Winter on Kauai – Ultimate 1 Week Itinerary

Winter on Kauai – Ultimate 1 Week Itinerary

When you think about taking a vacation, you probably dream of visiting the state of Hawaii. Like you, we had dreams of visiting one of these paradisiacal islands. They popped into our mind every time we planned a new trip. After traveling to several other places we finally decided it was time to visit Hawaii. Our main attraction to the state was the Garden Island, Kauai. It’s the oldest island in Hawaii and is home to the famous Na Pali Coastline and the “Grand Canyon of the Pacific” (Waimea Canyon). Sam spent a lot of time researching and planning this trip for us, and I booked everything with her suggestions. Though our trip was far too short, we made the most of spending part of winter on Kauai with this ultimate 1 week itinerary. Keep reading to see how.


Kauai is one of the more expensive islands in Hawaii to visit. Since accommodations are usually cheaper during winter, we planned our trip for January. The south coast of the island typically has less rain and calmer waters than the north coast in winter so we chose to stay near Poipu in the south. There weren’t many good hotel or resort options under $200 USD a night, even in winter, so we looked at Airbnb as an alternative. We ended up finding plenty of options under $200 USD per night in every area of the island.

The Airbnb listing we chose was next to Prince Kuhio Park near Poipu for $169 USD per night. The one bedroom condo (with TWO lanais) was a perfect home base to explore the island and relax when we needed.

Exploring Kauai

Kauai is beautiful anytime of the year, but winter on Kauai can be especially breathtaking. The oceans are rougher and cooler (which makes swimming in some spots unsafe), but watching the massive waves crash against the dramatic coastline was unforgettable.

Getting Around

Having a rental car isn’t absolutely necessary, but we definitely recommend getting one to make the most of your time. With our own car we were able to get to any point on the island without any hassles of booking shuttles, cabs, Uber or Lyft. Renting a car for the week made it easy to explore Kauai at our own pace. It also enabled us to do some self-guided tours instead of booking tours for things we wanted to see. We rented an intermediate SUV for just under $400 USD (with taxes and fees). You can cut that cost by 40-50% if you rent a  standard or economy car, but we wanted the SUV for the extra room since we planned on having a special passenger during our trip (keep reading for more about our special guest).

winter on kauai - ultimate 1 week itinerary
Found this little waterfall on the side of the highway – so worth it to rent a car!

Jaw Dropping Views and Rainforest Hike

On the western side of Kauai, Waimea Canyon (aka “The Grand Canyon of the Pacific”), is one of the must see natural wonders of the island. The view from the Waimea Canyon Lookout is spectacular. From the left you’ve got a view of a waterfall, in front you have the wide canyon with lots of valleys, and to the right the canyon leads miles away to the coast. The soil on the island is full of iron which gives the canyon a beautiful red hue that contrasts well with the blue skies and random greenery.

If you want to take some good photos from the lookout spot I recommend taking them in the afternoon. The photos we took in the morning had a lot of shadows in the valleys of the canyon so we didn’t get the best pics. The waterfall that’s visible from the lookout will show up better in the afternoon light too. Although we thought we took enough photos (it wasn’t nearly enough), we got back in the car and drove further up highway 550 into the mountains. Our destinations were a couple of lookout points that overlooked the famous Na Pali coast.

The first stop was Kalalau Lookout which had plenty of parking for a morning in the off season. The view here is pretty, but if its crowded (it wasn’t when we were there) you’ll have to wait for a chance to get the best spot for taking pictures. If you’re planning to go to the next lookout or do a hike after this, like we did, you may want to stop and use the restroom here. The last lookout at the end of the highway doesn’t have any restrooms.

Before we headed to the next lookout, we hiked the Kaluapuhi trail across the highway from Kalalau Lookout. This rainforest trail is about a 2.3 mile loop which includes walking on the road. It is a easy/intermediate level hike depending on which direction you go. If you want the easy way, hike downhill on the road back towards Waimea Canyon. If you want the intermediate way, walk further up the highway towards the next lookout. Unfortunately we didn’t know this before hiking the trail and we ended up doing it the hard way. By the time we made it back to our rental car we were huffing and puffing due to the elevation (about 4,000ft) and for having to walk back uphill at the end of the hike.

Next stop, Pu’u O Kila Lookout. This lookout is at the end of highway 550, roughly a 5 minute drive from Kalalau Lookout. Parking at this lookout is limited and we had to park nearby on the side of the road. We got much better views and pictures here than at the Kalalau spot because there was more clear space to see down the valley. In addition to this being a viewing point and one of the wettest spots on earth, its also the start of the Pihea Trail that leads you to Kilohana Lookout (8 miles there and back). Since we already hiked the Kaluapuhi trail, we opted to just take some pics and head back to Poipu and get some lunch.

First glimpse of the magical Na Pali coast!

Kauai Humane Society

This is where we picked up the special passenger we had planned for. The Kauai Humane Society is located off of highway 50 about 4 miles west of Lihue. They have a program called Shelter Dogs on Field Trips that allows anyone 18 years or older to take a dog out of the shelter for the day. I was so excited when Sam told me about this program, we both love dogs and were happy to give one a break from the shelter.

The Kauai Humane Society requires a credit card to have on file in order to put a $200 USD deposit on the card if the dog is not returned by the end of the day. Once we got to the shelter we checked in, filled out some paperwork and signed a liability waiver. After that was taken care of, we got to meet some of the dogs and take them into a play yard to see if we were a good fit. Once we found our match, Humphrey a sweet and mild mannered middle-aged black pit bull mix, the staff gave us a quick orientation and provided us with a leash, treats, and doggie bags. Humphrey was given a vest that said “Adopt Me” to wear on his field trip.

When we got Humphrey to the car, we could tell that he was used to the field trip program because he jumped right in. We took him on a 3 mile round trip hike at Maha’ulepu Heritage Trail along the bluffs. He seemed to know the way and led us to the trail. While he got to take in all the smells along the path, we took in the beautiful views. On the way back, we stopped at Shipwreck’s Beach near the trailhead and relaxed on the sand for a bit. Since we still had some time left after the beach, we took Humphrey with us to get a late lunch at Puka Dog. We ate our hot dogs and then took him back to the shelter before time ran out. If you are a dog lover, don’t miss out on this memorable and fulfilling experience.

Hiking the Maha'ulepu Heritage Trail with a shelter dog.
Humphrey was the perfect hiking partner.

Kalalau Trail to Hanakapi’ai Falls

This is probably the most famous hike on the island and it was one of the top reasons we chose Kauai for our trip to Hawaii. We were inspired to visit the Kalalau Trail thanks to watching the movie A Perfect Getaway far too many times. It was partly filmed along the Na Pali coast and Kalalau Trail. The scenes in the movie were so beautiful that we knew we had to see it in person.

The trail starts right at Ke’e beach which is at the end of Highway 560. The hike to the waterfall does not require a permit, but you are now required to make a reservation before your planned visit. The reservations can be made up to 30 days before and no later than 1 day before your planned hike. The fees for the reservations are cheap, $1 USD for walk in and $5 USD for vehicles. I recommend reserving at least 1-2 weeks in advance because the voucher times do sell out.

The hike from the trailhead to the waterfall is around 4 miles each way with Hanakapi’ai Beach being the halfway marker. Hanakapi’ai Falls is a 300 foot waterfall that pours down into a natural pool that you can swim in (warning: the water can be freezing). This trail is sometimes closed due to recent rains making it slippery and dangerous to hike, so I recommend wearing hiking boots/shoes and not sneakers or sandals. Its definitely worth the effort to hike this trail because you’ll get some beautiful views of the Na Pali coastline and the towering 300ft Hanakapi’ai Falls. After the hike we hung out at the picturesque Ke’e Beach for a while before heading back. If you’ve still got enough energy left after this hike you should check out Queen’s Bath in Princeville.

winter on kauai - ultimate 1 week itinerary
Gorgeous views of the Na Pali coastline along the Kalalau Trail.

Kipu Ranch Adventures’ Ultimate Ranch Tour

This is one of the two tours we booked for our one week vacation in Kauai. We like adding a little adventure to our trips and we both agreed that this was a good way to do just that. Kipu Ranch has been used as a filming location for plenty of movies, most important of which is Jurassic Park (one of Sam’s favorites). That fact alone was enough to convince us to book this 2-seater ATV tour. The 3 hour Ultimate Ranch Tour is about $150 USD per person, and it takes you to some of the best sites on the property. You can drive in your own ATV or hop in with one of the guides instead.

When you get to the ranch, you’ll first have to sign a liability waiver, get a quick orientation, and receive your helmet and goggles. After that, the guides will give you a rundown of the rules and how to operate the ATVs. They even have a small course for you to practice on and get comfortable with the “extreme golf carts” before you head out for the tour of the ranch. When everyone was ready we headed toward the first location of note. At every stop our lead guide gave us lots of information on the history of Kauai and the ranch. He pointed out all of the locations for the popular movies filmed on the land and gave us time to take some pictures. We got to see some breathtaking views on the tour and I personally enjoyed the history of the island, its people, and ranch the most.

winter on kauai - ultimate 1 week itinerary
Epic views at Kipu Ranch. Can you spot any dinosaurs?

Na Pali Coast Snorkel and Sail Tour : Holo Holo Charters

Just in case you’ve forgotten already, the Na Pali coast is one of the top reasons we took our trip to Kauai. Sure, we’ve already hiked along a portion of it by the time we took this tour and we also saw parts of it from lookout points up in the mountains, but we hadn’t had a chance to get a big picture view of it yet. If our budget could have fit in a helicopter tour, I’m sure that we would have done that too. My point is that the northern shore of Kauai is one of the most beautiful coastlines in the world and you should definitely go see it.

This 5 hour tour included continental breakfast, deli style lunch, beverages (like beer and wine!), one snorkeling stop (with gear) and a grand view of the Na Pali Coast. The day started at the Holo Holo Charters office in Eleele where everyone had to check in and sign liability waivers (so much paperwork on this trip). After all of that boring stuff was over, we all walked down to the Port Allen Commercial Pier to collect our snorkel gear and get on the fifty foot catamaran.

We then left the bay and sailed to the snorkeling spot which was about 35 minutes up the coast. Before the boat was anchored, somebody spotted a sea turtle and we got super excited. By the time we had our gear on and jumped into the water, the sea turtle was nowhere to be seen. We swam around for about half an hour checking out the fish and reefs before we were called back to the boat. Sam and I were reluctant to get back on the boat without seeing the sea turtle so we were some of the last few people that got back aboard. When we finally did get back onboard, the sea turtle appeared again about a minute later. After the snorkeling was over, FREE beer and wine were available for the rest of the tour.

Heading out from there, we sailed further north toward the Na Pali coast and passed Waimea Bay and Polihale State Park. Along the way our luck picked up because started seeing humpback whales breaching the surface all over the place. We even had a dolphin swimming upside down in front of our boat for a little bit. When we finally made it to the Na Pali coast, we achieved our goal of getting a grand view of the cliffs. The sight was amazing even though we had to keep the boat at a distance due to the rougher winter waters on the north shore. Unfortunately we only had our cell phones and a GoPro with us so we couldn’t get any pictures that could do the spectacle justice.

Once everyone had their turn at getting their photos, the captain set a course back to the port. She had the engines running instead of using the sails so we made it back to the port in about 45 minutes. This was a great tour thanks to the fun staff and incredible views.

winter on kauai - ultimate 1 week itinerary
Thanks to 12 foot winter swells, this is as close as we could get to the beautiful Na Pali Cliffs.

Food and Drink

Our Kauai ultimate one week itinerary would not be complete without eating some great local food and enjoying a relaxing drink or two (or three). We also stopped at a grocery store on our first day on the island – which I would only recommend if you are looking to grab a couple of snacks or breakfast items. Grocery stores on Kauai are NOT cheap. Actually, food in general on Kauai is on the pricier side but depending on where you go, it can be totally worth it. See below for our favorite spots:

Eating House 1849 Koloa

($$$) This second floor Asian fusion restaurant is a great spot to catch the sunset while eating dinner. Their food and drinks were very good but they were a little pricey. Eating House 1849 Koloa is located in The Shops at Kukui’ula Village (a shopping center next to the roundabout in Poipu). You may want to make a reservation if you want a good table for viewing the sunset.

Koloa Fish Market (Poke)

($$) If you like poke, you probably won’t find a better place to get it on Kauai. Koloa Fish Market has fresh, quality fish and you can taste that in the poke. The market is on Koloa Road across from the post office. If you like spicy food we both had and recommend the spicy tuna poke.

Savage Shrimp

($$) This hole-in-the-wall restaurant is in the same shopping center as Eating House 1849 Koloa. Savage Shrimp has such flavorful and juicy shrimp dishes that we ended up eating it twice. They didn’t really have much seating, so we ordered it for take-out and brought it back to our Airbnb to eat. Just FYI, the shrimp are peel and eat unless you pay extra for peeled shrimp. We ordered the super tasty Grasshoppa and Fire Rock plates (two of their spicy options).

Brennecke’s Beach Broiler

($$-$$$) Another second floor restaurant, Brennecke’s Beach Broiler overlooks Poipu Beach Park and is another great spot to watch the sunset while eating. They’ve got a “world famous” Mai Tai and other great drinks. They also have a bakery and deli on the first floor. Happy Hour is probably the best time to visit but it can get busy since it’s near a lot of resorts.

Keoki’s Paradise Restaurant

($$-$$$) This was my favorite restaurant to dine-in at. It had an open air dining area that was bordered by a beautiful garden. We got seated right at the edge of the garden where the stage for live music was. The calm island music really added to the ambiance of the experience. I’d definitely recommend a reservation for this place as it is near many resorts. Keoki’s Paradise is in Poipu Shopping Village on Poipu Road.

Anuenue Café

($$)  Anuenue Café is in the center of Poipu Shopping Village. This small café serves great coffee and breakfast. They’re open from 7 am to 1pm every day of the week, except Thursdays and they have a small covered seating area outside. The service was quick and made for a nice, filling breakfast before the day’s adventures.

Puka Dog Hawaiian Style Hot Dogs

($) This famous hot dog stand is located in, none other than, Poipu Shopping Village. We stopped here with Humphrey after our hike to refuel and see what all the hype was about. Maybe it was just because I was starving from the hike, but I don’t think I’ve ever had a hot dog that good. I think the real stars of the dish were the fresh bread and Aunie Lilikoi’s Hawaiian mustard. They also have a Veggie Dog if you are meat free. Either way, you have to try Puka Dog.

poke lunch at shipwreck's beach, Kauai
Eating super fresh poke from Koloa Fish Market.

If you are planning to take a vacation to Kauai, winter or not, we hope you make use of this ultimate 1 week itinerary. After spending a week in Kauai it was very clear that the nickname “Garden Island” is very fitting due to the dramatic landscapes and lush greenery. Let us know in the comments if you have been to Kauai and what you loved (or didn’t love) about it the most. If you are thinking of traveling to Kauai let us know if this post was helpful. For other itineraries featuring locations with jaw dropping beauty, check out one of our other posts, Costa Rica or Belize. Thanks for stopping by and happy travels!

winter on kauai - ultimate 1 week itinerary

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