Curator’s statement
Our family’s first time in Maui was unforgettable. We celebrated my 40th birthday while discovering the island's magic as a family, from thrilling new adventures to peaceful moments that made us fall completely in love with this place. It's safe to say Maui has left a permanent mark on our hearts. This itinerary is a perfect balance of relaxation and exploration.
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Day 1: Arriving in Maui

Sunset from Pilina at Fairmont Kea Lani
You made it to Maui! You probably had a long travel day that included a layover, so you’ll be excited to have arrived and breathe in the tropical air. I highly recommend renting a car so you can explore everything the island has to offer.
Once you have your car, you’ll drive about 30 minutes from the airport in Kahului to your hotel in Wailea. I recommend staying in Wailea for a more upscale vibe. The area has beautiful beaches, an amazing beachfront walking path, and great hotels and dining. Our family chose to stay at The Fairmont Kea Lani. Not only is the property beautiful, but every room is a suite. It was the perfect choice for our family of four (kids ages 9 and 11) to spend eight nights.
After settling into the room, go for an evening swim at the pool and grab a quick dinner at the hotel marketplace. Enjoy pizza and salads by the pool as you watch your first Hawaiian sunset.
Day 2: Beach day & exploring Wailea

Today is all about enjoying the golden beach and resort amenities. The Fairmont sits on Polo Beach, and I highly recommend taking a walk along the beach as the sun rises. Have breakfast at Kea Lani restaurant—the breakfast buffet is incredible and offers something for everyone. After breakfast, it’s time to head back to the beach for the morning. You can rent snorkel equipment, boogie boards, paddle boards, and even scuba diving gear.
Take a break for lunch. You can eat at the casual AMA Bar & Grill or order food poolside. I loved ordering poke to enjoy by the pool. After lunch, go for your first walk along the Wailea beachfront path. It’s a three-mile (round trip) paved walking path along Wailea’s main hotels and beaches and offers stunning views. Cool off with a dip in the pool or ocean after your walk.
In the evening, enjoy golden hour drinks and sushi at Pilina. The specialty cocktails are great, and you’ll likely be treated to a gorgeous sunset.
Day 3: Waterfall hike

One of the many waterfalls on our hike
Drive to East Maui for a guided waterfall hike. You’ll hike through the rainforest learning about the plants and even get to try some edible ones. The guide will lead you to a few different waterfalls and teach you how to safely cliff jump! If you don’t want to jump, that's ok, you can swim under the waterfalls and just soak in the beauty. This hike was such a highlight for the whole family. On the way back to Wailea, stop for classic Hawaiian shaved ice.
Back at the hotel, take a swim and relax the rest of the afternoon. Our family was exhausted from the active morning and jet lag, so we opted for room service and called it an early night. If you’re up for it, have dinner at one of the hotel’s restaurants, Kō or Nick’s Fish Market. There is also a quick-service option at Makana Market.
Day 4: Learning to surf

When in Maui, you’ve got to try surfing. Book morning surf lessons with the friendly instructors at Rivers to the Sea. They have everything you need for your lesson. When you’re done, head toward Lahaina for lunch at Mala Ocean Tavern. This oceanfront restaurant is the perfect place for brunch, which is served daily.
On the drive back to Wailea, stop at Leoda’s Kitchen and Pie Shop for the best pies and banana bread. Highly recommend buying extras to keep in your hotel room.
Back at the resort, check out some of the activities like hula and ukulele lessons, lei making, and other great cultural offerings. For dinner, head to Monkeypod Kitchen in Wailea. Try their famous mai tai with lilikoi foam.
Day 5: Resort day & beachfront dinner

The view from our table at Ferraro's at Four Seasons Wailea
Have a resort day. Book a cabana at the pool, get a beachside massage, and have a relaxing day. Cabana rentals at the Fairmont Kea Lani include nonalcoholic drinks, fresh fruit, and ice cream treats. It’s a perfect way to spend a leisurely day in Hawai'i.
After the relaxing day, it’s time to dress up for a special dinner. Make reservations at Ferraro’s Italian Restaurant at the Four Seasons Maui. This restaurant sits right over the beach, and, if you time it right, you will get a spectacular view of the sunset as you dine. This is a great reservation to make if you are celebrating a special occasion.
Day 6: Discover Ka'anapali snorkeling tour

Discover Ka'anapali tour with Sail Trilogy
Wake up early and drive to Ka'anapali for one of the best snorkeling excursions with Sail Trilogy. This half-day tour includes cinnamon rolls for breakfast, a delicious Hawaiian lunch, and drinks. You’ll stop at two different bays to snorkel with sea turtles and see marine life. If you’re lucky, you might even see a pod of spinner dolphins playing in the waves next to the catamaran.
When the tour is over, explore Ka'anapali Beach. Walk along the beach path, enjoy the beach, and stop into Whaler’s Village for some shopping. There are plenty of restaurants to choose from for dinner here. Alternatively, stop at Star Noodle on your drive back to Wailea.
Day 7: Iao Valley & South Maui beaches

Visit Iao Valley in the morning. You will need to make reservations for entry. Take a short hike on theʻĪao Needle Lookout Trail for breathtaking, lush views. Stay and explore this peaceful, sacred valley for a little while. Nearby, you can visit Kepaniwai Park & Heritage Gardens and Maui Tropical Plantation, and stop in the town of Wailuku for lunch.
Drive back towards Wailea and explore some of South Maui’s golden beaches. Maluaka Beach is known as turtle town and is a good bet for seeing sea turtles and other marine life. Makena Beach is a big, wide sandy beach that is great to visit, but I’d avoid swimming here as the waves are powerful. Secret Cove Beach offers stunning views, and you can’t miss Le Perouse Bay with its dramatic lava fields.
For dinner, you have some great choices. Gather on Maui has panoramic views of the ocean, Koast offers elevated food, or Matteo’s Osteria has traditional Italian.
Day 8: Upcountry or another pool day

It’s your last full day in Maui. Start the day by going on a Hawaiian canoe experience through the hotel. Then, head to breakfast and, if you haven’t already, try a Loco Moco bowl.
The rest of the day is up to you. You could have another pool/beach day and enjoy the resort amenities. Traveling with kids requires matching their pace, and swimming always keeps them happy.
If your family is rested and up for an adventure, you could drive upcountry. The views and scenery are spectacular, and you’ll likely have cooler temperatures. There are cute towns and general stores, and you can visit farms. Check out Surfing Goat Dairy, Maui Alpaca farm, Kula Country farms, and the Maui Gold pineapple plantation. Other fun stops include Ocean Vodka Distillery and Maui Wine. You’ll be on the slopes of Haleakala, so this is also a good option if you want to hike and explore the crater.
End the night with a memorable dinner at Nick’s Fishmarket at the Fairmont as the sun sets. I recommend ordering the fresh island catch piccata for your main entree and strawberries panzini for a showstopping dessert.
Day 9: Head home

Photo: Victoria Faith Photography
Before heading to the airport, soak in Maui’s beauty with one last walk along the beach path. This might also be a perfect morning to take some family pictures on the beach.
Need to know
A week in Maui gives you the opportunity to explore a lot of the island. However, you won't be able to do it all. Embrace the laid-back Maui vibes and plan a return trip!

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Monica Hoss
Monica Hoss
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