Maui Must Do’s

by | Nov 2, 2018 | travel | 0 comments

I first visited Maui back when I was thirteen with my family. It was one of those trips that my parents saved air miles and a lot of money for so that we could have a memorable trip together. And memorable it was. I still remember the first smell of ocean air and palm trees that greeted me when we got off the plane. I was so excited to be in Hawaii – Hawaii!!

I loved the island so much in fact that I told my husband, Adam, we had to go for part of our honeymoon. It was on the way to New Zealand after all (where we were spending the majority of our honeymoon). Adam had never been, but we only had four days in Maui, so I knew I had to be strategic about what we did while we there. Because our New Zealand trip was going to be more of the ‘adventure’ part of our trip, Adam explained he wanted to do more relaxing while on the island of Maui. Nooo problem! We did just that.

Beers on Kaanapali Beach in Maui

We didn’t get to do everything I had hoped to do together, but lucky for me, I had already done most of them the first time around 🙂 Based on my last two trips, I’ve compiled a list of Maui must-do’s – things I highly recommend doing if you’re planning a trip there. You won’t be disappointed! Aloha!

Maui Must Do's Pinterest Pin

Rent a Convertible

MUST. DO. There’s nothing better than having the top down and having the Maui breeze run through your hair. You just feel so free. Beware though that everyone has this idea so it can sometimes be a mad dash or a wait for the convertible you want. We arrived mid-afternoon when a lot of other planes had landed, so we unfortunately had to wait in a line for the convertibles specifically and I may or may not have fought a guy for this red beauty. But isn’t she pretty!? We had so much fun driving this baby all around the island.

Red convertible patiently waiting for someone to drive it in its parking spot.

See Haleakala at Sunrise

If you didn’t already know, Haleakala is a dormant volcano that makes up most of the east side of the island. It’s known for it’s gorgeous sunrises and has many tours that go up each morning. I recommend doing the Halekala Crater at sunrise either the second or third morning you are there. If flying from the States, you will still be adjusting to island time and waking up at 2am actually won’t be too bad (note: that was 7am Chicago time for us).

You have options to get there too. You can book with a company like Bike Maui to pick you up and drive you so that after the sunrise, you can ride a bike down the volcano. We chose instead to drive ourselves so we could be on our own time schedule and because biking down a volcano didn’t immediately thrill me. If you go the route of driving yourself, you’ll need to make a reservation (as of February 1, 2017) ahead of time at The fee is only $1.00, but it is nonrefundable. To be safe, we made reservations for two days and monitored the weather to ensure we’d have a clear sunrise! Keep in mind there’s also a $25 fee to enter the Haleakala National Park once you arrive (credit cards preferred). If you do decide to drive yourself, just be prepared to drive in the pitch black for about two hours and go up a lot of switchbacks up the volcano. I promise you though – it’s worth it. Check out those views!

Kelly and Adam stand at the top of Haleakala. Pro Tip: Dress warm! It gets very cold up top![/caption]

Kelly and Adam smile with the amazing views behind them.

Adam & I above the clouds at Haleakala Crater in Maui, HI.

Explore Kaanapali Beach

Kaanapali Beach is Maui’s most pristine beach as is stretches over three miles and was once known as America’s Best Beach. Many hotels and condo buildings line the coastline, but there’s still plenty of beach to kick back and relax. You can choose to rent lawn chairs and umbrellas to lay out and tan, get your snorkel gear on and take a look at Maui’s beautiful fish, or get a massage oceanside. We opted with all three and did not regret it. You’ll also get views of Lanai and Molokai off in the distance!

Kelly stands under a small palm tree.

We loved walking Kaanapali Beach in the mornings!

The view from Aston Mahana Condos.

The view from our condo, the Aston Mahana. How much closer can you get?!

Drive the Road to Hana

I did this with my family the first go around. Adam and I didn’t have time to do this on our honeymoon, but I still couldn’t recommend it enough. I’d argue this is Maui’s most famous thing to do on the island. If you plan to do it, definitely get up early and go. There will be loads of tourists doing the same thing and the road to Hana can get very clogged with traffic.

The road to Hana is just that – a road to a town called Hana. Along the way, you’ll drive past waterfalls, ocean lookouts, black sand beaches, and national parks. The drive is truly what makes the trip magical. But you also have to be on high alert as there are many one way bridges and blind turns. (Fun fact: the road to Hana is the 5th most dangerous road in the world.) The road ends in Hana, where you can get some homemade banana bread and some other delicious snacks for the remainder of your trip. You then have the option to turn back around and go the way you came, or if you’re brave, you can keep going around the other side of the island.

Note: I recommend turning back around. My family decided to keep going and needless to say, this part of the island was much more rugged and less traveled. There were times we were driving on the sides of cliffs, with no rails or anything. It was terrifying and something my dad has said was one of the scariest things he’s ever done in his life.

Experience Ocean Life

What I mean by this is – snorkel or scuba dive! Back in 2002, my family and I went on an excursion that took us to Molokini, a moon-shaped island just off the coast of Maui. It’s where you can find many turtles, fish, and other ocean creatures. Although, it was on that trip though that I realized I hate the taste of salt water 🙂 Nevertheless, it was amazing to see all the different types of wildlife in the ocean.

Adam and I didn’t do an excursion on our honeymoon, but we opted to snorkel at Kapalua Beach, which is known for its snorkeling. It’s a great alternative if you want to save some cash. There was a ton of coral right off the beach (note: wear water shoes – Adam and I both got slightly cut!) and Adam even got to swim right next to a turtle! To be honest, snorkeling is not one of my favorite things to do as I get pretty claustrophobic, but I’m still glad I did it!

Eat at Mama’s Fish House

Mama’s Fish House is quite possibly the most popular restaurant on the island. I had heard about it for years and knew it was a place Adam and I wanted to visit on our honeymoon. If you plan to go, I recommend making a reservation far in advance (preferably before sunset) and head there an hour before your reservation. Mama’s sits on the north side of the island and has beautiful views you can take in before dinner.

Kelly and Adam stand on the beautiful grounds of Mama's Fish House.

The meal will definitely cost you a pretty penny, but I thought it was worth every bite. Adam went with the mahi mahi and I with the opah. Highly recommend the mahi mahi and macadamia nut crab cakes. I’m not a huge seafood eater, but those two parts of the meal were absolutely spectacular.

Mama's Fish House dinner.

The opah fish entree!

We also indulged in dessert and recommend the Maui Banana Macadamia Nut Crisp and the Kaua Chocolate Pie! YUM!

Mama's Fish House Dessert

How can you go wrong with dessert like this!?

Check Out Lahaina’s Front Street

If you’re looking for some casual shopping, searching for souvenirs, or simply want to go for a walk and explore, then look no further than Front Street in the town of Lahaina. It offers souvenir shops, art galleries, restaurants, and great views. I particularly liked going here about an hour and a half or so before sunset. This allowed me to check out some shops, stop by the Banyan tree (a tree with over 16 trunks and a canopy that stretches all over a beautiful park!), and walk along the waterfront before dinner.

Adam stands under the Banyan Tree in Lahaina.

There are plenty of options for dinner while you are there such as Lahaina Grill, Lahaina Fish Co, Fleetwood’s on Front Street, and my favorite, Kimo’s. If you head to Kimo’s, make sure to ask to sit upstairs, where you’ll get a view of the sunset!

Go to a Luau

You haven’t experienced Maui until you experience a luau. Growing up, I was infatuated with hula girls and even was one for Halloween one year. Going to an actual luau and seeing the hula girls dancing when I went with my family was so much fun. My sister and I even got to go on stage and dance with the younger hula girls! There are a bunch of luaus all over the island at various hotels. If you are staying at a particular hotel, you’ll likely head to the one that’s on our hotel grounds, if they offer one. However, if you’re staying in a condo, I recommend going to the Old Lahaina Luau, as it’s rated the top luau on the island. Keep in mind luaus are on the pricey side, but when else are you really going to go to a luau? Do it at least once! The pig roast, the tropical drinks, the history, the music and dancing make it all worth it. 

Pink lipstick stain


Welcome to Lipstick & Ink®, your home for everything career and wellness inspired. I’m Kelly, a Chicago-based career coach, writer, speaker, and events host.

Whether we’re working together on your career aspirations, refreshing your professional documents, or keeping your mental health in check, I encourage you to own your power and make your mark.




Submit a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.