Five Days on Kauai – The Garden Isle Guide


Our Hawaiian adventure kicked off on the garden isle of Kauai.  Kauai is the oldest and westernmost island in the Hawaiian archipelago.  It is known for the lush jungles, rugged coastlines, and gaping canyons.  This is the island Steven Spielberg selected to film Jurassic Park.  We spent five days exploring this island, and we departed thoroughly impressed by its undeveloped natural beauty!

Air Travel/Transportation

  • Delta Airlines – $33/ea (Used 25,000-UR points RT/ea, booked via Korean Air)
  • Rental Car5 days – $0 (Used 14,699 Citi ThankYou Points)

We used our Chase Ultimate Rewards points to book Delta flights via Korean Airlines.  The total cost for both of our round trip flights was $67 and 50,000 UR points!  Learn how to book this incredible deal here.

To properly explore Kauai, you must have a rental car.  We used our Citi ThankYou points to book a five-day rental with Thrifty through the Citi Travel website at a rate of 1.25 cents per point.  They set us up with a Nissan Altima, which was perfect for our purposes.



We booked the Sheraton Kauai resort using SPG points and the 5th night free deal.  The usual nightly cost is 12,000 SPG points, but with the deal, our five-night stay cost 48,000 points.  Since Delta screwed us over during our outbound flight from SFO to LIH, we missed our first night at the Sheraton.  We reached out to Starwood customer service to ask them to refund points for the night we missed, but they refused since we missed the “free” night.  After some discussion with a manager, they offered a 5,000-point courtesy credit.  The hotel also charges a $30-per-night resort fee.

About a month before our trip, we got a call from Jenny, the concierge at the resort.  She wanted to touch base and check if we had any special requests or were celebrating anything.  I was impressed by the initiative, and she was very nice.  When we arrived, we checked in at the desk and were given free drink tickets and a suite upgrade for our gold status (earned via the Amex Platinum card).  Jenny greeted us, congratulated us on our anniversary, and gave us a couple more free drink tickets and a voucher for champagne.  We asked if we could also get complimentary breakfast included with our room (not a perk of SPG gold), and she was able to find a manager to approve the request!

The resort itself was nice, but not mind blowing.  Our room was across the street from the beach, but we spent so much time out exploring that this did not bother us.  The room itself was a suite upgrade, with a living room, bedroom, and two bathrooms.  We did get a view of the secondary pool and garden area from our double balcony.  The primary pool was very nice, and we also enjoyed nightly walks along the beachfront path.  Sunset views from this area of Poipu Beach are phenomenal (see photo below)!  The Sheraton also offered a nightly happy hour, including two glasses of wine per person at the perfect time to watch the sunset.

Sunset Sippin
Sunset Sippin


Day 1 – Rum & Helicopters

  • Safeway

What an odd way to start… haha.  The first place we visited on Kauai was the grocery store to load up on snacks and beer!  We knew that we would be hiking, so we grabbed a few granola bars and some dried fruit snacks.  We also grabbed a six-pack of Maui Brewing Mana Wheat to prevent spending $10 per beer at the resort.

  • Koloa Rum Factory

Now we’re having fun!  Stop #2 – Rum!  The Koloa Rum Factory has a gift shop and tasting room.  Rum tastings are a lot of fun.  They are also free, include a few samples, some mixed drink recipes, and a history of rum production on the island.  We really enjoyed the new Kauai Coffee-infused rum.  Tastings are every half hour starting at 10am, according to the sign-in sheet.

  • Mauna Loa Helicopter Tour

This was one of the absolute highlights of our vacation!  We booked a private, doors-off helicopter tour with Mauna Loa Helicopter tours.  Our guide, Guy, was incredible!  He really knew the island of Kauai very well, and made the ride very smooth for us.  He taught us about the history of the island’s formation and made great recommendations for places to visit.  Since most of Kauai is not accessible by land, helicopter tours are the only option to see the many beautiful waterfalls, coastal cliffs, and massive canyons on the island.

I highly recommend setting up a helicopter tour early in your visit to Kauai for two reasons.  First, if the weather is bad, this will give you the opportunity to reschedule for a later day.  Second, it will give you a great perspective on the layout of the island, so you can better plan your adventures for the following days.  Mauna Loa offers a few different tour options.  We opted for the private island tour with the doors off, so we could really get the full experience.  If you plan to take pictures, doors-off is the way to go, because there will be no glare from the glass dome.  Also, wear long sleeves/pants, because you will be high up and traveling around 140 miles-per-hour!

After the helicopter tour, we headed toward Poipu Beach to check in to our resort.  On the way, we found a little spot for lunch, which boasts the best sushi and poke on the island!  To find Makai Sushi, you will have to step inside the Kukuiula Market, a random grocery store on the side of the road.  We ordered the Gorilla Bowl and the Hapa Roll, which were HUGE and absolutely INCREDIBLE!  We chatted with the owner while we ate, and he told us about how he personally drives across the island to pick up fresh fish every morning.  They start serving lunch at 11am, and they close when they run out of fish.  Get there early!

  • Resort – Happy Hour & Sunset

We checked in to the resort, grabbed our wine glasses, and headed out to enjoy the sunset… this would become a daily occurrence.


  • Dinner – Puka Dog

By dinner time, we were exhausted!  We decided to do something low key, so we ventured over to the nearby Poipu Shopping Village for some Puka Dogs.  If you’re not familiar (neither were we), a Puka Dog is a polish sausage stuffed into a soft, fluffy Hawaiian roll.  The roll is only open on one end, and they fill it with condiments of your choice before adding the sausage.  We went with pineapple relish and lilikoi mustard!  Add a bag of Maui onion potato chips, and you’re all set.  Mmm mmm good!


Day 2 – Hiking, Baths, & Beer (East Side)

Poipu Beach is a great place to stay, because this allows you to divide the island in half for exploration.  The Na Pali (north) Coast is impassable by car, so you can explore the east side of the island one day, and the west side the next.

  • Kalalau Trail – Na Pali Wilderness Park

Day two started early!  We woke up around 5:30am, packed our day bag with snacks and water, and headed out.  We wanted to reach the Kalalau trailhead before 8am, because parking is scarce, and the trail gets crowded later in the day.  The drive from Poipu Beach to Na Pali Wilderness Park takes almost two hours if you don’t stop.  I recommend driving directly to the trailhead, while making notes of places to stop on your return trip.

We reached the trail around 7:45am, parked, and stretched our legs.  The trail itself is not particularly difficult, but it does have quite a bit of elevation change.  We hiked along the beautiful coastal cliffs for two miles until we reached Hanakāpīʻai Beach.  The beach itself is covered in rocks of all shapes and sizes.  As we approached, we noticed hundreds of cairns (stacks of rocks balanced on each other).  Of course, I had to build one myself to mark our trip!

We sat and ate some snacks at the beach before opting to return to the trail.  At this point, you can continue another two miles to a waterfall, or turn back.  We had too much else to explore to commit to eight miles roundtrip, so we headed back the way we came.  We finished the hike around 10:30am, and the traffic on the trail definitely picked up by that point in the day.

On the drive back from our hike, we stopped for lunch at Pinks Creamery.  This tiny restaurant’s feature menu item is the Hawaiian Grilled Cheese – sweet Hawaiian bread, kalua pork, pineapple, and muenster cheese, grilled to perfection!  Add one of their signature smoothies and enjoy.


Moving along down the road, we came across Nani Moon Meadery.  If you’ve never tried mead, you really should give it a shot.  Mead is somewhere between wine and beer – fermented with honey, yeast, and water.  Here, you can sample the whole lineup, including Pineapple Guava Sunset and Deviant Beehavior (spicy!).


  • Queen’s Bath, Princeville

The Queen’s Bath is a relatively well-kept secret spot on Kauai.  To access it, you must drive into a residential neighborhood and find a tiny parking lot.  DO NOT park outside of this lot, or you will be towed.  When you park, look to the far right side of the lot, and you will find a small, unmarked trail.  Follow this trail through a wooded area and out to the rocky coast.  Turn left and follow the coastline until you see a large pool of still water in the rocks.  This is the Queen’s Bath – a space where the rocks form a bowl and the ocean waves crash over the wall and become trapped.

Climb down the rocks and into the bath.  Feel free to lounge a bit, but beware of the little fish in the area… they can be jerks.  Brooke was bitten twice on the foot while trying to take a picture.  Also, be careful on the rocks, because water crashed up and over them.  A sign indicates that more than a few people did not heed this warning.

Kauai Beer Company is a local microbrewery with a very impressive food menu.  We stopped in to get a beer flight, but we had to try the Brewhouse Mac N’ Cheese with butternut squash!  Combo that with a Tropical Armadillo Pale Ale… you’re welcome!


  • Resort – Happy Hour & Sunset

Another great day in the books… time to sit back with a glass of wine and take in another gorgeous sunset!


Day 3 – Coffee & Canyons (West Side)

All good days start with a nice cup of coffee, but great days start with an entire coffee plantation… and free samples!  Kauai Coffee boasts the largest US-based coffee plantation, with 3,100 acres of trees!  They offer free guided walking tours every two hours, starting at 10 am.  The tour will take you through the coffee production process, teach you the history of the estate, and explain what makes Kauai Coffee unique.  When you arrive, be sure to grab a few samples of the various blends, single-origin, and flavored coffees.  Whole-bean coffee bags are available for purchase in the gift shop.

To level off the coffee buzz, we headed down the road to Kauai Island Brewery for a beer flight.  They offer a solid selection of house-brewed beer, including the Lilikoi Ale… a golden ale, brewed with Passionfruit.


  • Glass Beach

Just around the corner from the brewery, through an industrial area, you can find glass beach.  The name “glass beach” comes from the tiny, smooth pieces of glass that make up the sand.  According to locals, this glass has been dumped into the water over time from the industrial surroundings, and then pulverized by the waves and rocks.  The result is a beautiful mixture of colored glass and sand unlike I had ever seen.

  • Hanapepe Swinging Bridge

We found a very narrow, wooden bridge in the historic town of Hanapepe.  As you walk across the bridge, it sways from side to side over the river.  Pretty neat, and worth a stop.  Also, visit the spice shop when you return from the bridge for some tasty samples.


This no-frills, white-brick building was a pleasant surprise.  They serve fresh poke without a ton of spices or seasoning.  This really allows the quality of the fish to shine through.  We picked up an ahi tuna bowl, side of rice, and a small side of octopus (Brooke refused to eat the octopus).  You will have to eat in your car, because there are literally no tables available.

  • Waimea Canyon Lookout

After lunch, we drove up into mountains in the northwest corner of the island, toward the Waimea Canyon Lookout point.  There are many lookout points to view the canyon.  We stopped at the first one and took the following pictures.  The panoramic views at this point were absolutely stunning.

  • Kalalau Lookout 

Once you’ve finished taking in the beauty of Waimea Canyon, hop back into the car, and continue along the road.  You will wind through Koke’e State Park for a while until you pass a few buildings on your left.  Keep rolling along for a couple more miles until you find the Kalalau Lookout.  If you’ve picked a clear day, you will be able to see into the gorgeous Kalalau Valley.  The day we visited, the clouds were very thick, but we hung around long enough for a brief clearing… and the view was totally worth it!

Kalalau Valley view
  • Pu’u O Kila Lookout/Wai’ale’ale

One more mile up the road will take you to the final lookout.  At a slightly higher elevation, this outlook is supposed to give the best land-based view of the Kalalau Valley.  However, it is perched at Wai’ale’ale, one of the “wettest places on Earth.”  When we arrived, the clouds were so thick and gray, we could hardly see 10 feet in front of our faces.  😦

Living up to its claim
  • Spouting Horn

On our return trip to the resort, we stopped by a spot called the Spouting Horn.  This is a rock formation along the coastline where incoming waves are channeled through a small opening in the rocks.  The result is a geyser-like spout, and it’s pretty cool looking.


  • Resort – Happy Hour & Sunset

Another night, another sunset!


  • Dinner – Bubba Burger

After a long day, we wanted an easy dinner.  We drove to the nearby Kukui’ula Village Shopping Center to grab some burgers.  Bubba Burger features a simple menu, but this specific location had the Kauai Burger with pineapple and teriyaki sauce!  Get it… that is all!

Day 4 – Drink & Golf

  • Drinks at the Pool

Our day started with a nice breakfast buffet at the resort.  We cashed in our free bottle of Champagne to make mimosas at breakfast.  Then we headed to the pool to enjoy our free Mai Tais.  It was nice to relax for a day after two full days of exploring.

  • Lunch – Da Crack & Anake’s Juice Bar

For lunch, we ventured just outside the resort, back to the Kukuiula Market.  I opted for a burrito bowl with fish from Da Crack, and Brooke went with the Chunky Monkey Acai Bowl from Anake’s Juice Bar.  Both were very tasty!

  • Kauai Lagoons Golf Club

In the afternoon, I decided to play some golf.  The Marriott near the airport features a Jack Nicklaus signature design golf course.  I chose to play the Kiele Moana “Ocean Nine” holes.  The course was very challenging, with high winds coming in from the ocean cliffs, plenty of water in play, and drastic elevation changes.  Twilight prices were reasonable, including club rental and a sleeve of Titleist balls.  The views were spectacular, and I managed to make it through nine holes without losing too many balls!

Day 5 – Chill & Depart

Day five was all about taking it easy, and then heading to the next island (Oahu).  We slept in, ate a late breakfast, and drove to the airport to drop off the car.  On the way to the airport, we had to stop for a picture of the iconic tree-tunnel street.


Total Trip Cost Breakdown

The following table breaks down our transportation and lodging costs.

Item Points/Miles/Loophole Actual Cost
Airfare x 2 from MCI to LIH (return flight from Maui to KC included) Roundtrip fare booked on Delta via Korean Air (25,000 UR points + $33.50 per ticket) $67
Rental Car – 5 Days 14,699 Citi ThankYou Points (1.25CPP) $0

Sheraton Kauai Resort

43,000 Starwood Preferred Guest points (see above) + $30 resort fee per night $120

Kauai was beautiful, natural, and filled with exciting adventures.  We truly enjoyed our time there, and I hope our activities provide inspiration for your visit to The Garden Isle!


8 thoughts on “Five Days on Kauai – The Garden Isle Guide

  1. Do you have the Citi Prestige? Doesnt that get you some free rounds of golf? If so, we’re you able to take advantage of that as well?


    • No, we used points to cover the flights, hotel, and rental car. That allowed us to have extra cash for awesome experiences. I highly recommend the doors off helicopter tour. Perhaps they will grant you a “local rate” if you ask nicely 🙂


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