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3 Days in Maui | Perfect Labor Day Weekend in Maui 2019

Planning a last minute trip to Maui and not really trying to plan? We have you covered on what to do, where to eat, and what parts of the Maui island to stay in to get the most out of your trip. There will be ample amount of time to decompress and enjoy this tropical climate. This itinerary is perfect if you’re looking to take three days off with Labor Day or Memorial Day Weekend.

Things to note before visiting Maui, Hawaii:

What is the recommended length of stay in Maui?:

– 3 days at the very minimum, 4 – 5 would be ideal for Maui

What is the language spoken in Maui?:

– English

Are there are any vaccinations required for U.S. Citizens when visiting Maui?:

– None required for US Citizens

Is Uber available in Maui?:

– Uber is not available in. A rental car is a must on your trip to Maui.

What is the value on the dollar in Maui?

U.S. Dollars are the currency in Hawaii and keep in mind that this vacation island is pricey.

What is the best time to visit Maui?

The best times to visit Maui is between April through May, and September through November.

What timezone is Maui in?

YO! Don’t forget you are traveling WAY out west to get to Maui. Maui is six hours behind eastern time and three hours behind pacific time. Perfect when you’re arriving.

Where to stay in Maui?:

Each part of the Maui island has something unique to offer. We spent two nights in Wailea at the Marriott Wailea Resort, and one night in Lahaina at the Royal Lahiana Resort. More deets to come here


Without further ado, here is the 3 day itinerary for Maui: 

Day 0: Travel Day, LAX → Maui


6:00pm: Flight lands

6:30pm: Grab rental car from the airport

  • Pro-tip: If you or anyone you’re traveling with can get a corporate discount with a rental company, do it. Our rental for 3 days cost $228! Otherwise it will cost you around $500+ for a rental.

7:30pm: Arrive at Mama’s Fish House for Dinner

~20mins from Airport

  • This spot is BEAUTIFUL. Definitely try to make it here before sunset
  • We weren’t able to get a reservation ahead of time, so we decided to do it the old fashion way by sitting at the bar where they serve the full menu. Worked out perfectly!
  • Do yourselves a favor and make sure to order the Panang curry


9:00pm: Drive to Marriott Wailea Resort

  • 40 mins from Mama’s Fish House
  • Property highlights: two outdoor pools, by the beach, slides for the kids, great  gym, luau entertainment, excellent pool side menu, restaurants, Starbucks, restaurants in walking distance, and comfortable rooms.
  • Booked for two nights using Marriott points
    • Pro-tip: This property for some reason doesn’t allow online booking via points. May list as sold out with points. In this case, call Marriott Rewards directly and have them make the reservation. Definitely do this in advance if you’re planning to go to Maui for Labor Day weekend or Memorial Day weekend. The property is more likely to be fully booked.
  • Cost in points: Category 8 hotel = 40,000 points/night.
  • Cost in dollars: ~$350+ a night

10:00pm: Crash early the night before the sunset.


Day 1: Wailea, Maui


2:30am – 11:30am: Haleakala Maui Sunrise Tour with Breakfast

  • What do you get on this tour? Picked up at an ungodly hour and taken to the Haleakala mountain to witness the sunrise above the clouds while you freeze in the windy cold. Nonetheless, it is indeed a beautiful sight! After the tour, the drive back to Wailea is gorgeous and you make a few stops along the way, including stopping for breakfast. The tour guide is informative and will give stories, facts, and myths along the way and back.
  • Price is $168.55 on Viator. Very expensive for what you get. If you want to avoid this cost, you must book months in advance to come visit this volcano as parking is limited.

11:30am – 4:00pm: Enjoy the Marriott Wailea

  • After starting the day at 2:30 in the morning, the best thing to do for the day is relax and enjoy the resort property you’re staying at

Make sure to hit up that pool side service:

4:30pm – 10:30pm: Te Au Moana Luau Dinner at Marriott Wailea Resort

  • You’re in Hawaii, so isn’t this like a tourist bucket list must? The Marriott makes it even more convenient by hosting these Monday, Thursday, Friday, and Saturday evenings.
  • Doors open at 4:30 and an open bar is included in the ticket price
  • Standard ticket price: $118, which includes the luau and buffet-style dinner. The dancers and entertainers are fantastic.
  • I will say, it’s beautiful watching the Luau with the sunsetting over the ocean. There truly is something magical about the sunsets in Hawaii. Try to catch as many of them as possible!

Day 2: Wailea → Lahaina


11:15am – 1:00pm: Brunch reservation at Merriman’s Kapalua

  • Stunning Farm-to-table oceanfront restaurant. Don’t miss the chance to eat here
  • Make a reservation in advance

1:15pm: Check into Royal Lahaina Resort in Lahaina

  • For the one night we stayed here, cost ~$285. You can book this directly or via Expedia
  • The property wasn’t anything  SUPER glamorous but definitely comfortable with private beach and ocean front rooms
  • The Royal Lahina Resort also has a Luau if you decide to skip the Marriott’s Luau.

You can take this time to enjoy the private beach at the Royal Lahiana property


  • Enjoy a nice juicy cheeseburger in paradise, courtesy of Royal Lahiana room service (see photo below)
  • Head to Lahaina on the West side – this is a nearby town that has a lot of history and shops
  • Grab a bathing suit and head to The Cliff House’ — This is an area you can jump off of to snorkel and see lots of fish and turtles. Look for the trail that leads you to the rocks that can be jumped off of — I would advise holding off on the snorkel if you’re planning to do the next excursion below

6:50pm – 8:50pm: Private night time Snorkel with Shorelines Snorkel

  • This night time snorkel was LEGIT. There is something that feels surreal about snorkeling at night with no one in the ocean but you and your small tour group
  • The company provides hotel pick-up and drop-off, wet-suits, snorkel gear, and a flashlight that can be used underwater
  • We got to see some massive turtles that were 100+ years old swim past us. This experience was worth the pretty penny. Definitely something magical and intimate about being close to these animals late at night.
  • Cost: $90 per person

Day 3: Road to Hana, Maui → LAX


6:00am: Trek out to the Road to Hana

  • What is the road to Hana? Get ready for an drive full of waterfalls, waterholes, hikes, lookouts, beaches, sand, and more. This is a definite must as far as experiencing Maui goes. There is just something epic driving on one road all day that is full of adventures.
  • Ok so you’re thinking, wow this all sounds great but how do I know where i’m going? GUYS, download the ‘Shaka Guide’ app to your phone. It has a feature that will continue to work offline as you’re likely to lose service during the drive. We did the original tour and left early to avoid crowded areas. The guide is great because not only does it provide entertainment, stories, and where to go, but it will tell you which areas are so so and which ones you definitely don’t want to miss.

Here’s a few of the stops we made

  • Twin falls – this was a quick walk for us. Didn’t spend more than 20 mins. I would pass on this if you’re short on time
  • Garden of Eden – Don’t miss this! Wow, this place is a tropical wonderland with amazing views. It costs $15 per person and it is WORTH it!
Road to Hana Garden of Eden – Maui, Hawaii

  • It was actually challenging finding food on the route. We had lunch at The Preserve Kitchen + Bar which had a great view. I would advise packing a lunch so you can enjoy it next to a waterhole of your choice.

Some other recommendations for the Road to Hana we didn’t make it to –

  • Black Sand Beach – fit for camping
  • 7 Sacred Pools – has bamboo trees and a giant waterfall
  • Koki and Homoa beaches – Voted as the two most beautiful beaches in the U.S. by Travel Magazine more than once
  • Lava Tubes – supposed to be dopeboifresh.

Overall – I get why Maui gets this hype. It is remote, it is quiet, and it is beautiful. Enjoy your journey and feel free to comment on any recommendations, suggestions, or questions below.


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