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#DiamondStories: Hawaii Island Hopping, Part 3 – Maui Magic

#DiamondStories: Hawaii Island Hopping, Part 3 – Maui Magic

By Stephanie Allen

Media & Content Editor

After spending 11 days island hopping in Hawaii, the Diamond Resorts media team couldn’t say goodbye.

Instead, we said “a hui hou” to Hawaii.

Throughout our journey, we showcased what it’s like to vacation in Hawaii with Diamond Resorts, providing members with tips and excursion recommendations to help them make the most of their next adventure.

We began our journey on Oahu at Diamond’s newest property, The Modern Honolulu for an unforgettable opening event featuring a concert by Diamond Celebrity and country music star Colt Ford. We then hopped to Kauai for a stay at The Point at Poipu to fly and float around the Garden Isle.

Finally, we finished our trip at Ka’anapali Beach Club on Maui.

Our social media manager, Christopher, disagrees, but Maui was my favorite stop on our hop. (He enjoyed our stay on Kauai best.) Located just minutes from historic downtown Lahaina, Ka’anapali Beach Club doesn’t have the same chic aesthetic as The Modern Honolulu, but it offers a comfortable, homey feeling. I honestly could see myself living at the resort. Side note: the one-bedroom accommodation is actually bigger than my one-bedroom apartment in Las Vegas. And Christopher’s two-bedroom unit was massive. It could easily accommodate a family of six or more.

We stopped by the ‘Iao Valley State Park on our way to the resort from the Kahului Airport. There’s a $5 entrance fee, but once inside, you have access to several short hiking trails and spectacular views of the ‘Iao Needle. The green-covered rock formation stands 2,250 feet above sea level and was once used as a natural alter. In addition to spectacular views of the lush landscape, the park has historical meaning, as the site where Maui’s tribal army lost to King Kamehameha I during the Battle of Kepaniwai in 1790.

After about an hour of exploring, we drove to The Mill House for a unique dinner experience. The carefully crafted restaurant is located on a historic plantation and embodies the true meaning of farm-to-table dining. You are literally overlooking the farms where your food comes from. Our waitress even pointed out a group of cows on a farm that my burger came from, which is a little creepy when you think about it.

We made it to the resort just in time to catch an unbelievable sunset that filled the sky with bright pink and purple hues. It was by far the best sunset we saw during our trip – possibly the best sunset I’ve seen ever.

Checking into our accommodations was breeze, and once again, the concierge team made sure we were all set for our exciting adventures. First up: snorkeling.


Early mornings were definitely the theme throughout our trip.

We were up and at ‘em by 6 a.m., heading to the Calypso boat slip at Maalaea Harbor for a half-day snorkeling trip at Molokini Crater. Check in was quick and included taking a cheesy photo in front of the boat. The crew then helped us find two open seats and directed us to a spread of breakfast pastries, fresh cut fruit, coffee and juices.

It was overcast and cool, but we enjoyed being out on the water. And the fish didn’t seem to mind! We spotted numerous different, brightly-colored species, including parrot fish and a massive eel.

After about an hour in the water at Molokoni, we re-boarded and moved to a second snorkeling spot dubbed “Turtle Town.” It wasn’t a town in the traditional sense – we were still in the middle of the ocean – but the spot definitely had turtles! We spent another hour or snorkeling there and checking out the sleeping giants. The crew provided us with a simple barbecue sandwich lunch and after Turtle Town, opened up the bar for drink purchases.

Of course, just as we started heading back to harbor, the sun made a glorious appearance. It provided just the bit of warmth we needed to combat the chilly sea breeze.

We decided to stop by downtown Lahaina on our way back to the resort. The historic streets are lined with shops and restaurants. We grabbed an ice cream cone and wandered around for a bit, taking photos by the massive banyan tree. Tip: Though Lahaina is beautiful during the day, it’s even more breathtaking at night, filled with twinkling lights and the sounds of live music from various restaurant performers. We spent our night back at Ka’anapali Beach Club, with dinner poolside at the O’hana Bar and Grill. We again called it an early night for an even earlier wakeup call the next morning.


We were so tired (pun intended) of our alarms going off before sunrise that on our second day in Maui, I accidentally told Christopher to meet for our tour 30 minutes too late. I realized my mistake about two minutes before our tour bus was scheduled to pick up us from the resort. I repeatedly called Christopher until he answered, only to learn that he had just stepped out of the shower. Needless to say, he wasn’t too happy with me that morning. But we rushed and made it outside only a few minutes behind.

We were on our way to conquering the Road to Hana.

And boy were we glad we didn’t attempt to drive it on our own. Our Valley Isle Excursions tour guide knew the road by heart. He knew what curves to slow down for, where to watch out for tourists and how to safely drive the highway in a way that made our ride as enjoyable as possible. Super important tip: if you get even the slightest motion sickness, take preventative medication. It is was a full day trip = sunrise to well after sundown – and it would be miserable if you weren’t feeling well for it.

The tour technically started before Hana Highway with a continental breakfast at a golf course in the middle of Maui. One word: coffee. We recommend filling up and using the restroom before leaving, as it was a decent drive before we hit a stop with proper facilities and snacks. We did stop at a small stand halfway to Hana (aptly named Halfway to Hana) that sold the best banana bread we’ve ever eaten. It stayed warm for more than hour! We’re not ashamed to admit that we each ate a whole loaf…before the end of the trip.

Valley Isle’s tour buses are small, yet comfortable and feature massive windows to ensure great views from any seat. Our driver had several stops planned out, including several waterfalls, a black sand beach and botanical garden. Christopher, an avid plant lover, was like a kid in a candy shop at the garden. I practically ran from the bus to the black sand beach, flinging off my sneakers and sticking my toes in the water. If you’ve never been to one of Hawaii’s famous black sand beaches, they’re different than I expected. The sand is thick, but extremely soft and provides an excellent contrast for cool photos.

We hit traffic just past Hana, which put our tour about an hour behind schedule. We didn’t get back to the resort until after 8 p.m. Exhausted, we grabbed a snack from the on-site gift shop and retired to our rooms for the night.


At least the sunrises in Maui make up for the early mornings. We had breakfast by the pool and then drove north, up the coast to Nakalele Point to see a natural blow hole. It’s a short, fairly steep hike down to the hole, which formed naturally and can shoot seawater 20 feet or more into the sky. There are numerous handmade signs on your way down, warning you to stay away from the hole. It’s incredible to watch, but can be extremely dangerous. On your way down, you may also notice several handmade crosses and memorials, as yet another reminder of the ocean’s true power.

We stopped at a few other lookout points and grabbed fantastically fresh smoothies from a food truck parked across from the Honolua Bay. We walked through the jungle to the bay, which is known as a great snorkeling spot, but that morning the water was churned and murky. We spotted roosters and feral cats, and took pictures of massive trees.

Back at the resort, we got cleaned up and dressed in our best Hawaiian-themed clothes for the resort’s weekly luau, Huaka’i: Journey through Polynesia.

A few drops of rain during dinner didn’t stop our fun. The resort staff handed out colorful ponchos and continued with the show as planned. And we were sure glad they did. The performers were spectacular and had a few tricks to keep everyone engaged. Tip: when they ask for volunteers to come on stage, nominate whomever you are with. Christopher was unwillingly voluntold to participate and that moment, watching him try to hula on stage, was one of the best moments of our entire trip.


We didn’t want to leave. Hawaii had become like a second home to us. The dedicated Diamond Resorts team members we met at each of the resorts had become like family.

After 11-days in Hawaii, we had fallen in love with the island state. We can’t wait to return to island hop some more with Diamond Resorts. 

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