Kauai to Maui to Oahu. Explore the vast beauty of Hawaii in 15 days and the diversity of three islands.

If you’re reading this, I hope a trip to Hawaii is on your horizon, as it remains once of the most incredibly magical places I’ve ever been.

Recommendation: If I did our trip over again, I would reverse the entire thing. I’d start with the bustling Oahu, then the adventurous Maui, and end in the most natural and beautiful island of Kauai.

Hey Honeymooners!

Our honeymoon trip to Hawaii exceeded my imagination in every way. As you scroll below, you may be thinking, how could I afford that? Well, we already had most of the household essentials after moving from 2 houses to 1 so we asked our guests to contribute to a Honeymoon Fund!

A gift card registry that's as flexible as cash. Sign up for Honeyfund today to start your dream registry.

Settling into the “Garden Isle”

Kauai – Day 1

After a long day of travel in early December, we settled into our cottage and enjoyed a glass of champagne along with a slice of our wedding cake that thankfully survived the journey intact. 

We stayed west of Hanalei on Kauai’s north shore. We had our own private place (indoor and outdoor) in a small cottage community, right on the beach.

Exploring the North Shore

Kauai – Day 2

We woke up in time to watch the sunrise (a rare sight for me, “thanks jet lag”) and went for a long walk on the beach. It felt like we were the only ones around as all the footprints had washed away. We saw our first of many Hawaii rainbows.

To stock up on fresh fruit and vegetables, we found a local farmers market in Hanalei. Troy bought me a bouquet of beautiful tropical flowers with which to decorate our cottage.

Then we headed to see the view of the Kilauea Lighthouse, a 100-year-old lighthouse and bird sanctuary. We made lunch at home then lounged around the cottage and read while “the wettest spot on earth” was getting its tropical rain showers.

When the sun returned, Troy and I went on a run to “Tunnels Beach” to check out one of the caves. From there, you may continue to the end of the road where it hits the Napali Coast mountains.

We watched the sunset on our own beach then Troy cooked us a delicious steak dinner to enjoy with a bottle of wine I brought back from Argentina for a special occasion.

We had the suitcase space so we traveled into Hawaii with a decent amount of alcohol. I recommend doing the same, it’ll save you an arm and a leg that you can spend on experiences instead.

Scenic South Shore

Kauai – Day 3

We drove through The Tree Tunnel, a mile long stretch of road lined with eucalyptus trees, on the south side of the island where there is a dryer climate.

We hiked Maha’ulepu Trail along the coast east of Poipu. There were beautiful views from there and the weather was absolutely perfect. We stopped by Poipu Beach just to see if there happened to be any monk seals or turtles on shore. No luck.

Spouting Horn was supposed to be an impressive geyser.  To our disappointment, it has lost its height over the years due to erosion causing the hole to widen.   It was fun to look through the souvenir shops there though. 

The Green Bay Packer game was just starting, so we rushed over to Kauai Brewing Company to catch some of the game and try a few local brews. They were pretty good and the Packers were winning so we left happy.

Near the Brewery, we came across Kauai Coffee (Hawaii’s largest coffee plantation) and thought we’d drop in for coffee to bring home as gifts.  When we walked in, a tour happened to be starting, so we tagged along for a bit.  I’m glad we did as we got to try fresh beans from the trees which tasted completely different than I expected. We also learned that Hawaii is especially popular for their coffee because of the unique flavor in the beans from the volcanic soil. 

We wanted to get back to the north shore to watch the sunset so we left in the afternoon.  On our way, we visited Wailua Falls, which are the prettiest falls that you can drive up to by car.   From the lookout point, the view was good, but if we were more daring that day, it would have been awesome to climb down the “restricted path” to see the falls from the bottom.   

We also pulled off the main highway to see Anini Beach, where our friends Kari and Andrew got engaged. Then we watched the sunset over Hanalei Bay at Hidden Beach.

Tunnels and Trails

Kauai – Day 4

I don’t know what it is about Hawaii, but it turned me into a morning person. Bright and early, we got up to walk on our beach. Troy chased crabs with the Go Pro trying to get the perfect underwater shot. A morning shower sent us running back to the cottage.

Later, we headed to Tunnels Beach hoping to boogie board, but I chickened out when I saw the high waves. Troy went for it, but after a few attempts, a large wave snapped our board into three pieces. We returned to our cottage to lounge in the yard, listen to the ocean, drink some beers, and read.

We wanted to time our hike on the Hanakapi’ai Trail so that we could see the sunset on our way back, so we set out in the early afternoon. The path was moderately strenuous, the worst were the sections of steep rocks covered in slippery mud. The views on the Napali Coast were stunning and I’ll never forget the sounds and the smells from our hike.

A Chopper & A Cruise

Kauai -Day 5

Today could not have been more perfect. This was my absolute favorite day of the trip.

We left the cottage before sunrise headed to the airport where our helicopter ride would start. Troy booked a Doors Off Helicopter Tour with the doors off so he could get some clear aerial photos. Our pilot was wonderful and had some great stories to share with us on our one hour tour. Our tour was 1 hour, costing $325. This was a once in a lifetime experience we received as a wedding gift from our Honeyfund registry.

My favorite water falls were the Seven Sisters Falls and Jurassic Falls (from the movie). We saw some incredible rainbows over the ocean too.

I hadn’t thought about the wind factor. If you book a doors off helicopter your, tie back your hair!

We had time to kill between our helicopter tour and our sunset cruise, so we checked out a couple historic towns.  The first, Old Koloa Town, where we browsed several small shops and Troy found his first Shave Ice of the trip.

I had read in a local magazine that a Wisconsin Native opened up a pie shop along the highway to Henepepe, so we felt obligated to check it out.  It was called Right Slice and was well worth the time/money to stop in.

Historic Henepepe, which translates to Crushed Bay is dubbed “Hawaii’s Biggest Little Town.” Here we found some cute shops and a unique swinging bridge.

Salt Pond Beach was not far from Henepepe, which is named for the traditional Hawaiian Sea Salts from the flats nearby.

Now it was finally time for our Napali Coast boat tour. We booked with the Blue Dolphin Charters tour company and loved our first mates Danny and Joe (who doubled as bartenders). We had a rough ride north, battling the waves, but it all paid off when we got to the northwest side of the island for a spectacular view of the 4,000 ft Napali cliffs.

Napali Coast – Kauai – Blue Dolphin Charters

I’ll say that the views from the helicopter were better, but the highlight of the boat cruise was seeing Humpback whales. That was a first for both of us. Before we got back to the docks, we caught a breathtaking sunset over the Pacific, a perfect ending to our most memorable day.

Humpback Whales Off The Napali Coast – Kauai – Blue Dolphin Charters

Beach Day and Queens Bath

Kauai – Day 6

We spent most of our morning walking a long stretch of beach from our cottage to Tunnels Beach.  Troy taught me how to identify Military helicopters, which we’d spot overhead quite often.  

We spotted a monk seal on our walk back to our cottage!  I was so excited as the species is on the brink of extinction and it is estimated that there are only about 35 left around the island. Troy captured him on the Go Pro and we named him Walter.

monk seal hawaii vacation
Monk Seal on Kauai’s Beach

We lounged in our hammock in the afternoon reading books, soaking up our last full day with our private ocean front cottage.

In the afternoon, we made the short drive over to Queen’s Bath, hoping conditions were right to relax in the tide pool.  No such luck, the water was stormy causing continuous powerful waves to crash over Queen’s Bath. It’s amazing how drastic the tides can change.

For a pre-dinner snack, we picked up some fresh ahi sushi at the Hanalei Dolphin Fish Market. 

Goodbye Kauai, Aloha Maui

Maui – Day 7

Opaeka’a Falls was the last waterfall on my to-do list and luckily it is the most accessible on the island. We were able to drive to a nearby parking lot just a short walk from the overlook.   Before heading to the airport for our flight to Maui we stopped at the Kilohana Plantation where the original Sugar Mill Plantation of the island thrived and the baron had his mansion.   On the grounds, we visited Koloa Rum for some samples and delicious rum cake.

It was late by the time we got to Maui and picked up our rental car (a convertible in anticipation of the Road to Hana journey!), so we headed for dinner at Mama’s Fish House, a restaurant that Troy had visited with his family years ago. His parent’s were kind enough to sponsor this dinner as a wedding gift.

The Fish House was much more established than I imagined. I suppose I was expecting a little shanty on the water. We had delicious cocktails, topped with an orchid and fresh pineapple and the best calamari I think I’ll ever taste. The menu there was unique as they note where the fish was caught and even the fisherman’s name.

Then we drove (with the top down, of course) to settle into our Maui condo in Kihei at the Kihei Garden Estates.  We had to be up early the next morning to check in for our Scuba Tour. 

Scuba, Snorkel, and Maui Culture

Maui – Day 8

Have you tried Scuba before? This was my first dive!

Our Scuba Tour was another Honeyfund wedding gift booked through Scuba Shack. It featured two dives: one at Molokini Crater and the other at Turtle Town. I could only Snorkel at Molokini as it was too deep for an uncertified diver. Being an underwater crater, it was incredible to see the steep drop-off of the reef walls and all the sea life that thrived there . Within minutes I saw a White-tip Reef Shark! Of course, while I’m out all on my own.

The second dive, at Turtle Town, I was able to scuba. We were probably underwater for about 45 minutes. The first 20 minutes were quite frustrating for me, as it took a lot of adjustments to get my buoyancy right. When I figured out how to use my lungs more efficiently, I could actually enjoy the views. We saw some incredible wildlife including: Moorish Idols, Butterfly fish, Goatfish, Needle Fish, Parrotfish, Parrotfish, Spotted Puffers, White-tip Reef Shark, Whitemouth Mooray Eels, Soldier fish, Surgeonfish (Troy’s favorite yellow tang), Wrasse, Barracuda, Triggerfish, Trumpet fish, Hawaiian Fantail Filefish, and Green Sea Turtles.

When we returned to the boat launch, we were warned that a drive up to the mountain within 24 hours would surely result in death!

After the dive we stopped at a Kihei farmer’s market to stock our condo with fresh foods for the week and picked up Poke (pronounced Poke-aye) for lunch.

Troy didn’t get his fill of Go Pro footage of turtles, so we found a beach near where we dove earlier. He snorkeled while I napped and read on the beach. He did get some amazing videos.

It was a Friday night, so we headed to Wailuku for their Music Festival held the first Friday of every month.  There, we tried traditional Hawaiian eats like Laulau (meat that is cooked wrapped in taro leaves) and Malasadas (doughnuts). 

Road to Hana and Beyond

Maui – Day 9

Today we were finally going to put the convertible to good use. We woke up early and drove in the rain to the start of the Road to Hana which consists of over 56 one lane bridges and more than 600 hairpin curves.

We stopped at Hookipa Beach to watch the sunrise before beginning our journey. The first hour of the drive we had to keep the top up as it kept drizzling.

We stopped often to hike and look at the waterfalls along the way. One of the best was Wailua Falls. There was hardly anyone on the road. We made it to the halfway point and found some delicious banana bread to eat as a snack. At a coffee shop that was built into the jungle, I was able to get my caffeine fix for the day (a mouth watering macadamia nut latte).

Next on the list was Wai’anapanapa State Park to explore the lava tubes and the Black Sand Beach. We found a secret cave with a hidden pool where all the locals were swimming.

Time to put the top down and continue on to Hana. We drove into town and down to the Hana Bay Beach Park. As we were warned, the beach wasn’t anything special so we decided to travel on the road less traveled beyond Hana. The road got really narrow and we practically had to scrape against the canyon walls to share the road with buses and other cars.

We stopped at Hamoa Beach and had a lunch of bananas and granola bars before continuing on to the Haleakala National Park and the Pools of Ohe’o (AKA Seven Sacred Pools). We hiked through the pools to get to the waterfall at the top and soaked in the view for a while at the park before embarking on the long, winding journey back.

Pools of Ohe’o (AKA Seven Sacred Pools)

Once out of the curves we stopped at Paia town to do some shopping before heading back to our condo.

Blowholes, Beaches, and Brews

Maui – Day 10

Today we packed up the car before lunch and headed to the west side of the island where we relaxed and watched a wedding on the Royal Ka’anapali Beach. We luckily got one of the 10 public parking spaces that they had for the whole beach.

We kept driving north til we arrived at Nakalele Blowhole and the heart rock. After I had a little quarrel with the port-a-john attendant, we walked down to the Cliffside. The geyser from the blowhole was at least 3 stories and we were afraid to get too close. We took a picture in front of the heart shaped rock as every couple on their honeymoon should do! We hiked back up the cliff and headed back toward Lahaina.

On our way back towards Lahaina, we stopped at D.T. Fleming Beach Park so Troy could try boogie boarding. The waves were crazy but at least he got some good videos! I was nervous the whole time.

We continued on to the Maui Brewing Company and really enjoyed the variety of quality brews we tasted.


Next, we were off to Lahaina to stroll around town before our Luau reservation. Thrift stores and expensive art galleries made for fun window shopping before ending up at the famous banyan tree in downtown Lahaina. It stretches over 200 feet over a park and has 12 major trunks supporting it. There was a neat craft fair with all the vendors and musicians setup under the tree.

After our long day of adventures it was finally time for our dinner at the Old Lahaina Luau. (Another Honeyfund wedding gift.) We were greeted with fresh Hawaiian Leis and Mai Tais.

Before dinner, we learned about Hawaiian traditions like how to make poi, how to play instruments, and then took pictures together with the sunset in the background. We enjoyed a grand buffet of all the Hawaiian specialties (like Kalua Pig, cooked underground) and sipped on various cocktails.

The show was great, but to our disappointment there were no fire dancers. We sat on the ground in the front row, it felt like we were part of the action.

Watching Sunrise from Above the Clouds

Maui and Oahu – Day 11

We woke up at 4am to drive up Mt. Haleakala (“House of the Sun”) to see the sunrise from 10,000 ft. We had a long winding journey up the mountain racing as fast as we could so we wouldn’t miss it. We reached the viewing platform just in time to see the sun poke up through the clouds. It was amazing to just stand there and enjoy the stillness of the morning.

After our long winding journey back down the mountain we felt much better getting back to sea level, the thin air at the top was noticeable.

To kill a few hours before our flight to Oahu, we had a picnic on the beach to finish all the random food and beers for lunch that we couldn’t take on our flight.

The Hawaiian Whale Institute is known as a location where you can spot humpback whales, unfortunately, it was too early in the season to see them close to shore.

That’s all for Maui!

Day 11 continued (Arrival in Oahu)

We arrived in Oahu early in the evening. We picked up our rental car and headed to Waikiki.

Our hotel was in the middle of downtown Honolulu and parking proved to be a major challenge.

We quickly got settled in our room and headed out to explore the downtown area. If you took away the tropical air and the palm trees it felt like walking down Michigan Avenue in Chicago.

We stopped at the Big Kahuna restaurant to try a Hawaiian specialty burger called Loco Moco which has a fried egg on the top. All the while, we suffered through some terrible Karaoke.

Waikiki Beach

Parasailing & the North Shore

Oahu- Day 12

Troy wandered around downtown Honolulu and found coffee and banana pancakes to surprise me with breakfast in bed before we set out for a couples’ massage.

Relaxed and reenergized, we headed straight to our wedding gift parasail adventure with Xtreme Parasail. They took us for a private trip along Waikiki Beach.

You could also hit the sky on an Oahu Helicopter Tour, especially if you haven’t done one yet on your Hawaii vacation.

For drinks and dinner we enjoyed the atmosphere at the Tiki Restaurant where patrons can watch the sun disappear into the ocean.

When we got back to our hotel we learned that a crew was filming Hawaii 5-0 nearby! (Finally, an explanation for the gunshots we were hearing!) Unfortunately we didn’t spot any actors, just all the props lined up on the street.

That was enough of the big city for us and it was time to head north to our apartment in Oahu’s famous North Shore. Picking up groceries on our way, we settled into the apartment pretty quickly.

We were entertained by the fact that we had live lizards chilling around our kitchen. We relaxed the rest of the night, drinking Rum drinks and playing card games.

Cultural Immersion

Oahu – Day 13

After some time at the beach in the morning, we took a short drive into the Waimea Valley to explore the Polynesian cultural center. (Waimea means “red waters”.) A spiritual and wise Hawaiian elder taught us how to play Hawaiian Checkers and weaved us a “possible” ball out of palm fronds to put in our house. (2021 edit: We still have this ball in a bowl in our living room. Since our honeymoon we have had two beautiful boys and purchased our forever home. I’m not superstitious, but I’ll keep this lucky treasure forever.)

We learned how to make woven bracelets from a perfectly tattooed Polynesian man.

As we continued into the valley, we came to the waterfall pool. The water was shockingly cold, but we braved it anyway so we could kiss under a waterfall on our honeymoon.

Despite some wind and rain we headed back to the car and decided to try our luck at golf, determined not to let weather slow us down.

Driving to the very northern tip of the island, we paid a total of $20 at Kahuka Golf Course to play and rent clubs. The location of the public course is prime real state and is constantly getting offers for commercial property.

After 9 holes of golf in the wind, we drove into Haleiwa to check out the famous surf town and find some food. We decided to stop at a Thai food truck for dinner and enjoyed amazing pad thai and sticky rice.


Oahu – Day 14

Time to check out the west side of the island. We drove around the north shore and ended up in Kailua and stopped at the famous Kalapawai Market for lunch sandwiches.

We snorkeled in Kailua bay to try and find some Humuhumunukunukuapua`a (Hawaii’s state fish) even though the water was choppy. I think I spotted one, but this sighting was not confirmed.

The Tetsuo Hurano tunnel was an excellent shortcut through the middle of the island, getting us to the Dole Plantation quite quickly. We wandered around the Dole gardens looking at all the baby pineapple, and had a slice of pineapple upside down cake. Pineapples were around $10 a piece and another $30 to ship home. Still, tourists were buying them like crazy.

We made it back to our condo right before sunset and booked it to the beach. Troy took incredible pictures of the waves with the sun setting behind them.

North Shore Surfing

Oahu – Day 15

Today we decided to “hang 10” and go check out the Billabong Pipe Masters Surf Contest. The North Side of the island was packed with people. Troy got some stellar photos of the professionals riding the massive waves.

Feeling inspired, we decided to go try surfing for ourselves. We rented surfboards in Hailewa town and strapped them to the top of our rental car.

We found a nice lagoon that had perfect sized waves. Neither of us were able to stand up on the boards. We didn’t stay out for long because i got distracted by the sea turtles that were swimming all around us and Troy crashed into some rocks breaking off some of his board.

We returned the surf boards feeling even more in awe of the pros after we failed. Luckily our rentals came with free shave ice which made it worth all the effort!

Pearl Harbor, Market, & Gas Station Poke

Oahu – Day 16

We packed up our belongings at our condo in the morning and headed to Pearl Harbor, our last tour before returning back to mainland US.

We took in the exhibits and boarded the ferry out to the U.S.S Arizona Memorial. It was eerie to see the hull of the battleship right below us and honor the nearly 1,200 people who went down with it. There are still sailors to this day that choose to be buried in the ship when they pass. We noticed oil in the water and when we looked it up, we found out that the ship still leaks about 2 quarts of oil each day and there is no way that they can stop it.

After leaving Pearl Harbor we went to Aloha Stadium to check out the flea market. We wandered around the whole outside of the stadium and I finally got the fresh coconut water I had been seeking the whole trip.

It was just about time to get to the airport but we decided to stop for some food before our flight. I picked a highly rated deli in the back of a convenience store located in the shadiest part of town.

There was a long line of locals getting food so we figured it was going to be good. We ordered Hawaiian BBQ, fish, and Spicy Poke (for Troy of course) and ate in the car.

A sad farewell to island life.

We drove to the airport and checked our luggage. The saddest part of the trip came when we had to change into our blue jeans before getting on the plane.

There were a lot of people doing the same thing, and no one looked happy about it.

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  1. Thanks for sharing such a great guide to Hawaii! I’ve always wanted to go, and your photos make it look so beautiful. I especially love all the beaches. I can’t wait to visit.

  2. Hawaii looks like areal paradise! You have some beautiful photos in this post and you’ve also shared some great tips! Thank you!

  3. Oh my goodness! The tree tunnel looks so so dreamy. Personally, I am an island person, and I can understand how hard it gets when the time comes to leave the place.

  4. What a magical trip! Hawaii looks like such a beautiful place! Those beaches and sunsets look unreal! I’d love to do the scuba diving tour, that marine life looks incredible! Thanks for the great guide!

  5. I love this post. I have been wanting to go to Hawaii for so long now, and I was wondering how many islands I can visit, this post is a great place to start my dreamy trip to Hawaii.

  6. Ahh, Hawaii looks so beautiful and I love the islands you’ve shared here! This is great inspiration for a future trip!

  7. […] you’re honeymooning in Hawaii or bringing the kids, the Dole Plantation is a fantastic place to taste Hawaii’s history and […]

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