Maui was pure magic—literally and figuratively. After a short flight, we checked into the Kaanapali Beach Resort, where nightly sunsets and the sound of the waves quickly made us feel at home. Our days were filled with memorable moments, from learning to surf at Goofy Foot Surf School (we both stood up on the first try!) to snorkeling with sea turtles at Honokeana Bay. We explored the legendary Road to Hana, hiked to waterfalls, and took in dramatic views at places like Waiʻanapanapa State Park and Wailua Falls. The Fourth of July brought an unforgettable dinner cruise with fireworks over Lahaina, and we even caught a magic show (Kupanaha) at our hotel.
The Feast at Lele was an unforgettable evening of gourmet island cuisine, mesmerizing Polynesian dance, and a breathtaking sunset right on the beach—an elevated take on the traditional luau experience.We greeted the sunrise from Haleakalā, biked down the volcano, and wrapped it all up with a beachfront meal at Mama’s Fish House. Every day in Maui brought a new adventure—from epic hikes to ocean breezes—and each one ended with the most breathtaking sunsets we’ve ever witnessed.

Itinerary

This itinerary is based on the Maui portion of our 2014 Big Island combo trip from July 1-7.

🛬 Day 1 – Maui Lei Greeting

• ✈️ 1:44 PM – 2:17 PM – Flight from Kona to Maui (Hawaiian 269)
• 🚗 Pick up Mustang convertible rental from Budget
• 🏨 Check-in to OUTRIGGER Kaanapali Beach Resort (6-night stay).
• 🌅 First sunset view of Black Rock and the island of Lana’i from the resort beach
• 🌺 Traditional lei greeting and kiss to begin our stay

🏄 Day 2 – Surf & Magic

• 🏄 Surf lessons at Goofy Foot Surf School (We both got up on the first try!)
  • 🧑‍🏫 Bonus: Group lesson turned into a private session with a great instructor
• 🧉 Personalize a tiki souvenir from a local whittler
• 🎩 Attend the Kupanaha Magic Show at the hotel (top-rated local attraction)
• 🌺 Daily ritual: pick plumeria flowers from the trees for Sarah’s hair

🤿 Day 3 – Scuba & Hula

• 🤿 Scooter scuba dive with Maui Scuba Mike
• 🌺 Take hula lessons at hotel
• 🛶 See a hand-built raft honoring a local child’s dream

🎆 Day 4 – Turtles & Fireworks

• 🐢 Snorkel at Honokeana Bay, a hidden spot full of sea turtles
• 🌺 Participate in a lei-making class at hotel and give each other leis, as tradition
• 🚢 4th of July Dinner Cruise with Pacific Whale Foundation
  • 🌅 Spectacular sunset views from the water
  • 🎆 Fireworks over Lahaina

🌿 Day 5 – Road to Hana Adventure

• 🚗 Drive the legendary Road to Hana with stops along the way.
• 🥾💦 🏊 Twin Falls (MM 2) – Easy-access waterfall with a short trail; great for a refreshing swim
• 🌿 Garden of Eden (MM 10) – Botanical gardens with stunning views
  • 🎥 Keopuka Rock Overlook – Jurassic Park filming location
  • 🐈 Meet adorable, stray cats
• 💦 🛣️ Waikamoi Falls (MM 10) – Small roadside waterfall often missed by passersby
• 💦 🐻 Upper Waikani Falls / “Three Bears” (MM 19) – Beautiful triple-tiered cascade right off the road
• 💦 🍽️ Puaʻa Kaʻa Falls (MM 22) – Accessible falls in a state wayside park with restrooms and picnic areas
• 💦 🌁 Hanawi Falls (MM 24) – Lush, dramatic falls seen from a narrow bridge
• 💦 🌁 Makapipi Falls (MM 25) – Unique view looking down into a rocky gorge from a bridge
• 🏖️ Waiʻanapanapa State Park (MM 32) – Stunning black sand beach, lava tubes, sea arches, and coastal trails
• 🏝️ Koki Beach (MM 49) – Red-hued sand and scenic shoreline near Hana, great for photos
• 💦 🏊 Wailua Falls (MM 45) – One of Maui’s most iconic and photogenic roadside waterfalls (our favorite spot)
• 💦 🏊 ʻOheʻo Gulch / Seven Sacred Pools (MM 42) – Series of cascading pools and waterfalls in Haleakalā National Park
• Optional post-Hana waterfalls that require a hike:
  • 🥾💦 Makahiku Falls – 200-ft waterfall viewable from the Pipiwai Trail overlook
  • 🥾💦 Waimoku Falls – 400-ft waterfall at the end of the Pipiwai Trail (4-mile round trip hike)

🌺 Day 6 – Luau

• 🏝️ Chill on the beach
• 🍹 Traditional luau @ The Feast at Lele

🌋 Day 7 – Volcano Sunrise & Bike

• 🌋 3:00 AM – Check-in for Sunrise Special Bike Tour (🎟️ Pre-purchase through Haleakala Bike Company, $234 total for 2)
  • 🌄 Watch the Big Island in the distance as the sun rises at Haleakala Summit
  • 🚴‍♀️ Bike down the volcano (thrilling and scenic)
• 🍽️ Lunch @ iconic Mama’s Fish House
  • 🌊 Oceanfront views and the famous Black Pearl chocolate mousse for dessert
• ✈️ 2:55 PM – 11:20 PM – Flight from Maui to Seattle (Hawaiian 30)
• 🏨 Overnight at Sleep Inn SeaTac Airport

🛫 Day 8 – Fly Home

• ✈️ 11:05 AM – 4:50 PM – Flight from Seattle to St. Louis (Southwest 289)

💡Maui Tips

• 🚗 Rent a convertible (and book early!) – A car is essential, and a convertible is a worthwhile upgrade for exploring the Road to Hana.
• 🛑 Drive the Road to Hana slowly and start early – Expect one-lane bridges (46!), hairpin turns, and dozens of scenic stops
• 🥾 Wear good shoes and bring bug spray – Many trails like Pipiwai Trail and Waimoku Falls get muddy and buggy
• 🐢 Visit Honokeana Bay for turtles – A lesser-known spot with incredible turtle sightings right off the shore
• 🧘‍♀️ Stay in Kaanapali for beach vibes and cultural activities – We loved the OUTRIGGER Kaanapali Beach Resort for its location and Hawaiian traditions
• 🏄‍♂️ Take surf lessons in Lahaina – Goofy Foot Surf School was great for beginners, and we got private-level attention in a group class
• 🌅 Don’t miss sunrise at Haleakalā – But be sure to reserve a permit/tour in advance and dress warmly. Weather can be hit or miss and there is a chance the view will be blocked by clouds.
• 🚴‍♀️ Consider biking down the volcano – A unique and scenic adventure following your sunrise visit
• 🥥 Pack snacks for Hana and don’t rely on cell service – Plan out your route and download offline maps
• 🎩 Check for shows and luaus at and near your hotel – We loved the Kupanaha magic show and The Feast at Lele traditional luau.
• 🍽️ Make a reservation at Mama’s Fish House early** – It’s popular for a reason (ranked #2 in the US in terms of OpenTable reservations), and the food + views are worth the splurge

Pictures

Here are our favorite Maui Pictures.

Keopuka Rock Overlook

Tucked within the lush Garden of Eden Arboretum along the Road to Hana, the Keopuka Rock Overlook offers one of the most iconic views on Maui. This dramatic cliff-lined vista, backed by emerald valleys and framed by the Pacific, was featured in the opening scene of Jurassic Park—making it a must-see for movie fans and nature lovers alike. The overlook perfectly captures the wild, prehistoric beauty that defines the island’s east side.

Maui and Big Island Highlights

Scooter Dive with Maui Scuba Mike

One of our most unique underwater adventures in Maui was a scooter-assisted scuba dive with Maui Scuba Mike—an unforgettable way to explore the island’s reefs with ease and speed. Using underwater propulsion scooters, we were able to glide through the ocean, covering more ground than a traditional dive while still enjoying up-close encounters with tropical fish, coral gardens, and even a curious sea turtle or two. Mike, a local legend with decades of experience, made the whole experience fun, safe, and laid-back—like diving with a friend who knows all the best secret spots. It was part thrill ride, part marine safari, and totally unforgettable.

Biking Down Haleakala

Check out our other Hawaiian blogs:

• Kaua’i
• O’ahu
• The Big Island