This guide feels like it’s long overdue but my trip to Hawaii was just a few months back in late May of 2021. I got engaged in Maui, Hawaii so it’ll always hold a special place in my heart and the trip really did surprise me. I would highly recommend visiting Maui and if it’s not on your list I’d add it on there now. This guide will give you all of my Maui recommendations as well as some insight into the history and my perspective plus a few Black Owned Businesses too.

I’m excited to share more about my trip to Hawaii and to share more about all of the things I learned. Over the past few years I’ve honestly been a little hesitant about heading to Hawaii because I thought that it would be tough to really delve into the local culture. I’m the type of traveler that can appreciate popular tourist attractions but craves more and Hawaii always seemed to have so much culture to explore. When I got the opportunity to volunteer on my trip and work directly with the Go Hawaii CVB team it made me really excited about the opportunity to be able to delve deeper and to give back. If you’ve visiting Hawaii I’d highly encourage you to check out the volunteer opportunities available. We loved our experience with the Lahaina Restoration Foundation and learned a ton. I’m all about impact so I was really appreciative of the opportunity to give back by restoring and categorizing artifacts with the Lahaina Restoration team.

I know that Hawaii has been a popular destination throughout the pandemic because it is within the United States so you don’t need a passport as a US citizen however there are some pretty strict COVID travel guidelines you’ll want to be mindful of. I’d recommend checking the Hawaii tourism website as well as CDC guidelines to ensure you’re up to date on everything before your trip. We flew United and as always it was a pleasure, the teams were super organized as they handled testing requirements. You can actually get a COVID test in the mail should you need one through a United Airlines and Hawaii tourism approved partner listed on their website. We used ADL Health and it was seamless, took the test on zoom, mailed it back and got the results within about 24-48 hours! So you have your test set up, your flights booked and now you’re headed to Maui…let’s get into all the amazing things to do once you get there.

Where to Stay

Hotel Wailea: Located in Wailea tucked away atop a hill with beautiful views and an amazing staff. I’d go back again in a heartbeat. While the hotel wasn’t directly on the beach there were quite a few nearby and I loved the on-site garden paths plus the beautiful pool. This is a splurge that I’d say is totally worth it, it’s lowkey in the most luxurious way. 

Montage Kapula Bay: This hotel is in Kapula Bay which is fairly close to Lahaina so on the opposite side of the island from Wailea. This hotel was on my list and is a great beachside option. It’s also a splurge but a family friendly property with a lot to offer!

Lumeria Maui: This is a unique hotel that’s on the north side of Maui in Upcountry. Lumeria Maui is an educational retreat center that, according to their website, seeks guests interested in experiential learning, personal growth and well-being in a peaceful setting that honors the natural beauty of Upcountry Maui.

The Best Western Pioneer Inn or Plantation Inn: Both of these are smaller B&B’s located in the historic LaHaina area. I stayed at the Plantation Inn and it was really cute, calm and the restaurant attached was conveniently located right downstairs. I loved that it was historic and the balconies that each room has are great. This was also a great budget friendly option.

There are some great Airbnb properties as well and we kicked off our trip staying in Kihei in an airbnb which was super centrally located. You can find great affordable condos for rent here and a lot of them are beach side which is great. If you’re looking to splurge or have a bigger group there are some amazing Airbnb Luxe options too.

A little note on the Plantation hotel name because it was something that made me feel a little uneasy as I thought about it. At first I was a little put off by the word plantation but as a part of our volunteer experience we explored what that actually meant in Hawaii. I thought slaves but that wasn’t quite the case. While the conditions and pay weren’t great, workers from nearby countries in Asia were paid for their service on the sugar plantations. The word plantation was just the best English word that could be used to describe it at a time when the native language was much different.

What to Eat

Overall I’d encourage you to make reservations in advance for dinner to avoid long wait times. A pro-tip from a friend before I arrived was actually that the best poke on the island would be found at the Foodland Grocery store. She was right, it didn’t disappoint. 

808 Deli: This locally owned spot was perfect after a morning beach adventure.The Pasta Salad was PHENOMENAL, we had it twice and the sandwiches were great as well.

Maui Coffee Attic: The thai iced tea gave me life and the pesto chicken quesadilla was bomb.

Tiffany’s Bar & Grill: This is a lowkey bar near the airport that actually had surprisingly good food plus a solid happy hour. 

Maui Brewing Company: Great food options plus outdoor seating. The local beers & hard seltzers were dope. In Lahaina we were able to enjoy a beer/seltzer while waiting for our table which was nice. There are a couple locations as well so you are likely to find one near where you’re staying. They also do tours as well.

Mama’s Fish House: We barely got in without a reservation but ate at the bar before our flight and it was honestly some of the best fish I had during the trip. They were so good about allergies too which always makes me happy.

Duke’s Beach House: We went for dinner and they had great drinks as well. Make a reservation or you’ll be waiting forever and get the fries (so good).

Gerard’s Restaurant (in Plantation Inn): Great French food but beware you cannot make substitutions so if you’ve got allergies or preferences look at the menu in advance. I enjoyed the items we got but wish I’d looked at the menu a little more in advance. 

Paia Fish Market: Great for lunch. They’ve also got multiple locations but can get super busy so try to go at an off peak time or before you’re really ready for food.

Star Noodle: Located in Lahaina, the food is known to be great and they’ve got some really amazing options.

Wailea Kitchen: Great selection of food options and also amazing drinks. Great selection of vegan, vegetarian and overall local options.

Black Owned Businesses

Farmacy Health Bar: A great place to go for breakfast or a snack. Their menu features delicious vegetarian options in the Wailuku town area.

Kihei Caffe: This is known to be the best breakfast in Maui, a really solid option loved by many. 

Sale Pepe Pizzeria e Cucina: Milan and Brooklyn come together in a beautiful way here to create an awesome Italian inspired restaurant.

Hikes

Waihe’e Ridge Trail: We definitely started with the hardest hike but the views were so worth it. These stunning views aren’t even at the peak! It took about 2 hours to do 4 miles (+2miles to the overflow parking) but we didn’t stop much. Go early (like 7am) to get a spot in the smaller parking lot at the trailhead. Stopped for Thai Iced Coffee at @mauicoffeeattic after we finished and it was so good!

Pipiwai Trail for Waimoku Falls: This is at the end of the Road to Hana which I will talk about in it’s own post. We started early so we made it! This is also a 4 mile hike and it’s a bit less challenging than the above but still not easy. The waterfall at the end and bamboo along the way make it such a great trail to really take in and enjoy.

Pools of ‘Ohe’o (aka Seven Sacred Pools): This is a shorter loop available at the Haleakala National Park and shares a parking area/entrance as the Pipiwai trail. It was only about a mile loop total but had some really great ocean views.

Haleakalā National Park: If you get the park entrance for the above two trails at the base of the you may as well get the most out of that $30 entry fee. Sunrise is prime time for the summit trails but they are all honestly beautiful any time of day. They are strenuous due to elevation but Pā Ka‘oao is a great shorter option. I’d recommend bringing heavier clothing because it’s much colder up at the top.

`Īao Valley State Monument: This isn’t really a hike persay, it’s more of a walk and took us 10-15 mins tops. Great views and really beautiful streams flowing past that you can swim in! There is a small entry fee of $5/per person but it was great to see because of all the history in the area.

Kapalua Coastal Trail: This trail came recommended but we didn’t have a chance to do it while we were nearby on that side of the island; however it’s a scenic short option.

Things To Do

Ocean Vodka Distillery Tour: We happened to drive by while exploring Up Country and had a great time. Learned so much about the business and the spirits were great. 

Ali’i Kula Lavender: Loved our visit to Ali’i Kula Lavender farm as a relaxing way to kick off the day. Beautiful for a picnic or just to walk around. 

Snorkeling Experience with Adam: We loved going out with Adam near Makena Beach. We were able to see great fish and he had all our gear prepped and ready. It was fun to have photos of the experience as well. 

Road to Hana: I wanted to do this but was on the fence at first because there’s one way in and one way out with one hospital in the Hana area. We were super safe in terms of wearing masks inside but I’m always cognizant of my local impact which I’d never want to be negative. Glad we did it and really glad I paid for @gypsyguides because it helped a ton!

Big Stops to Make:

1. Hamoa Beach
2. Ho’okipa Beach
3. Ke’anae Arboretum
4. Ke’anae Peninsula
5. Lava Tube & Heiau
6. Pipiwai Trail
7. Rainbow Eucalyptus (seen roadside or at the arboretum)
8. Twin Falls
9. Wailua Falls
10. Wai’anapanapa Black Sand Beach (advance reservations required, booking opens up 14 days in advance)

Pro Tips:

• The start of the road is near the airport so if you’re staying in Wailea or Lahaina you’ll have to calculate some extra time when planning your route.
• Make your reservations for the black sand beach early because tickets sell out and you’ll get turned away if you don’t have one. We did the 7am-10am slot and it was early but we saw very few people. We left Hotel Wailea at 530am and made minimal stops before the beach.
• ️Don’t cross peoples private property to try to see something you saw online. You’d be pissed if someone random walked into your front yard, it’s the same thing. There’s more than enough to see that’s accessible.
• Bring cash and snacks. There are some places open on the road but the more stops you’re trying to make the less time you’ll probably want to spend waiting for food.
• ️Drive carefully, the route is no joke and the later in the day it gets the more people are going back and forth.
• You can do the full route in one day but you’ve got to prioritize and know you won’t see every single thing. We loved Gypsy Guides because it helped us decide where to stop and we loved the history info we got on the way back. Best $6.99 I ever spent! Also super helpful because we had no service most of the route and this worked on GPS alone.
• ️Haleakalā State Park has a $30 entry fee so definitely maximize! Wish we’d gotten to the top but if you do the summit first, keep your ticket info.

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A Few Things I Learned

Learning more about the history was an important part of this trip for me and there’s so much more than I can fit in a short blog post but here are a few things I learned during my time. A lot of this learning came from my volunteer experience with the Lahaina Restoration Foundation.

• ️Lahaina was the capital of the Kingdom of Hawaii from 1820 to 1845 before the capital was moved back to Honolulu.
• Hawaii has been known to focus on one major crop at a time (learned the word monocrop). After tending to whaling ships slowed down, sugar was the next big thing and now tourism has become a big focus for the islands.
• ️Hawaii’s last sugar mill in Pu’uene, Maui did their last run in 2016 closing a 175 year chapter in Hawaii history.
• The word “plantation” was an attempt to find an English word to describe the system used to manage sugar production. The workers were paid although the principles were similar in some ways. It was great to hear that there’s recent talk of shifting the terminology to ensure that slavery as we knew it in the American South isn’t minimized.