striped wide leg pants

To say our vacation to Maui was amazing, is almost an understatement! It was so relaxing, beautiful, and fun, even with a toddler in tow! Great weather, beautiful hotel, and awesome food (maybe a few cocktails too) – what more could you ask for?! Keep reading for more details on traveling with a toddler to Maui, where we stayed and where to eat!

Forever21 Striped Wide Leg Pants // Rails White Button Down Blouse // Cult Gaia Turband // Warby Parker Crystal Sunglasses

On Smith: Cotton On Kids Rolling Stones Tshirt // Cotton On Kids Camo Pants // Gap Kids Water Shoes

maui lemonade cocktail

striped two piece set

Lottie Moss Striped Pants // Lottie Moss Tie Back Top // Sensi Studio Mesh Bucket Bag // Joe’s Jeans Cropped Denim Jacket // Ann Taylor Yellow Slides (on sale!)

black lace pants

Victoria’s Secret Lace Pants (similar HERE) // Rails White Button Down Blouse // Janessa Leone Packable Hat //

On Smith: Tea Collection Pineapple Tshirt // Cotton On Kids Camo Shorts // Gap Kids Water Sandals

Traveling with a Toddler

Despite Smith’s face in the photo, he had an absolute blast in Maui! My mom thought I was crazy when I told her I wanted to take Smith with us to Maui, but I knew he would love it so much, I just had to! Yeah the flight there was misery, but it was worth it! Travel mom tip: get extra legroom seats if you can on the plane and/or don’t forward face an unruly toddler in a car seat like we did on the way there! Smith kicked the seat in front of us the entire time (5.5 hours from LA) and as much as we said stop and held his legs, we were virtually imprisoned in our seats when he was fighting us, there was not much we could do. Needless to say, when extra legroom seats were not available on the way home we rear-faced the car seat for a much smoother ride, even though the seat in front of him could not lean back because the car seat was so big… I digress lol. For what we packed for Smith on the plane and for the trip, make sure to check out THIS POST!

One more TIP: call the hotel (any nice hotel) before you go and ask about a babysitter. Our hotel recommended a company they work with called The Nanny Connection and they vet babysitters, and they all have great experience, etc so they are easy to book without meeting them. I actually worked for a company just like this in Louisville while I was in college and trusted that they had background check them and a lot of great references. We booked an amazing lady for three days and loved her so much. Smith did too! It allowed us to have Smith in Maui with us, but to still really relax and enjoy the vacation. She played with him at the pool and waited upstairs while he napped, while we got to lay back, relax, enjoy cocktails and get some sun!

maui kea lani

ann taylor white pants

Wayf Off Shoulder Top // Ann Taylor White Wide Leg Pants // Ann Taylor Yellow Suede Heeled Sandals // Cult Gaia Arc Bag

pink high waist bikini

Tularosa Bikini Bottoms (similar HERE) // Ann Taylor Scarf

supergoop spray sunscreen

Janessa Leone Packable Hat // Supergoop Spray Sunscreen // Kate Spade Gingham Wallet // Warby Parker Crystal Sunglasses (drink is Maui Lemonade

wayf floral blouse

Wayf Floral Blouse // L’agence Destructed Jeans // Ann Taylor Suede Slides // Baublebar Earrings // Sensi Studio Mesh Bucket Bag

on Smith: Tea Collection Tshirt // Cotton On Kids Sweatpant Denim // Tea Collection Native Shoes

maui kid friendly hotel

Rails Palm Tree Blouse // Madewell Denim Shorts // Havaianas Sandals

On Smith: Snapper Rock Swim Trunks // Tea Collection Tshirt // Gap Water Sandals

Where to Stay in Maui

Back to the trip, Smith had been asking and asking for hotel, beach, pool and ocean and I knew this would be the best spot for all of us to vacation because it’s remote, beautiful, the water is warm, the weather is beautiful and everything is clean and safe! When I started hotel hunting I knew that we needed a kid-friendly hotel that was still super nice, but that had a toddler pool and came across the Fairmont Kea Lani in Wailea. Doug and I got married on Wailea Beach 5 years ago and loved that side of the island, so I pretty much knew we wanted to stay in Wailea and the Fairmont looked amazing. And it did not disappoint! We arrived to the most gorgeous lobby and were given leis. The property is stunning, the staff was so friendly and room was even better! Each room is a suite with a little kitchenette, huge living room with l-shaped couch, a huge bedroom, the best bathroom and a patio of patios with a table and chairs and lounge chair for sunning! Plus, the best view of the pools, ponds and ocean! Everything is upscale, but still kid-friendly.

The grounds of the hotel are stunning too! There are fountains everywhere that Smith loved walking around to in the morning, a little rainforest type of area, bridges, 4 restaurants (plus a market), 1 adults only pool, one toddler pool, and two other pools with a slide connecting them! My husband and I were obsessed with the slide! And plenty of chairs for laying out that you never had to save chairs or get out there early. Also, the location on the beach was amazing. It’s so private and literally right on the beach and so nice that the hotel offers chairs and towels for the beach, plus free snorkel rentals are included in the resort fee (as well as parking!) The food was also really great. We ate at Ama the poolside restaurant everyday for lunch and it was a great diverse menu with all the pool favorites and local specialties too! The best part – kids eat for free at all the restaurants on the property when an adult entree is purchased! Love it! They also have KO Restaurant that we heard is amazing and Nick’s Fish Market that we were recommended by several of my Instagram friends! We ate in the little Ciao Bakery/Market, every morning for breakfast and were also able to get snacks and drinks there for the room since we had a fridge.

Where to Eat in Maui

While we are pretty much by the pool and beach people during the day, at night we love to get out and see a bit and try more local spots. of course if you have asked anyone where to eat in Maui they say Mama’s Fish House and I have to agree! We had such an amazing meal last time we were in Maui, but this time I didn’t make reservations in enough time so we didn’t get to go! Make sure to plan in advance if you want to eat there. Get the almond crusted fish for sure and a delish cocktail to take in the view. It’s beautiful there, especially if you can catch a sunset!

This trip we had an amazing Italian dinner at Matteo’s Osteria where they make their bread and pasta fresh in house! It was delish and everyone was so nice there. Great for date night! Then the next night we had Smith with us and went to the MonkeyPod Kitchen that we had actually been to the last trip when we got married and forgot about it, but went again on a recommendation! It is really good! They have lots of fresh seafood and wood-fired handmade pizzas! Smith and Doug got pizzas and loved them and I got the best fish sandwich I have ever had! It’s super cute and kid friendly and they have great drinks! For our final night in Maui we went for sushi, because after all we are in the best place for that and got a great recommendation. It’s called Sansei and is also kid friendly and they get fresh fish everyday. It’s a huge menu with lots of specialties and the usual sushi fare. Also a great drink list! One last rec if you re looking for a simple lunch – and I love a good sandwich! It’s called The Market and it’s basically a gourmet deli and they literally have the most amazing sandwiches. One of the best grilled cheese, turkey sandwich and my husband loved his steak sandwich!

A few other places that my Insta fam shared with me, but we didn’t make it to:

Spago – for a nice dinner sans kids

Millhouse Restaurant – for lunch or dinner

Kihei Caffe – for breakfast (I hear it’s crowded, but worth it)

Paia Fish Market – for casual lunch or dinner

Eskimo Candy for lunch – poke bowls and kalbi ribs

Koiso – fancy sushi, need a reservation


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