Hawaii Trip Guide - Maui


Maui truly dazzles with its breathtaking diversity. One moment you’re lounging on the golden sands of Kaanapali or Wailea Beach, and the next you’re navigating the lush, winding road to Hana or standing atop the mist-shrouded summit of Haleakalā. As your plane circles the island, the vibrant blues of the Pacific intertwine with the emerald hues of tropical forests and the rugged volcanic landscapes of the island’s interior. Nestled within these stunning natural wonders are luxurious resorts and acclaimed restaurants offering farm-to-table delicacies. You’ll depart with memories to last a lifetime, already plotting your return to Maui’s enchanting shores.

*Traveling from almost anywhere in the mainland to Hawaii involves a long haul; for us, flying from the Midwest to Big Island, then departing from Maui, meant enduring 12-hour flights each way. Given this, you’ll want to plan for at least a week in Hawaii, even if you’re only exploring one island. We spent 13 days visiting both Big Island and Maui, which was just perfect to really dive into what each unique spot had to offer.

Quick Guide

  • Suggested Time: 5-10 Days
  • Highlights: Trilogy Lanai Snorkeling Tour, Haleakalā National Park & Road to Hana Drive
  • Best Time to Go: March (Great Weather & Whales are still around)
  • Other good times to go: May and September (Low Crowds)
  • Highest Elevation: Haleakalā Summit 10,023′
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Vacation Packages

Hawaii is the ultimate bucket-list destination, but it’s no secret that it demands both thorough planning and a hefty budget. The best approach? Book early to catch the best deals:

  • Costco Travel: For a seamless DIY option, Costco Travel is a game-changer. We tapped into our stash of points for our trip, but our friends who joined us went through Costco and snagged a seriously hot deal. Planning ahead really pays off when you’re headed to paradise!

Value Hotels & Resorts

If you’re hitting up Maui, kick off your adventure with a 4 to 7-night stay at the vibrant beaches of Kaanapali or the serene bays of Kapalua. For those seeking top-tier resorts, the Wailea Beach Resort area won’t disappoint. And if you’re craving a slice of local life, Kihei offers a more down-to-earth town vibe.

Post-Road to Hana, which is a must, consider unwinding for a night or two in Hana to really soak in the lush, laid-back atmosphere. Despite Maui’s commercial buzz, there are plenty of stellar stays away from the mainstream hustle:

  • In Kapalua Bay/Kaanapali Beach: Our buddies snagged a spot at The Kapalua Villas Maui through Costco—talk about scoring with great pricing on spacious townhomes and killer ocean views. Another gem is the Aston Maui Kaanapali Villas, offering good value right near the beach.
  • In Hana: Check out the Hana Maui Resort. It’s on the pricier side but offers a luxe escape, and you can even book using Hyatt Points for a bit of a break on the wallet.

Maui Hotels with Credit Card Points

For a getaway to Maui and using hotel points, here are some of our top picks across major loyalty programs:

For Hyatt Fans:

  • Hyatt Regency Maui Resort and Spa: We cashed in 175K points for a 5-night stay, which might seem steep but delivered tremendous value. We enjoyed an ocean view upgrade and club access, saving us a considerable amount on meals. The resort boasts excellent pools and a thrilling water slide, and it’s ideally located right on Kaanapali Beach.
  • Andaz Maui: This is a fantastic option for those looking for a slightly quieter option. It has a trendy vibe and can be booked for 45K points a night.

For Marriott Enthusiasts:

  • Sheraton Maui Resort & Spa and The Westin Maui Resort & Spa: Both located in the Ka’anapali Beach area, these resorts offer superb facilities and can be booked for 40K-70K points per night. An added perk is the proximity to the departure point for epic Trilogy snorkeling tours next to Sheraton.

For Hilton Lovers:

  • Grand Wailea, A Waldorf Astoria Resort: This standout resort features a waterpark and beachfront access, offering a paradise for families. Last I checked, it was going for 300K points per night, which is quite high. However, if you can find a good redemption rate, it’s one of the top family-friendly stays on the island.


When planning your flight to Hawaii, we recommend using Google Flights for a comprehensive view of your options. Always aim to book direct for the simplest travel experience. :

  • Most travelers heading to Maui fly into Kahului Airport (OGG), a conveniently located but smaller airport. If you’re exploring multiple islands, consider booking multi-city flights for better deals and flexibility. There are always plenty of options to find competitive cash rates or make the most of your points. 

*On our last trip, we snagged return flights from the Midwest using 41K Avios each through American Airlines. We even stumbled upon a fantastic deal with United—return flights for just 16K each through Turkish Airlines. Unfortunately, the dates didn’t work for us, so we stuck with AA, but it just goes to show the deals are out there if you keep an eye open!

Itinerary for Maui - 6 Days

Day 1: We caught a morning flight from Big Island to Maui, hit up Costco for essentials, and checked into our resort. The day was spent unwinding as the kids reveled in the resort’s water slides and pools—a chilled start to our Maui adventure.

Day 2: We embarked on the scenic yet challenging drive to Haleakala National Park around 10 AM. Nearing the summit, the strong winds were a force to reckon with, but the breathtaking views were well worth it, reminiscent of Mauna Kea’s landscapes.

Day 3: An early start propelled us on the iconic Road to Hana. Thanks to the Guidealong App, our journey was enriched with historical insights and timely pit stop suggestions. We enjoyed multiple scenic stops, a leisurely roadside lunch, and capped off the exploration near Hana before returning to the hotel. A lengthy but incredibly rewarding day.

Day 4: Another early rise set us on the Discover Lanai Snorkeling tour by Trilogy, a definite trip highlight. The excursion to Lanai offered spectacular snorkeling straight off the beach. It was our 7-year-old’s first snorkeling experience, and he adapted like a natural! The return trip was graced with humpback whale sightings—a truly memorable day.

Day 5: After several action-packed days, we took a day to relax at the resort. In the evening, we explored Ironwoods Beach and strolled the Kapalua Coastal Trail, capturing stunning family photos at sunset—an idyllic end to the day.

Day 6: Our final day in Hawaii was packed with a visit to the Maui Ocean Center, where the Humpback 3D show at the Sphere was particularly impressive. We squeezed in a last-minute trip to Iao Valley, absorbing its breathtaking views, before bidding “Aloha” to Maui and catching our late evening flight home.

This blend of exploration, culture, and relaxation made our Maui trip an unforgettable family adventure.

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