How to Do Maui in Three Days

Should you ever, like me, find yourself in a temporary fit of insanity realizing you simply cannot step foot into the state of Florida and in desperate need of a complete escape, book yourself on a flight to Maui.

Obviously, this is easier to do if you’ve already taken the days off work, booked boarding for the dog, arranged with your parents to watch the other dog, and set aside the funds for your trip. And, also obviously, doing this with less than 3 days notice of the actual trip is less than ideal.

But nevertheless, should you for whatever reason find yourself in Maui for three days, I can tell you a terrific way to spend those 72ish hours so that you get the most out of your whirlwind vacation.

Day Zero – Fly to Maui

Travel to Hawaii on a bonus day. We picked Saturday and the flights were not at all ridiculous, even booked three days out. We flew through LAX to Kahului and arrived at about 8:45 PM island time.

Rent a car. As delightful as Maui is, it’s near impossible to get around without a car. You’ll want one anyway to enjoy the non-public-transit-able sights and the freedom that having a car affords you. While you can Uber (and you should, if you have booked any “drinks included” activities), one cannot traverse the island with Uber alone. So rent a car and don’t let them sell you the two-door speck that can barely hit 40 miles per hour and will get blown off the coast should a big wind hit. Get a normal car at the airport, then head to your hotel.

Your body will be tired, as it will feel much later than it is, but suck it up and have a drink at the hotel bar. Have a mai tai, in fact; that’s just the right thing to do.

Day One – Haleakala & Luau

Wake up early, because your body wants to, and hit your hotel’s buffet. We stayed at the Hyatt Regency Resort & Spa in Ka’anapali and breakfast started at 6:30 AM; we were in line at 6:20 AM, and we weren’t the first. While we took a few minutes before hand to walk the grounds and get a lay of the land, our 10:20 AM CST tummies were ready to eat. 

Eat all the fruit and fish you can get your hands on. We had more pineapple and papaya and smoked salmon at those breakfasts than I thought possible. And drink the POG! Pineapple-orange-guava juice is like nectar and will never taste as impossibly good as it does in Hawaii. Gorge yourself on these things.

Once you have fueled up appropriately, head to the town of Haiku to check in with Haleakala Bike Company for your Express Ride down the volcano. These good folks will drive you in a van full of other tourists to the entrance of Haleakala State Park. You then hop out, hop onto your surprisingly comfortable bikes, and give in to gravity. 

Express bike ride down Haleakala
Ultimate cool.

You will look a perfect mix of silly and badass in your helmet. Your hands will go numb approximately every 15 minutes from the cold and from gripping the brakes. You will go faster than you thought you were okay with, and it will be amazing. The 23 miles goes by in an 80-minute flash and the three rough hills are worth the sweat.

Having survived the strenuous bike ride, you’ll need to feed your tummies again. It’s time to try that famous island poke, and our bus driver recommended, “some liquor store that’s famous for it.” Yelp says it’s Tamura’s and it’s in Lahaina, but well distant from the main drag. Enjoy having your own car as you drive there and sample two or three flavors before deciding on a winner. We grabbed a bottle of Trader Vic’s dark rum and a bottle of his Mai Tai mix for blue collar hotel room cocktails and headed back to the hotel.

The poke and mai tais on the patio are incredible. You will toast with your plastic coffee cups and revel in the salty, amazing, umami chunks of ahi and scallop atop brown rice. It’s everything Maui should be.

Take a beat and hit the ocean. Stroll around in the sand and surf, feel the wind in your hair and the salt on your skin. Maybe get another mai tai at the beach-front bar then get ready for your luau.

Grab an Uber to get to the Feast at Lele luau, by the team at Old Lahaina Luau. Enjoy all the mai tais and other tropical cocktails, dig into the five-course feast and relax. The dancing and singing and fire-dancing are all wonderful and memorable and classic and you must go. And then get an Uber home and go to bed.

Day Two – Beach & Sailing

Wake up early, still, and be the first in line at breakfast this time. Rent a beach-front cabana afterward (even though it costs $75, and we didn’t know this) and enjoy three gorgeous morning hours of reading and watching the waves. 

Cabana View from Hyatt Regency Maui
Worth it.

Rent a couple of boogie boards, and find out that the beach by your hotel is too rocky to safely play. The rental guys will tell you about D.T. Fleming Beach Park, this wonderful beach about a 10-minute drive away. Drive there and bounce in and out of perfect 4-6′ waves on your boogie boards. Your hair will be a right mess, but this is what you came for and it’s perfect.

Boogie boarding at D.T. Fleming Beach Park
How about those old fat dudes in the background?

Stop in for lunch at Maui Brewing Co. on your way back to the hotel. Try a few of their local beers before settling on a pint (or two) and order the flatbread with kalua pork or the local, grass-fed burger. You won’t regret it.

Pop back into your cabana (you have it all day, anyway) for some complimentary pineapple and more reading. Feel pure relaxation wash over you as you realize home doesn’t exist until you’re there again.

Start walking toward Whaler’s Village (we mistook the distance and called an Uber, but here’s how you should do it) about 20 minutes before your sunset sail. We took the Hula Girl out on the water, a proud and proper high-tech sailboat with the coolest ladder that dropped right into the sand for boarding. We enjoyed several beautiful rainbows during our cruise and cuddled up in the bean bag chair suspended over the water. Three mai tais apiece and some fresh seafood made the trip complete. What a perfect way to watch the sun set behind the islands!

Sunset Sail on the Hula Girl

Once your sailboat has returned you to shore, stop in Leilani’s on the Beach for a few more tropical cocktails and more poke. Wind your way home along the beach and check out all the different resorts along the way.

Day Three – Lahaina & Hana

 Wake up to a bittersweet last day in Maui and savor your pineapple, papaya, and POG even more. Revel in the treat that is coconut french toast during your last breakfast buffet and stare out over your cup of green tea at the swans and ocean. 

Treat yourself to an extra hour reading and listening to the ocean poolside before the sun heats up, then pack everything up and hit the road. Head to Lahaina to walk nearly the entire length of Front Street in search of the perfect tiki shot glass, some Hawaiian-print attire for your nephew, and a Dole Whip. Positively squeal with delight when you realize that buying an I <3 DOLE WHIP shirt will also unlock a free cup of the creamy pineappley goodness. 

Gaze with wonder upon the mighty Banyan tree. Feel small as you stand in its acre shadow and 16 trunks. Then pack up your souvenirs and big Lahaina adieu.

Set your GPS to Tin Roof, in Kahului near the airport, the place your Uber driver from day one told you about. Order the mochiko chicken tin and sub out kale for rice. The kimchi delights with the perfect piquant spice and the chicken is the crispiest, juiciest you’ll ever try. With power food in your tummy, hit the road to Hana.

Drive 45 minutes or so until you hit the Garden of Eden Arboretum, but opt out of the $15 per person tour. Instead, buy some starfruit at their fruit stand and enjoy its fresh bright flesh, bursting with tropical sweetness. Return the way you came and stop at a few of the more dramatic switchbacks for a breathtaking photo opp.

On the road to Hana
Everything the light touches, Simba.

Stop short of the main open stretch of road and park at the entrance of the Twin Falls hiking trail. Stumble around on the wrong path for 15 minutes or so before realizing you can lift the chain “lock” at the gate warning EXPERIENCED HIKERS ONLY and keep on trekking.

Soak in the 20-minute hike through streams and vegetation of all shapes and colors. When you arrive at your waterfall destination, don’t be afraid to get in. Yes, the water is cold, but you’re in Maui and when is the next chance you’re going to have to swim in a waterfall like this?

Swimming in the Twin Falls pool
I mean it’s pretty epic.

Complete the path back down to where you started and enjoy the intermittent rainforest showers. Continue your drive back towards civilization, stopping in Paia for a spell. Grab a few happy hour drinks at Cafe Mambo and get your last mai tai for under $5. Walk through town and admire the works occupying the numerous artist galleries. Finish your night in the covered patio at Cafe Des Amis with their stupendous curries.

Finally find yourself back at the car return and airport, a few hours early for your redeye flight home. Curl up and look out at the inky darkness and remember they don’t make island-dark nights at home. Give your husband a hug and a kiss and feel grateful that you got to share this amazing adventure together. 

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