How to Spend a Long Weekend in Maui, Hawai’i

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Advisor - Misa Kabashima
Curated By

Misa Kabashima

  • Active Travel

  • Beaches

  • Food & Wine

  • Maui

  • Hawai'i

  • Local Food

A serene sunset scene with a person immersed in water, silhouetted against a sky ablaze with vibrant sunset hues and palm trees.
Curator’s statement

Sometimes you just need to get away, and on the West Coast, we’re lucky that we can retreat easily to Hawai'i when we have a little extra time. Why Maui? Why not? The Valley Isle has it all. It’s the perfect blend of gorgeous scenery, lots to do and, most importantly, lots to eat, without the hustle and bustle of a big city. You may not find any skyscrapers here, but you’ll be surrounded by plenty of local culture, charm and aloha.

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Day 1: Arrive

A serene beach scene with clear blue waters, boats and palm trees, under a sunny sky.

When you get off the plane and board the Maui Airport Tram, designed after the plantation-style trains of old Hawai'i, the first thought you should have should be, “What to eat first?” To be in Hawai'i is to be hungry — otherwise, you’re missing out! Rev up that rental car and head straight for Tin Roof Maui for some local grindz. Tin Roof is the casual creation of Chef Sheldon Simeon, former Top Chef finalist and Big Island native. The restaurant serves up local favorites, like mochiko chicken and garlic shrimp, in a bento (lunchbox) with your choice of carb. Since it's portable, you can head straight to your hotel or make a pit stop at Kanaha Beach Park to enjoy the scenery whilst you feast.

Pro tip: The garlic noodles at Tin Roof are not to be missed. If you’re staying in an accommodation with a kitchen, buy a few things you want to try and eat it over multiple meals. It reheats great — I can say from experience.

If you’re in the mood for something sweet — or know that you will be later — Shikeda Patisserie is not to be missed. Their desserts can hang with France’s finest and bring a tropical twist — think flavors with ube and lilikoi — to perfectly executed pastries. If you’re lucky, you’ll be able to stock up bento and onigiri (rice balls), perfect snacks for any excursion.

Head on over to your accommodation, wherever that may be. If you’re me, you’ll be staying in the Kihei/Wailea/Makena area, a popular place for those who like beaches, water activities and golf. If you arrive during the day, it’s the perfect time to hit the beach! There are several amazing options in the area and the water is always warm, so jump on in! If swimming or beaching isn’t your thing, check out the Shops at Wailea where you can buy everything from a designer purse to the perfect Aloha shirt.

For dinner, consider Monkeypod Kitchen, a venture by Peter Merriman, a leader in showcasing island-grown foods though preparation that reflects Hawai'i’s multiculturalism. Food at Monkeypod is quality and accessible, sure to please everyone — plus, they have a live music calendar. Try to make a reservation if you can.

Day 2: Explore

Molokini Crater, a small curved island surrounded by ocean.

What better time to get outside and explore what Maui has to offer? A visit to the Molokini Crater is not to be missed. Experience this natural phenomenon through taking a snorkeling or scuba diving tour. Make reservations in advance as Molokini is a popular destination. It’s one of Maui’s must-see attractions and is not to be missed. Many tours pair Molokini with a visit to Makena’s “Turtle Town,” the best place to snorkel if you like seeing sea turtles in their natural habitat. Makena Beach is a fantastic beach to visit in and of itself, so if snorkeling isn’t your thing, just enjoy lounging on the powder-soft sand.

If you’re more of a land person, today might be the day to hike Maui’s famous Haleakala, a national park with a variety of trails. Haleakala is a sacred place to native Hawaiians and houses many sacred cultural sites inside of the park. It’s a true privilege to be able to experience it.

Pro tip: Many activities don’t run in Maui on Sundays, so check before you get too attached to a plan.

It will be time to eat again before you know it. If you’re seeking food after adventure, consider visiting Kitoko Maui, a gourmet food cart located in South Maui Gardens in Kihei. Fresh, local ingredients are used to make elevated local favorites like the fanciest loco moco you’ll ever have. This is not a place to skip or share dessert — get your own and savor every bite!

When in Hawai'i, one must eat Foodland poke at least once. It’s consistently delicious and what the locals do. There are Foodlands throughout the island, so you can get your poke fix wherever you are.

After you relax and refresh from your day out, dinner will be here in no time and Paia is the perfect destination. There are three locations in Maui, all serving up the freshest, tastiest catches with craveable sides like Cajun rice and crispy potatoes.

For dessert, it’s essential to head to Lappert’s, which I consider one of the best ice creams of all time. Made fresh in Kauai every day, it’s flown to their various locations throughout the state. They scoop traditional flavors and some only-in-Hawai'i offerings like macadamia nut, Kona Lava Java and ube haupia.

Day 3: Surf

A surfer in an orange swimsuit and straw hat riding a wave, set against an overcast sky.

If you’re like me, you’re taking a red-eye back to the mainland so you can make the most of the last day in paradise. What better way to send yourself off than spending the day surfing? I’ve taken lessons with Maui Wave Riders and had a blast. Even if you’ve never surfed before, you’ll have fun! The instructors are really kind and patient, and they help you to ride as many waves as possible. If you’re a more experienced surfer, you can also rent equipment from them, including stand-up paddle boards.

After surfing, you’ll for sure be hungry. This is a prime opportunity to go to South Maui Fish Company. Not even exaggerating, this is the best fish taco you will ever have in your life. The fish is THICK, cooked perfectly and drizzled with unagi sauce so good you’ll want to lick the plate. They only outdo themselves in the poke department, which tastes like it just came out of the ocean — which it did. Guy Fieri came here, so there’s also that. Get it all because it’s so good you will eat it all. They sell out every day, so hurry there!

After you gather up your last souvenirs, shower off and pack, it’s time to journey to the airport. For one last meal, check out Balai Pata, which is conveniently located in Kahului, making it easy to stop by before your flight. A celebration of Filipino cuisine, this is the perfect way to say aloha to your perfect long weekend.

Advisor - Misa Kabashima

Travel Advisor

Misa Kabashima

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This guide is part of our ongoing series on travel to Hawai'i. For more travel tips, check out my guide, The Ultimate Guide to Breakfast & Brunch in Honolulu, Hawai'i.