Maui Top Ten Guide

As I sat on the plane to Maui, they handed me the customs form to fill out. When asked to check the box of how many times I’ve visited Hawaii, I was so excited to check the highest option of 10 or more. It’s truly magical there and one of my favorite places in the world. I'm fortunate enough to have visited all of the six major Hawaiian islands. My parents absolutely fell in love with it when I was young, so we would spend a week or two there most years. Ultimately we favored Maui and kept going back. My favorite area to stay on the island is Wailea, which is more of the South-Western side of the island.

This list is a compilation of my favorites from visiting over the years. I can honestly say that this past trip was the most adventurous Maui trip I’ve ever had and by far the best trip to Hawaii as well.

Top 10…In No Particular Order

1. Road to Hana

This section could honestly have it’s own top 10 list! I braved the Road to Hana when I was young and remember hating it. Because let’s be real, it’s a super windy road, I got carsick easily, I wanted to play in the pool and mostly hang out with my new-found friends at the condos we stayed.

Now in my mid-30’s, you could say I have a different appreciation for this windy road and all it has to offer. There are so many spots to pull over and take photos. I was super lucky to have Richie along side of me (obvi…but stick with me). Richie is an incredible drone pilot which means we had access to areas off the beaten path that most people cannot either get to or take photos of. You’ll find tons of waterfalls along the Road to Hana. There are the traditional Twin Falls & the Seven Sacred Pools, but I recommend exploring the pools that are off the beaten path.

2. Highway 340

BEWARE: This is listed as the most deadly road on Maui, and there is a reason for it. Many rental car companies will make you sign an agreement that states you will not drive on this road. Just keep an eye out for that before jumping on this activity. We’re talking one lane roads with absolutely no room to pass and dramatic cliff sides on the other side. It’s not for the nervous passengers, I’ll say that much. But geeeeez is it worth it or what?! Some of the areas we found were so beautiful and felt so untouched.

3. Lava Fields - Makena

This place feels like a movie set. It’s so wild to see lava rock all the way down the volcano and out to the ocean. I recommend checking out the book The Lonely Planet Maui Guide. It has a few notes about following a path of white rocks which is separate from the normal path. Regardless, if you make it to the light house, you’re in for a beautiful photo. DON’T FORGET TO BRING WATER and wear protective shoes. The lava rocks can get pretty sharp so you’ll want to watch your step which can be hard to do with the views around you.

4. The Path

“The Path” is my favorite walk on Maui. Not necessarily for any reason outside of it just being sentimental from childhood. I remember walking down the path with my parents in the mornings (back then it was wayyyyy less busy than it is now). The path is a narrow walkway that starts at Polo Beach in Wailea and goes all the way down past the Andaz. It’s definitely a LOT busier now than it used to be, but still makes for a great morning walk or jog, just be prepared to dodge some peeps.

5. Sunset Time

Find a spot, grab a drink and watch the sun go down. Sunsets in Colorado are pretty incredible, but there’s something special about watching the sun set off the shores of Maui. I recommend taking a seat on the beach, because why wouldn’t you want your toes in the sand to watch the sunset?

6. Lahaina/Kaanapali

This is definitely a tourist area but a must see when you’re on the island. Most people stay on the Kaanapali side, there are a ton of resorts, shops and restaurants there. Lahaina is the next town over and has a really cool walking area (Front Street) with tons of shops right next to the water. There’s a massive Banyan tree there as well which is a fun spot to take photos and walk around. Our favorite coffee spot was tucked away off of Front Street. They had cereal creamer to go with the coffee….just trust me, check it out. It’s called VigiLatte Artisian Coffee, oh and bring your wallet, you’re gonna need it. Expensive, but worth it.

7. Rent a Boat

Look, not everyone is going to have a Captain Dick available at their boating leisure…lucky for me, my handsome man has his Captain’s license from being a badass in the Coast Guard. The boat day was top of list for activities. We had such an incredible time out on the ocean, but I think that was due to the ease and trust of being with Richie out there. We used Maui Boating which is pretty much the only boat rental option on the Wailea side of the island. They were super easy to work with and had everything ready to go for us upon arrival. There was a pretty big oil leak upon our arrival back so just make sure you’re checking over the boat when you arrive and keep an eye on it when you’re out on the water.

8. The Dumps

Unexpected, incredible, and one of the most memorable experiences from the trip. There was a tropical storm that was off the coast of Hawaii named Darby. It fizzled out prior to making it to the islands, but the waves that came from it were unreal. The National Weather Service stated it as a “historic swell”. Locals said it was the biggest waves the island had seen in 15 years. We ended up at the Dumps and Richie took the most incredible photos there of the waves and surfers. The Dumps are just before the lava fields in Makena. Not sure what it’s like when there aren’t massive waves but still a cool place to hike around and check out.

9. Paia

I love the vibes in Paia. It’s basically Boulder 30 years ago on the beach. It’s a hippie style beach town with the cutest little shops. We found a coffee shop, Paia Bay Coffee, that was hidden away from the main walking area and looked like it’d be fabulous at night if you’re sticking around the area. It’s definitely worth it to walk around Paia for a half day trip….and you better check out Mama’s Fish House while you’re in the area too. Food Recs on Maui coming soon.

10. Shopping

Maybe shopping isn’t your thing on vacation, but it is definitely a highlight for me, always. If you’re staying in the Wailea area, the Shops at Wailea are the go-to spot. They have a good variety of shops as well as price ranges. I love the surf shops like Honolua Surf Co. and Quicksilver but they also have the Gucci and Louis Vuitton storefronts if you’re a baller. The woman who sat next to me on the plane ride back to the mainland told me that the Louis Vuitton stores are much cheaper in Hawaii than they are on the Mainland. I cannot confirm that, but if it’s your thing, it may be worth checking out. There are also a few cute boutiques up the street from the Shops at Wailea. They’re in the same parking lot as Manolli’s (one of my go-to restaurants there….see below.)

As mentioned above Lahaina and Kaanapali have great shopping as well. More of the tourist type of shops available there but a few really cute boutiques sprinkled in. My favorite spot is a little hidden shop on the main walking street in Lahaina. It’s called Pakaloha Bikinis (they have the best selection and they’re all mix and match style).

You may notice that I left off a VERY crucial aspect of vacation…the FOOD!!! I started the food as one of my top ten’s above and quickly realized that it needed it’s own post! Check back to read my Top Ten Food Spots on Maui.

If you’re interested in purchasing any of the incredible prints from 998 Millibar check out his website! You can order directly from there, and may I suggest a metal print?? They’re incredible. Mahalo!!