One of the advantages of winning a trip to Maui was staying at four resorts. It was also the disadvantage. But despite being on-the-go every two nights, our nomadic lifestyle gave us the opportunity to visit various parts of the island and discover what properties worked best for us.

Each was family-friendly but that was where the similarities stopped. Napili Kai Beach Resort was the most budget-friendly and had our favorite views. All of the accommodations at the Honua Kai Resort & Spa are luxury suites overlooking the world-famous North Kaanapali Beach. Travaasa’s experiential resort in remote Hana was dripping with beauty, relaxation and on-site activities. The Fairmont Kea Lani’s only all-suite and villa luxury oceanfront resort on the white sands of Wailea’s Polo Beach looked like it had been plucked out of a scene from Arabian Nights.

It was the best of four worlds.

Napili Kai Beach Resort

After a long day of travel and a three-hour time difference, we were exhausted when we arrived at the open-air lobby at the Napili Kai Beach Resort.  “Welcome home,” the front desk clerk’s melodic voice sang and we immediately felt wrapped in her warmth as we eagerly downed a tropical beverage.

This affordable (at least by local standards) and charming full-service Hawaiian hotel does indeed feel like home. Set on 10 oceanfront acres on tranquil Napili Bay, the area is bereft of high rises and ultra-resorts, and the 163 lovely yet unpretentious plantation-style hotel rooms and condos make it the perfect place to unwind with your family on the white-sand beach.

Napili Kai stays true to its promise “we don’t nickel and dime you,” and they had the most complimentary services of any of our resorts. The resort infuses the tradition of Aloha with activities such as lei making, creating a Puka shell necklace, building a canoe, sand art and a Mo’o (lizards) Safari. And did I mention their seasonal “Keiki Club” for kids ages 6-10 is complimentary and that kids stay and eat free?

When we weren’t eating at the glorious beachfront restaurant the “Sea House” or playing in the four small swimming pools or 18-hole putting green, we were on the beach. Renowned for its tranquil waters, Napili Bay is perfect for snorkeling and stand-up paddleboarding. My husband realized he had brought only his fins and not his mask and snorkel (a minor oversight) and we were delighted to learn the Activity Center had complimentary loaners for guests. Too bad we weren’t really home.

Prices start at $280. Address: 5900 Lower Honoapiilani Rd, Lahaina, HI 96761. (808) 669-6271

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 Honua Kai Resort & Spa

Polished. Beautifully appointed. These were my first impressions as we entered Honua Kai’s  stone entryway. Grandparents, parents and kids roamed the lush tropical grounds, testifying that this newish property that was completed in 2010 is an ideal multi-generational gathering place.

So, what is the draw? This resort on famed North Kaanapali Beach is comprised of 628 spacious studio, one, two and three-bedroom suites that range from 595 sq. ft. to 2,650 sq. ft. If you’ve traveled with kids you know just how convenient it is for everyone to have their own space and private bathroom. Our condo had a partial ocean view overlooking the islands of Molokai and Lani with the West Maui mountains looming in the east and it was tough to drag ourselves from our glorious open-air deck.

At Honua Kai, each living space has a professionally-equipped gourmet kitchen with high-end Bosch appliances so we were able to save money by preparing most of our meals in our room. But if we’re being truthful here, as a mom, I most appreciated our in-room washer/dryer. It was a relief to throw in a couple of loads of laundry after five  days on the road.

Beyond the rooms (if you can drag yourself outside), the manicured 38-acre grounds offer an Aquatic Playground with three spectacular pools, a waterfall, waterslide, children’s play area, four hot tubs and water slides. Beach and pool items like boogie boards, snorkel gear, pool floats and rafts are available to purchase or rent by the hour, day or week.

And then just steps away is Kaanapali North Beach. As one of the most famous beaches in the world, the north section is actually less crowded than its southern counterpart. We spent an entire afternoon jumping waves and whale watching but skipped the snorkeling due to the unprotected, snarky waters.

One morning, I arose at dawn to go for a run along the 1-mile Ka’anapali Beachwalk that starts at the Hyatt Regency Maui Resort & Spa and stretches to Pu`u Kekaa (Black Rock) at the Sheraton Maui Resort & Spa. Cut through the Sheraton and the pathway will keep going for another 2 miles, the perfect way to explore this famous coastline.

Suite prices start at $324 and beachfront condominium residences are available for purchase. 130 Kai Malina Pkwy, Lahaina, HI (808) 662-2800.

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Travaasa Experential Resorts, Hana

If you’re planning to navigate the gorgeous yet precipitous 52-mile road to Hana, do yourself a favor and spend at least one night to thoroughly explore the area. But there’s a complication: Hana has very few hotels, most of which aren’t family-oriented. After an extensive search on VRBO.com, I ascertained the majority of the vacation rentals either required a minimum two-night stay (we only wanted one) and many of those properties banned children (the opposite of kid-friendly).

Though a friend recommended AAA Four Diamond Hotel Travaasa, when I called to inquire, I was dissuaded from coming because “we only cater to families seasonally” and our late-February visit was apparently not in season. I understood, really I did. Travaasa focuses on a renewal of body, mind and spirit through five different à la carte pathways: Adventure, Culinary, Culture, Fitness and Spa & Wellness and having hooligan kids takes away from the luxe resort.

But I booked it anyway. This boutique resort is made up of 70 plantation-style cottages and suites on Maui’s picturesque eastern shore Kaihalulu Bay (though most of the property is not ocean-front). Our queen suite was spacious, underwhelming in its amenities yet elegantly simple with a memorable sitting area overlooking the golden fruit palm tree-framed lawn.

At sunrise, I hiked the 1-mile trail across the street to Fagon’s Cross with views of where the mountains meet the sea’s rugged black lava in a wet and wild world and the summit smelled like a plumeria garden. Back at Travaasa, we played at the Makena Center for hours, which could have extended into days. In addition to the tennis courts and a pool, the activity center offered plenty of free options including sand toy checkout, bikes, Frisbees, snorkel gear, boogie boards and my kids had their first real golf experience on the 3-hole pitch and putt golf course. 

The center also prides itself on authentic Hawaiian pursuits such as lei making, hula, snorkeling, throw net fishing, opening a coconut and garden tours. My kids took a ukulele lesson and after only an hour they not only learned basic chords but how to play “You Are My Sunshine.”  Staffers Doug and Andrew delighted us with stories of Hana’s history and natural resources

Travaasa felt like the real Hawaii, far away from the tourist traps and despite the original pushback I felt, we were delighted and entertained. Really, the only negative parts to our visit were the weather (it rained for part of the time) and sheer exhaustion at repeatedly picking our jaw off the ground at Hana’s grandeur.

A la carte prices start at $400. Address: 5031 Hana Hwy, Hana, HI.

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The Fairmont Kea Lani, Wailea

Growing up in Canada, the Fairmont Hotels and Resorts are renowned for being among the country’s most iconic. The Fairmont Banff Springs Hotel. Fairmont Chateau Lake Louise.

This Canadian-owned hotel chain now operates in 19 countries and I was thrilled to finally stay in one of their properties. We saved the Fairmont Kea Lani for the last two days of our trip and it was the perfect way to go out in grand style.

Wailea, on the leeward side of South Maui, is renowned for its luxurious beachfront resorts and the Fairmont Kea Lani on Polo Beach has a prime location. As Hawaii’s only all-suite and villa luxury oceanfront resort, you’ll find 314 spacious one-bedroom suites and 37 private two and three-bedroom villas.  Translation? Every room at the hotel is a suite and has a 150-300 sq ft lanai (balcony) that is perfect for families. When we checked in, we were outfitted with fragrant leis and Hadley and Bode also received a turtle/whale necklace or a sand bucket with a shovel.

“Kea Lani” means “white heaven” and the resort looks like a dreamy escape you’d find in Casablanca. Despite its pomp and circumstance, we were delighted it was extremely kid-friendly on 22 acres of lush tropical landscape with two fantastic activity pools connected by a 140-foot waterslide, various beach activities and an adults-only pool where my daughter observed that “no one is ever in the water,” proving that grownups don’t know how to have fun.

Except for when it comes to exploring Wailea’s 1.5-mile Coastal Walk.  One morning, there were plenty of adults having the time of their lives watched the hump backs at dawn on this beautiful oceanfront trail that runs from Polo Beach to Keawekapu Beach.

Hands down, our favorite activity was the Hawaiian Canoe Experience. Complimentary to guests ages 10 and over (though be sure to book early because it fills up), my daughter and I become like the Island’s seafarers of yesteryear as we learned the basics of paddling, native chants and then set out on an adventure in our 6-man outrigger canoe. During our hour-long adventure, our two guides led us into the ocean where we grabbed some snorkel masks, jumped in and reveled in a gorgeous coral reef teeming with Nemo’s buddies.     

The Fairmont Kea Lani also offers Keiki Lani, a kids club for ages 5–13 with daily seasonal programming with gems like erupting volcanoes, crafting sandcastles, feeding koi fish and painting coconuts. The resort also offers the “kids eat free” program for children five years and under at their three restaurants. Their fine-dining Kō restaurant’s Hawaiian, Chinese, Filipino, Portuguese, Korean and Japanese  cuisine was awarded Best Restaurant of the Year 2013 in Maui No Ka ‘Oi Magazine.  The keiki (kid) menu is divided into two sections: recommended for kids under 7 and children ages 8 to 12 with delicious dishes like Huli-Huli Grilled Chicken Fajitas and the Caterpillar Roll (vegetable sushi).

 Prices start at $599. Address 4100 Wailea Alanui Dr, Wailea, HI 96753 (808) 875-4100.

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Join us on our week-long journey to Maui! In case you missed them:
Maui Family Travel–Your guide to 7 days in paradise Days 1 & 2
Maui Family Travel: Days 3 and 4 in the Glorious Upcountry and Beach Bums
Maui Family Travel: Days 5 & 6 The Road to Hana and Maui’s Best-kept Secret
Maui Family Travel: Day 7’s “Sunny” Wailea and a Luau Farewell