Maui: everything you need to know for a stylish family vacation


Maui family vacay

Stylish globe trotting with small shouty kinder seems like The Amazing Race for the delusional, right? Wrong. So many shades of Chanel lipstick wrong.

As a die-hard beauty and style aficionado plus a mum-of-two our recent family vacay to the USA starting in Maui had to checklist the chic with the realistic. Doing the hard* (not considered technically a “hardship”, like, say breaking rocks in the hot sun) travel research yards before wheels up meant a 100% post-trip rating by all sized/aged travellers. Read on for the stylish family intel on what to see, where to stay, get beautified, standout shops, and must-eats in show stopping Maui.


Hawaiian Airlines do a good line in direct flights ex Sydney to Hawaiian entry point Honolulu. On disembarking in aloha airport, don’t let the ‘70s heavy wood, concrete and stained carpet stylings confuse you into thinking the rest of your holiday will be similarly décor deficient, airports are never good indicators of a country’s holiday destination potential. Except Singapore. The airport there is exactly like the rest of the country – your luggage arrives at the carousel before you do. The rest of your stay will be just as efficient. Anyway Hawaii. So long as you don’t get arrested at Customs in a case of mistaken identity like the husband did (true story) you’ll skip through the airport quick sticks onto the short Maui flight.

Chanel Airline Spring 2016, Image: into the gloss
Chanel Airline Spring 2016, Image: into the gloss


There’s lots to see on Maui and freeway walking with small hangry children is not the Prada way to see this fine island. Collect your up sized hire car and drive directly to Wailea.

You’ll know you’ve arrived in this ‘hood by the luxe markers. One minute it’s all ugly freeways and pick up trucks, the next minute a group of angels emerge in front of your car playing soft welcome music. Kidding. Sort of. The freeway does suddenly turn from pot hole heavy, greenery-free to a perfectly smooth ride flanked by beautiful manicured bougainvillea filled gardens, towering palm trees and sandy beach vistas… Aloha!


If I was in the all the single ladies/gents or loved-up couple genre I’d save my pennies and stay at the Four Seasons Wailea. The location on Wailea beach is worth the $$$$. For the luxe family stow your Vuitton at the Ho’olei Villas. Book an ocean deluxe for a top-notch view of the perfect tropical island sunset.

Décor varies, ours was upscale dark designer wood over two levels with three bedrooms, 3.5 bathrooms, marble kitchen and dreamy view. The complex is rounded out by a drop-dead gorgeous pool, plus excellent gym and sauna.

The Ho’olei Villas are part of the Waldorf Astoria Grand Wailea Hotel, which is a short hop across the road. The best thing about the villas (apart from everything) is you have access to all the bells and whistles of a five star resort (spa, gym, restaurants, shops, shaved ice cart, water slides, beach service), without the small hotel style room situation. Also, stunning Wailea beach is a tiny five-minute walk through the Grand Wailea Hotel.

Grand Wailea Maui. Image: panoramio
Grand Wailea Maui. Image: panoramio


As any glossy gal worth her salt scrub will agree there’s nothing like international air travel to add approx. 100 years onto the visage and physique. Naturally the best way to get back to social media sharing hotness, cough, I mean relaxed holiday mode, is to immediately hit the spa. Not the heated pool version popular with couples who key swap, but the life essential pampering variety for card carrying members of the glossy gang*. (*No, I don’t have an “application form” for the glossy posse gang. It’s metaphorical.)

Spa: I booked into the Grande Spa at the Grand Wailea Hotel online prior to wheels up. At villa check in our pre-booked items were helpfully printed out. Good thing too, the husband saw in clear black and white that I was required to present myself at the spa within approximately 25 seconds of check in.

The spa service menu is extensive covering everything from your standard Swiss massage to facials, body treatments, blow outs, and mani/pedis. Word on the zen street is it’s currently undergoing a refurb but they’ve set up temporary shop in the resort chapel, giving it the liturgical tick of approval. Amen to that.

Treatment time: My miracle cure of choice was a Sugar Cane Exfoliation and Deep Tissue Massage. The spa staff encourage early arrival for your treatment so you can enjoy the spa’s hydrotherapy pools prior. Top tip? The hydrotherapy pools are gender specific and swimsuit optional. Opt in. And take a spare suit because spas love watery treatments (style sidebar: those disposable one-size-fits-no-one spa underwear are style nemesis numero one, avoid like you would polyester).

Verdict: The salt scrub and massage turned the airplane pudding skin into bikini ready smoothness. Also it completely alleviated jet lag. A+ on the spa scorecard.

Spa for kids: The spa also offers cute-as-pie kid services, one of my kinder had a kid-specific manicure, which she told me after was a highlight of her life, #makingdreamscometrue.

Retail therapy: The spa boutique is well-stocked with the skin/hair goods. I discovered a completely fab pre-blow dry heat protecting product, Perfect Blowout Cream from Alterna’s Caviar hair range which is a frizz-free style saver.

Off piste: If you feel like going further afield to find your bliss, head to the super luxe Spa Montage at the Montage Resort Kapalua Bay for a signature Hawaiian Lomi Lomi massage then float down to stunning Kapalua Bay beach for a dip, sun ray catch or a sandy stroll.


Water water everywhere:  Layer up on La Prairie 50+, Gucci shades and Pucci hat, the sun has serious wattage in these parts. Walk over to the Grand Wailea, collect towels, hit the soft Wailea beach sand – the resort beach boys will set your lounges and umbrellas shore-side. After saltwater good times, hotfoot it to the pool at the Grand Wailea. All slide sizes on site, a swim up bar, poolside catering service, and if you’re feeling flush book a cabana at $350 USD for the day. It comes with shade and a, er, safe, in case your bikini comes with large wads of cash and serious bling.

High-end hands free: Book the kids into the super swish and fun Grand Wailea kids club The Rock (or The Spot for teens, which is less kids club more cool chill lounge), then choose your own adventure: hang 10 on the beach, get a surf lesson, take a dip in the grown ups only pool, lunch long it at one of the many dining options (we loved Bistro Molokini)… you’re welcome.

Hula how-to: The evening Grand Luau at The Grand Wailea is kitschy buffet, two words not usually in the glossy vocab. But the sunset was one-of-a-kind wonderful, and the kinder loved it, especially seeing the cooked pig brought out of the ground and the hula how-to. Worth the cringe factor.


The big blue:

Maui is bounded by one of the most beautiful ocean areas in the world, it’s a must-see. The stylish (and turbo) family option is the Molokini Express by Kai Kanani Sailing Co.. Check in is 6am at the Makena Beach Resort for a 6.30am cast off. It’s an “express” so you’re on/in water for under two hours and will be back on the beach by 8.45.

The Makena Beach Resort is a short drive from the Ho’olei Villas and at that early bird hour the in-house Starbucks is a beacon for the bleary eyed. If you have the stamina, bypass it, the charming boat crew serves piping hot beverages and gourmet breakfast on deck.

Style sidebar: wear your swimsuit plus a warm sweater. Boarding is from the beach, not a jetty. The handsome sailor types will get the boat as close to shore as possible, but you still have to wade through the water to climb on. The sweater is to wear between the two Molokini Crater snorkeling locations, and it’s pretty nippy motor boating between dive ins.

The fine print: they have flotation devices for the less strong/little swimmers. Our game four year old wore a flotation belt and hopped a boogie board which I towed her on while I checked out the sea deck below. Which was fish, coral, giant turtles. Lots of cool sea life stuff.

Molokini Reef Maui
Molokini Reef Maui

Racquet club: Tennis anyone? Hit the Wailea Tennis Centre for fabulous courtside or on court action. It’s a 10-minute walk from the Ho’olei Villas, and on the day we played, the court beside us was packed with ladies-who-lunch dripping in diamonds, titanium blow dries, and killer backhands. Surrounded by lush beautiful gardens, the pretty surrounds (and hilarious tennis neighbours) made us all play better. Racquet and ball hire available.

Tee up: For the golf enthusiast, three stunning championship courses are within five iron throwing distance of the Ho’olei Villas but for a super sonic fun variety tee up for mini golf at Maui Golf Sports Park. It’s about 20 minutes drive, has two x 18 holes and is an all ages ‘80s good time. The semi-pro golfer in our group came dead last, despite informing us “a good score keeper beats a good player any day.”

Go to town:

The town of Lahaina claims bragging rights as the Kingdom of Hawaii’s capital many eons ago. It carries the trademark old timey architecture and landmarks to prove. Set your GPS to Front St, do the speedy signposted walking tour, followed by an essential I Scream for Ice Cream segue into Maui’s top gelato joint, Ono Gelato Company. Eye-poppingly good gelato is house-made each day, plus cold brewed coffee and brownies straight out of the oven. Still sweating? Cool down with the national Hawaiian dish of shave ice from Ululani’s Hawaiian Shave Ice.

Ululani's Hawaiian shave ice Maui
Ululani’s Hawaiian shave ice Maui

Lots of stylish beachware and made-in-Hawaii gear to purch from the Front St retailers. Breakout discovery? Maui Wood, a local brand making über chic wooden sunglasses, light as a feather and designed to float on water. Genius.


Lahaina’s style scene covered, onto the retail promised land of Wailea. Set your on-trend Valentino gladiator sandals a five-minute walk from the Ho’olei Villas to the aptly named The Shops at Wailea. It’s a sleek open-air mall with brands like Gucci, Prada, Louis Vuitton, BCBGMaxazria, and Tiffany and Co. on deck. Stock up on cocktail frocks, rocks, bags, and heels. It also does a solid line in American basics like GAP, Banana Republic, Tommy Bahama, and if you’re thinking a new bikini for each day on the beach (no judgment), hit cool surf brands Quicksilver, Billabong or Ripcurl.


Babysitters club: Before we chat good eats, let’s settle the should we/shouldn’t we take the small family members out for dinner question. Whining is not glam dining. Avoid by outsourcing to the experts. The Ho’olei Villa concierge booked fab babysitting from the premier Maui nanny agency. The kids loved staying in, we loved going out. Win-win.

Cool crowd and cuisine: SpagoMust eat here. It’s at the fashionable Four Seasons (five-minute walk from the Ho’olei), has swank interiors, a seasonal-produce driven ethos and shows strong drinking game for pre or après dinner cocktail sipping.

Spago Maui
Spago Maui

#IheartItalian: Matteo’s Osteria. This cute continental cucina is a five-minute drive or 15-minute walk away in the Wailea Town Centre. The reviews on Trip Advisor were solid gold for the food and they spoke the truth. Delish traditional Italian garlicky, tomato flavours in a busy, buzzy urban vibe space. The service at the start was loose but picked up after appetizers for a completely fabulous, delicious evening out.

Catch of the day: Humuhumunukunukuapua’aThis lobster-led restaurant with the longest moniker on the planet (named for the state fish) at the Grand Wailea is firmly on the luxe to-dine list. It’s over water, ocean side, thatched roof Hawaiian style and serves up serious seafood tastes. The lobster is Fresh (yes, capital F), they take you to the net (cage? No pretty way to say it) area where they’re caught and you select your dining lobster date. It’s got a roof but otherwise it’s open-plan, as in, open to the elements. Wear repellent and bring a torch.

Food supplies cupboard: We had a grocery delivery done by the fab Ho’olei Villa staff prior, they can stock for your entire stay, but if you’re happy to DIY for weekly snack attack, breakfast eats etc., there is a good foodie fill up station option. I understand supermarkets exist outside Wailea but word is they’re not pretty so avert your eyes and your wallet. Instead head to The Market by Capische, a 10-minute drive from the Ho’olei Villas at The Gateway Centre. It stocks homemade pasta, artisan bread, cold pressed juices, house-made pastries, and meat you might actually want to eat (think wagyu steaks).


No glam travel guide would be complete without an action plan for staying in the svelte zone. The gym at the Villas is suitably stacked, but dial up the sweat-o-meter via a personal training sesh or two at Reps Training Centre in the Wailea Town Centre (near Matteo’s Osteria Italian). State-of-the-art equipment compliments state-of-the-sweat trainers. My trainer, Mark, took me through my paces until I had no more pace to give, while also providing excellent commentary on his side gig treading the Hollywood boards (he was in A-list flick Just Go With It).