Published: 6/10/23

Our Complete Itinerary To Circumnavigate Kauai in 5 Days

It was an absolute dream to spend 5 Days on Kauai in December 2022.

Hawaii’s Garden Island had been on my short list of must-see travel destinations for the better part of a decade. I spent a lot of time researching and planning this trip before it was anywhere close to being a reality. Suffice it to say, if you’re wondering what to do on Kauai, I’ve got you covered!

Finally, during a fit of pique during a mid-April snowstorm  – having just returned from Cincinnati and Jackson Hole – I took my entire Skymiles balance and threw them at round-trip Comfort+ tickets into Lihue – the Kauai airport –  for myself and my partner, Andy. We combined our time on Kauai with three days in Honolulu.  I don’t think I’ll ever forget this amazing first island-hopping Hawaiian adventure.

During our 5 Days on Kauai we (almost) completely circumnavigated the entire island. After our time in the big city of Honolulu, Kauai’s lush jungle and beautiful beaches were a balm to our rural, northern souls. 5 days on the island proved the perfect length for a first-time visit Kauai visit. 

Read on for our full Kauai 5 Day Itinerary including where to stay, what to eat, and our favorite Kauai hikes and adventures. 

This post may contain affiliate links. When you purchase something through these links, I receive a small commission that helps me create this blog’s content. There’s no extra cost to you.

Wondering how to spend 5 Days on Kauai? Read on!

Sunrise over the Royal Coconut Coast on Kauai’s East Side 

A Brief Introduction to Kauai

Kauai is the most westerly of the four main Hawaiian islands. (The other “main” Hawaiian Islands are Oahu, Maui, and Hawaii, aka Big Island.) Located on the far edge of the Hawaiian archipelago, about 70 miles from Oahu, you can reach Kauai in about a 25-minute flight from Honolulu.

One of the oldest Hawaiian Islands, Kauai is known for its striking and varied scenery. It’s a favorite Hawaiian destination among outdoor adventurers including hikers, scuba divers, and bird watchers. More than a million tourists visit Kauai each year, easily making tourism the island’s main industry. The island is also home to the Pacific Missile Range Facility, Barking Sands.

With a population of about 75,000, the island has a distinctive small town vibe, especially when compared with Honolulu’s nearly one million residents. Although you can drive from one end of the island to the other in about 1.5 hours, the island is divided into four distinctive areas: North Shore, East Side (aka Royal Coconut Coast), South Shore, and West Side. The rugged Na Pali Coast on the island’s west side prevents you from actually driving around the entire island.

Hanalei Bay as seen from the Okolehao Trail

How Many Days in Kauai

Our 5 days on Kauai proved the perfect amount of time to make our way around the entire island. However our itinerary really didn’t offer the opportunity to return to spots that especially piqued our interest. If we’d done that, we would have missed out on another corner of the island completely.

Because of that fact, I recommend a minimum of 5 days on Kauai. With the island’s four distinctive “zones” (North Shore, South Shore, East Side, and West Side), you’ll want at least a day in each of these quadrants. While not every zone of Kauai will likely be your jam, it’s nice to be able to linger once you find your Kauai sweet spot.

Ideally, I’d recommend a full week in Kauai bookended by your travel days for a nine-day vacation. During that week, you’re going to want to move lodging. This will save you some tangles with Kauai’s notoriously fickle traffic. Plan to spend half your time somewhere south of Lihue and the rest of your time in or north of Kapa’a.

During our five days on Kauai, we stayed on the East Side, near Kapa’a and the mouth of the Wailua River. 

How We Spent 5 Days on Kauai

Our time on Kauai was pretty unstructured. As I planned our Hawaiian adventure, we looked into guided tours, fishing charters, and more. In the end, we decided to experience Kauai on our terms rather than hurtling from one planned activity to the next.

We spend our 5 days on Kauai slowly circumnavigating the entire island. In fact, I think there was just one teeny portion of the island that we didn’t see: the section between Tunnels Beach and Ke’e Beach.

While a destination as popular as Kauai doesn’t have many true hidden gems, we were able to see most of Kauai’s “must see” spots as well as some less hyped areas during our 5 days.

Tropical forest along the Okolehao Trail on Kauai’s North Shore

Day One: Arrive Kauai

We have a leisurely morning in Honolulu, then headed to Daniel K. Inouye International Airport to take a 25-minute island hopper flight to Lihue.

In all my research about Kauai, I read over and over again about how gorgeous the Na Pali Coast is on Kauai’s west side. With that in mind, I was totally unprepared for the beauty of my first glimpse of eastern Kauai from the plane window. The entire island is stunning!

After collecting our luggage and grabbing our rental car, we received our second Kauai surprise. Although our VRBO was only 6 miles north of the airport, it took us nearly 40 minutes to reach it in bumper-to-bumper midafternoon traffic!

Eat

I’m always apprehensive to make reservations on the day we’re scheduled to arrive somewhere, but the only opening at the highly rated, and extremely close by Hukilau Lanai was this night. I’m so glad I didn’t let worries about potential travel hiccups prevent me from booking the table. This meal was stunning – a true highlight on a trip filled with delicious food.

Waypoints

After a few nights in the big city of Honolulu, it felt wonderful to settle into the charming little Hale Iki Cottage on the 17 Palms Kauai property in Wailua. Our first 10-minute Kauai afternoon rain shower rolled in as I started a load of laundry in the cottage’s washer and dryer. We made the first of many forays to the Coconut Marketplace right across the road to grab breakfast items and get our first taste of Hawaii grocery prices!

Day Two: Kauai’s East Side and Interior

Shorter days are a definite downside to visiting Kauai in December is that the days are pretty short. By the time we’d settled into our cottage the night before, it was pitch dark. It just made sense to devote our first full day on Kauai getting to know our immediate neighborhood.

Although I’d say the East Side is the most underhyped area of Kauai, I felt drawn to its jungles and mountains. It’s home to the “arguably” wettest place on earth – Mount Waialeale – gets more than 400 inches of rain annually! What can I say, as someone who’s spent a decent amount of time in England and Ireland, I just feel at home in rainy places.

I’m so glad I followed my instincts and took time to explore Kauai’s East Side. Our hike on the Kuilau Ridge Trail was an instant highlight of the entire trip.

Soaking in all the Jurassic Park vibes on the Kuilau Ridge Trail outside Wailua, Kauai 

Eat

While you can’t actually dine on the beach in Kauai, you can get pretty close with the Lava Lava Beach Club in the Kauai Shores Hotel. Their restaurant opens up onto a manmade sand “beach” outdoor seating area.

Despite the novelty of beach dining, we went twice and actually dined inside both times. Personally, sitting in chairs slowly sinking into sand wasn’t particularly appealing! However, we loved the fun atmosphere, great drinks, and the convenience of excellent dining a one-minute walk from our cottage.

After dinner I popped over to Jojo’s Shave Ice in the Coconut Marketplace. I’d never had shave ice before and expected something along the line’s Dairy Queen’s Mr. Mistys. Well I was wrong and I not mad about it. It was so good, I came back the next night!

Waypoints

We never truly adjusted to the time change during our entire Hawaiian adventure, so we explored nearby Waipouli Beach shortly after sunrise. The beach offers a great view of the Wailua River mouth, one of the most sacred places in all of Hawaii.

After a wander on the beach, we grabbed some produce from the Coconut Marketplace Farmer’s Market. There’s pretty much guaranteed to be a farmer’s market on somewhere in Kauai every day. We felt lucky that the one within walking distance for us happened the morning after we arrived!

We hopped in our car and drove inland to the Kuilau Ridge Trail. This easy 3.5 round-trip trail goes through intense jungle that gave me definite Peru vibes. Although the path was very muddy, this easy, scenic trail was well worth the red Kauai mud stains!

After our hike, we wandered around nearby Keahua Arboretum. We rounded out our day of East Side adventures with a drive to Wailua Falls. While this photogenic waterfall is definitely a Kauai “top 10” site, it really only warrants a quick stop for a couple photos.

Day Three: Kauai’s North Shore

Turns out 5 days on Kauai isn’t very long! We headed north today to start our “circumnavigation of Kauai.” We set out with the goal of doing another hike and seeing some marine biology.

Unfortunately, one of the best spots to view marine wildlife from shore on Kauai, the Pools of Mokolea, can be pretty treacherous during the winter months. Since I’m no expert on surf conditions, we decided to skip it rather than risk being sweep out to sea by the winter waves. Despite this, we really enjoyed the dramatic lushness of Kauai’s North Shore.

Eat

I grabbed some treats at Passion Bakery Café after taking in another beach sunrise. The coconut hand pie was delicious – everything else was a little lackluster.

We hit up Sam’s Ocean View for dinner and I highly recommend it for its great view, food, and happy hour. I had the poke nachos over rice, which is really just an appetizer, so don’t worry . . . I had plenty of room for another stop at Jojo’s Shave Ice when we got home!

Waypoints

We settled on the 2-mile round-trip Okolehao Trail for our hike. Extremely muddy conditions for the first quarter mile almost caused us to turn around. I’m so glad we stuck it out. The panoramic view of Hanalei Bay made all the slipping and sliding worth it! As a bonus, on the drive to the trailhead we got a close-up look of a taro plantation.

After our hike, we enjoyed a picnic lunch at Hanalei Pier, then continued on to Tunnels Beach. On the way, we braved Kauai’s famous one-lane bridges. Turns out they’re not nearly as death-defying as they sound on paper.

We actually started our day at the Kilauea Point National Wildlife Refuge, but didn’t realize you needed to reserve an entrance time. We returned in the afternoon, reservation in hand, which thanks to my America the Beautiful pass, only cost us the $2 online booking fee. (The entrance fee is $10 per person so I felt pretty smart for packing it.)

Not only is this wildlife refuge home to Kilauea Lighthouse, it’s also a haven for Hawaiian wildlife, including the rare nene goose. A little later in the season, this point is a great spot for whale watching. We enjoyed beautiful weather and lots of bird sightings.

Day Four: Na Pali Coast

I only had one nonnegotiable about our 5 Days on Kauai: the Na Pali Coast.

When Andy vetoed a helicopter tour because “helicopters don’t fly, they repel the ground,” I immediately booked a boat tour.

There are several boat tour companies in Kauai that will take you to the Na Pali Coast. However I’m pretty sure we found the best with Liko Kauai Cruises.

We opted for the small boat experience on the Makana which takes a maximum of 12 passengers. Although we weren’t the oldest passengers aboard, we felt a little elderly for this boat. However, we had an absolutely unforgettable time sailing with a massive spinner dolphin pod, ducking into sea caves, and snorkeling with sea turtles.

While it’s a little more challenging to see the Na Pali Coast in winter, it’s well worth it. In summer, you can reach the dramatic coastline in just a short, eight-mile sail from Hanalei.

But North Shore winter seas are too rough for sailing. Instead, you need to pound through about 17 miles of bumpy winter surf starting at the Kikiaola Small Boat Harbor on the island’s west side. You do get a great view of the Pacific Missile Range Facility, Barking Sands when you take this route.

It was an absolutely stunning afternoon when we disembarked and if we’d had more energy, we would have headed into the nearby Waimea Canyon. However, the non-drowsy Dramamine hit us both hard. I’ve subsequently learned that I’m not prone to seasickness and won’t be making this mistake again!

The famous Kalalau Beach tucked in the Na Pali Coast. Our morning sail meant we got shadowy photos, but smoother seas. By the time we returned the harbor, the seas were so rough, the afternoon sailing was cancelled. 

Eat

After two failed attempts to score grocery store poke bowls, we settled on takeaway from Coconut Thai in our old haunt, the Coconut Marketplace. While it wasn’t the best Thai food I’ve ever had, it was very pleasant to enjoy it on our cottage’s porch.

Day Five: Kauai’s South Shore and West Side

Despite the popular claim that Mark Twain called Waimea Canyon the “Grand Canyon of the Pacific”, Twain never visited Kauai. The canyon does look a lot like the American Southwest though .  . .

We doubled back to the island’s South Shore today to hit up all the sites we’d skipped the day before in our post Na Pali Coast boat tour Dramamine haze.

Eat

After missing them in Honolulu, I finally got my hands on a Hawaiian hot dog at Puka Dog. Not only did they live up to the hype, but people-watching at Poipu Beach (lifeguard jet ski rescues!) made the experience even better.

For dinner, we returned to Lava Lava Beach Club. If you go, definitely try their Bambu Pupu, an appetizer sampler of ahi poke, coconut shrimp, and fritto misto.

Waypoints

Sadly, we squandered our gorgeous day for Waimea Canyon. Instead of sweeping views, we got fog when we tried to do the Pihea Trail at the end of Highway 550. Still, we had a nice quick hike to the first overlook on the Waipoo Falls Trail.

Maybe we’d hit our sightseeing quota for the trip, but I struggled with Waimea Canyon. With little to no interpretative information available in the visitor parking areas, but prominent fee pay stations, I walked away feeling a little jaded.

Could I have done more research ahead of time? Absolutely! Should I have? Apparently!

I’d heard mixed reviews about the Kauai Coffee Company, but I really wanted to see the largest coffee farm in the United States. I actually think this stop was one of my favorites on Kauai. While the coffee isn’t as celebrated as Big Island’s Kona Coffee, we had a kickass iced mocha and I put a hefty dent in my Christmas shopping!

We also finally saw the famous tree tunnel on our way to Poipu Beach.

Day Six: Kapa’a, then homeward bound

If your stay is anything like yours, 5 Days on Kauai simply disappear!

Our day started with grounds workers knocking on our door because they were about to start removing coconuts from the trees surrounding the cottage. We’d noticed the coconuts starting to fall around the parking area during our stay, so it was definitely time for the ripening fruits to go! 

We also took the workers’ arrival as our sign to go. Although it was sad to say goodbye to our beloved little cottage, we still had an entire morning to spend in Kauai. It’s hard to give your full attention to the day you fly out on, I think we did a decent farewell tour of Kapa’a and the East Side. 

Eat

I wish we’d have gotten here earlier, but we finally made it to the very popular Kapa’a coffee shop, Java Kai.

View of the Pacific Ocean from the Ke Ala Hele Makalae path outside Kapa’a, Kauai

Waypoints

Conveniently located right next door to Java Kai, I popped into Kauai Nut Company to grab some souvenirs.

After savoring my final coconut latte of the trip, we drove north to walk on Ke Ala Hele Makalae path from Kealia Beach to Pineapple Dump Pier.

This multi-use trail built on an old pineapple plantation railroad grade provides super easy walking (or biking) and stunning views. 

Tunnels Beach on Kauai’s North Shore 

What I’ll Do Next Time In Kauai

5 Days on Kauai simply isn’t enough time to do everything that will pique your interest. These activities will be at the tippy top of my next Kauai itinerary!

Hanapepe Swinging Bridge – Although I’m not a Lilo and Stitch super fan, the little town of Hanapepe sounded so charming. Next time I hope to check out their famous swinging bridge and small shops!

Kukuiolono Park – We passed this park located just east of Kalaheo twice and would have stopped our second time if we hadn’t been so hungry! The park features walking paths, a Japanese garden, and a golf course. It’s also the site of Hawaiian Heiau, or temple.

Spend way more time on the Ke Ala Hele Makalae Path – You can’t beat the ocean views on this super user friendly path.

Take that helicopter tour – Having seen how beautiful Kauai is from land and sea, I really want to see it from the air.

Watch the sunset over Hanalei Bay – Next time I’m definitely scoring reservations at Bar Acuda to enjoy their spectacular tapas and sunset views.

Kayak up the Wailua River – I fully planned to do this on this trip, but the stars just never aligned for me to arrange a kayak rental, despite spending our time on Kauai embarrassingly close to the river’s mouth.

Go tubing through an old sugar plantation – I didn’t know about this activity until I was talking with friends after returning. Now I’m keen to try out tubing through an old sugar plantation irrigation system myself!