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After my mother passed in 2015, I was determined to come up with a new family tradition that was solely ours. Someplace to reflect on the prior year and ring in the new. In 2017 we started our annual trip to the Hawaiian Islands, where we would celebrate the New Year as a family, boogie board, to our heart’s delight, and discover all the hidden gems of the islands. Every year we’ve taken the trip to Maui, and with several direct flights from Los Angeles, it’s never been easier and quicker (under 5 hours which is shorter than getting to the east coast for us). We spend a few days decompressing and letting island life soak in. It really hits by the 4th or 5th day and I’m always grateful that we book an extended stay and don’t have to rush back to life of school drop-offs, work, sports, activities, and obligations.
I stashed a few beach totes for this trip that doubled up as bags for evenings out and mornings at the beach. I love the cheerful colors on this straw clutch and can pull out my necessities for quick errands or a morning coffee run. Make sure to pack plenty of sunscreen, a couple snacks, water bottle and beach toys (these are great for travel as they’re collapsible and have held up for years!) P.s if you find yourself in Wailea, this is my go to coffee spot. Make sure to grab the banana bread!
Knowing we’ll be for the most part living at the beach, I always pack an armful of Turkish towels for trips like this. They’re so compact, dry quickly, and can be used for multiple things like picnic blankets, a pareo or a throw when the kids are cold or need a blanket in the car. Not only are these towels cute but they come in several colors and can be personalized.
This large tote was perfect as an extra carry-on and doubled down for all the beach gear, buckets and shovels. My favorite thing about this beach bag is that it’s a washable material. At the end of the day, I could empty the sand and give it a rinse.
We’ve always stayed in the Wailea area. There’s the entire west end of the island left for us to navigate and explore (which I admittedly haven’t covered here!). I prefer renting a condo for our extended trips. They’re great for families and can accommodate laundry, cooking in the kitchen, and room for the kids to sleep while we stay up late and enjoy a glass of wine. There are plenty of amazing hotels in the area as well, which would be perfect for a couple or for a really quick trip with kids. I think the Four Seasons and Fairmont are my two favorite properties although the Wailea Beach Resort is lovely too, being right on the water with a beautiful adult pool. And the Grand Wailea is wonderful for families with an over-the-top kids’ pool with a swim-up bar and a beautiful restaurant on the property. We were lucky enough to stay at that property on our honeymoon and babymoon so it has a special place in my heart.
I truly love Maui because it’s the perfect intersection of having plenty of things to do while really feeling like you’re away from it all. There are so many amazing things to explore on the island, places to shop, and restaurants to indulge in. Here’s a few things I love to do when we’re not laying on the sand.
- Go for a hike! The Waihee Ridge trail is one of my favorites and has incredible views of the island and north shore.
- Take a scenic drive around the island via the famous Road to Hana. Make sure to stop at the beaches, waterfalls, and lookouts. Every turn is more breathtaking than the last.
- Go snorkeling and explore the vibrant coral reefs and diverse marine life. The Molokini crater is a must if you’re staying in the Wailea area.
- Take a guided tour of Haleakala National Park and experience the breathtaking views from the summit. If you’re feeling adventurous, you can book a bike tour through a local company that will drive you up for sunrise and you can enjoy a guided cruise down the volcano on bike.
- Visit the Iao Valley State Park and take a walk through the lush tropical rainforest.
- Join a whale-watching tour and catch a glimpse of the majestic humpback whales. We have yet to do this but have heard the Pacific Whale Foundation is the best.
- Spend a day at a luxurious spa and pamper yourself with a massage and other treatments.
- Take a helicopter tour over the island and experience the stunning views from above.
There are some really incredible restaurants on the island that are not only a culinary delight but also offer stunning views. Here’s a few of my favorites that we keep going back to every year.
- Spago’s – This iconic restaurant is located on the Four Seasons property. It’s similar to its sister restaurant in Los Angeles and follows the farm-to-table approach by serving dishes that are inspired and sourced on the island. The views are the best in Wailea and the service is impeccable.
- Mamas Fish House – We’ve been going to Mama’s for nearly 15 years and sadly it’s not the hidden gem that it used to be. Reservations can be made 5 months in advance and you need to be on top of your reservation to secure a spot. If you missed out give them a call and ask if they have any same-day availability. That’s how we always get a last-minute res. Come a bit early and enjoy some time on their beach. It’s one of my favorites on the island.
- Monkeypod is a must if you’re in Wailea. It’s owned by Peter Merriman, a culinary celebrity on the islands, known for opening Merriman on the Big Island (you must go if you ever find yourself on Hawai‘i ). He’s considered the founder of the Hawai‘i Regional Cuisine movement, with a mindset on showcasing Island foods with a sense of conscience for the land and sea. Monkeypod is a derivation of his original restaurant with a laid-back yet elevated menu. Definitely book a reservation in advance if you find yourself in Wailea during peak season but you can always walk in with a bit of a wait. It’s great for lunch and dinner. The Mai Tai and Banana Cream Pie are a must, no exceptions. And of course kid friendly.
- We enjoyed dinner at Hotel Wailea and drinks at The Birdcage for the first time during our trip this past year. The restaurant was lovely and romantic. The Birdcage bar on the property offers a similar a la carte menu and has jaw-dropping views and parrots resting on the eaves. The next time we go back we will probably just pop into The Birdcage for a glass of champagne and a burger while enjoying a few hours away from the kids.
