Where To Stay in Kauai

They say opposites attract. My husband is a thrill-seeker and I’m happiest with a book in hand. So when it came time to choose hotels in Kauai, negotiations were in order.

“I put together a list of the best places to stay in Kauai,” I said, gesturing for my husband to come join me at the kitchen table to review a list of luxury resorts on the Island.

“Let’s stay in a dump,” my husband suggested, taking a seat next to me. “Let’s just camp,” he continued. “Let’s get one of those VW rentals and camp on the beach. You’ll love it.”

That last part was because I’d never camped with him. I was a skilled glamper, having stayed in a retro RV park surrounded by vineyards in the Willamette Valley, an eco-resort in the Belizean jungle, and an eco-lodge in the Canaries. But any camping I’d done had been in my youth, when the sleeping bags were thin, the ground was jagged, and my unrequited love for the boy in the next tent kept me up at night. Not to mention my need for a warm shower, a ledge for my contact lens case, the list goes on. My husband practically grew up in the wilderness of Central Oregon, but over the years I’d warmed him up to the softer side of life: plush pillow menus, couples' massages, balcony views…or so I’d thought.

“I’m not just going to lay around on a beach all day,” he went on, “I want to hike, go on a boat trip, snorkel, I don’t just want to sit around in a built up resort.”

He was right. Even if my perfect scene involved drinking a frozen cocktail out of a pineapple, I knew I could only spend so long on the beach when there was an entire island to explore. 

I sat quietly for a moment, surrounded by guidebooks, two laptops, AFAR magazine, even Pinterest queued up on my phone. I weighed my options.

“We have eight nights and the Island’s not very big,” I began. “Let’s start up north. I’ll take a look at beach camping permits for a few days, and if not I’ll find an Airbnb. We can hike the Na Pali Coast, wander around the beaches and shops in Hanalei Bay, find a boat tour, go horseback riding—maybe even kayaking—and slowly make our way south,” he was nodding his head, “where-we-can-stay-in-a-resort-for-the-second-half-of-the-trip.” I slipped in.

It was a compromise. If the first part of our trip was all about adventure, the second half was all about luxury. 

A Hotel Tonight Flop

Although I am an avid planner, sometimes having no plans is the best plan (and sometimes it’s not). When we arrived in Kauai, we knew we were headed north. There were no campsites available (darn!), so we decided to travel north until we found a place we’d like to stay. We noshed on fish tacos and wandered along the beaches near Anahola.


It was a gorgeous day, sunny in the high 70s, but it wasn’t long before we were exhausted and ready to find a place to lay our heads. I searched hotels in Princeville and Hanalei, two towns we were fast approaching as we headed north on route 56. Using TripAdvisor and HotelsTonight, I landed on Hanalei Bay Resort. There were a few less expensive options in Kapa’a, but it meant we’d have to turn around.

I completed the transaction for a one night stay at Hanalei Bay Resort on HotelsTonight. Big mistake. Given my hotelier background, I know that direct bookings are always the way to go. But something about the convenience of the app and the sense of urgency (1 room left!) caused me to book via the online travel agency (OTA).

OTAs have become a dirty word in the hotel industry: they claim to have the lowest rates when in fact booking directly with a hotel will often get you the best deal (if a hotel is managing its occupancy effectively). Hotels have gotten wise, and often limit their inventory to their lowest quality rooms, reserving their best for guests booking direct. The OTA guest tends to be deal-seeking without loyalty to any particular brand or hotel and less likely to become a repeat customer. 

Our fate was sealed as we walked through the stunning resort, passing the beautiful lagoon-style pool and hot tub, through manicured paths of orchids and plumeria, winding around the back of what looked to be an event space, passing a loading dock, then a bunch of janitorial carts, trucks, and then down two flights of stairs to our $400 room. To say it was disappointing would be an understatement, and that’s when I realized my mistake. Had I just booked direct, we would have had a better room for the same price. The room didn’t have a garbage can, or tissues, it was very basic. The best thing about it was a patio that was home to some vagabond chickens and more beautiful foliage. Despite the disappointing room, mediocre food at the resort restaurant, and the pool bar being closed even though the hotel was supposedly sold out, we had a restful night’s sleep.

private stretch of beach near Hanalei Bay Resort

The next morning, we woke early due to the time change and wandered down the manicured paths in the dark to witness the sunrise on the beach. Although the room itself left a lot to be desired, the resort was beautiful but it was time to explore more of the Island. We packed up our things and left a few hours prior to check out. 

A Gem Of An AirBnB in Hanalei Bay

When we arrived at Waterfalls, our Airbnb in Hanalei Bay, we couldn’t help but compare it to the resort experience we’d had the night before. There are many reasons Airbnb does it better than hotels. For half the price, we had an entire second story loft - complete with a full kitchen, spacious living area with a couch and television, bathroom with a claw foot tub, a private bedroom, and a patio with a grill. The location was better than the resort, too. It was a five minute walk to the beach and a ten minute walk to the center of town, complete with a variety of restaurant options. Cruiser bicycles were included in the reservation, and our host had a bottle of sparkling wine and a can of macadamia nuts waiting for us. These gestures made us feel special - the same level of service is only provided to VIPs in most hotels and resorts. 

The Airbnb in Hanalei was the perfect launch pad for adventures. Our first day, we explored the beaches just beyond popular Hanalei Bay, finding Lumaha'i Beach, which was somewhat hidden through a forest path, just beyond a lava rock outcropping. The beach's only inhabitant was a rooster. The rip tide was strong which meant no swimming, so instead we walked along the coastline all the way to Wainiha Beach Park.


The next day, we drove to the end of the road and traversed the Na Pali Coast's Kalalau Trail. I count this as one of the most breathtaking and toughest hikes of my life - the views were worth it, and cooling off in a waterfall was the cherry on top. Read more about my hike and other things to do in Kauai, here.


A Hotel Walk-In    

I wasn’t going to make the same mistake I’d made on night one, but we were facing a similar dilemma. We had another night without a place to stay. That day we’d begun the journey south, stopping in Kapa’a for a kayaking adventure on the Wailua River. There were a lot of hotel options in the area. Using my Fodor’s Guidebook, I started calling down the list. Sold out. Sold out. Sold out. It seemed occupancy was running at 100%. We drove up to the Aston Islander and I hopped out to see if they had a last minute room available. Thankfully, they did, and offered us a complimentary upgrade to a third story room with breathtaking views of the resort grounds, the ocean, and a ridge behind which the sun would set exactly how it's supposed to in Hawaii.


Birds were chirping and the scent of orchids hung in the air. Our room was perfectly charming and just what we needed, complete with a comfortable queen bed, complimentary local coffee, and a laundry facility which we desperately needed after four days of adventure.


All Too Rustic Retreat in Waimea

I'd booked a night at an Airbnb in Waimea with the intention of getting up early and spending the day exploring Waimea Canyon and the wild and scenic beaches further west. It was only $100 and the bathroom appeared to be en suite. I was expecting a glamping experience my husband would appreciate, and this was our last night before the luxurious final leg of our trip began. 


The movie Room came to mind as we pulled into the driveway and realized we’d be staying in an oversized plywood shed. If I’d been alone I would not have stayed, but my husband always makes me feel safe, even when our room for the night felt more like a place to hide a body than a vacation rental. We carried our suitcase in, put on some clean clothes, and headed out to find a bite to eat in the town of Waimea.

We pulled back into the driveway a few hours later, and our headlights revealed the door of our cabin (if you could call it that), was wide open. My mouth dropped as a dark figure stepped out. It was our host we’d met a few hours earlier, exiting our cabin wearing a headlamp, and carrying what looked like clothes. What was he doing in our room? Turn down service at 10pm was highly unlikely.

My husband jumped out of the car, “Hey man, what’s going on?” 

Nervously, our host answered back, “I was just, um, bringing you towels and toilet paper.” 

I’d predetermined earlier that I would not be showering. The sink/shower combo was a hose with a heater attached, and the shower itself a human-sized plywood box attached to the bedroom. The bathroom was constructed in similar fashion, made from plywood, with a toilet rigged up and a curtain separating it from the bedroom. Walking around barefoot was not an option. That night we slept very little. Between dogs barking, bugs biting, and the uncomfortable feeling (and smell) of polyester sheets, we couldn’t get out soon enough.

Suffice to say I never had a chance to leave a review of this stay on Airbnb, the listing seemed to have vanished into thin air shortly after our stay.

Luxury At Last

We arrived at Sheraton Kauai having filled up on adventure: an eight mile hike along the Na Pali Coast, kayaking on the Wailua River, hiking to Secret Falls, a boat tour to the Forbidden Island, and even a helicopter tour of Kauai. My husband was horribly sunburned, my feet were covered in blisters, we hadn’t slept a wink the night before, and it was finally time to relax. Our room wouldn’t be ready until the afternoon, but we were invited to valet our car and enjoy the pool and beach until it was time to check in. 

The setting was just as one might expect from a resort in Poipu, Kauai: a lagoon-style pool surrounded by pool chairs, a hot tub, and an open-air restaurant/bar. There was a pristine lawn - the site of weekly luaus. 180-degree views of the ocean stretched out before us. Sheraton Kauai offers the best location among its neighbors because it is situated right on the beach, and although it houses nearly 400 hotel rooms, it is designed more like a boutique hotel than a resort - everything is within reach. 

We rented a shaded daybed situated between the pool area and the beach ($50 for all day access) which included a dedicated attendant via a little flag we’d raise when we needed anything at all. Before I knew it, the frozen-mojito-inside-a-pineapple of my dreams appeared, along with something strong and blue for my husband. Paradise found.

Blissfully unaware that he'd even wandered off, my husband emerged with a boogie board in hand. Located at the pool, the Adventure Desk offers boogie board rentals, snorkeling equipment, and even surf lessons. While I dove into the latest issue of Women’s Health, my husband was having a grand time learning how to catch a wave. 


Although toning my abs with my own body weight sounded intriguing, I thought between sips of pineapple mojito, it wasn’t long before I was out there in the ocean trying to catch a wave myself.

The Room

I reserved a Garden View guest room at a discounted rate through my Starwood employee benefits (perks of running the marketing efforts of a hotel group), so when the chance to upgrade to an Ocean View room was offered, I jumped at the opportunity. In the end, we had an upgraded room for around the same price as the room I’d initially booked had I not received the employee discount. 

Our room was well appointed with a four poster bed, an infinite number of pillows, plush mattress and ironed sheets, desk and chair, TV, arm chair, and outdoor furniture on our spacious balcony overlooking the ocean. The bathroom was spacious, separated from the room by a double sided closet which made my usual trying-on-multiple-outfits easy. The bathroom featured a double vanity, a shower and large bathtub, full length mirror, and plush robes perfect for sipping morning coffee. Luxury at last.

After the night we’d spent in Waimea, we sunk into the king bed like the Titanic. There was no coming back. By 9:00pm we were fast asleep.


The Amenities

Sheraton Kauai was a great choice for us given the little extras - daybeds along the beach, a hot tub which we braved during the craziest rain storm we’d ever seen, boogie board rentals, daily outdoor yoga, and surf lessons which my husband tried (and loved) on our last day in paradise.

The only amenity that left a lot to be desired was the food. Although Rumfire restaurant has an unprecedented location with panoramic views of the ocean, the ambiance inside was lacking. The restaurant was cooled to an icy temperature that wasn’t in sync with the breezy, warm feeling just outdoors. The casual, pool side restaurant was another miss - this time because of mediocre, overpriced food, and lack of service. When paying resort prices, I expect more or dine elsewhere. The luau was also a miss when it came to the food, although the dancers, performances, and host were incredible and provided an evening of entertainment we won’t soon forget.

Kauai is one of those places you'll visit and quickly realize you'd like to stay forever. The tropical landscape begs to be explored, the variety of fresh fish and fresh fruit never gets old, and endless miles of golden sand beaches ensure even the most devout adventure junkies find time to relax. Staying in a variety of hotels, resorts, and vacation rentals all over the Island was a great way to get to know different areas and experience the many sights, sounds, and tastes of Kauai. Looking for more? Read this next.



Hanalei Bay

Where To Stay

Hanalei Waterfalls, 5-5428 Kuhio Highway A, Hanalei, HI 96714, Airbnb.com.

Where To Eat

Cafe Turmeric, 5-5100 Kuhio Highway, Hanalei, HI 96714, Yelp.com.

The Dolphin, 5-5016 Kuhio Highway, Hanalei, HI 96714, http://www.hanaleidolphin.com/.

Things To Do

Kalalau Trail, The End of The Road, Hanalei, HI 96714, http://kalalautrail.com.



Where To Stay

Aston Islander on the Beach, 440 Aleka Place, Kapa'a, HI 96746, http://www.astonislander.com.

Where To Eat

Hippie Cafe, 4-369 Kuhio Highway, Kapa'a, HI 96746, http://www.hippiecafekauai.com.

Paco's Tacos, 4-1415 Kuhio Highway Kapa'a, HI 96746, http://pacostacoskauai.com.

Things To Do

Wailua River Kayaking, 4565 Haleilio Road, Kapa’a, HI 96746, https://kayakwailua.com.

Helicopter Tour, 3225 Akahi Street, Lihue, HI 96766 http://www.safarihelicopters.com.



Where To Stay

Sheraton Kauai, 2440 Hoonani Rd, Poipu Beach, Koloa, HI 96756, http://www.sheraton-kauai.com

Where To Eat

Living Foods Market, The Shops at Kukui’ula, 2829 Ala Kalanikaumaka, Koloa, HI 96756,  http://shoplivingfoods.com.

Anake's Juice Bar, 2827 Poipu Rd, Koloa, HI 96756, yelp.com.

Eating House 1849, Shops At Kukui'ula, 2829 Ala Kalanikaumaka Road, #A-201, Koloa, HI 96756, http://www.eatinghouse1849.com.

Things To Do

Chartered Boat Tour, Port Allen Marina Center, 4353 Waialo Road, Suite 5A, Eleele, HI 96705, https://www.holoholokauaiboattours.com/.

Horseback Riding, Maha'ulepu Heritage Trail, Koloa, HI 96756, http://cjmstables.com.