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.)

 

Flights

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 a direct United flight on Turkish Airlines that would have cost 45K miles per person. Even better, I 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! (I did this deal one more time, but it has since become much harder and more in miles.

 

 

 

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 Marriott Bonvoy Brilliant® American Express® Card to stay there. Unfortunately, that changed when Marriott devalued its points and raised redemption costs for most of its hotels. A stay here now costs about 80K-100K/night in points.

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, including 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 would love to come back here. Our stay was one of the best parts of our sister’s trip to Maui for under $600!

 

 

 

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.

 

 

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 delicious.

 

 

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 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 at one of the Hyatt’s. Again, I wanted to book with points and had two 50K certificates to use, so I decided to do that instead. The cost was 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 was an excellent use of a 50K certificate hotel with a fantastic beach. Read my review of this hotel here.

 

 

Restaurant Recommendations

Coconuts

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

 

 

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.

 

 

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.

 

 

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.

 

Activities

On this trip, we spent a lot of time lying around the pool or going to the beach. We also took 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 three for later!

 

 

 

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 splurging for activities!

 

 

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!