Sister’s Trip to Maui for Less than $600


Every year my sister and I do a fall trip together. Last year was our epic Greece and Italy trip, but we stayed closer to home this year. Previous trips include one to Puerto Rico and one to Puerto Vallarta. We did our sister’s trip to Maui this year for less than $600 in hotel and flights. (Actually, I had resort credits on two Marriott Bonvoy Brilliant cards that covered this $600 which was the resort fee and the parking.)



Without a doubt, the best part of this trip was how I paid a mere 30K for us both to get to Maui roundtrip! I did this by booking on Turkish Airlines for a direct United flight that would have been 45K a person. Even better, I then asked Turkish to put my United Mileage Plus number in. They added my mileage plus number (I’m Gold Premier) so we each got Economy Plus seats! (On my second booking, the Turkish agent said they couldn’t do it but United later did for me). Yes, it wasn’t the easiest flight to book but I’ve since done it another time. You can read how I did it here.  My Citi Premier  and its signup bonus made this trip possible because Turkish Airlines is a transfer partner with them. The cost was only $11.20 each for taxes and fees! Can’t beat that.


Two women on plane

15K Turkish miles and $11.20 in taxes and fees got us to Maui from Denver.


Screenshot of United flight Denver - Maui


Marriott Wailea Beach Resort

One of my favorite hotels in Maui is the Marriott Wailea Beach Resort. In the past, I could use one of my 50K annual night certificates from the American Express Marriott Bonvoy Brilliant to stay there. Unfortunately, that changed last year when Marriott devalued their points and raised them for most of their hotels. A stay here now runs about 80K-100K/night so I can’t even top off a certificate to stay.

Just before they did this, I booked a 5-night stay for my sister and I so I could go for one more stay. I had points to use and with their 5th night free on award stays policy for Marriott redemptions, it was a great way to stay once more. Unfortunately, Marriott passes on resort fees. A daily resort fee of $45 plus tax is added to the room rate and includes bike rentals, internet, activities, and more. Parking was an additional $35 a day for self-parking or $45 for valet.

We loved the Wailea Beach Resort and you can read my complete review about it. I 100% would love to come back here. The Wailea Beach Resort stay was one of the best parts of our sister’s trip to Maui for under $600!


woman standing on balcony in front of palm trees and ocean

Alex and Mitch were at the Wailea Beach Resort the week before me!


Screenshot of hotel reservation

This is what I paid for my room but now you can expect to pay about double.


I have Platinum Premier status with Marriott so we received free breakfasts every morning from Starbucks, enhanced internet, and an upgraded room. Our breakfast consisted of a pastry, a fruit cup, and a choice of beverage every morning. I sent a letter for upgrades to the concierge before we arrived, and we also had welcome treats in our room.


Umbrellas and lounge chairs near blue water

The ocean views at Wailea Beach Resort are incredible


We ate most of our lunches at the resort. We are light eaters for lunch, so we usually shared an item. The burgers served poolside were delicious as were the coconut shrimp. We had loaded tater tots with Kalua Pork one day from Mo’ Better Food Truck near the pool with the waterslides. They were also very good.


Mo' Bettah Food Truck

This food truck has some great Kalua Pork loaded tater tots!


Sheraton Maui

The award redemption price increased after the 5th day for the Wailea Beach Resort and Spa so we opted to switch hotels and go up to the Kaanapali area. I kind of like doing this anyway just for a change on the beaches. Here we stayed at the Sheraton Maui. I love the Kaanapali Beach area and usually stay there at one of the Hyatt’s. Again, I wanted to book with points and had two 50K certificates to use and decided to do that instead. The cost was actually 56K Bonvoy Rewards so I topped off each certificate with an additional 6K in points.

While I love the area of Kaanapali, this hotel is not as nice as the Wailea Resort or the Hyatt Regency nearby. But it was pretty darn nice and I would come back. It is a great use of a 50K certificate hotel with an amazing beach. Read my review of this hotel here.


White hotel with palm trees

Sheraton Maui Resort & Spa


Restaurant Recommendations


Our must-stop restaurant in Maui is Coconuts. We love the fish tacos and the coconut shrimp. Fast food at its finest!


Sign that says Coconut's Fish Cafe

One of our favorite places to eat in Maui

Monkeypod Kitchen

Close to the hotel, is Monkeypod Kitchen. I’ve been there several times and my favorite dish is the Pumpkin Ravioli. Sounds a little weird, but it is delish. They have several cream pies with strawberry being my favorite so save room for it if you go!


ekolu Kitchen1279

The next night we went to ekolu Kitchen1279 because Alex had been there the week before. The double pork chop was a thing of beauty and easily feeds 2 people. Highly recommend this restaurant.


Pork chop and mashed potatoes on white rectangular plate

This double pork chop did not disappoint!


Kihei Food Truck Park

Not sure what you want to eat? Head to the Kihei Food Truck Park where you can find multiple food trucks. Everyone can find something to suit their taste buds here.


Food trucks around wood gazebo with lights

Food trucks are located near Kihei and also up in the Kaanapali area!

Paia Fish Market

Paia Fish Market has two multiple locations in Maui. If you love fish as I do, this is a perfect spot to eat. I had.  My sister, who doesn’t like fish, had a chicken teriyaki sandwich and enjoyed that.



We did a lot of laying around the pool or going to the beach on this trip. We did a nice walk on Thompson Road near Kula and saw the area where Oprah lives – it is gorgeous. Sadly, we weren’t invited to lunch so we stopped at the Kula Bistro which was very good. We couldn’t decide on desserts so we ordered 3 for later!


Large White House in green meadow.

Supposedly, this is Oprah’s previous home.


Bakery case filled with desserts

So many desserts! How do you pick?


We did go to Warren and Annabelle’s Magic Show one night. I highly recommend it – not only was the magic amazing, but the comedy was hilarious. It was a really fun time! When your sister’s trip to Maui costs under $600, you don’t mind a splurge for activities!


Man in black and white suit in front of red curtain

Such a fun night of magic!


Bottom Line

Our sister’s trip to Maui for under $600 was a success! We had a fabulous time relaxing and reconnecting – I love that points and miles allow us to create memories with family members!

Sand, turquoise water and turtles

Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. American Express is a Travel Mom Squad advertiser, but we always show the best public offer even when we don’t earn a commission. Terms Apply. 

Share this post

  1. Julie Woods says:

    I am so lucky to have a sister who takes me on these wonderful trip! I love her and spending time with her! She knows how to create the best memories!

Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.

Leave a Reply

Your email address will not be published. Required fields are marked *

Want to know the most popular card for beginners? 

click here

Advertiser Disclosure: Travel Mom Squad has partnered with CardRatings for our coverage of credit card products. Travel Mom Squad and CardRatings may receive a commission from card issuers. This compensation may impact how or where products appear on this site. Travel Mom Squad has not reviewed all available credit card offers on this site.

Editorial Note: Opinions expressed here are author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.