A weekend trip to Maui? Are you serious? Yes, we are serious and let me tell you, it was totally worth it. Sometimes the craziest ideas are the best ways to maximize your paid time off. This trip provided the perfect escape from reality while also allowing us to travel without using any of our vacation days. We were able to relax in Wailea and explore the Road to Hana all in a holiday weekend.
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Why Maui for a Weekend?
The reason Hawaii makes sense for a Labor Day weekend trip is because of the time change and reasonable flights.
- You can frequently find reasonably priced flight sales to any Hawaii island. Keep an eye out for them.
- Our flight left Dallas at 11:20am on Saturday morning. We landed in Maui at 2:20pm and were at our resort pool with a Mai Tai in hand by 4:00pm.
- Our flight returning to Dallas left at 8:00pm and landed at 7:00am Tuesday Morning. We were able to relax for a full day before having to return to the airport. We slept on the plane and drove directly to work the next day. Yes, we were a bit sleepy, but for us it was totally worth it!
Yes, this is a bit of flying for many but if you don’t mind a long flight, a weekend trip to Maui is definitely a vacation to consider.
Unwinding in Wailea
If you are heading out to Wailea on a weekend trip or a week long adventure, Wailea is the place to be.
First things first, that sunset view…I mean, it’s incredible.
Multiple luxury hotel options. Here are a few of note:
- Four Seasons Maui
- Grand Wailea, A Waldorf Astoria Resort
- Marriott Wailea Beach Resort
- Andaz Maui At Wailea Resort
There are also more reasonable hotel options available to check out.
In addition, to wonderful hotels, this area has fantastic shopping and restaurant options. We enjoyed exploring the luxury stores at The Shops at Wailea and had an incredible dinner at Monkeypod Kitchen by Merriman. Monkeypod Kitchen is a must have if you are staying in Wailea as they have the best Mai Tai that we have ever had.
Golf your thing? Kipp was drooling over the incredible Wailea Golf Club courses. If we return, we will definitely be spending a day on the beautiful course.
Need a great beach? While Wailea Beach leaves a bit to be desired, it is only a quick 10 minute drive to Makena Beach which offers white sand, clear water, and great views.
Grand Wailea, A Waldorf Astoria Resort
We chose to stay at the Grand Wailea, A Waldorf Astoria Resort. A you may know, if you have been following our blog, we utilize credit card points to stay at luxury hotels way out of our price range. The Grand Wailea is a part of the Hilton Hotels collection and offers rooms at 80,000 points per night. While this sounds high, our American Express Gold Card transfers from AmEx to Hilton at a 1 to 2 ratio which makes this hotel a great deal. The wonderful staff at the Grand Wailea even upgraded us at check-in, providing us an ocean view room. Short on points? Hilton Hotels allows you to purchase additional points and they usually have bonus opportunities (click here to see the rates).
The resort is beautiful inside and out. The open air facility sits on 40 acres of lush tropical landscape right off of Wailea Beach. The resort is home to fantastic pools, wonderful restaurants and views for days.
We enjoyed taking in the incredible view of the sun setting over Lanai while sipping on our Mai Tais in a lounge chair.
The resort also hosts a Traditional Luau on multiple days through the week for a classic Hawaiian experience.
Exploring the Road to Hana
The number one thing that most Maui guides have in common is the Road to Hana. You will need a large part of the day for this adventure but it is well worth it. Make sure you get started early in the morning as well. Paia Town is the Road to Hana’s starting point; however, from Wailea, plan on it taking around 30-45 minutes to get to the starting point.
With winding roads with incredible views in every direction, the Road to Hana is lined with fun hikes, beautiful waterfalls, black sand beaches, and homemade banana bread.
Here are the stops that we made on our Road to Hana adventure
- Twin Falls – great waterfalls to start your journey accessible from a short hike
- Nahiku Marketplace – great little coffee shop and checked out some local art
- Waianapanapa State Park – the most incredible black sand beach
- Haleakala National Park – home to Waimoku Falls (if you are up for a long hike), Falls of Makahiku (accessible by a shorted hike), and the Ohe’o Gulch (also known as the Seven Sacred Pools).
- Wailea Falls – located right off of Hana Highway between Haleakala and Hana
- Hana Town – we enjoyed a wonderful lunch in Hana Town. There are a handful of food trucks and restaurants to relax in before the long trek back to Wailea.
- Baldwin Beach Park – We enjoyed a short driving break at the white sand beach park just outside of Paia before driving the final leg back to Wailea.
In total, from Wailea to Haleakala and back to Wailea with 7 stops and lunch, the drive took us around 10 hours. This beautiful day trip on Maui is a must no matter how long you plan to stay on the island.
Want more details? Check out our Road to Hana Guide.
Tips and Recommendations for Corporate 9-5ers Trying to Save PTO
Don’t be afraid to take a long flight for a short getaway. Sometimes these trips are better than a 3-4 flight when you consider time change.
Remember, just because you check out of your room, it doesn’t mean the trip is over. On our final day on our weekend trip to Maui, our itinerary looked like the following:
- Enjoyed the morning on Makena Beach
- Early lunch at the Jawz Fish Taco Food truck. A must!
- Quick shower and hair wash at the hotel before check out (so we would be presentable at work the next day).
- Hotel Check out and leave bags with the front desk for storage. Most hotels offer this service for free.
- Mai Tais and relaxation at the resort pool for hours.
- A little shopping at the resort stores.
- Picked up our bags and changed from our swimsuits into travel clothes.
- Headed to the airport around 5:00pm for rental car turn in and to head home.
With a quick trip, you don’t have to spend any extra time with checking bags. A carry on and a backpack will suffice. Make sure you check out our favorite travel tool.
Maui Post Lahaina Fires
We did a lot of research prior to our trip to Maui. Labor Day was a short amount of time after the devastating fires in Lahaina. We found mixed camps of people noting to stay away from the island while others were encouraging people to visit. After much research, we decided to go.
At check in, we were so glad we decided on this destination. We spoke to many within the first few hours of being on the island and they all had the similar view that can be summarized in the following statements:
- This is a tourism based economy and in order to heal and rebuild, the island needs the continued visitors that the island always sees.
- This is a large island and the area affected is relatively small.
- Please encourage your friends and family to visit.
When we were on island, the crowds were very small. While great for us, this is negative for the island. Immediately after the fire, the island needed a couple of weeks to assess the situation but now they are hurting due to cancelled reservations. We would encourage you to visit the island just stay away from the Lahaina area out of respect.
Our Itinerary
We hope this guide helps you consider a weekend trip to Maui. It may seem like a crazy idea but it is a wonderful long holiday weekend experience. In case you were wondering, here is our itinerary for our entire stay.
Saturday
- Land in Maui and pick up rental car – we would highly recommend a rental car while on the island
- Check into hotel and explore property
- Relax by the pool and enjoy Wailea Beach
- Dinner in Wailea (Monkeypod is a must)
Sunday
- Road to Hana
- Sunset on Wailea Beach
- Dinner at Olivine at the Grand Wailea
Monday
- Makena Beach
- Lunch at Jawz Food Truck
- Check out of Hotel
- Mai Tais by the pool while enjoying a great book (or watching Ted Lasso on an iPad)
- Shopping at the resort
- Head to the airport to fly home
Final Thoughts
Yes, you can obviously spend a week in Maui and never run out of things to do and see. But this weekend trip to Maui was a great experience for us and we loved every minute of it.
Remember, getting yourself out of the everyday 9-5 grind to relax and adventure will help you return to work more focused and positive.
Thinking about utilizing a holiday for vacation? Make sure you check out our Guide to Taking Advantage of Holidays for Travel.
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Maui is magical! Thank you for the fun ideas for a quick getaway!
Wow the pictures are taking my breath away soo beautiful, My work is flexible I can work from anywhere only con would be I’d have to delay my packages going out.
I did a weekend trip to Oahu from Seattle, WA, and it was wonderful! Would love to do another weekend trip soon… maybe to Maui! This was such an awesome post!
That is awesome! If we lived on the west coast, we would definitely do it more often!
Maui looks amazing! From
Europe a weekend trip would be a much short but I guess from the US it’s easy to get too. I’d love to visit for sure!
I’ve never been and I can’t wait to mark this one off my list. Thanks for the itinerary suggestions!
Hawaii is magical…I loved my time on Maui and definitely would like to go back soon. Thank you so much for this blog post with all the great information and inspiration, much appreciated.
Maui is beautiful and I’m hoping to visit in the new year!! Thanks for some ideas on what to do 🙂
Weekend trips are the best, especially if you don’t always have enough time or money to go for longer. Never thought about doing a weekend in Maui, it’s a very long flight for me so maybe not the best but it definitely sounds intriguing!
Haleakala National Park is my favorite part of Maui, especially the drive to the top and all the colors up there. That, plus all the sea turtles!
All in one weekend? Who would have thought! It’s not that long of a flight from where I am either, about the same as a trip to the East Coast – and I have done 24 hour trips there so I might give a weekend in Hawaii a try!
I love this idea, however, it’s five hours longer from Melbourne (where I live). But never say never. Just the thought of being on Maui is wonderful. I really liked the itinerary suggestion.
I went to Maui once years ago and loved it! I loved it way more than I even thought I would. So beautiful there. Was so sad about the fires that wrecked so much beauty.
I’ve always wanted to go to Maui! This is such a cool resource and it’s good to hear that there’s a desire for tourists to visit after the fire. Thank you for sharing!
Great info! I’ve always wanted to go to Maui!! Thanks for sharing!
Sounds like a perfect weekend trip to me! I’m sure the locals appreciate the return of visitors on their island, you are right they depend on tourism and need it to help heal from the devastating wildfires.