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#DiamondStories: Hawaii Island Hopping, Part 2 – Kauai Adventures

#DiamondStories: Hawaii Island Hopping, Part 2 – Kauai Adventures

By Stephanie Allen

Media & Content Editor


There is nothing better than walking into a resort and immediately feeling at home.

If you missed our previous post, the Diamond Resorts media team recently went island hopping to showcase the best ways for members to vacation in Hawaii with Diamond. We began our 11-day adventure on Oahu at Diamond’s newest resort, The Modern Honolulu. (Side note: it’s gorgeous, you should check it out.) After three jam-packed days, we then hopped on a flight to the Garden Isle of Kauai to continue our #DiamondStories experience at The Point at Poipu.

Located on Kauai’s southern tip, The Point at Poipu overlooks the sandy shores of Shipwreck Beach and offers spacious, well-appointed two-bedroom accommodations. The grounds are secluded enough that you feel like you’ve escaped reality when there, but it’s still only a short drive to many shops and restaurants, so you aren’t giving up any conveniences.

It was overcast when we arrived, so we took our time checking in to our rooms, and checking out the newly-renovated lobby and buildings. The front desk team graciously offered to help us with our bags and the concierge made sure we were all set for our excursions. They even volunteered restaurant recommendations to ensure we hit all the best local spots, including Brennecke's Beach Broiler, which is less than a mile walk and serves up tasty seafood favorites. We tried it out for dinner that first night and were not disappointed.

After dinner, we walked around the resort, stuck our toes in the soft sand and spotted sea turtles in the rough surf, just offshore. We called it an early night and the next morning, we took the skies to explore what makes the Garden Isle, well, the Garden Isle.


Only about 10 percent of Kauai is accessible by vehicle, but there is much, much more breathtaking landscape to see. To help us get around, The Point at Poipu concierge team booked us on a helicopter tour with Blue Hawaiian Helicopters.

Driving to the helipad is a breeze. We followed our GPS to the Lihue airport and then the signs for the helicopters. Blue Hawaiian Helicopters has free parking just outside their building. Once inside, you check in – and get weighed – and are instructed to place everything except your phone and camera in a complimentary locker. You watch a short safety video and briefing, before the ground crew gives you your pilot’s name and seat location. We got lucky with the two seats right up front. Views from the backseat wouldn’t be terrible, but the front seat is definitely where it’s at.

Our pilot, Brian, flew us around the entire island, pointing out all the interesting landmarks, including the waterfalls from the Jurassic Park movie. We had incredible views of the Nāpali Coast, circled inside the crater of Mount Waialeale to see the “weeping wall” of waterfalls and flew inside Waimea Canyon. Christopher, our social media manager, was so in awe of everything, he didn’t say a word throughout the entire flight.

After touching down, we decided to drive up to Waimea Canyon for a different view of the “Grand Canyon of the Pacific.” There are several lookout points and a few hiking trailheads throughout the state park. Though we didn’t have time for a proper hike, we did stop at several of the lookouts to take pictures. The last stop provided by far the best view, but it didn’t last long, as thick rain clouds rolled in right after we arrived. (Tip: bring a rain jacket or umbrella. The weather changes quickly and we were drenched after just a few minutes outside.)

We (OK, maybe just me) had started to get a bit hangry on our way back to the resort, so we stopped at The Lanai Restaurant and Bar, which turned out to be an exceptionally cute and quaint little place. The restaurant is just a small patio, so we had a short wait, but we filled the time by wandering in the neighboring shops. We gave the hostess our phone number and she called when our table was ready.

 The food was some of the best we had during our entire trip. Christopher ordered the Miso Fresh Catch and I opted for the Steak and Potato, which was perfectly seasoned and cooked. Everything tasted fresh and the portions were hefty. It’s a good thing The Point at Poipu has a full-sized fridge and microwave for late-night leftover snacks.

The resort also has a washer and dryer, so I threw in a load of laundry when we returned for the night. It was nice knowing I wouldn’t have to pack all my dirty, rain-soaked clothes when we left.


We took the next morning at our leisure, exploring more of the resort’s sprawling grounds and amenities. Christopher woke up early to catch the sunrise and then enjoyed a hike along the Maha’ulepu Heritage Trail, which takes you past Shipwreck Beach and up a rocky cliff. I opted to enjoy a coffee and oatmeal on my patio.

We were scheduled on a sunset dinner cruise that evening and needed to be in Port Allen by 2 p.m., so we left the resort a little early to grab lunch at the Port Allen Sunset Grill & Bar, which is directly next to Capt. Andy’s – our charter for the evening. We scarfed down a couple of shrimp and fish appetizers to hold us over until dinner, and then explored a couple nearby gift shops before checking in for our cruise.

The catamaran sailboat is shoe-free, so don’t plan your outfit around your sneakers and then get upset when you end up going barefoot (ahem, Christopher). The crew had us lock away our shoes in a container until after we got back to dry land.

Originally, we were supposed to head north to the Nāpali Coast, but our captain feared some strong winds would prevent us from enjoying the ride, so we headed south, past Poipu to Kipu Kai. The water was exceptionally calm and there was only a slight breeze (we hit a top sailing speed of about 3 knots). The crew helped us spot a whale, spinner dolphins and sea turtles before serving us appetizers, and then dinner. Everything was delicious – you would never know it was all cooked on the ship!

I have to stress though, if you are at all concerned about seasickness or you know you don’t do well with motion, please take medication. Christopher took motion sickness medicine before we boarded, just in case, and said he probably didn’t even need it. A few others didn’t take any and, to put it nicely, they not only ruined their trip, but put a kink in ours, too. And once you’re out at sea, there isn’t much the crew can do to help you feel better.

Overall, we thoroughly enjoyed the sailing trip and were exhausted when we finally returned to port. We would absolutely choose to sail with Capt. Andy’s again. The crew went above and beyond to serve us and ensure our safety.


The only downside to island hopping? The packing. We spent the next morning packing our bags (again) and saying goodbye to The Point at Poipu. If you can, I recommend traveling light and taking advantage of the in-room laundry services. I had just a carry-on for our 11 days, so it didn’t take me long to get everything back together. I even had time to relax in the lobby rocking chairs our last morning, while Christopher finished getting his three checked bags together.

It nearly broke Christopher’s heart to leave Kauai – he said it was by far his favorite island that we visited – but it was time to hop.

Maui, here we come!