Vacationing in Maui at Wailea Beach Resort- Marriott & Tropical Destination Outfit Inspiration

Hawaii is without a doubt, my happy place. Italy pulls at my heartstrings too, but because we’ve vacationed in Hawaii three times now and because frankly, I feel like Hawaii doesn’t get enough recognition for its honest-to-God magic, I’m officially proclaiming the tropical and oh, so lush group of islands my happy place.

Chris shares my sentiments. In fact, he may even be more obsessed.

Wailea Beach Resort's beautiful "backyard"

Both the first and the second time we visited Hawaii, we stayed on the island of Oahu. Truthfully, that island is crazy diverse with so much to see and do, we felt we had to go twice to really see and do it all. But this time around, we were yearning for a more relaxed, resort kind of experience- with some adventures spread out during our week’s stay. So naturally, we picked Maui.

Black bikini top, Abercrombie & Fitch. High-waisted bottoms, Forever 21. Yellow Tassel earrings, BaubleBar

It didn’t take a lot of research to decide on Wailea Beach Resort. This lavish Marriott property has it all. Starting with the restaurants. The resort’s signature restaurant, Humble Market Kitchin, provided us with the very best dinner we had on the island (and that includes Mama’s Fish House, which did live up to the hype). Between the panoramic view of sunset on the Pacific and the Szechuan Spiced Baby Back Ribs (Good God, those meaty, fall-off-the-bone ribs), we were in culinary and ambiance paradise.

The resort’s poolside restaurant, Kapa didn’t disappoint, either. Their poke and fish tacos were stand-outs as the fish was so fresh, it had likely been caught that very day. The cocktails were everything you could desire in a tropical adult beverage too.

Blue cold shoulder dress, Urban Outfitters. Tan thong sandals, Tory Burch. Floppy hat, Nordtrom. Blue aviators, Ray-Ban.

The Wailea Beach Resort also came complete with two beautiful infinity pools, an elaborate kids pool (with giant twist-y slides that Chris and I totally indulged in), gorgeous native landscape everywhere you looked, and a gym along with class offerings, like morning yoga by the ocean, which Chris dragged me to, promising it’d rejuvenate us after too many Mai Tais the night before. He was right. In fact, it was one of the better yoga classes I’ve ever been to.

Cream crochet cover-up, Urban Outfitters. White bikini with leather hardware, Vix Swimwear- similar here. Starfish clip, similar here. — Cream crochet cover-up, Urban Outfitters. White bikini with leather hardware, Vix Swimwear- similar here. Starfish clip, similar here.

I could go on and on about the Wailea Beach Resort- Marriott but, I want to tell you about our adventures. You’ve probably heard of the Road to Hana. But has anyone given you the details on this long and windy road trip? Ok, so...locals and tourists alike will tell you all about the Road to Hana but not about the road back. That’s because the road back, aka, “backside of Haleakala” includes a 10-mile stretch of a rocky, unpaved, and unmaintained cliffside road. But guys, it is worth it. However, if you’re too worried about the rental car, you can always book a tour, which includes the road back as well as some serious peace of mind knowing that you won’t have to endure any of the driving.

Sceneic stop on the "back road" from Hana. — Sceneic stop on the "back road" *from* Hana.

The road back is actually so much sweeter than the road to Hana. Because while there are lots of exploration opportunities on the way to Hana (hikes, waterfalls, etc.) there were only two that felt especially memorable. The enticing black sand beach - Waianapanapa State Park, is pretty incredible with its lava caves, ocean arches, blowholes, and of course, pure black sand, which gives quite the contrast to the clear, turquoise waters. You’d be silly to miss out on this stop.

Black one piece swimsuit, Urban Outfitters. Similar here.

After Waianapanapa State Park, you have another hour until you reach the grand finale - the “Seven Sacred Pools.” At this final stop before returning home, you’ll enjoy an awe-inspiring 4-mile round-trip hike through the most magical bamboo forest you could ever dream of and at the very top, feast your eyes on a 400-ft. waterfall that makes way for the seven pools down below, which are supposed to offer an experience of a lifetime (unfortunately they were closed when we were there).

Now, you can double back on the same road or take the road less traveled. We chose the later, even if it did give Chris a near heart attack a couple of times. The scenic road back is just, breathtaking. Views of the Pacific from sweeping cliffs, picturesque and untouched “Old Hawaii” cattle ranches with the Haleakala crater lurking so enchantingly behind it all, we were beside ourselves as we marveled at all of the beauty surrounding us. Quite honestly, it was the highlight of our trip.

In addition to Hana, we also took surf lessons from Surf Club Maui, which was another vacation highlight. It had been 4 years since my first surf lesson in Waikiki and while Chris has surfed on his own several times since, I’ve been hesitant. But I must say, the semi-private lesson in Maui was all I needed to gain much confidence and also, motivation to get on the board back in Los Angeles. I got up more times than I can count and was loving every minute of the adrenaline-pumping rides to shore.

Banana Palm Dress, Show Me Your Mumu. Pink Tassel earrings, BaubleBar.

For the final evening in Maui we treated ourselves to a sunset sail via Kai Kanani sailboat charters. Wow, what a way to end our vacation - these guys pulled out all the stops. Definitely the most extravagant sail I’ve been on, the crew really took care of us with non-stop service of drink refills from the full bar, music from a talented ukulele player, and a glorious spread of delectable snacks. We couldn’t have ended the trip in a more perfect way. All the frills, all the bells and whistles...I highly suggest sailing with these guys if you desire some serious R&R and VIP treatment.

Maxi Dress, Flying Tomato - similar here.

And that’s all, folks! Truth- I actually hate the word, “folks” but it seemed appropriate just then. We definitely left some activities for next time, namely, exploring the Haleakala crater. But all in all, we felt accomplished, and most importantly, relaxed after our week in Maui.