Maui Travel Diary

My husband and I have had the joy and privilege of doing quite a bit of traveling throughout our relationship. We love it! Whether it’s exploring a new U.S. city or crossing the border into other countries, we both enjoy discovering new ways of life, restaurants, pretty sights, and different cuisine (amongst the many other things!). Since traveling is important to us and something we love to do together, we make a strong effort to make it happen. If we get to spend two days or two weeks somewhere, we feel grateful to even have the opportunity to hop on a plane or in a car and take the time to explore. While we’ve been to a good amount of places that we love, Maui is definitely atop that list now! We’ve talked about wanting to go to Hawaii for years and saw an opportunity to do it, so we seized it! While our trip was short, especially compared to most travelers’ time in Hawaii, we enjoyed every last second of it. We knocked a couple things off the list of to-do’s, and have a good idea of the other things we would love to do, if we have the opportunity to return again. On our last evening there, we did a little trip “review”, discussing what we loved and what we wish we had been able to do. It was then that we decided that we will definitely make a great effort to return sometime, hopefully exploring more islands and spending a bit more time on Maui.

Even the view flying in was beautiful!

While on our trip, I heard from quite a few of you that you have upcoming travel to Maui (or the other islands) or would love to visit one day! A travel diary was highly requested, so I’m happy to share what we did, where we ate, and more. One thing that I want to point out before diving into it is that every person and every couple/family travels differently, of course. What Mike and I enjoy doing or value (I.e. are willing to spend money on) may be different than what you would enjoy or value. I’ll share the things that we did, ate, liked, but this is certainly not a comprehensive guide to traveling there. There are so many resources online about what to do, eat, where to stay, and more, so consider this just one person’s perspective! Alright, let’s jump in!

stunning view from our hotel room

Where We Stayed

My family traveled to Maui for a spring break trip when I was in middle school, so I had a bit of experience there before. We ended up staying at the same hotel that my family stayed at, almost 20 years later! We stayed at the Hyatt Regency on Ka’anapali Beach and had a wonderful experience. The resort is beautiful, restaurants provide good food, and the location is hard to beat! It’s along a strip of other resorts and hotels and within walking distance of a popular restaurant/shopping center called, Whaler’s Village. We walked down to Whaler’s several evenings of our stay to grab dinner at one or the restaurants or for dessert.

Tip: If you stay here, they have happy hour twice a day and their Mai Tai’s are delicious!

Note: if you’re planning on renting a car or traveling around the island (which you should!), consider the places you want to drive to and the distance that they are from the hotel/place you stay at. Since we were on the west side of the island, we had to do quite a bit of driving to get to just about every activity we did. It was worth it to stay at the resort, but just something to keep in mind!

The sunsets are unbeatable!
Mama’s Fish House

Where We Ate

Here’s a list of the restaurants we ate at and would recommend checking out, along with any highlights from what we ordered:

  • Japengo (at the Hyatt) – spicy edamame, rainbow roll
  • Leilani’s on the Beach (Whaler’s Village) – fish tacos
  • Monkeypod (Whaler’s Village) – mai tai and fish tacos
  • Mama’s Fish House* (Paia) – stuffed mahi mahi (my dish – so good!) and bouillabaisse
  • Lahaina Pizza Co** (Lahaina) – chopped salad
  • Hana Picnic Lunch Company (Paia) – for our drive along the Road to Hana
  • Umalu (at the Hyatt) – we only ate lunch here, but it was good!
  • Breakfast – I received a lot of recommendations for different breakfast joints to try out – there seems to be a lot of options! We had breakfast included with our stay, so we took advantage of that.

*Note about Mama’s Fish House: if you do any research about where to eat when visiting Maui, Mama’s will show up on the list. It’s like an institution there. The setting is beautiful and the restaurant itself is definitely cool to see and eat in. The food we ate was delicious, probably one of the best meals that we had while we were there. That said, it is expensive. Like $50+ an entree expensive. Mike and I are not big food people – we love food, but we don’t love spending a lot of money on food. My recommendation: if you want to go because you want to see what you’re missing out on and don’t mind spending well over $100 on a meal, do it! You’ll have great food and a cool experience. If you’d rather keep that money to spend on something else, don’t feel like you’ll be making a huge mistake by not going. We don’t regret going, but it’s not a restaurant we would visit again if we go back. Just my two cents!

**Note about Lahaina Pizza Co: as a Chicagoan, nobody else does deep-dish pizza right. The pizza is good, but if you’ve had Chicago deep-dish before and are expecting that, you may be disappointed!

The views from the zipline tour were beautiful!

What We Did

We had discussed our list of “must do’s” before heading to Maui, making sure that we made time to do those things while there. Since we were in a pretty tight window, we wanted to make sure we spent our time wisely! Any of the time we weren’t doing these activities, we were taking advantage of our resort area and swimming in the ocean. Here’s a look at some of the activities that we did:

  • Ziplining – this is something we’ve talked about doing for awhile, but hadn’t made a priority to. I did some research about options on Maui and we ended up doing it through this company. It was so fun! I’m a bit afraid of heights, so it was a little nerve-wracking at first. But after the first line, my nerves were gone. We got to see pretty views along the way, too!
  • Road to Hana – I’ll dedicate a whole section to this below!
  • Watched kite surfers at Kanaha Beach Park – if you’ve never seen kite surfers in action, you may enjoy checking this out!
  • Downtown Lahaina – we walked around after dinner one evening – it’s a cute little downtown with shops, restaurants, and Banyan Tree Park
  • Boogie boarding in the ocean – we bought cheap boogie boards at Walmart and had some fun riding the waves. If you’re planning on going in the ocean, I highly recommend packing or planning to purchase some water shoes –  it can be rocky.

We didn’t get to do much snorkeling, for a couple reasons. Taking a snorkeling cruise or boat out somewhere and snorkeling is not my idea of a good time – I get seasick and snorkeling gives me anxiety, the whole hearing yourself breathe thing really throws me off and I have a hard time enjoying it. The other reason is we simply ran out of time! Also, Mike was having more fun riding the waves on his boogie board. We did get to see quite a few sea turtles off the beach of our hotel, so that was cool!

Ching’s Pond, Road to Hana

Road to Hana

This is another one of those things that you’ll find on nearly every, “what to do in Maui” list. It’s a 65 mile highway along the coast to Hana Town and beyond. It’s a beautiful drive with a ton of hiking, waterfalls, beaches, and pretty photo ops along the way. We had rented a car at the airport because we knew we wanted to drive this, along with being able to freely travel around the island. If you’re planning on doing the Road to Hana, you may be tempted to rent a Jeep Wrangler. My advice: stick with a small rental car! It’s much easier to maneuver on the one-lane bridges, hairpin turns, and to park in the tiny parking areas along the road. This is a very popular tourist activity, so be prepared for some traffic, crowds, and slow going in parts. If you’re not a confident driver or you get carsick very easily, I recommend doing plenty of your own research on the Road to Hana and determining if it’s actually something you want to do!

My #1 recommendation is to download one of the Road to Hana apps that acts as your tour guide. We utilized the Shaka Guide App (search in App Store) and thought it was great. It tracks you via GPS and calls out stops (both visible and hidden), shares tips and tricks, and provides some history and background information while driving. There’s very spotty cell reception along the drive, so be prepared to not use your phone for much of it.

We both went into the experience open-minded – we had heard mixed reviews from people. Some say it’s a must do, others say it’s not worth your time. We wanted to check it out for ourselves, but were willing to turn back if we found we weren’t enjoying ourselves. We really enjoyed it! I’m not sure it’s for everyone, but it’s definitely a unique experience. We ended up spending about 5 hours or so on it. We started at mile marker 0 at 10:30am and were back in Paia by about 3:30/4pm. We knew we weren’t going to go all the way to Hana, especially since we got a late start, but the places we stopped along the way were very cool.

Our Stops:

  • Kaumahina State Park – there’s a little picnic area and restrooms, so we utilized both on our first stop. If you look at a map, you’ll see that we drove in for quite a ways, about an hour, before stopping. We wanted to bypass a lot of the traffic/crowds that we heavy at the first several stops.
  • Ke’anae Arboretum – a quick hike into the forest will have to seeing rainbow eucalyptus trees (so cool!) and more
  • Ching’s Pond to Swim – this is the first “swimming hole” we stopped at. It was right off the road, so super easy to get to. The water was freezing cold, but it was definitely fun to jump in and swim.
  • Halfway to Hana – a little snack stand where we enjoyed some banana bread and shave ice
  • Wailua Iki Falls and Hike – this was maybe a 15-20 minute hike but so worth it. We saw the most stunning waterfall and got to swim in another pond. Since it’s a decent hike (not difficult, just longer than some), there were very few people there, which was a nice change of pace!

That was it! We had dinner reservations back near our hotel that evening, so that was all we had time for. I’m definitely glad we ended up making time for it!

Wailua Iki Falls, Road to Hana

Final Thoughts

We had a wonderful time! We had four full days, plus a little time on our travel days. I felt like we could’ve used 2 more full days there (or more!), but also think we did a pretty good job of how we spent our time.

Another thing for consideration: it’s expensive. Certainly some things are more expensive than others, but if you’re going to be in any of the tourist/vacation areas, be prepared to spend some money!

The “beach” area at the Hyatt is not super substantial – some spots of the beach are very short. You can find larger beach areas if you walk down towards Whaler’s Village or if you go to different spots on the island.

Something we definitely want to do if/when we return is to go to Haleakala National Park – it looks stunning!

Hi there!

Lauren Loves is an online destination where I share my personal style, beauty finds, and bits of life in hopes to inspire other women to feel good in their skin and find the beauty in the ordinary.

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  1. 8.28.19
    Sara said:

    What did you wear on the road to hana? Specifically, footwear? This is on our list of things to do – but I’m thinking I probably need to bring comfy shoes for hiking and sandals for swimming? Or did you just wear water shoes?

    • 8.28.19
      Lauren said:

      I just wore the sandals that I had with me on the trip. If I were to do it again, I would wear water shoes, since we swam! We didn’t do any intense hiking, so I didn’t feel the need for tennis shoes. Depends a bit on what you’re planning on doing and where you want to stop! You could also bring options in the car with you 🙂

  2. 8.28.19
    Jordan said:

    Love, love, love Maui! It is on the top of my favorite places ever visted as well. Next time, yes, go to Haleakala National Park. Do a sunrise tour. It is breathtaking! A little cold so dress warm, but definitely breaktaking. We did a sunrise tour with downhill biking afterwards and it was so much fun! So many beautiful views on the way down and we got to stop at a local food truck half way down to get coffee and breakfast. I can still taste it!

  3. 8.28.19
    Angie said:

    My husband and I were actually there the same time as you and actually did the Road to Hana the same day! Small world! We loved swimming near that waterfall, it was amazing! Glad you had a great trip! 🌸

    • 8.29.19
      Lauren said:

      So cool! Hope you had a great trip!