Maui: A Guide I Have Curated Over the Past 23 Years

OK, 23 years might be an exaggeration, but the point is, I have been going to Maui since I was born. It is my family’s favorite destination, so we have been able to experience a lot over the years. This post only scratches the surface, but I share all of my favorite things.


The two main areas people like to stay are either in Kaanapali (north west-ish part of the island) or Wailea (south-ish part of the island) – there are more places including Kapalua, Paia, Lahaina, and Kihei which are also popular for visitors. Personally, I will go to my grave defending Wailea to be the best part of the island, but that is just my own personal preference. Besides, you really can’t go wrong on Maui.

A few tips

  • You will probably want a car unless you plan on staying in your area. Maui has so much to see and ubering everywhere isn’t the best option. Most of the hotels in Wailea have free car shuttles which are great for the area, but if you want to explore any other parts a car is necessary.
  • Book Mama’s Fish House way before you go! I put this here because going here is a MUST.
  • January-March is whale season
  • The Cheapest times to go are from August-October
  • ABC stores are everywhere and great for getting alcohol instead of spending $18-$20 on every cocktail by the pool

Where to stay in Wailea

Fairmont Kea Lani – This place is home to me. I grew up coming to this Fairmont so my opinion is definitly biased. You know when you grow up going somewhere and it’s just special to you? That is this for me. I love the pools here, swim up bar, and beach. The perk to this hotel is that ALL of the rooms are suites which pretty much all of the other hotels have very small rooms for about the same price. For example, my parents, brother, Keegan, and I all stayed in the same room and we fit comfortably.

Andaz – This is where Payton had her wedding and I was able to spend a good amount of time here. The Villas are AMAZING if you have a lot of people and are looking to splurge. The normal rooms are very nice but small. I loved the pools and how tranquil the whole vibe is here. It feels very modern!

Four Seasons – I mean, you can’t go wrong. Their pools and restaurants are my favorite. The whole place feels very private and intimate which I love.

Grand Wailea – Outdated but amazing for kiddos! Their property is HUGE and has the best luau on the island.

Airbnb – A lot of my friends found great Airbnbs! If you are wanting a non-hotel option or something a bit more affordable, be sure to check it out!


Miso Phat – Amazing sushi. They have a couple locations on the island.

The Mill House – The hottest new restaurant on the island. HIGHLY recommend. Ask for a table outside.

Mama’s Fish House – The best restaurant on the island – IMO but a lot of others will agree. You HAVE to go. Make sure to book in advance! If you can’t get a dinner reservation, lunch is great too (same menu).

Monkey Pod – A great causal spot in Wailea

Ferraro’s – Italian at the Four Seasons. The ambiance is romantic and they have live music which I loved.

Duo – Steakhouse at the Four Seasons. Get the lobster bisque.

Down the Hatch – Causal fish spot in Lahaina. Would be fun for watching a sports game too.

Brekkie Bowls – Acai bowl truck. In a weird spot and not the easiest to find, but yummy!

Ka’ana Kitchen – At the Andaz

Fleetwood’s – Rooftop in Lahaina

Paia Fish Market – This was on our list but we didn’t manage to make it this time.

South Maui Fish Co (food truck) – My family LOVED this truck when they went. I didn’t get to go but my brother swears it was amazing (he is an even bigger foodie than me…almost!)

Humuhumunukunukuapua’a – At the Grand Wailea, super fun! It’s like a grass hut over the water.

Botero Lounge – One of our favorite spots to get drinks. It is in the Grand Wailea lobby!

Things to do

Big Beach & Little Beach – One of the most beautiful beaches in the world. Little beach is a nude beach and too much fun not to go. If you are a little skeptical, don’t go on a Sunday.

Kai Kani Sailing – Snorkeling, whale watching (winter), sunset cruise.

Alii Nui Sailing – Snorkeling, whale watching (winter), sunset cruise. Payton and Jack had their rehearsal dinner on here! It was a blast.

Road to Hana – it is not for anyone who gets car sick, but it is a must do on the island. Plan a full day for this!

Lahaina shops and restaurants – walking around Lahaina is always a favorite. Make sure to see the banyan tree!

Paia beach town and shops – cutest little surf town. We always stop here before going to Mama’s Fish House.

North Shore – we always go here to watch the surfers and turtles before or after Mama’s Fish House too!

Maui Ocean Center (Aquarium)– they have an amazing whale exhibit that opened recently that is a must see. I haven’t done it, but next time for sure!

Twin Falls “hike” – you can swim in a waterfall and it really isn’t a “hike,” it is more of a walk

Nakalele Blowhole – heart shaped rock that you see in all the pictures

Haleakalā National Park – Take a helicopter tour, it is incredible

Processed with VSCO with a4 preset
Processed with VSCO with a4 preset




Leave a Reply

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.