(Writer’s Note: This trip took place ahead of the deadly fires that have swept the Maui community. Unfortunately, some of the locations I mentioned below have been destroyed. Rather than remove the mention of them altogether, I decided to keep them in to remember what beautiful places used to stand there and with the hope it inspires travelers to support the Maui community and its generous people with donations and eventually a visit to support the tourism industry.)

As an adventure junkie, Hawaii was never at the top of my adventure list. I thought it was all palm trees and luaus. That may sound like heaven to some, but my work usually has me chained to a computer therefore sitting still is the last thing I’d want to do on vacation. My family knows this and when they told me about the family trip to Maui, their caveat to my invitation was that I invite a fellow adventure junkie to keep me occupied. No way were they waking up early to go hiking on their vacation. What followed was the creation of two itineraries. One for those that can’t sit still, and one for those who can’t wait to sip Mai Tais under palm trees and do nothing else. Both have been vetted and tested by my family and even have the stamp of approval from my 80-year-young abuela.

Day 1

• Rental Car Pick-Up – Kimo’s Rent-A-Car
  • It’s the cheapest option I could find in Maui. Be warned that requesting the newer vehicles still means you end up with something from 2012. The A/C works and gets you from point A to B which is really all you need and there’s not much else to brag about. The SUV also handled the back-to-back road trip of the Road to Hana and the Haleakala summit. Taper your expectations and simply enjoy the savings.
• Food – Costco and Coconut’s Fish Cafe
  • Once at the hotel, we unloaded our luggage and everyone went their separate ways to decompress post-flight. We already picked our dinner spot so no one had to deal with decision fatigue after a long travel day. No kid complained about being hungry or asked what was next because we all knew Coconut’s Fish Cafe was our next stop. On our way back from dinner, we stopped at Costco to experience a treasure hunt. We planned to stock up on snacks but we spent half an hour looking at all the Hawaii-specific items we didn’t have at home. We bought Pau vodka, a box of mangoes, papaya, guava ice cream, and cookies from the Honolulu Cookie Company. They were out of the guava cheesecake unfortunately, but it should be on your list if you can get to the store early. It was after this that our Maui experience diverted into two separate adventures.
• Adventure – Explore
  • We stayed in Kihei across the street from the beach so after dinner my adventure buddy and I watched the sunset and then wandered the neighborhoods to scope out the nightlife. It’s imperative to assess your surroundings the first day so you know what cafes, bars, and grocery stores you can fall back on in case your fancy dinner reservation falls through. In our exploration, we came across bars with a dance floor, an Irish pub, a Guy Fieri-approved restaurant, and a dope poke spot with a live band that plays late into the night which was all important information that came in handy later in the week.

Day 2

• Adventure – Snorkel Molokini Crater Tour 
  • While my resort-loving family planned to camp out at the pool, I headed to a snorkel tour of Molokini Crater. I’d never been snorkeling and there was a chance we’d spot sea turtles. It was a full-day excursion that included a continental breakfast, lunch and an open bar. I also got insight from the locals running the event, met fellow travelers, unleashed my inner child by playing on the boat’s waterslide, and then enjoyed unlimited Mai Tais until we got back to shore.
• Relax – Drinks By The Pool
  • Once back at the resort, we met up with my family living their best life poolside sipping their drink of choice in their own version of Hawaiian paradise. I’m the type of person that actually plays in the pool. Whether it be volleyball, diving for treasure, or playing Marco Polo, this pool is going to play a major role in my entertainment. Also, by learning to lay back and be patient, I was entertained by the family stories that slowly bubbled to the surface once the more mature adults of the group were finally able to relax and not worry about their kids, work or home responsibilities. The chisme that my aunt dropped from her teenage years had me crying with laughter and was a good reminder that we all had different ways of bonding with our loved ones.
• Relax – MonkeyPod Kitchen
  • For dinner, we all gathered at the highly recommended MonkeyPod Kitchen. It’s a formal restaurant that delivered an exceptional dining experience. I must say the mocktails were worth the usual upcharge and everyone was fawning over each other’s plates. We ordered lobster deviled eggs for the appetizer and for the entree, I got the chef’s special which was fish drizzled in a delicate cream sauce over mashed potatoes. It sounds heavy but it was actually filling and light and hands down the best thing I had on the island. I would also recommend the macadamia-crusted mahi mahi. For dessert another chef’s special, a mango mousse pie. Basically, if you head here, just get anything that the chef recommends because it will not disappoint.

Day 3

• Adventure/Relax – Makena Beach
  • In the morning the familia set out toward Makena Beach. It was a state beach, twenty minutes south of us. The “relax” group of the family stayed on the sand while the “adventure” crew dove into the large waves, body surfing, and open water swimming. The lifeguards were adamant about us avoiding the powerful crashing waves and we did see some pretty rough wipeouts by people on their boogie and skimboards.
• Relax – Luau at the Hyatt Regency
  • In the evening, we headed up the coast of Maui to the Hyatt Regency where we attended a luau. The manicured scenery was jaw-dropping as we walked in the open-air lobby to see parrots and penguins on display. Everywhere we turned was another photo opportunity and our best family photos took place here. At the luau, we were served a five-course dinner with unlimited drinks as we watched our talented local performers share some Polynesian history. They danced, swayed, yelled, and juggled fire. A single adult ticket cost $210 plus fees but the show itself was worth it. The seating arrangement ensured we all had a great view and enough space to learn the hula when asked for audience participation.

Day 4

• Relax – Front Street
  • We decided to head to Front Street which is a tourist street lined with shops filled with souvenirs. There were also specialty stores that sold delicious Hawaiian cookies in gift packages that you could sample. FYI, these were the same cookies at the local Costco in case the cute wrapping isn’t a big selling point for the frugal-minded. The street also had countless bars, Dole whip vendors, and spots for shaved ice. There was a park with several historic banyan trees that beautifully twisted around each other in an intricate web and looked like something out of Fern Gully. Reflecting back on this street that no longer stands, I think of the simple pleasures those few blocks held and even though the street’s buildings were humble, they were luxurious because in one glance you had the sweeping ocean views, the banyan trees and the crowds of people relaxing in paradise.
• Explore – Kihei Bar Hopping
  • Refusing to call it an evening, the adventure crew set out to explore all the local bars we passed on our first evening yet hadn’t visited. Here is where Maui redeemed itself as we ate some delicious sashimi at Three’s Bar and Grill This place is the Guy Fieri-approved spot I mentioned earlier. We had some bomb poke at Ohana Seafood. Here is where we also got a rock and roll-worthy show from the local band playing classics that even got the people in the parking lot next door dancing. Afterward, we went to the South Shore Tiki Lounge where I had some delectably crispy chicken wings. I also want to commend them on their expertly crafted Painkiller. When I went to the Irish bar next door and asked for a Painkiller, the bartender said she could try to find some ibuprofen. After a good laugh, I decided to stick with ginger and Jameson. Here is where I stayed for another live band that played more alt-rock and brought down the house with Sublime. (RIP Bradley) I may be a hypocrite for doing exactly what I said I didn’t want to do on Front Street, however amongst the local crowd, enjoying live music and actually good food, I finally found some things worth sitting still for.

Day 5

• Adventure – Road to Hana
  • Despite our late night, the adventure crew woke up early to hit the iconic Road To Hana which consists of driving on the wet side of the island filled with lush greenery, hikes to waterfalls, and enduring the intermittent rainstorms responsible for all that beauty. It’s not possible to attempt all of the waterfall hikes in one day but I would be content with packing a picnic and spending all afternoon at any one of the spots. The actual route should take less than four hours without stops, but the whole point is to be astonished by every turn and very safely pull over to admire the vast ocean views. Be warned that the highway is narrow and feels more like playing Mario Kart on a one-lane road. When it comes to knowing when to stop, Google Maps has several icons pinned but there is limited cell service so download the map beforehand. Stops I recommend are Twin Falls Waterfall, Garden of Eden Arboretum, and Upper Waikani Falls. I never made it to Kaihalulu Red Sand Beach, Hamoa Beach, or The Pools at ‘Ohe’o but they also are highly recommended. Here is also where all those Costco snacks came in clutch. There were several food options on the way but after being burned with subpar options, I can only confidently recommend Uncle Harry. This place is a bright red stand on the side of the road which offered a Hawaiian melt that resembled a grilled cheese with pulled pork, pulled pork tacos, chili cheese fries, shaved ice, and a dessert called malasadas which reminded me of fresh doughnut balls. When we reached the very end of the road, we ended up at a black sand beach called Hana Beach Park. This is not to be confused with Black Sand Beach which is a state park that requires reservations to enter. The views on the trip were astonishing and inspiring but plan accordingly in regards to the return trek because you absolutely don’t want to be driving back on such a windy road in the dark.
• Adventure – Haleakala Summit
  • Everyone I talked to suggested catching the sunrise from the Haleakala summit. It takes at least an hour and a half to drive to the top which means a very early morning that the “relax” crew was not about to make. We also realized that we needed to make a reservation at least two days (not one like I initially thought) in advance to access the state park and drive up the volcano before 7 am. Since the “adventure” crew failed to take that into account, we decided to continue our expedition back from Hana and straight up to Haleakala to catch the sunset. This was another case of playing real-life Mario Kart on a windy road that wasn’t for the faint of heart. Worse still, fog had started to settle in so we could only see about twenty feet in front of us. Yet the summit was so high, we finally broke above the fog and clouds and pulled over just in time to catch the most beautiful sunset in my life. The brilliant orange, reds, and purples that colored that sky left everyone speechless and every few minutes the colors would evolve to present a new art canvas to be admired. No one wanted to miss a minute of the spectacular display so we actually didn’t head back down until nightfall. This is where we joined a caravan of cars slowly making their way down the side of a volcano. We were all going well below the speed limit, but at this point, our priority was to make it home safely, no matter how long it took.

Day 6

• Relax – Lavender Farm and Pineapple Farm
  • The family members who didn’t do the insane 10-hour road trip were amped for their own version of an adventure: a tour of a lavender farm. There was also the option of visiting a pineapple farm where they handed out pineapples as souvenirs. Pretty and informative was the review I got but after some research I realized they were underselling the pineapple place. Turns out you can learn about the process and even sample the product along the way. As for the lavender farm, apparently, the views can be pretty impressive when the flowers are in bloom and the farm can even host weddings.
• Relax – Beach and Turtle Spotting
  • Now that the adventure crew was all “adventured” out, we decided to spend our last day beachside. We whipped up some vodka pineapple-guava slushies and set up on the soft sand. Here is where some Hawaiian magic took place. I was out in the water past the break when I spotted something rather large and dark right by me that sent me running back to shore. When I shakily told my crew I thought I spotted a turtle, they all jumped up and asked me to show them where. With reinforcements and feeling a bit braver, I went back into the ocean, and about fifteen minutes later, we all jumped and then cheered when we spotted a sea turtle swimming right by us. We stood back as it glided by unbothered and made it back to shore to watch our final Hawaiian sunset.

Aloha to Hawaii!

By the end of the trip, everyone had experienced what they wanted out of the vacation and while we had different experiences, we all came back tan, rested, and happy. By acknowledging our own expectations and needs, there were fewer miscommunications and stress attempting to force everyone to do a single activity. We all bonded when we could and we still chose to come together almost every breakfast and dinner to recount our Hawaiian adventures with our ohana. It’s that separate time that gave us more to talk about and stories to laugh over which made this the perfect family vacation.