Getaway Guide: Family Trip to Maui

January 21, 2020

Last November, we took a family trip to Maui and had an absolute blast! It wasn’t the first time for any of us, but it was such an incredible way to connect as a family. We spent almost a week in Hawaiian paradise eating local food and soaking up the views. Here’s our experience and my family-tested Maui travel guide!

Why We Chose Maui

Erik and I first came to Maui on our honeymoon, then we brought Harper here when he was 2 years old. He had a blast, but was too young to remember. So when our dear friend invited us to come back, we jumped at the chance to go! This trip to Maui was also our family Christmas gift for the year. Rather than giving Harper a bunch of toys that he might get tired of, we’ve been gifting him big family trips for a few years and so far we’re loving this Christmas tradition! Harper ended up loving Maui so much that we made his room a total surf-themed room.

Where to Stay: Andaz Maui at Wailea Resort

Located in the Wailea area of Maui, the Andaz Resort is located on one of Maui’s gorgeous crescent beaches and is only 30 minutes from Maui’s main airport. The whole resort is gorgeously designed, with a luxurious and modern feel, which sets it apart from many of the similarly priced hotels in Maui. The rooms are spacious and nice, and Andaz also offers villas for an even more luxurious stay.

Our favorite part of the Andaz Resort was definitely the pool area. The pool is situated on the most beautiful beach area, making it perfect to hang out by during the day. As a resort guest, you get umbrellas and chairs, and the resort employees occasionally walk around the pool with coolers filled with complimentary mochi. Harper loved the daily bingo games and even won free smoothies by dancing along to Michael Jackson. 

Overall, there are tons of amenities at the Andaz Maui Resort, including the kayaking scuba trips and multiple restaurants we took advantage of while we were in Maui. It’s just beautiful!

What to Do: Maui 6-Day Travel Guide

Day 1

We arrived at the Maui airport and rented a car to get around the island for a week. After settling in, we headed out for dinner at Matteo’s Osteria. Maui Restaurant Week was going on while we were on the island, which meant that a lot of great restaurants were offering a three-course meal deal for $49. Matteo’s Osteria is a charming Italian restaurant with a big outdoor patio seating section. We started with a kale Caesar salad and arancini. Then we had lasagna and chicken cacciatore. For dessert we had tiramisu and profiterole. Harper had spaghetti and meatballs; he loved it!

Since there’s a 5-hour difference between Charleston and Maui, we were totally exhausted and decided to have an early night to rest up for the next day’s adventures!

Day 2

Our second day in Maui was snorkeling day! In one word, it was unreal. Our trip left from the Andaz Maui Resort and we went out on this really cool outrigger canoe. Erik and I got to help paddle while Harper got to sit on the side (called the “ama”) and stay on the lookout for sea turtles. Our incredible local guide showed us an eel, urchin, octopus, lots of fish, lobster, coral and a TON of sea turtles. At first, Harper had a hard time with the snorkel and mask, but by the end of the trip he was a pro. It really was a wonderful experience we will never forget.

We spent the rest of the day at the resort, visiting the pools and hot tub while looking out at the gorgeous beach. We splurged for a cabana rental so we could have our own space throughout the day. For lunch, we stayed by the pool and ordered from the Andaz restaurant. Harper had grilled cheese and lemonade, Erik had a fish sandwich and a Mai Tai, and I had a wagyu beef bowl with a Lava Flow. Everything was delicious!

Restaurant Week saved the day again with an amazing dinner at Tommy Bahama. Erik had the sea bass and I had the brisket, while Harper ate chicken fingers and fries. Even though it’s a chain restaurant, Tommy Bahama had a great vibe inside, with comfy chairs and Hawaiian decor.

Day 3

We started our day at a cute local breakfast joint called Piko Cafe. The cafe is all fitted out with light wood and modern decor; totally dreamy! Piko Cafe serves a variety of Hawaiian breakfast and lunch dishes as well as a bunch of espresso drinks. I had banana pancakes, Erik had fried rice and eggs, and Harper had pancakes and an iced chai. He definitely gets that from me!

Every time we go somewhere new, Erik likes to collect the local Starbucks mug from that city, state or country, so we hit up a Starbucks to pick up a Maui Mug. We also made a Target run for some snacks and beach essentials that we’d forgotten to pack. Yes, there is a Target on Maui!

Our beach day was actually at the Andaz Resort’s beach, which is so magical. Harper loves swimming in the ocean, so that was great. We stayed at the beach for most of the day before freshening up for a little spa day! Our friend watched Harper while Erik and I hit up the spa at The Grand Wailea. For the first hour, you enjoy the healing waters of the Maui baths. Then, we all had an hour massage.

Afterward, we got dinner at Monkeypod, a farm-to-table Hawaiian restaurant filled with wood and teal accents. We shared a bunch of dishes, including fish tacos, pizza, gyoza and potstickers, and pumpkin ravioli.

Day 4

We started our morning at the Cafe O’Lei parking lot in Kihei. There’s a little shack called “Beach Street” that’s known for their Kona Bean shakes. They were super yummy and Harper had a rainbow Hawaiian ice. We then spent another day at the beach at the public beach in Kihei. Luckily, a stranger let Harper borrow a boogie board and he had a blast!

After a long day at the beach, we drove to Paia and had dinner at Mama’s Fish House, an oceanside seafood restaurant that was decked out in old boats and ocean scenes. It was the perfect place for an incredible meal and view. Local surfers were catching waves that we could see from the nearby lookout, so we watched them for a bit before heading to the Four Seasons to watch the sunset and some traditional Hawaiian dancers.

Day 5

On our second-to-last full day in Maui, we woke up and watched the Buffalo Bills game (we lost). Then we drove back to Paia to start the day at Tobi’s Shave Ice. I actually had the most amazing seared tuna dish, and we all had Hawaiian ice. We spent the whole day exploring the cute town of Paia. Paia is pretty touristy, but a lot of Maui is, and this area had lots of cute shops, art galleries and restaurants. Shopping and sight-seeing was a great break from the beach while still soaking up the Hawaii atmosphere. We ended our excursion with round 2 of Hawaiian ice at Ululani’s Hawaiian Shave Ice before heading to a friend’s house where Harper got to swim in their pool. We watched yet another gorgeous Maui sunset and had food truck meals for dinner. The boys got burgers and I had fish tacos.

Day 6

Our sixth day on Maui might’ve been the most exciting, and it was definitely what Harper was looking forward to the most: we went surfing! We booked surf lessons through Aloha Ocean Adventures and it was a fantastic experience all around. Our surf instructor, Ikaika Kawai, had such a fun personality and took the time to make sure we were safe, comfortable, and having fun! I was SO proud of Harper. He got right up and rode the wave all the way in. After surfing, we headed back to Andaz Resort. The boys went body surfing on the beach before meeting me back poolside, where I was enjoying some mochi and reading.

For dinner, we went to Nutcharee’s Authentic Thai Food. We started with Tom Yum soup, made with shiitake mushrooms, tomatoes, onions, lemongrass, cilantro, and chicken. I had chicken and cashew nut for my main course and it was AMAZING! I also recommend getting sticky rice on the side.

Where to Eat

Our favorite dinner of the trip was at Mama’s Fish House. The seafood there was so fresh and deliciously prepared. I had the mahi-mahi, ono and ahi in panang curry and Erik had onaga with Maui onions, chili pepper, and avocado. It is a bit of a splurge but we all agreed it was worth it. If you pick one restaurant on your trip to Maui, I would pick Mama’s. 

Of course one of the highlights was going to be all the Hawaiian ice we had. After “testing” several locations, our favorite spots were Local Boys Shave Ice in Kihei, Tobi’s Shave Ice and Ululani’s Hawaiian Shave Ice, both in Paia.

After such an amazing trip to Maui, we’re already looking forward to our next trip! Maui is a great island for beaches, food, and shopping, plus it’s an amazing family destination. We can’t wait to keep taking Harper back to Maui and more!

Professional photos taken by: Catherine Ann Photography

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