Wailea Marriott

Guide to Maui

Aloha, friends! My husband and I spent our honeymoon in Hawaii and we wish we could re-live it all over again! We spent two weeks in Hawaii, the first seven days in Maui, three full days in Kauai, and another four days in Maui. Originally we were supposed to be in Maui for seven days and Kauai for the last 7 days, but we decided to make a spontaneous trip back to Maui. I’ll explain why in my Kauai post! Before I continue, book every restaurant through OpenTable for points and indicate that it’s your honeymoon or anniversary if you want to score some free champagne and desserts throughout your trip.

Lots of you are planning on Maui and Kauai. If you’re going to split your time, I would spend the most time in Maui and anywhere from 3-4 full days in Kauai. Kauai requires more self entertainment, hiking, and lots of site seeing. So it all depends on what you’re looking for in your vacation, but you can’t go wrong with either choice!

Secret Cove
Secret Cove

I’m writing this because a significant number of followers have reached out regarding places to stay, things to do, and favorite restaurants to check out on the next (or first) trip to Hawaii. I’d say at least five people reached out regarding honeymoon recommendations, but everything below will apply to both a honeymoon or a nice family and/or friends getaway!

I’ll get started with our favorite part of Hawaii. Wailea, Maui! We stayed at the Wailea Marriott Beach Resort right on the water. We booked this hotel through the Southwest Airlines hotel portal. I HIGHLY recommend booking your hotel through Southwest or any airline you frequently fly if you’re trying to get a status with the airline. We earned 70,000 points for booking with SW, and these points got us to Companion Pass right away (I use my SW priority card for everything so I had a big chunk of points banked up to begin with). Another recommendation is to book the hotel (for any trip) directly through Marriott or Hilton depending on how often you travel. My husband travels for work, but he does a lot of day trips as opposed to night trips, so he didn’t have many points to begin with. We charged everything to our room and paid with our SW card, so we were able to get points for the expenses we incurred throughout the trip (a lot LOL). However, if you’d rather book directly through your hotel account, you’ll get a TON of points from the cost of the stay and expenses incurred as well. Please note you cannot get points through the Marriott for your full stay if you book through Southwest or a direct airline.

Southwest Airlines Hawaii
We flew from Chicago to Oakland and Oakland to Maui! Southwest also flies in between islands as well! Highly recommend SW, especially if the layover is very short.

Before I mention the hotels, our first piece of advice is to stop at Target or Costco right after you get off the plane (they’re RIGHT next to the airport after you get your car). Grab some snacks and booze if you want to save a little bit at the hotel. We bought some vodka and La Croix for the week at Costco but we didn’t use much (so go to Target in this case). We ordered every day from the bar, but we mixed some drinks in our Yeti’s to save a little bit as well.

Wailea Marriott
Wailea Marriott Serenity Pool

Where to stay in Wailea, Maui:

Back to the good stuff (i’m very passionate about Southwest if you can’t tell). The Wailea Marriott was absolutely beautiful, staffed with the most friendly employees, and relaxing. There were plenty of people with families here, but this hotel truly had more of an adult and serene feel. They have a kids pool with slides (and a bar for the adults to stay sane), a huge game room, escape room, and plenty of little attractions to keep the kids entertained. The hotel also has 3 other pools. One infinity pool is for adults only – the serenity pool. It’s a large beautiful infinity pool with plenty of chairs (get there early for a seat), options to buy up on Cabanas (pointless in my opinion unless you have a big group to split the cost), and Terry as your staff member to take your order. If you plan on staying here make friends with Terry right away! She was the most kind hearted and personable person we’ve ever met! She’ll also know your names right after she meets you for your entire stay. This pool looks directly out at the ocean and makes for a great sunrise and sunset spot. Please note that some members take the “serenity” meaning pretty serious. So if you want to talk loudly and have one too many Mai Tais, check out the next two pools. We heard a guy ask the girl behind us to be quiet (I honestly didn’t even hear her talking, but to each their own). The other two pools are located near the serenity pool right near the bar and restaurant. You can do ask many cannonballs as you’d like in this one! This pool was definitely more active, but it’s much smaller. You’re right in front of the bar, so if you want to catch a sports game you’ll be able to see the TVs. There is also an infinity pool right in front of this pool as well with two hot tubs. Another amazing view and not as crowded as the serenity pool. We only went to this pool one day because we loved Terry so much, but this was another good option! Wailea Marriott is a 4 star hotel.

Grand Wailea
Grand Wailea – A Waldorf Astoria Hotel

We decided to check out the Grand Wailea – A Waldorf Astoria Hotel upon flying back to Maui for another 5 days. We got 22,000 points for booking through Southwest. The Grand Wailea is right next to the Marriott, so you still have access to the walking path, and restaurants within all of the hotels. If you’re traveling with kids or a fun group of people – this is the hotel for you! We would stay here over and over again. We also think it’s a good choice for those who can’t just lay on a beach chair in the sun all day. If you’re like Jeff and I, we need to be entertained a little bit and we felt like children all over again! The Grand Wailea is a 5 star hotel according to Google and we can attest! The hotel has 9 pools (one is an adult pool) that connect via little slides, caves, and the world’s first & only (at this time) water elevator! The owner designed and built the water elevator back in 1991 to accommodate his disabled son. How sweet is that!? It was under repair the first day we got there, but we waited in a 25 minute line on day two just to experience the attraction. There is a section of the pool that has sand and looks like a beach for your youngest children. They also have a rope swing attraction that we took advantage of multiple times. I’m not sure who had more fun… all of the kids or Jeff an I! We never even visited the adult pool. This hotel was stunning, our room was much bigger and much much nicer than the Marriott. It was also cheaper too. We booked this through Southwest again for points, but we also got points through Hilton for our stay an expenses incurred. They waived our resort fees and upgraded our room to an ocean view for free simply because I was being kind as the long was a little line while we waited. It costs nothing to be nice!

Grand Wailea
Grand Wailea Pool

Where to eat in Maui & at the hotel:

Now, where to eat! All of the restaurants were good if you’re planning to stay at the Marriott and don’t feel like leaving the resort. We really enjoyed Humble Market Kitchin for breakfast/brunch (get the buffet)! One of the days I just ordered avocado toast (which was one of the best I ever had…but $23). We did the buffet twice and didn’t regret it. They switch up the buffet a little each day so you’ll be able to have some variety. KAPA Bar & Grill was also a good choice for lunch or dinner! We got the asian chicken wings, vegetarian tacos, fries, onion rings, edamame (make sure you ask for the hot version), and burger. All were delicious (especially the onion rings). Nothing outstanding, but i’d go back and eat there again. Get the Guava Cooler and Mango Tango drink at least once if you go! You also get two free Mai Tais when you check in. I’m not a fan, but if you are that’s a win right there! There is a Starbucks in the hotel, but we highly recommend checking out Whale’s Tale in the mornings. Take a little stroll on the path towards Wailea Beach and you’ll find the cute little hut filled with paninis, smoothies, treats, and coffee/tea options! We had the panini a few times and loved it. The coffee was also delicious. Mo Bettah Food Truck was also another good option. Expensive but just ok. My husband got a pork sandwich which he said was good, but nothing great. I had tater tots that seemed to be a day old. They were fresh but the humidity made them a little soggy.

Humble Market Kitchin
Avocado Toast (DELISH) from Humble Market Kitchin

You MUST check out The Mill House restaurant in Maui! This was recommended by a good friend and i’m so glad we went. It was unique, delicious, and the views blew all the other views we experienced out of the water. The restaurant has a mountain and plantation in the backyard as opposed to the typical ocean views you see in Maui (still beautiful). They also have a cute little store and ice cream shop on the plot of land as well. The store reminded us of a giant Cracker Barrel…but the Hawaiian version. We got the chickpea cakes which came with a delicious jam and we’d get it again! We didn’t know what they were going to look or taste like, but they were outstanding. We also ordered the burger, fries, and Italian Sausage Pizza (without the sausage but I recommend getting the sausage to add flavor). Order the LATITUDE ADJUSTMENT drink if you like margaritas! It’s served with pineapple juice in a cute pineapple glass. The vanilla ice cream was also unique and definitely recommended to end the meal on a good note.

The Mill House Maui
The Mill House Maui

Mama’s Fish was another frequently mentioned place. It’s at least 30 minutes from the Marriott and Waldorf, so don’t have to much fun at the pool before driving. I don’t eat fish, so I didn’t care for the menu at all, but Jeff got the crab cakes and Stuffed Fish option and enjoyed both! I actually tried the crab cakes and thought they were pretty tasty! This is a tourist attraction nowadays, so if you want a restaurant that’s pretty much right on the water – this one is for you. Even though Jeff thought it was good, he said he wouldn’t tell someone they HAD to go. If you’re planning a vacation in the future MAKE A RESERVATION NOW! This books up fast. Make the reservation around 5 or before if you want to see the sunset. We’ve been to two restaurants in Florida that are RIGHT on the water, so we felt this was very similar. The sweet bread, banana dessert, and drinks are delicious. Don’t pass these up. Again, if you LOVE fish then this isn’t a bad option, but there are million restaurants on the island with good fish and even better views.

Mama's Fish House
Mama’s Fish House Views

Sarento’s on the Beach was a good option for a sunset dinner, views, and Italian and fish! Great service and good food! It’s less than 2 miles from the Marriott which was nice. The grilled asparagus appetizer was very yummy! It was a little salty but still delicious. They also give you complimentary focaccia bread. We thought it had good flavor but it was way too oily. I got the spaghetti (without the meatball), and Jeff ordered the Seafood Mixed Grill. Mine was tasty (but it’s hard to mess up spaghetti and marinara). Jeff loved his dish and said it’s a must if you like a mix of seafood over a bed of risotto! I’d choose this over Mama’s Fish given the convenient location, good food, and views. The sunset here is beautiful.

Sarentos on the Beach
Sarentos on the Beach

Monkeypod Kitchen was easily one of our favorites! We went twice and actually went to the sister company in Kauai. It’s in walking distance from the two hotels we stayed at, and the menu has something for everyone. The truffle fries are required in our opinion. We loved them so much that we put in TWO orders for them the first time we went (I did not feel well after that). I ordered the pizza special of the day – Truffle white pizza without the mushrooms (I hate the texture). Jeff ordered the fish tacos, wings, and margarita. Everyone we met on the trip kept taking about Monkeypod and one of the hotel employees said it’s ALWAYS busy. Great service and good pies (we got the chocolate)!

MISOPHAT Sushi and Sansei are both good options. I only eat vege sushi (cucumber, carrot, asparagus, avocado), but Jeff said MISOPHAT was his all time favorite so far. The quality of the fish was outstanding in his opinion. They don’t take reservations, so get there early if you can. We ate here on one of our last nights, so we decided to go around 3:30. They have happy hour from 3-5 and the food is 15% off during that time. Sansei is about a mile away but not as delicious in our opinion. They do take reservations, so book one through OpenTable to get points! We got the kombucha margarita and enjoyed it. Sushi was still good, but it wasn’t anything spectacular. People actually line up outside hours ahead (idk why because they take reservations). Head on over to Surfing Monkey for ice cream after. Rocky Road, Cookies & Cream, and the Root Beer Float were scrumptious! All of these sushi and ice cream options are a few miles from the hotel!

HumuHumu is at the Grand Wailea but we didn’t eat here. However, we met a couple from San Francisco that absolutely loved HumuHumu and highly recommended the Filet & Lobster.

The Mill House

We ate at the Bistro Molokini at the Grand Wailea and enjoyed most of it! Jeff & I got a Hibiscus Margarita. I actually ordered the Frose at first but it tasted like water so I KINDLY asked if I could swap for what Jeff had ordered. I’ve never sent anything back at a restaurant but they switched with no questions asked. Their bread was delish, and the onion rings were our favorite! They were breaded perfectly with a little flavor as well. I ordered the truffle pizza again without the mushrooms and it was one of my favorite white pizzas! It had sweet maui onions that truly cave it a unique flavor. Jeff ordered the Shrimp Wrap, but it only had lettuce and very little shrimp + olives so he was not impressed. An employee recommended the breaded buttermilk chicken sandwich. He’ll try that next time because we WILL be back! Good service and reasonable! We really enjoyed the views and option to watch the Bears game as well. Head to the bar in the middle of the grand entrance, Botero Lounge, after if you’d like another drink. The margarita (without spice) was a good one! Live music here as well until 9 some nights. They also have a breakfast buffet restaurant and a little cafe on the main level if you want something quick. The little cafe sells liquor for much less than the pool bars, so pick some up there if you didn’t stop at Target or Costco to save money.

The Mill House Chickpea Cakes
The Mill House Chickpea Cakes

We also ate at Roasted Chiles which is right near MISOPHAT. This was a delicious Mexican restaurant with great customer service and kind employees! The chips and salsa were delicious. We thought the guacamole just tasted like mashed up avocado, but it wasn’t terrible. The margaritas were large and tasty as well. I got vegetable fajitas which were tasty! They don’t have black beans but their beans are vegetarian and pretty unique! We both enjoyed them. Jeff got the fish tacos and loved them. We’d go back here!

Wailea Marriott
View from KAPA Bar & Grill – Wailea Marriott. Two pools located right next to this photo as well.

If you want to take a little drive and experience a different area of Maui, head to FleetWood’s in Lahaina. The restaurant is known for its live music and rooftop views. Unfortunately the rooftop was closed for an event when we went, but everyone said it’s one of their favorite spots for a few drinks and appetizers. We got fries and Jeff got the calamari. Nothing great…just bar food in our opinion. This is located in a cute little beach town with a bunch of little shops. You can spend a little time here + they have plenty of beaches.

Things to do at the hotel:

Humble Market Kitchin
View from breakfast at Humble Market Kitchin

As mentioned above, the resort has plenty of entertainment. They have a movie room, an Escape room (save this for a rainy day), game room, fun signs and swings, and snorkel/kayak options. We got suckered into the snorkeling activity at the resort and we thought it was over priced. We took a kayak right in front of the resort and floated around for about an hour in the water looking at turtles and fish. It was cool to see but we were over it after the first couple of turtles. I’d say take a sail boat tour that offers the snorkel / scuba option as you’d get your monies worth. Our friends did the boat and loved it! We had a very scenic and long sunset boat planned for Kauai, so we didn’t feel the need to hop on another boat. If you don’t feel the need to snorkel, save any boat option for Kauai as it’s much more scenic and breath taking. You can also do a Luau right on the resort. In our honest opinion, save your money. It was cool to see and the food and drinks were good for being a buffet catering to hundreds of people. Overall we wouldn’t have had any regret if we didn’t do it. Our friends asked us to join so we were happy to tag along and be together! Definitely talk to the people at your table and get to know people throughout your stay! One of our favorite parts of the honeymoon was associating ourselves with people and having conversations with people from all over the US! We’re social people and we’re so glad to have met others in the same boat!

Grand Wailea
Grand entrance to the outdoors at Grand Wailea

The pool itself is all you need at the Grand Wailea. It’s so much fun! There is a bar in the water under a cave with TVs which happened to always be crowded due to the football games! Tim was our bartender and he was super fun and easy to talk to. We met lots of people at this little water bar. The resort also offers scuba diving lessons in the pool as well. Check with the employee upon check in regarding these details. Only issue I had here was there seemed to be a lot of flies at this pool compared to the Marriott. It wasn’t bad the first two days, but I was being swarmed with flies the last day for some reason (I did rain a little later on so maybe that’s why). Given we were only here for 4 nights, we just stuck around the pool and walking path the entire time. They do have ocean activities as well. This hotel is also RIGHT on the water, so you have free beach access.

Grand Wailea
Beautiful paths to get to the beach or pools at Grand Wailea

Things to do outside of the resort:

Piiholo Ranch Zipline in Maui
Piiholo Ranch Zipline in Maui

The Piiholo Ranch Zipline 5 line 3 hour tour was a blast! Highly recommend this tour, especially if you’ve never zip lined before (we have not). There are 5 different lines that you get to try and they’re so much fun! You’re surrounded by a rain forest, ocean views, and mountain top views the entire time. If you’re extremely afraid of heights i’d advise against this. Otherwise it’s not so bad. You do climb some shaky (well secured) bridges to get to the top post on a few lines. Nate was our tour guide and he was very goofy and entertaining. We actually ended up being on the tour with the people we sat next to on our first flight in. What a small world! TALK TO PEOPLE when you’re on tours, boats, and at the pool! Book this in advance as they only do 2 a day and sometimes only 1 during their “winter” season. LOL, what we would do to have their “winter” in Chicago.

Emerald Course Wailea Golf Club
Wailea Golf Club – Emerald Course

If you like to golf you will not be disappointed on the Maui courses! The views were stunning and the weather was favorable as expected. We played the Emerald course at Wailea Golf Club. The course was about $180 a person, but the grounds were in great shape and every hole had an absolutely stunning view. We played behind a slower group, so I would recommend booking a Tee time in advance to get the earliest slot possible. Then you’ll have the whole day after to spend at the pool! We also played at Maui Nui. This was another pretty course, but we started on the 10th hole due to the crowd. We actually went back to 10 and did the same holes again because there was a huge line for hole 1. We didn’t play the holes with the mountain views, so I can’t speak for that. Overall, good course but nothing outstanding in my opinion.

Big Beach Maui
Big Beach, Maui

If you have time, head to Big Beach (and little beach if you want to see a nude beach) and Secret Cove in the morning for a sunrise. We think beaches are beaches as they all are pretty similar and serve the same function, but these beaches were two of our favorites. The Secret Cove beach is a tiny little area with a bunch of rocks and huge waves. Something to check out for a few minutes or even enjoy a little picnic. Big Beach was… well…as you imagine, BIG! The waves were also huge!

Secret Cove

Things we didn’t get to but were recommended:

From my friends Kelly & Dillon (check out their blog)! Haleakala Crater – state park. With a credit card payment, it’s about 1.5 hour drive all the way to the summit, without stops. There are some cool pull offs on the way up if you have more time. Sunrise needs reservations. BUT, sunset doesn’t need reservations. (we did sunset, and it was the most breathtaking experience.) Dress REALLY warm, bring tons of snacks. And stay a bit after the sun actually sets, colors are amazing. Iao Valley very quick hike surrounded by trees. Nakelele Blowhole drive there is beautiful. The blowhole itself isn’t too grand, but the views near are stunning. Driving the west side of Maui – drive CLOCKWISE back around the island. One lane road for an hour. Actually a bit scary, but so cool. Right through the rainforest, incredible views, but not an easy drive. Twin Falls for a little walk or swim. Waianapanapa State Park for a big black sand beach, but crowded.

From many: Road to Hana- We’ve heard mixed reviews. Everyone who’s done it hasn’t come back saying you absolutely have to do it. They’ve said its beautiful and a cool trip, but they never said we should absolutely do it, so we didn’t feel inclined. One, it’s exhausting. You’re in and out of the car for about 15 hours if you’re making stops. You should get up at about 3 or 4 AM to get on the road. You have the option for some little hikes on the way, otherwise it’s a trek where you’re hopping in and out of the car to see some amazing views and beaches. We didn’t feel like wasting a full day pool day in the sun, nor did we want to sit in a car that long. Someone in Maui AND Kauai said if you’d rather do a shorter version then just drive the island of Kauai and it’s the same thing in about 4 hours lol. We will definitely be back to Maui, so we MIGHT do it when we go back but we don’t regret skipping it. If you’re a big explorer and like site seeing, do the Road to Hana!

  • Road to Hana Notable stops (from my cousin)
    • Twin Falls
      • Kenanae Arboretum
      • Keanae Peninsular
      • Niihau Market
      • Wainapana Park (probably one of my favorite parts from Road to Hana)
      • Koki Beach
      • We went past to the Seven Sacred Pools- no one tells you you have to pay to go in (National Park) however if you plan well you can use your ticket to get in to Haleakala within 24 or 48 hours (however the day we went was free to get in to Haleakala)

Fabiani’s to eat. This one is right near Monkeypod. Good little Italian restaurant.

Snorkeling through Pride if Maui – Turtle Town & Molokini.

UFO Parasail near Lahaini / Kanapali – Do the highest one

To wrap this all up (if you’re even still reading this):

You will LOVE MAUI! The nice thing about Maui is that while it’s commercialized due to the tourists it has so so so much to offer! You’ll never be bored (especially no the resorts)! The island is large enough to keep you entertained for a long stay. Check out all areas of Maui if you can. There are multiple cute little towns and plenty of shops and restaurants. If you’re really looking to straight up relax in a serene environment, stay at Wailea Marriott Beach Resort. If you want a little more entertainment and fun pools, stay at Grand Wailea – A Waldorf Astoria hotel. Please message me on the blog or instagram with any questions!


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