4-Day Kauai Itinerary

I fell asleep in the sky somewhere over the Pacific Ocean and woke up to an island of possibilities. Beach hopping, hiking and sailing through the sunset were just a few of the adventures on the Kauai bucket list.

First day in Kauai, Hawaii and the last time I saw those sunglasses.

Kauai Itinerary:

Day 1: Beach hop through northern Kauai.
Day 2: Swim at Queen’s Bath and take a photo at the top of the Na Pali sea cliffs.
Day 3: Hike to a waterfall in Waimea Canyon.
Day 4: Practice stand-up paddle board (SUP) yoga at Hanalei Bay and drink out of a coconut.

Day 1: Trying to Beach Hop Through Northern Kauai

If you travel a lot then you most likely already know that being flexible is important. Sometimes you have to throw your itinerary out the window because things just don’t go as planned. We learned that day one in Kauai. The plan was to go beach hopping and in a way we did. We tried visiting four different beaches until we finally found an open beach with available parking, two hours later. After so much hustle, we decided to stay in our secluded alcove surrounded by black volcanic rocks until the sun dipped into the ocean. We caught our first glimpse of a Hawaii sunset at Anini Beach on April 27, 2019 and it was magical.

Staring out at the ocean from our private corner of the Earth—Anini Beach.
Staring out at the ocean from our private corner of the Earth—Anini Beach.
The clouds blanket the sun as it sets in Kauai, Hawaii.

Day 2: Attempt a Swim in Queen’s Bath & Check Out the Na Pali Coast

Terrified of not finding a parking spot at Queen’s Bath, we started the day early—6 a.m. to be exact. We dragged our jet-lagged butts out of bed and made our way to the trailhead leading to Queen’s Bath. The jaw-dropping views were worth the rough hike. At 7 a.m. the gentle light coming from the rising sun somehow made the ocean and the dark rocks look even more beautiful. Just after low tide, the pools were full to the brim with calm blue ocean water, perfect for swimming. And since I never pass up an opportunity for a swim, I cannonballed into one of the deep blue pools before Jake had time to pull out the GoPro and hand it to me. The rush of saltiness was invigorating and shocking, and totally worth it. Nothing like an early morning dip to get the day started.

The sun rising over Queen's Bath, Kauai, Hawaii.
The sun rising over Queen’s Bath, Kauai, Hawaii.

Since the beaches and trails around the Na Pali Coast were closed due to flooding in April 2018, Jake found another way for us to explore the sea cliffs—by boat. We boarded Captain Andy’s sailboat and enjoyed a four-hour sail down the Na Pali Coast. The sea cliffs were only made more impressive by the stories of shark wrestling in caves and royal burials and reincarnation. I still remember the feeling of the salt water splashing onto my face as we whipped through the water. If I close my eyes I can see dolphins jumping through the water and the ocean eating up the sun. And I have to admit, exploring the Na Pali sea cliffs by boat was one of the most spontaneous and romantic adventures of my life.

Dolphin sighting during Captain Andy’s Na Pali Coast boat tour.
The fog descending on the Na Pali sea cliffs.
View of the sunset from Captain Andy’s sailboat.

Day 3: Try to Stay Dry at Waimea Canyon

We woke up to rain tapping on the windows around 6 a.m.; and while the forecast promised rain all day long, we didn’t let it stop us from packing up the rental car and crossing off the next item of our Hawaii bucket list: Waimea Canyon. It rained the entire one-hour drive to the canyon and by the time we got to the top-most viewing point, we were walking through clouds. Eerie doesn’t begin to describe it. We experienced the feeling of being the only two people in the world as we hiked the Pihea Trail. Instead of gazing through the lush valley of the canyon, we were blinded by fog on all sides. All we could see was the path ahead and the trees lining it. I guess you can’t always see what you’re heading toward, but you can still laugh as you splash through the puddles on your way there. The at-first gentle rain gave way to clothes-soaking downpour. Laughing at our luck, we turned around after just passing the half-way point on the trail and ran back to the car. On the drive back, I managed to sneak a photo of the Waimea Canyon between torrential downpours.

Waimea Canyon, Kauai, Hawaii.
Waimea Canyon, Kauai, Hawaii.

Next came the beach portion of the day. As we drove toward the coast, the rain slowly eased into a light drizzle. But by the time we made it to Polihale Beach, which is flanked by the Na Pali sea cliffs on one side, the rain was back. We patiently waited in the car, snacking on strawberries and tortilla chips while the clouds unloaded on the sand and ocean. As soon as it started to stop, we leapt out of the car and ran toward the waves. We enjoyed 30 minutes in the ocean and ran back to the car as the clouds grew dark overhead, narrowly missing the next downpour. We drove back to the Airbnb as the rain pounded on the car, big goofy smiles on our faces the whole way home.

Monstrous waves crashing onto Polihale Beach in Kauai, Hawaii.
The Na Pali Coast just before another downpour of rain.
The Na Pali Coast just before another downpour of rain.

Day 4: Give Up Trying and Just Go to the Beach

We woke to another rainy day; so we threw our schedule out the window and enjoy our last full day on Kauai the way the locals do—slowly. We savored breakfast—avocado toast with fresh mango—and leisurely made our way back to Anini Beach (since we knew it was open). As the clouds parted, allowing the sun to make a gentle appearance, I flowed through a short yoga sequence on the rocks instead of a paddle board. Hours of sitting had made me stiff and I welcomed the sensation of my muscles stretching out and releasing tension. As partly cloudy skies gave way to mostly sunny skies, we set up our beach chairs under a wide-leafed tree and strolled happily along the beach.

The clouds breaking up over Anini Beach, Kauai, Hawaii.

Once the rain returned, we packed up and drove into Hanalei for lunch. With patio-seating and tropical drinks on the menu, Kalypso Bar & Grill was a no-brainer. We enjoyed our first taste of Hawaiian-style food and ordered drinks that featured local Kauai rum. And while it didn’t come in a coconut, my Kauai-tai was dangerously tasty. After a laid-back lunch hour (or two), we spent the rest of the day exploring the local shops in Hanalei, taking care to only buy things that we really needed, (which included a baseball cap with a wild chicken on it).

One last salty soak in Kauai before taking off to Maui.
One last salty soak in Kauai before taking off to Maui.

We packed at the speed of light to make our late morning flight to Maui. As we waited for our flight to start boarding, I pulled out my Kauai bucket list and made some modifications.

Day 1: Beach hop through northern Kauai. Find a gorgeous beach and camp out till sunset.
Day 2: Swim at Queen’s Bath and take a photo at the top of the Na Pali sea cliffs. Cannonball into Queen’s Bath and enjoy the majesty of the Na Pali Coast.
Day 3: Hike to a waterfall in Waimea Canyon. Get lost in the Waimea Canyon.
Day 4: Practice stand-up paddle board (SUP) yoga at Hanalei Bay and drink out of a coconut. Relax at the beach and explore the local gems of Hanalei.

I smiled to myself as I realized something revolutionary—it’s not about finding every item on your bucket list, it’s about creating adventures for yourself out of the little things. My smile broadened as I looked over my Maui bucket list. I couldn’t wait to see what changes I would make to that one.

Until next time,

Leah Pinkus


2 thoughts on “4-Day Kauai Itinerary

  1. Leah, I love reading your blog, you are such a good writer! I definitely understand the feeling of things not going according to plan when traveling but it sounds like you guys had a blast nonetheless! I hope to visit Hawaii one day as well 🙂


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