The Ultimate Kauai 5 Day Itinerary For The Garden Island

Kauai 5 day itinerary
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Welcome to our ultimate Kauai 5 day itinerary. This epic adventure through the fabled Garden Isle of Hawaii will showcase some of the most stunning natural landscapes in the whole of the Aloha State. It’s an adventure that offers a taste of all the most famous facets of the island, from its sugarcane-growing past to its sublime mountains.

Yep, we’ll begin by revealing the luxurious enclave of country clubs and golf courses up north, then pass through the coconut-dotted beaches of the eastern shoreline, skirt around the family-friendly beaches of the south, and then delve into the peaks of Na Pali and Waimea.

We’ve planned the route to go clockwise around the island, but you can do it in either direction. It largely follows the main highway that runs a loop around Kauai, although remember that both ends don’t connect, so this is a point-to-point itinerary.

Day 1 – Hanalei and Princeville

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Our Kauai 5 day itinerary starts in the far north of the island. That means you’ll probably need to make the drive up the 56 highway straight after landing at the airport in Lihue, but that should take less than 50 minutes in normal traffic, so there’s not too much legwork to do before you reach the beginning mark.

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Anyway, these two towns kick us off with a hefty dose of R&R. A chilled breakfast at one of the lovely local cafes (a personal fav is the Hanalei Bread Company) can be followed by a relaxing stroll along the horseshoe of sand at Hanalei Beach.

We’d also recommend taking time to venture a little further west into the mountains that rise past Hanalei town. They peak over old taro fields and farms, quickly turning into dramatic cliffs where you can discover hidden bays like Lumaha’i Beach and Tunnels. There’s not too much swimming to be done in these parts as the Pacific has strong currents on the Kauai north shore, but you can go snorkeling in the reef pools at Ke’e Beach and Haena.

For the afternoon, drive east to the town of Princeville. Welcome to the jet-setter hub of Kauai, the home of the most luxurious hotels and resorts on the island. If you’re keen to sample the luxury, be sure to book one of the deluxe stays ahead of time – the Makai Club Vacation Resort and The Cliffs at Princeville are both well-rated options with swimming pools and Pacific Ocean views.

Princeville is a haven for golfers. If you’ve brought the clubs in tow then you’ll definitely want to pay the green fees for a round at the Princeville Makai Golf Club, which is considered one of the most stunning in the Aloha State. Alternatively, there’s loads of chic shopping opportunities, along with farm-to-table food at Nourish Hanalei.

Day 2 – The Royal Coconut Coast

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The Royal Coconut Coast might not be as dramatic as the Na Pali Coast (more on that later) but it’s still one of the loveliest regions in Kauai. It’s proved popular for families and couples mainly thanks to its beaches and the accessibility of it all – the airport is just a 15-20-minute cruise down the 56 highway.

You’ll be traveling from north to south out of Princeville. If you went without pausing, that drive could be completed in just 45 minutes. However, we’d say make a whole day of it. There are oodles of things to see along the way, including postcard-worthy beaches and stacks of detours to make inland for those feeling the pull of adventure.

Here are just some of the spots that we’d ensure were part of our Royal Coconut Coast itinerary:

  • Anahola Beach Park – This protected bay fronts the small town of the same name. It’s got calm waters for swimmers thanks to the ring of reefs out in the ocean.
  • Donkey Beach – Not a great place to take a dip, but perfect if you want to watch the lashing waves of the Pacific Ocean rolling in beneath the coconut palms.
  • Ho’opi’i Falls – An overgrown hiking path weaves through the jungles to this waterfall, where you can jump off the mossy ledges into the plunge pool if you’re feeling brave.
  • Wailua Falls – Unquestionably one of the most dramatic cataracts in Kauai, the Wailua Falls can be reached on a semi-challenging jungle hike. The water here is swimmable but bracingly cold.
  • Kapa’a Beach Park – One of the east coast’s prettiest beaches, complete with seagrasses that run right up to the wavy shoreline.

Day 3 – Lihue to Poipu

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Wake up in Lihue. It’s the busiest town and main commercial center of Kauai Island. But it’s also a pretty great place to get stuck into local history and heritage, mainly thanks to the Kauai Museum. It’s housed in an old-school building that dates from the 1920s (the Albert Spencer Wilcox Building) and hosts collections that chronicle the ages of the Kauai kings and queens before Hawaii even joined the union.

If you’ve got the time, a stop at Grove Farm is another historical POI that’s great for history buffs. A onetime sugar planation that’s now been totally preserved to look like it did back in the 1800s, it reveals the secrets of the island’s agricultural past.

From there, get back on Route 50 and drive west. Soon, you’ll come to a junction where the tarmac veers off to the south turning into the Maluhia Road. The first part of the drive after the turn off takes you through the so-called Tree Tunnel, a gorgeous stretch of highway that’s flanked by venerable eucalyptus trees that have grown into a natural tube over the asphalt.

Soon, you’ll reach Old Koloa Town. It’s a Wild West-style settlement that has a long past, with saloon doors and wood-fronted buildings. After you’ve got the compulsory Instagram shots, keep going south because you’re close to Poipu, arguably the best-loved beach town on the whole island.

Yep, Poipu Beach is the place where you’ll spend the night of day 3 on our Kauai 5 day itinerary. Try to arrive before the sun goes down – there’s a conch-shell-shaped arc of pure gold sand backed by lanky coconut trees to go and laze on, not to mention some of the best-protected swimming and snorkeling in the whole state.

Day 4 – Waimea Canyon State Park

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Day 4 is where our ultimate Kauai 5 day itinerary takes a turn for the more adventurous. You’ll start by following the wiggling Kaumualii Hwy (also called Hawaii Route 50) in a westerly direction out of Poipu. For that breakfast brew, be sure to detour off onto Halewili Road. It’s now called the Coffee Highway because it’s the home of Kauai Coffee, where you can sample beans grown and harvested on the very same island.

Then, plot the sat nav for the north and the protected reserves of the Waimea Canyon State Park. The turn off to enter is just past Waimea, and you’ll notice that the road narrows and the route starts winding up and into the mountains. It’s not long before you get a chance to pull over at some striking lookout points – the Niihau Lookout has visions of verdant gorges, but the Stream and Canyon Lookout showcases a strange land of Mars-like red rock.

All the while, you’ll be working your way towards the heart of the Waimea Canyon State Park. Depending on the time you arrive and how energetic you’re feeling, this is a top spot to pull on the walking boots and hit the Hawaiian trails. There are a few different paths that take varying times, but we can recommend:

  • The Cliff Trail (rated as easy) – Just after mile marker 14, there’s a dirt path that offers a short walk of less than 30 minutes, but with pretty spectacular views of the Waimea Canyon.
  • Iliau Nature Loop (rated as easy) – Another chilled walk through wooded highlands, this path offers info about the various flora of Hawaii’s Garden Island.
  • Koaie Canyon Trail (rated as moderate to difficult) – A steep path descends into a side canyon where there are gurgling rivers.
  • Kohua Ridge (rated as difficult) – You’ll need a 4WD to even reach the trailhead. Then, you’re onto a three-hour ridge walk that sometimes opens onto sheer-cut cliffs that are thousands of feet high. Not for the vertigo sufferers.

Day 5 – The Na Pali Coast – natural grandeur to finish our Kauai 5 day itinerary

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Day 5 caps off our ultimate Kauai 5 day itinerary with a sighting of arguably the most striking natural feature on the whole island. Cue the Na Pali Coast. Over just 16 miles of shoreline on the far northwestern edge of Kauai, the mountains and the forests converge on sheer-cut cliffs and ridges that soar more than 2,500 feet above the pearly blue Pacific Ocean here. The result is a whole region of stunning vistas that every traveler to this corner of Aloha simply has to see.

However, the Na Pali Coast is also famously impenetrable. In fact, the whole reason that you can’t cruise the full circle around Kauai is that the cliffs are just too darn rugged for any roads to be able to weave their way through. That means you’ve got a choice for the finale of your Garden Isle adventure.

There are four ways to go: By car, by foot, by boat, or by plane/helicopter. Let’s take a look at each in turn…

  • By foot – There’s nothing that can beat the Kalalau Trail in our opinion. It’s an epic undertaking that will add three days to this itinerary but showcases the finest views of Na Pali that exist. There are also shorter hikes, like the path to the Kalalau Lookout or the Black Pipe Trail Loop.
  • By car – You can’t drive that far into the Na Pali region but there are some lookouts on the Kokee Road. This isn’t the best option as you don’t get to see the famous cliffs and coastline up close.
  • By boat – There are loads of day trips by motorboat leaving from Port Allen in Eleele that can whisk you up to see the pure drama of Na Pali from out in the Pacific. Alternatively, you could hop in a sea kayak and let your arms be the engine – it’s rewarding but challenging.
  • By plane – Prepare to strike a line from the bucket-list, because flyovers of the Na Pali Coast let you see all the incredible mountain ranges and the sweeping rainforests that make the region so famous.
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Joe has been a freelance travel writer for over nine years. His writing and roaming have taken him from the colonial towns of Mexico to the chowks of Mumbai to the Southern Alps of New Zealand. When he's not putting together the next epic blog on the best Greek islands or ski fields in France, you can usually find him surfing or hiking – his two top hobbies.