Maui: What I Wore

I’ve partnered with the makeup company called Seint for 8 years and have earned almost all of their incentive trips. This year, I earned a trip to Maui! They paid for my hotel and food and we got free plane tickets from our credit cards points. My husband and I spent 5 days on the Hawaiian island and had the best time! I’m sharing what I wore, ate, and did during our time in paradise. Hopefully it will be helpful for you as you plan your trip…



Where I Stayed

We stayed at the Regency Hyatt in Kaanapali. Our room had an ocean view and it was gorgeous! The pools and gardens on the property were so beautiful. We rented a car for two days and were able to explore more of the island and eat more variety that way. On the days we didn’t rent a car, we either walked to where we needed to go or used an Uber or Lyft.

The hotel had fun wildlife: penguins, swans, ducks, and geese. You felt like you were living in a tropical oasis!

There’s a nice walking path along the beach that you can take to other hotels and to Whaler’s Village. We really enjoyed the Napili area and will probably stay there the next time we go. But the Regency Hyatt was really nice!


Maui Travel Guide

Maui Travel Guide

What I Wore

I always travel with just a carryon suitcase and a personal bag so I have to be strategic in what I pack! I spend time well before I go to plan out what I’ll be wearing while I travel. I look at the weather, consider the activities we’ll be doing, and determine how I want to look and feel. This helps me pack intentionally.

Since this was a tropical vacay, I knew I would be spending most of my time in my swimsuit. So, let’s start there… Here’s what I wore on the beach!


Maui: What I Wore

SWIMSUIT | SUNGLASSES


Maui: What I Wore

SWIMSUIT | SUNGLASSES


Maui: What I Wore

SWIMSUIT | SUNGLASSES | SANDALS


Maui: What I Wore

SWIMSUIT | SUNGLASSES | SANDALS


Maui: What I Wore

SWIMSUIT | SUNGLASSES | COVERUP


In the evening, we cleaned up and went out to dinner. Here’s what I wore:


Maui: What I Wore

DRESS | SUNGLASSES



CULOTTES | TEE | SANDALS | BAG | SUNGLASSES


Maui: What I Wore

SKIRT | TEE | PURSE


Maui: What I Wore

DRESS | SANDALS | PURSE


What I Ate

For us, food is one of the best parts of traveling!! We put a lot of thought and research into what we eat. I had a lot of friends, family, and followers recommend some great places to eat and we also found some great places on our own through Google Maps. We never eat anywhere that’s not rated a 4 or higher. We shoot for 4.3 or higher to guarantee a yummy meal!

Here were our favorite places we ate:

  • Merriman’s- This place is pricey but SO WORTH IT! Plan ahead and get a reservation. Dinner and dessert for two was about $200, but it was the best food of my life. We had the macadamia nut crusted mahi mahi for dinner. For dessert, we got the banana bread pudding topped with macadamia nuts, caramel, and vanilla ice cream and the chocolate purse. If you love chocolate, you HAVE GOT TO GET THIS! It was the most decadent chocolate treat I have ever had. It was divine! My mouth is watering just thinking about this meal!!
  • Monkeypod Kitchen- This is in Whaler’s Village, surrounded by fun places to shop. We got the Kalua pork and pineapple pizza and it was delicious!! Even people that don’t believe pineapple belongs on pizza will love this meal!
  • Island Vibes Cafe- This was a find from Google Maps and it was so good! We got a breakfast burrito, the Hawaiian panini, and an acai bowl. So yummy and fresh! And we loved that there was no long wait. Win win!
  • Joey’s Kitchen- This was another Google Maps find. People loved this place so we thought we would too…and we did! We got our orders to go and ate it on the Napili Bay at sunset. It was heavenly!
  • The Gazebo- My brother recommended this place to me and said if we wanted to avoid waiting in line, then we should go about an hour before closing. We did not heed his advice and had to wait an hour in line. But, the wait was worth it! We got an omelet and the macadamia nut white chocolate chip pancakes with coconut syrup and it was soooo good! The pancakes were more like a dessert so the omelet helped balance out the sweetness.
  • Ono Tacos Hawaii- This was a simple food truck in a parking lot but the tacos were fresh and yummy!
  • Ono Teppanyaki & Seafood- On our way back to the airport we wanted one last good bite to eat. We found this food truck place that was highly rated and it was amazing! We got the garlic shrimp and lobster and the ginger soy sauce to dip it in was out of this world!
  • Hula Scoops Ice Cream- You can’t go to Maui without having shaved ice! And it’s even better with ice cream. This place was walking distance from our hotel and it was a yummy sweet treat.

Maui: What I Ate

Maui: What I Ate

What I Did

We wanted this trip to be relaxing but also enjoy exploring the island a little. Here are a few highlights that are worth going back for:

  • Snorkeling- We packed our masks and snorkel but rented fins from our hotel (the Regency Hyatt). But Snorkel Bobs is also a great place to rent gear. We snorkeled right along our hotel beach and swam with a massive turtle. But the next day, we went to Honokeana Bay and were blown away by all the turtles!! We probably saw 20 turtles as we snorkeled that bay! My husband went snorkeling around Black Rock Beach and saw a monk seal! The coral isn’t vibrant, but you will definitely see lots of sea life along any beach you snorkel. We could also hear whales calling to each other under the water. It was super cool!
  • Napili Bay Beach Trail- We took this trail often from restaurants to beaches. It’s a great place for pictures and the tide pools are cool to look at around low tide.
  • Nakalele Blowhole- We drove on the 340 along the coast and stopped at this blowhole. You can take a short walk to watch the blowhole from a distance or you can walk all the way down to the water to be close. Either way, it’s a cool site to see! But back to the 340…only drive this if you are comfortable with windy and narrow roads. Many times it goes down to one lane, with cliff on one side. It’s quite the journey!
  • Haleakala- We went here for sunset and it was AMAZING! It was raining the entire way up and we almost turned around but decided to keep going. And we’re so glad we did! As soon as we parked at the Kalahaku Overlook (this place is less crowded than the summit), the clouds parted and the rain stopped. We felt like we were on top of the world! But be warned…it is FREEZING up there. Literally. It’s so cold and windy, you’ll definitely want to bundle up. Like, wear more clothes than you think you’ll need.

Maui What I Did


Maui Travel Guide

What I Packed

I don’t go anywhere without my favorite makeup to travel with and my trusty skincare! Seint makeup is TSA approved so you can carry it on with you without any spills and messes and without worrying about it getting lost in your checked bag!

Everything (minus mascara) fits into your palette! I love how simple, compact, and versatile it is! Take the makeup shade matching quiz to find your right shades!


Best Makeup for Traveling


When you travel, you want to invest in good traveling bags! It matters! I recently replaced my carryon suitcase with a new one and I’m in love!! It held a ton and moved so smoothly. And the bag that I use for my personal item was like a Mary Poppins bag!! Quince has great options for suitcases and bags for traveling!


Best Suitcase for Traveling

SUITCASE | BAG



And my go-to brand for purses is Sapahn! There are so many sizes, shapes, and colors to choose from! They make the perfect travel accessory! You can save 20% on any Sapahn bag with this discount code: JOELLEN20

Check out these perfect bags for traveling!


Best Purses for Traveling


And I always pack my Mixhers supplements to help my menstrual cycle stay regular (HerTime) and to get more greens in (Greens)…because we know that doesn’t happen much when you travel!

Save 15% with this code: JoEllenW15

Learn more about Mixhers!




I hope this was helpful for you as you plan your trip to Maui! We had a great time. We took lots of notes for when we take our kids back with us next time.

If you need other travel style inspo, then check out these other style posts from where I’ve traveled:


Skincare Quiz

Shop Here!

Here are other blogposts that you might enjoy:


Maui: What I Wore

About the Author

JoEllen is a licensed aesthetician, certified makeup artist, and certified John Maxwell coach, speaker, and trainer. She works with women helping them look and feel confident. She loves teaching women simple beauty techniques so they can feel empowered to try it at home. Her motto is that when you look and feel good, you do good!


Maui Travel Guide

*This post contains affiliate links. If you choose to purchase an item featured in this post, I get a small portion from the sale. Thank you! It does not affect you at all.

Newsletter