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The Perfect Long Weekend in Kauai, HI

The seductive seclusion of Kauai is not to be missed. Being one of Hawaii's smaller islands, it tends to get overlooked in favor of bigger, more touristy places like Waikiki and Maui, both of which have become synonymous with visions of loud Hawaiian shirts and the overuse of words like Aloha and Mai Tai.

And while, Oahu and Maui certainly have their beauty and unique charms, Kauai feels like the place you want to run to when you're craving something a bit more wild.

Stepping off of the plane, you're immediately enveloped by this hypnotic balmy, sea breeze that greets you like and old familiar song as you make your way down the jetway stairs and across the tarmac. This, the first encounter with the gentle slowness of the island seeps into you like a drug, delicately peeling off your stress with each breath. You can't help but close your eyes and drink it in slowly.

In the ride from the airport in my old rented Jeep, I found myself a little taken back at how I would possibly see everything I wanted to see on the Island in a long weekend. In truth, I didn't. In typical Type-A form, I had lists, and plans, and an ambitious itinerary to taste little bits of everything the Island had to offer. But before I got to my Airbnb, that wildness that I was repeatedly drinking in at every turn of the road was calling to me to slow wayyy down. It transformed my default, breakneck, I gotta see it all speed, to a more chill, I'll see where the day takes me speed.

And so, this is by no means a fulsome list of all the Island has to offer, but it is my recipe for a perfect long weekend made by blending a well-rounded assortment of activities, the slow wildness of the Island and a limited time period to experience it. No matter what adventure you choose, I would imagine its fairly difficult to have a bad weekend surrounded by all the lush beauty of this place.


Where to Stay:

There aren’t many resorts on the island and in truth, I would avoid most of them (with exception of the One Hotel in Hanalei) if you’re looking for peace and solitude. So, in most instances I’d say that Airbnb or VRBO are your best options.

Look for something walking distance to the water in either the North End of the Island like Hanalei or the Northeast side of the Island like Kapaa.

Where to Hike:

I would have loved to do a multi-day hike in Napali Coast State Wilderness Park, but as I mentioned time was a factor here so I opted for a few other shorter hikes for more variety.

The hikes listed below are all moderate with gorgeous views and can be done in the morning or a half a day or so depending on your speed and how early you start.

Sleeping Giant Trail Summit

Best Beaches:

You won't find a bad beach on Kauai. That said, some are better for swimming, or seclusion, or sunsets (depending on what you're looking for) than others.

The three below were my favorites (its a must to ride a bike up the path from Kealia Beach to Donkey Beach for some incredibly breath-taking ocean views)

  • Hanalei Beach - Best for swimming

  • Kealia Beach - Best for accessibility and sunsets

  • Donkey Beach - Best for seclusion

Hanalei Beach

Donkey Beach

What To Do:

  • Napali Coast State Park (by boat is ideal)

  • Snorkel at Poipu Beach

  • Drive the Tree Tunnel

  • Visit the Kilauea Lighthouse (get tickets in advance)

  • Drink champagne at Donkey Beach at Sunset

What To Eat:

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