North America, United States

Traveling Hawaii: Maui there yet?

The beaches – and sunsets – in Lahaina are worth one or two night’s stay

No island hopping here, we chose Maui for an eight-day excursion and took our time traveling the island. We spent time in Wailea, Hana and Lahaina and appreciated each for surprisingly different reasons. Find out which we wish we’d stayed at longer, and what can’t-miss stops you need to include on your own visit. Also, please note that Trevor named this blog post ;)


JESSICA: I had traveled to Hawaii for work years before, staying on the remote side of Maui the entire time. It was stunning and beautiful and one of the places that I swore I’d visit with my one-day husband.

TREVOR: Insert me. Game time.

J: Yea, you were game to visit Hawaii, but remember how concerned you were about it being an overly commercialized stretch of chain hotels with exorbitant pricing?

T: Yep. With eight days to work with, we thought it would be better to become best friends with one Hawaiian Island, rather than acquaintances with two or three islands. We picked two areas to stay – Wailea and Hana – and ended up adding a day in Lahaina at the end of our trip.

J: We owe major props to our friends (more than one!) who recommended that we pick up the Maui: Revealed guidebook.  I can’t overstate how helpful it turned out to be in planning our visit, as well as during our stay, guiding us to the off-the-beaten path waterfalls all to ourselves, and the best roadside food stops. {Side note: I downloaded the ebook on Kindle, so it was easy to toss into my bag and carry everywhere. Until now, I haven’t been sold on digital guidebooks … but now I can attest, it works!}

Views of the beach (look at that rainbow!) from the Andaz Maui property


T: If you’re looking for the bougie side of Maui, this is it. Grand resorts with smaller beaches, but loads of luxury. One of the things I most appreciated about Wailea was the walkway that runs along the water, connecting a large section of  waterfront resorts and making it really easy to bar crawl. Our favorite stop was the lobby bar at the Grand Wailea called Botero Lounge, which was abuzz with live cover music, plenty of people and a simple but good charcuterie board.

The entrance and lobby of the Andaz Maui has a very zen vibe (see sand pit)

J: We spent our first three nights at the Andaz Maui, based on great feedback from two sets of good friends – one of which had honeymooned there. It was relaxing and not over run by beach combers, tucked behind a craggy coastline that just about hides the property from folks who may not be too familiar with the area. But it’s also new and trend-driven, with minimally styled rooms and a sushi restaurant overlooking the water (If you’re on Instagram, you’ll likely recognize the hotel’s chic tiered-pool set up.)

T: Knowing we’d be doing our exploring in Hana, we spent our time at the Andaz lounging by the pool.

Tiered pools at the Andaz Maui offer plenty of poolside seating

J: For the love, please order yourself the loaded pork waffle fries from the pool menu.

T: …and walking the beach. I even dragged you out into the ocean during an epic storm that rolled through (YOLO!), but regretted it the second you tore your ankle on a rock in the water.

J: Seriously, that hurt. I still have that scar.

T: Bring water shoes, guys!

The dreamiest view of the black rock beach from Hana Kai Maui Hotel


After a few days of relaxation in Wailea, I was ready to head out and explore Hana. We checked out of the Andaz, but picked up a rental car right at the hotel before we left, and headed directly to a grocery store to stock up on booze and groceries, anticipating – correctly – that we’d find few restaurants on that side of the island.

J: Right. We had booked a room with a kitchen, which I absolutely recommend. If you do the same, you’ll definitely want to load up a soft-sided cooler before before beginning the trek to Hana.

A classic view on the Highway to Hana: lush greenery and twisting roadways

T: Then we hit the road! If you’ve heard about the Highway to Hana being an iconic route, it’s true. But, it’s only iconic if you stop and get out of the car and explore. That guidebook Jessica referenced earlier lists all the amazing unmarked stops by mile marker. You’d never think they were anything special from the road. We pulled over at Mile Marker 13 to crawl over a guard rail and hike up a creek bed quite to a stunning waterfall pouring into a swimmable lagoon. We were the only ones within miles and were able to easily swim up to and under the waterfall.

J: Of course (eye roll) we made several other stops before we pulled into the small, beachfront Hana Kai Maui Hotel and found ourselves mesmerized by the black stone beach it sits in front of.

We stayed in Unit 2, which was a small studio style guest room with a kitchen and queen bed and the most beautiful oceanfront balcony view I’ve maybe ever seen. {The sound of the waves rolling over the smooth stone beach was magic, y’all. I mean, sound machines have nothing on this!} The property is a small one with less than 20 rooms, but the views are gorgeous and we found the location to be perfect.

T: Breakfast was fresh banana bread picked up along the drive to Hana, which I ate on the balcony as I watched the sunrise each morning. Maybe it was being on vacation, but you really do plan your days around the sunrises and sunsets here. There’s a life lesson there I need to figure out.

There aren’t any signs and the trek is a bit tricky, but Red Sand Beach is worth a visit

J: Lunch was apples, cheese and wine while we laid on Red Sand Beach for our first full day. We end-capped it with a couples massage and hot tub soak at the nearby (and only) luxury resort Travaasa, followed by cocktails at the bar, before we went back to our room and cooked crab cakes and fresh asparagus for dinner. Side note: Can I please replay this day in my head over and over and over? Our second day in Hana would’ve been hard to compare, but I’d booked a surprise birthday activity for you…

T: It’s a good thing I wasn’t aware of this in advance.

Preparing to hang glide from the Hana Airport

J: Power hang gliding! We arrived at the tiny Hana airport, where Hang Gliding Maui is based out of a small hanger. The tandem gliding experience probably seemed a bit intimidating at first glance, but after you landed from your 45-minute tour, I’d say that you were on a true high.

Up in the air! Aerial views while Trevor hang glides over Maui

T: 100 percent. It was awesome. The coolest part was seeing a whale from the air. Or maybe when he gave me the wheel – or whatever you call it – and let me take over flying. From up in the air, you get an entirely different perspective of the island. We negotiated the cost of the high-res photos that the owner offered, which was well worth it.

J: That afternoon, we ventured to the Pipiwei Trail, part of the national park system, south of Hana. Just about two miles, the trail is a popular one, which winds upward – and through an essentially magical bamboo forest – before ending near a 400′ waterfall.

The gorgeous bamboo forest along the Pipiwei Trail

T: Put this on your must-do list. Seven Sacred Pools trail is also right near the trailhead and is an especially popular stop, although the pools were closed for swimming when we were there, unfortunately. Still, totally worth it.

Our sunset drive from Hana to Lahaina, along the more remote south end of the island

J: After our hike on our third day in Hana, we headed to the opposite side of the island – to Lahaina – and we opted to take the less-traveled southern road out of Hana. If you do the same, be ready for lots of long bumpy dirt roads and hairpin turns. Also, wildlife. Like the bull that was standing in the middle of the road when you were behind the wheel. Terrifying.

T: And if you can, pre-plan and hit the open-and-rolling-hill middle of the route just around sunset. It was shockingly beautiful, enough so that we pulled over alongside a handful of cars just to watch the glowing sun settle beneath the hills, washing the southern part of Maui in golden hues before it dipped out of sight.


Gifted champagne and chocolate-covered strawberries for our anniversary!


J: I hadn’t really planned on tacking on another “stop” during our stay, but you wanted to stretch the trip out a bit, and let’s be serious, I wasn’t complaining. So, we opted to head toward the more populated part of Maui – Lahaina. I had realized when booking our stay at Andaz – part of the Hyatt brand – that by booking Hyatt properties through Costco you received a member discount (woot!). I ended up booking the Hyatt Regency Maui since it seemed like a solid, easy choice and a different atmosphere than our previous properties.

T: It’s a BIG family-style resort that has its own network of pools, restaurants, bars but also a fantastic stretch of pristine sand beach.

I mean, I had to get this shot … champagne, rainbow, sunset, Trevor appreciating it all ;)

J: But we had great ocean views from our room on the top floor and the hotel even left us a complimentary bottle of bubbly and chocolate-covered strawberries in honor of our anniversary, which was an extremely appreciated touch.

T: My only gripe was that this was the type of resort where you’re required to wake up early and stake claim to decent lounge chairs if you want to hang by the pool. Which we did … don’t get me wrong … after you nudged and prodded me too go do it. And gripes aside, we ended up sitting quite close – literally – to a cool Australian couple who unexpectedly, but delightfully, imparted their words of marital wisdom to us over the course of the morning. Good on ya.

J: We toured downtown Lahaina and its cute shops and restaurants and also found time to drive through the clouds to the top of Maui’s volcano, which one half of our traveling duo loved and one half (me) sort of thought was not that impressive..

T: You’re crazy. We drove through and then above the clouds. It was sweet. On one drive in one hour, we went from 80 degrees and humid to 40 degrees and very thin air.

The Mars-like environment that is the top of the volcano

J: And then, it was time to head back home. Tanned and buzzing with that sort of zest for life that you really only get when you’re not working and in one of the world’s most beautiful settings, we left Maui. We’ll be back ;)

*Actual travel date: March 2017

Lounging in a tide pool at the end of one of many hikes


Day One

  • Our Delta flight arrived into Maui late in the evening, so we grabbed a taxi straight to the Andaz Maui at Wailea and grabbed a bite at the only restaurant on the property still serving food – the Lehua Lounge
At the Andaz Maui, taking advantage of its well groomed lawns

Day Two

  • Bright and early, we headed out on a catamaran whale watching tour, coordinated through the hotel and departing from the beach {we didn’t spot any whales up close, but we could hear them and barely see them, much farther away than we could paddle}
  • The sun came out and we walked the beach, starting to the right of our hotel, then tracing our way back for a long walk along the resorts to the left {beach facing} of the Andaz
  • We settled in for some pool time back at the Andaz, ordering up those Loaded Pork Waffle Fries from the pool bar {delish!}
  • After a leisurely afternoon, we grabbed the hotel shuttle and headed out to dinner at a nearby restaurant, the Monkeypod Kitchen for a change of scenery. Good energy and vibe.
Poolside at the Andaz, just before those loaded waffle fries

Day Three

  • Up early again {damn the time change}, we walked the beach before it was crowded with tourists then grabbed a quick bite of breakfast to go from the Andaz cafe
  • We settled back in at the pool just before a massive storm came rolling through; when it didn’t quickly let up, Trevor convinced me into an ocean swim in the rain, which ended up in two bloody ankles – don’t recommend. Trevor highly recommends but maybe just sit in the sand with your feet in the water.
  • When the skies parted, we began our own bar / restaurant crawl, walking along the beach path and stopping into various resort restaurants … the Marriott for appetizers, Grand Wailea‘s Humuhumu for a light dinner, and then for drinks and a cheese board at the Botero Lounge

Day Four

  • After checking out of the Andaz, we picked up our Enterprise rental car onsite and went directly to a grocery store to load up on food that we could cook in our Hana hotel kitchen
  • Ready to head to the remote side of the island, we began the long and twisty Highway to Hana, relying heavily on our Maui Revealed guidebook for the best places to stop along the way.
  • Pit stop for roadside stand banana bread, which would be our breakfast for the coming days.
  • Arrival at Hana Kai Maui, a quaint independent property with a variety of guest room styles.
  • A stroll along the black rock beach with a bottle of wine that we’d packed; this is where we sat down and watched the local kids surf until the sunset.
  • Homemade dinner back at our guest room kitchen
Posing at Kahanu Gardens, an interesting and quick – but fun – stop

Day Five

  • Sunrise breakfast on the balcony
  • A birthday surprise for Trevor’s birthday – power hang-gliding at Hang Gliding Maui, a 45-minute piloted tour for one departing from the teeny-tiny Hana Airport
  • A visit to nearby Kahanu Gardens, where one of the largest lava-rock structures still stands; a great stop for wandering and soaking up the scenery for an hour or so
  • Then, a quick walk to find a trail we’d read about in the tiny village of Nahiku that ended with this sweet little tidal wave pool {see photo above!}; I honestly can’t remember what this trail was named, but it was in the guidebook that we’ve since lent to other friends
  • Pre-booked afternoon massages booked at the only spa – well, only resort – in Hana, the Travaasa, followed by lounging in their outdoor spa space, then a drink at the restaurant bar
  • Back to our hotel for another leisurely dinner in, followed by some drinks and ukulele playing on the balcony (the room came with a ukulele)
Post-meal views outside of Huli Huli Chicken beachside food stand

Day Six

  • Checked out of Hana Kai Maui and packed up the car
  • Grabbed lunch at the Huli Huli Chicken beachside stand and then headed toward the infamous Red Sand Beach, which isn’t open to tourists, but is accessible if you know how to get there {great people watching, there were nude swimmers}
  • Drove out to the Kīpahulu District National Park, home to the Pipiwai trail, which we’d absolutely recommend hiking {a moderate trail that took us approximately two hours}
  • Then, the two-and-a-half hour drive over to the west side of the island, Lahaina {we took the lesser traveled southern route, which was remote with stretches of dirt roads, but offered really stunning views}
  • Arrival into Lahaina! We walked the downtown and grabbed a bite to eat at one of the many restaurants before checking in at the Hyatt Regency Maui

Day Seven

  • We started our day at this BIG family resort the only way that one should, by getting up way too early to reserve two pool chaises {sigh}
  • Spent most of the morning and afternoon chatting, swimming, enjoying cocktails and eating pool bar lunches
  • Late afternoon naps, of course
  • Nearing sunset, we took a bottle of champagne down to the beach and got cozy; a rainbow appeared and we clinked to our last night in Maui as the sun dipped behind the ocean
  • With a bit of energy left, we changed and headed to the resort next door to enjoy a casual dinner al fresco
The road up the volcano side to Haleakala National Park

Day Eight

  • Checked out of the hotel and made our way to Haleakalā National Park for the last activity of our trip, a drive up the Mars-like ecosystem that is a 10,000-foot volcano crater
  • Took our rental car to the airport and boarded our flight home
More gorgeous rainbow views from the Andaz Maui


  • Buy the guidebook! Maui Revealed is the one that not only helped us understand the island’s microclimates when booking our stays, but led us to the best hole-in-the-wall beaches and trails.
  • Stay a night in Hana! Better yet, stay two. While many wouldn’t think that there’s enough to occupy your time on that side of the island, we found that it was our favorite part of the trip, and I (Jess) loved our spa visit to Travaasa. The weather can be a crap shoot though. High risk, high reward.
  • Check out AirBnB and VRBO for rental properties that offer beach views and access better than many resorts once you’re outside of the touristy areas. I found our Hana Kai hotel room via AirBnB, in fact, but then reached out directly to the property to book.
  • Bring swim shoes. No, really. I didn’t pack any and somehow, never purchased any during our stay. I have three scars on my ankles to prove that there are some super sharp (likely volcanic) rocks in Hawaii’s shallow waters.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s