6 Incredible Days in Kauai on Points & Miles

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Kauai, the Garden Isle, home to hiking, surfing, general chillaxing and the famously dramatic Na Pali Coast, is a gem of the Hawaiian Islands. It offers travelers all the opportunities of a major destination in a mix of tours and tiny towns, yet all the seclusion and nature one could want with luxe hotels and world-class outdoor activities. But traveling to this diverse paradise can set you back more than a few Mai Tais.

For me, trying to visit only one Hawaiian Island is like trying to convince myself to have only one Cool Ranch Dorito — I'm not stopping until I've "experienced" each "chip." But instead of getting full by power-grazing carbs alone in a dark closet at my company holiday party, I'm looking to fill up on the personality that each island carries with it, on a lanai at a five-star-hotel. Plus, they still have Cool Ranch Doritos in Hawaii. With many travelers heading to Honolulu and its renowned Waikiki Beach, and with a trip to Maui and the Big Island completed last summer, it was the less-traveled island of Kauai that was next on my list. Here’s how I booked six days in Kauai almost entirely on points and miles.

Getting There

With nonstop daily flights offered from Alaska, American, Delta, Hawaiian and United, getting to Kauai’s Lihue Airport (LIH) from West Coast cities such as Los Angeles, San Francisco, Phoenix and Seattle is a breeze. At roughly five and a half hours, the flight is refreshingly easier than the LAX to JFK route I fly regularly. But rather than pay for flights that typically range from $500 to $800 from the West Coast, you can get some great value when booking with miles. I took advantage of a few different transfer partners to book two nonstop round-trip flights from LAX to LIH for only 25,000 miles and $11 per seat.

A few months back the Starwood Preferred Guest Credit Card from American Express was offering a 35,000-point sign-up bonus. The offer has since gone down to 25,000 points after spending $3,000 within the first three months. Once I had earned my bonus I was left with just over 40,000 SPG points, which I then converted to British Airways Avios with ease on Starwood's website. The best part about the transfer is that SPG offers a bonus of 5,000 miles for every 20,000 points that you convert. This left me with 50,000 Avios, and British Airways has a sweet spot for reward flights to Hawaii (HNL, OGG, LIH, KOA) at 25,000 miles round-trip in economy or 100,000 in business from the West Coast via its partner American Airlines.

The two tickets I booked would have cost a total of $1,452 if I paid in cash, but redeeming points left me with a very strong redemption value of 3.5 cents per point (based on the 40,000 Starpoints I transferred). So, just by getting the SPG Amex and hitting the minimum spend, I was able to redeem for $1,452 (minus the $22 in taxes) in value — a very nice return! If you're looking for another way to earn some Avios in a hurry, there's always the British Airways Visa Signature Card, which offers a bonus of 50,000 Avios when you spend $3,000 in the first three months.

A Few Nights on a Budget

Our flight arrived at Lihue around 9pm (which is basically when Kauai shuts down for the night), so we were just looking for a place to crash. I chose the Courtyard Marriott Coconut Beach for the first two nights due to its convenience to the airport, central location for some hiking we had planned and for its cost. I could have paid $165 per night in cash or redeemed 35,000 Marriott Rewards points, which is just a so-so value. However, I had a decent amount of Citi ThankYou Points that I had earned with the Citi Premier Card. You can also get a 40,000-point sign-up bonus (when you spend $4,000 in the first three months) and even better features with the Citi Prestige Card. Using Citi’s travel portal, which gives you a value of 1.25 cents per point when redeeming for travel, I found the same oceanfront room for only 12,228 Thank You points per night (plus an $18 daily resort fee).

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This was the best over-all Courtyard Marriott I’ve ever stayed in, especially for the price. Overlooking the Pacific, the pool and hot tub serve as the center of all the action with the $4 — yes, I said $4 — poolside drinks during happy hour. Sure, the property was simple and the rooms were on the smaller side, but in Kauai size only matters in wave break and tuna fish.

You’ll Need Wheels

Rent a car. There’s no way around it; you'll be doing yourself a disservice if you try to see what the island has to offer without one. Get a Jeep, or a convertible. I again used the Citi ThankYou points travel site to book a Jeep for 22,850 ThankYou Points plus $108. It's possible to book an intermediate-level car for about 40 percent less, but it's also possible to paint everything you own beige, put all your money into municipal bonds and to start eating your soft-food-only dinners at 4pm. Cruising around in the fresh island air is well worth the extra cost.

Even if you unplug your alarm clock, put your phone on do-not-disturb and slip a few Baby-Ambien™ into your toddler’s virgin Mai Tai — I dunno, I don’t have kids — you will still be getting up early. A time change from the mainland mixed with a rooster population ensures the most natural of wake up calls. Seriously, there are so many chickens on the island. If you're neither a bird nor a morning lover, call ahead to your hotel make sure it's a fowl-free resort.

Get Outside

After breakfast, leap in your Jeep and head north, then west past Princeville until the Kuhio Highway turns to dirt and simply ceases into the sea. You don’t need directions, just make sure the ocean is on your right and drive until you land in the Ha’ena State Park parking lot. You’re about to hike the Kalalau Trail along the breathtaking Na Pali Coast past the secluded Hanakapiai beach through an ancient, untouched valley dotted with bamboo rain forests to a 300-foot waterfall that bears the same name.

This hike is a very long, very wet, very slippery eight miles. If you have some weird fetish of being drenched with rain yet still somehow covered head to toe with red clay-mud, then Move. Here. Immediately. Weirdo.

Too much for you? No problem. You can cut the hike in half with a four-mile round-trip to Hanakapiai beach. But you might not want to go in the water — there were signs everywhere warning us of impending doom. Instead, bring a backpack with some snacks and watch water turn from cloud to rain to river to sea in the matter of minutes.

Points in Poipu

We purposely planned to check out of the Courtyard Marriott, tackle our Na Pali Coast hike early in the day and then drive south to Poipu, to check in to the property I was excited to check out: The Grand Hyatt Kauai Resort and Spa. This Category 6 property requires 25,000 points per night or starts around $400 for a standard room. I wanted to stay three nights with a full day lying around the massive interconnected pool system constructed from volcanic rock along with a private salt-water lagoon.

The dates that I was staying would’ve cost me $1,821.76 for a standard guest room if I had booked with cash, but I had signed up for the Hyatt Credit Card 11 months beforehand and had only 30 days left to use the two free nights at any Hyatt property that comes as the card's sign-up bonus. I also had about 22,000 Hyatt points from recent stays — 3,000 shy of an award night. Luckily, Hyatt is a 1:1 transfer partner of Chase Ultimate Rewards, so I instantly transferred points I had earned with my Chase Sapphire Preferred Card over to Hyatt and booked my third night. And since the Hyatt card comes with Platinum status (no longer available), we were upgraded to a Deluxe Ocean View room for the stay — over a $2,000 value booked with points!

The Hyatt is a big property for a little island. Spread out over several wings, this 602-room, open-air hotel is surrounded by meticulously kept grounds, the Anara Spa, 18-hole golf course, kids camp, tennis facilities and — wait for it — no roosters. And the pool was, well, the best. Multiple pools are connected by a lazy river with a few adults-only spots and daily organized water slide races.

If you're not flush on Hyatt Gold Passport Points there are still plenty of other luxury hotels you can book with Points. The St. Regis Princeville Resort and Spa (SPG Category 7) is located directly across the island from the Hyatt, and can be booked from ~$500 or 30,000 Starpoints per night. If that's too rich for your blood, there's also the Marriott Beach Club in Poipu, available from $225 or 35,000 points per night if you can find a PointSavers award.

Poke man, go.

If you want to overpay for good (but not great) sushi and low-tier service while watching a once-in-a-lifetime sunset, then Stevenson's Library at the Hyatt is the place for you. Also keep in mind that portions are small; I had a lot of feelings leaving this place, but mostly it was just hunger. If you're looking for a quick bite that still leaves you able to pay your rent, The Shrimp Station in Waimea is for you. Or, head to the Kilauea Fish Market where they will grill you up today's fresh catch. And the one restaurant that I wasn't able to try but came highly recommended was Red Salt at the Ko'a Kea Resort.

Hang Loose

Poipu is a quiet town, so this is your chance to really relax. Can't sit still on a beach? Go jump off a cliff. Standing 40 feet above the waves and jutting out into the sea is the Shipwreck Beach cliff, where you can impress onlookers by attempting the worlds-deepest-ocean-wedgie. This jump isn't for the faint of heart or the soft of bone, and serious injuries are reported on the regular, so please be smart. The day I went to jump, a storm was on its way in and I'm pretty sure the ocean would have eaten me alive.

From the Air

Even though the island is small and you can drive around it in a few hours, Kauai is a treacherous landscape with few roads to take you to its most beautiful secret spots. So consider ditching the wheels for a ride in an AS-350 from Island Helicopters, where hour-long tours start at $175. However, for ~$330 you'll have a spot on the Jurassic Falls Landing Adventure, where your pilot will fly you on an extended trip with a jungle landing at the same waterfall they landed at in the movie Jurassic Park. They even played the famous theme music as we cut deep through the sharp valleys towards the 400-foot falls.

Rising up 4,000 feet, straight from sea-level, the Na Pali coast stands as a natural metaphor of Hawaii's own strength and longevity. Showing off his skill on our approach, our pilot Isaac banked left then immediately hard right to what felt like 90 degrees above and around a sea-cliff crest. The views of this beastly coast are forever ingrained in a tiny box in my brain called my happy place. This place is zen, and this helicopter tour added the rush I need to that. As we came down, I felt high and immediately wanted more... what are they pumping through that cabin?

'k den...

That's an informal goodbye in Pidgin, the slang of the island. And this was ours. We made our way to Lihue airport to board our red-eye flight back to Los Angeles. As I settled into 11F I did some quick math to see what the trip had cost me with out including food, drinks and the helicopter tour.

Flights: $22.40

Hotels, including resort fees: $126

Rental car upgrade: $108

Divided by two people: $128.20

Had we not used points and miles, this trip would have run ~$4,500.

I wanted to run off the plane and do it over again, but it was time to go. For now. Even as a traveler who rarely returns to the same place, I can confidently say that I'll be back to this beautiful island. It's one of the few places in the world with parts still untouched. And besides, at $128.20 I'm practically losing money by not being on vacation in Kauai all the time.

What are your top recommendations for visiting Kauai? Share your tips in the comments below!