headed to Outrageous Surf, where we took a surf lesson. The staff were very laid back, kind, and encouraging. We were given instructions before going into the water and took turns with our guide learning to riding the waves. These waves were calmer, but I can officially say I have surfed now! It was so much fun, and I have to admit I wasn't feeling very confident going into it. I am so glad we did it, and I gave it a try.

We worked up an appetite while playing in the water, so next we headed to the famous Paia Fish Market on Front Street, SO GOOD. Their tartar sauce is the only tartar sauce I have ever liked in my life! We all cleaned our plates. Unfortunately, I read this restaurant closed due to a fire since we have visited, but there are several locations on the island. After our delicious meal, we explored a nearby park where we spotted a chicken and several adorable baby chicks walking near a banyan tree. Adorable. The area also had some cute shops, perfect for a leisurely stroll and souvenir shopping.

In the afternoon, we relaxed down on the beach, soaking up the sun. For dinner, we picked up some tasty local food and snacks from a convenience store and enjoyed a chill evening at the condo, reflecting on another wonderful day in paradise.

Day 8- A Relaxed Morning, Haleakala's Majesty, and Breathtaking Starry Nights (May 29, 2021)

We started our day off slow, drinking coffee, watching the sunrise, and listening to the ocean waves. Before heading out for the day, we laid out the beach close to the condo and I enjoyed reading a book before getting cleaned up and packing the car for a road trip to Haleakala. We made a quick stop at a busy Walmart along the way where we grabbed some lunch from the attached McDonald's and obviously had to try their exclusive FRIED apple pies.

Equipped with layers of clothing and a few blankets, we made our way up Haleakala. We stopped at several viewpoints to take short hikes and marvel at the breathtaking scenery. There were so many different landscapes heading up to the summit. Upon reaching the summit, we found the perfect spot to sit, bundle up and watch the sunset. It felt surreal being above the clouds. We witnessed the sun gradually dip below the horizon, creating a stunning visual. Despite the cold- it got COLD- we stayed to watch the stars come out. I didn't think anything could look more incredible than the sunset sitting above the clouds but stargazing in total darkness was even better!

There is an observation center at this location, though it is not accessible to the public as far as we know, but it was fascinating to learn about. Something else to note, is at one point the National Park was limiting visitors to go up to see the sunrise, but to my knowledge there isn't a limit on those traveling up during the day to watch the sunset.

Day 9- Snorkeling Adventure at Molokini Crater (May 30, 2025)

One of the many highlights of our trip to Maui was spending an entire morning snorkeling at Molokini Crater. This crescent-shaped, partially submerged volcanic crater is renowned for its crystal-clear waters and vibrant marine life. We started our day early, around 6am, boarding a boat that took us to the crater. As we approached, the view was simply stunning—turquoise waters surrounded by the rugged beauty of the crater's edges. Once we arrived, we put on our provided snorkeling gear and went into the tropical waters.

Snorkeling in a tropical water was a first for us too! The underwater world at Molokini is like nothing we've ever seen. The visibility was incredible, allowing us to see a diverse array of marine life up close. We encountered colorful coral reefs teeming with tropical fish. Then we got back on the boat and went to what they called Turtle Town where we snorkeled and saw sea turtles. They did emphasize the sea turtles were protected and there is a large fine if someone touches them. Additionally, when snorkeling it was advised to not snorkel to close to the reefs because touching it can be harmful. It's also important to have reef safe sunscreen for this reason.

After hours of snorkeling and taking in the beauty of Molokini, we returned to the boat, basked in the sun, and enjoyed the complimentary lunch. When back at the condo we all took showers, and relaxed until it was time for our last event in Maui.

Since luau's are a classic Hawaiian tradition, I thought that would be the perfect way to end our Hawaiian adventure. I looked into a few and ended up choosing Old Lahaina Luau. It was everything I hoped it would be and more. We were greeted with fresh Orchid leis and sat at our table. We were provided a 4-course meal- including traditional Hawaiian foods and drinks-including alcoholic beverages. Sitting outdoors, watching the sun set over the ocean, and watching traditional hula dances with my family, quite literally brought me to tears. It was such a treasured moment. It truly was the cherry on top of a beautiful trip.

Day 10- Leaving Maui and Heading to San Jose (May 31, 2021)

Our unforgettable adventure in Maui came to an end. We packed our bags and checked out as late as we could then made our way to the airport. It was hard saying good-bye to this beautiful island. We got to the airport at bit early, and luckily there were no delays with flights getting back to the mainland, but we did arrive late, so we chose to stay the night at a hotel close to airport to catch an early flight home the next morning. I chose the Homewood Suites by Hilton near the airport in San Jose. We arrived late, got a bite to eat, and went to sleep.

Day 11- Journey Back Home: From San Jose, CA to St. Louis (June 1, 2021)

Again, there were no flight delays getting back to St. Louis. The flight was smooth, and as we soared above the clouds destined for home, we reminisced about the amazing experiences we had in Maui. From ziplining through the lush jungles and snorkeling at the stunning Molokini Crater to exploring the road to Hana and witnessing the breathtaking sunset at Haleakala, each moment was unforgettable.

Upon landing in St. Louis, we were greeted by familiar sights and the warmth of home. Our trip to Maui was filled with adventure, relaxation, and delightful surprises, making it a journey we will always hold close to our hearts. As we settle back into everyday life, I can't help but feel incredibly grateful. Mahalo nui loa, Maui. We hope to see you again someday.

With Gratitude,

Rachelle