The Ultimate Maui Hawaii Vacation Adventure

A prelude from the author

Aloha, I’m Austin Distel – tech entrepreneur and adventure seeker. When I’m not growing our startup Jarvis in Austin, Texas, I’m exploring the natural beauty around the world. My trip to Maui in September 2021 was one of my favorite experiences thus far. In this guide, you’ll discover everything you need to know to plan the ultimate adventure vacation to Maui, Hawaii. I’ll be very transparent with you, sharing exactly how I booked my round trip flight for just $320 to my top 7 favorite excursions you must experience while on the island. For a behind-the-scenes look into startup life and travel hacking, follow my journey on Instagram @austindistel.

Austin Distel
Written in a window seat above the Pacific Ocean
Tuesday, September 21, 2021

The Backstory of Maui

Legends have it that the demigod named Māui was fishing in the ocean with his brothers and caught the islands of Hawaii on his magic hook. To please his mother with more time in the day, myths tell the tale of Māui weaving a long lasso out of coconut fibers, snared the sun, and made it slow down for longer daylight. These stories have been passed down for centuries in Hawaiian folklore, some of which you may hear along your trip to Maui, Hawaii!

Best time of year to visit Maui, Hawaii is Early & Late Summer

The best time of year to visit Maui, Hawaii, is between April-May and September through November. The late spring and early fall will give you pleasant weather to enjoy in Hawaii without the high costs and big crowds that come with the summer and winter months. I went in September and had an amazing experience, with daytime temperatures averaging in the mid-70s and low 80s with very little rain.

If you decide to go to Maui to watch the whales’ migration in the winter, come prepared with a rain jacket. During the winter months of December through April, Maui County's leeward waters are home to the world's greatest humpback whale population. Every year, over 10,000 humpbacks migrate to Maui’s warm, shallow seas and create thunderous splashes and aerial displays not seen in other species of whales.

Watch whales in the winter in Maui, Hawaii

How I booked a cheap flight to Maui

What if a round trip flight to Maui for you and your partner could be found for less than $1,000? It’s true – our total cost from ATX to OGG was just $320 RT per person! Plus, this was in September, a perfect time of year to go! How did we find such a great deal? We’re members of a traveler insider’s email called Scott's Cheap Flights. For just $49/yr, Scott and his team will let you know when amazing deals like this popup. Other flights I’ve booked by being a member include $180 to Puerto Rico, $420 to London, and $240 to Costa Rica!

Once I saw the SCF deal, I looked to see if Southwest was running a similar deal since they aren’t an airline that Scott emails cheap flights on… and sure enough, they did! Why did I look to see if Southwest Airlines was running a deal too? So I could use my Chase Sapphire points. Chase points can be turned into Southwest Rapid Rewards with a 1:1 point transfer. So I ended up buying my flight to Maui with just 17,000 points! Since my girlfriend Paige didn’t have points yet, she bought her flight in dollars for $320.

Where to Stay in Maui

The Hawaiian island of Maui isn’t that big. The airport is on the North coast, just a 45-minute drive to the west coast of Lahaina. Here is where most of the resorts and hotels are, with the most beautiful beaches and tasty restaurants. If you’re looking for a more small-town local experience, look into getting an Airbnb in Paia – a cute beach town towards the Road to Hana.

My friend Eddie Coleman lives on the island and gave us all kinds of great recommends which I’m passing along to you in this article. It was essential for me that the location I chose was good for an entrepreneurial retreat where many people could find spots nearby, so the resort area in Lahaina was best for me. We went to Honua Kai Resort & Spa, which we loved! We paid $3,320 for 7 days ($475/night), which I think was a fair price for a Maui resort. But you can get a private Airbnb condo for as low as $300/night.

Wailea Beach Resort Marriott, Maui

Should you rent a car in Maui? Absolutely yes – and make it a Jeep.

If you plan on just staying at your hotel’s beach for 7 days straight, then don’t get a car. The price of an Uber from the airport to Lahaina is ~$75 each way. But if you want to explore the island and do all kinds of excursions (see my Top 7 Maui excursions below), then you’ll want a car for sure. And not just any car – get a Jeep or convertible! Drive around the island with the top down, smelling the salty air, and while getting a tan.

A quick search on Kayak will give you the best prices. I went with to rent a white Jeep Wrangler 4 door for 7 days, costing just $403.95. It was totally worth it since many excursions were scattered around the island. Out of all the places I’ve rented cars around the world, Maui had the easiest check-in and return process by far! No hassling or negotiations – just here’s the price, keys, and you’re on your way. Return was as simple as parking the vehicle in a spot and leaving the keys on the dash. I usually dread dealing with car rental companies, but this time was a breeze. Mahalo!

Road trip around Maui in a Jeep Wrangler
Pro Tip: Do you have a travel credit card like Chase Sapphire? Then one of your included cardmember benefits is Collision Damage Waiver for car rental insurance. Usually, this is a fee you have to pay when renting a car that costs ~$12-20/day, so by being a cardmember, you can decline the car rental insurance and save that money! Most car rentals require written proof from your bank that they will cover your insurance, so request a Member Benefits Letter. Learn how to waive car rental insurance with your credit card benefits.

Best places to eat in Maui

Be prepared to enjoy the freshest Ahi Tuna and fruit bowls in the world in Maui! Below are our favorite spots on the island ranked in different categories. Just

Upscale dining

Try to book a reservation at these places on OpenTable for arriving.

Beach bars

Vegan cafes & food trucks

Top 7 most fun excursions to do in Maui, Hawaii

I didn’t cross the Pacific just to sit on a beach! I wanted to adventure, see wildlife, and get outside my routine to the edge of my comfort zone. Travel to me is all about sharing incredible experiences with my partner, friends, and family. So what if I spend $1,000 on adventures? That’s way more valuable to me than fancy food or shopping. No judgment there, but my money dials are turned way down on buying stuff and turned up on buying experiences. Below are my top 7 favorite excursions in Maui.

#7 - Surf in the North Shore of Maui

Maui is known for the most epic surf in the Pacific. Summer months have more calm waves, for starters. If you’re a beginner, take a lesson from Sea Maui. They will get you up in no time! If you’re already comfortable, rent a surfboard and head to the north shores of Ho’okipa Beach or Honolua Bay.

In the winter, sizeable southward-moving winter storms generate swells that reach Hawaii. Even though the storms are over 2,000 miles away, Hawaii feels the brunt of this energy. Consequently, waves in Maui, Hawaii in the winter months can grow up to 30 feet. In instances such as Peahi (also known as "Jaws"), the waves may reach more than 70 feet high during the biggest winter swells. On the north shore of the island, 20-foot waves provide the best surfing in Hawaii. It's a bit nippy – you're going to want to wear a wetsuit!

Surf in the North Shore of Maui
Pro Tip: If you decide to book any excursions with Sea Maui, talk with Jim and let him know Austin Distel referred you – he'll give ya a high five (or something better).

#6 - Sunset sail with open bar

This was the perfect way to get everyone together for a relatively cheap evening. For just $95/person, enjoy a beautiful 2.5-hour sunset cruise with an open bar to catch a sunset buzz. The Sea Maui staff was so attentive and fun! There was no better way to end our entrepreneur mastermind than to bring the attendees and their spouses together to celebrate a great event and transition to fun island time.

Sunset sail with open bar with Sea Maui

#5 - Sound Healing with Spiritual Shamans

It was a full moon our last night in Maui and we wanted to celebrate this past phase and set our intention for the next. I was recommended to do a Sound Healing session with a local spiritual guide. Maybe you’re like me – I had never done this before. I had no idea what to expect but was open-minded to the possibilities. We got a private session with Maui Sound Healing for $250, where we arrived at a bungalow, took off our shoes, and walked into a quiet room with incense burning. The shaman Rasa Priya was awaiting us cross-legged and surrounded by bowls, gongs, chimes, and guitars. He welcomed us in an inviting, soft voice and asked our intentions today. After introductions, we laid down and closed our eyes as he played instruments and chanted native American mantras, which spiritually guided us through an hour-long journey of healing. The experience was different for each of us – some cried, some giggled out loud. Everyone walked away in a better spiritual place with closure and new beginnings. What may come up for you?

Sound Healing with Rasa Priya in Maui, Hawaii

#4 - Drive the Road to Hana

To the west of Maui is a beautiful national park called Hana. The road there is quite a winding journey, with 620 hairpin turns along the coastal cliffs. It may be wise to take Dramamine before taking the trip. You can drive it but be warned, it's more relaxing to be a passenger than a driver. If you plan on getting a tour, my local friends recommend Hana Tours. There are two routes – many recommend the paved road to Hana as the dirt road is often protected by local Hawaiians who don’t take kindly to tourists. I’ve heard stories of locals on four-wheelers aggressively driving up on cars who take the local path. After all the stops to sightseeing, the Road to Hana will take you approximately 5 hours to drive from Lahaina, so it’s certainly a full day trip. 

#3 - Snorkel in the gorgeous Honua Bay

Where’s the best place to snorkel in Maui, Hawaii? Any local will tell you the same answer – Honua Bay. Sea Maui hooked us up with a great deal of these 5-hour excursions! For just $120/person, we boarded a catamaran from Whalers Village and sailed the rough seas for about an hour, where we arrived in the calm Honua Bay. Jump in with your fins and snorkel to see thousands of fish, giant sea turtles, and maybe even little nursing sharks! Have no fear; they are harmless and often sleep during the day. Since I love freediving, the 30-foot deep coral reef was the perfect distance for me to practice my skills to see wildlife. Once you’re back on board, the bartenders come out with champagne and cocktails to send ya back on the beach with a buzz. Don’t forget your GoPro for this one!

Snorkel in Honua Bay with Sea Maui

#2 - Morning Horseback Ride along Maui's cliffs

Along the cliffs in North Maui is the famous Mendes Ranch, named after the family that’s kept it for generations. This Hawaiian family is very influential in Maui, employing hundreds of people throughout its ranch to take care of their animals. Paige and I went here for a morning horseback ride for $140 – which was a first for me! The staff taught us how to ride these beautiful animals along the rocky road to the coastal shelf. Since you’re up in the mountains, it’s often foggy with scatter drizzles. While it’s not cold, you may be more comfortable in long pants and a shirt that you don’t mind getting a little dirty. The horseback ride leads to the most picturesque panorama of Maui’s most beautiful cliffs. Check out my story on Instagram of our ride here. 

Funny enough, my mom and dad went to Mendes Ranch when they were my age 25 years ago!

My dad at Mendes Ranch in Maui in 1996 and me in 2021.

#1 - Helicopter tour above Molokai

Want to feel like you’re staying in Jurassic Park? Take a helicopter ride around the island of Maui to it's sister island of Molokai to see the most epic jungles, cliffsides, beaches, and volcanoes from above. If you didn't know, Molokai is the dormant volcanic Hawaiian island home to the world's highest sea cliffs and largest coral reef in the United States. A giant earthquake caused half of the volcano to fall into the ocean leaving 4,000-foot sea cliff sharply cutting into the reef. Hawaiian legends state their ancestors originated from this island, which is also the birthplace of deep-rooted traditions like Hula dancing.

We went with Maverick to tour the Hawaiian island of Molokai. Be warned, the winds and sea are one of the most treacherous in the world, but the helicopter pilots at Maverick are experts at navigating through them safely. But maybe take some Dramamine before to calm your stomach so you can enjoy the ride without motion sickness. While this was the most expensive excursion at $350/person, it was a once-in-a-lifetime experience.

Helicopter tour above Molokai with Maverick

My Maui Experience Summarized

What an epic trip! Hawaii used to be so expensive to get to and stay that many wait till retirement – but I’m here to tell you it’s not only affordable, it’s a trip of a lifetime! There are cheap flight deals from most cities, locals put their place on Airbnb, and adventures are truly exotic. Whether you love exploring ocean wildlife or just want a relaxing beach getaway, Maui is a paradise born of fire. I’ve written about many other beach trips in my life, from Puerto Rico to Costa Rica. What makes Maui unique is that it has the safety and infrastructure of a 1st world country with the exotic wildlife adventures of a remote island. It’s perfect for solo backpacking, couples getaway, family trip, or even a business retreat. Explore the beauty of Hawaii.

Austin Distel
Written in a window seat above the Pacific Ocean
Tuesday, September 21, 2021

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