Hawaii Guide: Oahu, Maui, Kauai

12 Days, 3 Hawaiian Islands

Napali Coast from the water on a Hawaiian boat tour


Picture of a perfect sunset in Hawaii OAHU:

After landing a job in the insurance business and taking eight tests over a 14-month period, I was lucky enough to attend the CPCU Conferment Annual Seminar in the city of Oahu. If that wasn’t great enough news, I was also told I could bring a plus one. So… off my mom and I went for an early 65th and 25th birthday celebration in Hawaii!

The conference itself only lasted three days and then we split off on our own to explore the islands of Maui and Kauai.

But first…. let me go ahead and share some of our favorite memories made around Oahu.

First night at the Hawaiian Luau

On Friday morning, we had a wonderfully convenient direct, 9-hour flight straight into Honolulu airport. Lucky for us, Delta offered free meals the whole trip and had hundreds of TV shows/ movies / games / music available at our fingertips. After watching You Before Me, Alan Iverson documentary and RACE ..eating a few airplane meals and taking a quick nap, we were making our final descent over the turquoise blue waters of Oahu!
We scrambled to get all our stuff off the plane, at the same time trying to tell ourself it was only 2PM  in the afternoon and not letting our bodies fall into the trap of jet-lag as we still had a long evening ahead.

Lucky for us, we ended up with a free upgrade, Jeep Wrangler (winning!) and raced to the Hilton Hawaiian Village to check-in before hitting the road straight to our kick-off luau.

In the midst of all the craziness, we saw not one, not two but FOUR vivid rainbows along our drive and arrived at the  Germaine’s Luau just in time for our first Mai Tai, live entertainment and a traditional Luau feast.

Our mornings before the conference started consisted of early wake up calls, tranquil beach walks, and fresh Hawaiian fruit and macadamia nut pancakes with coconut syrup. Not too shabby when it comes to a work trip!

Cruising around the island of Oahu in a Jeep Wrangler


  • Hike Diamond Head: While hiking smack dab in the middle of the heat of the day…. .probably not the smartest decision but we made it to the top and the views were worth it! From there, we could see sweeping views of the Honolulu skyline and Waikiki Beach coast. Definitely worth it
  • Snorkel at Hanauma Bay: We spent the first few minutes at this state park watching an informative history video of the nature preserve and how it has gotten to it’s current state today. Then it was time to head out into the crystal clear blue waters for an afternoon full of snorkeling. The bay is filled with all the perfect different hues of blue and filled with colorful fish and coral galore.
  • Hike to the summit of Koko Crater: PSA– This is not for the faint-hearted. The hike consists of endless staircases (1,000+ steps to be exact). The entire journey up and down takes approximately 75 minutes and I would highly recommend following the signs of advice to *bring water*. The views at the top are indescribable. After taking it all in, the ‘fun’ part starts… there’s only one way back down which ends up being equally as tiring. It requires careful climbing and finagling your way down railroad ties and steep dirt hillsides.

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  • Road-trip to the North Shore: A relatively quick drive away from the city feel of Honolulu will take you to what feels like a whole new world. The road trip consists of beautiful scenic views that resemble scenes from Jurassic Park.
    • Stop at the food trucks for a road-trip snack (Garlic Shrimp at Giovanni’s Shrimp truck should not be missed)
    • Pit-stop at Turtle Bay Resort  (If you’ve seen Forgetting Sarah Marshall, this resort should ring a bell)
    • Watch the sunset at Waimea Bay as cliff jumpers dive into the waters with the sunsetting in the background .. are you convinced to visit Oahu yet?

Enjoying a big cup of shaved ice on the island of Oahu


  • Breakfast at Goofy’s Cafe & Dine: This hidden gem was walkable from the Hilton Hawaiian Village hotel. Words of advice – there will be long “waiting lists” but the time flies by. Don’t leave to walk around or you will likely loose your spot. We frequented this spot 2x during our stay and we could not get enough.  100% local Hawaiian coffee served steaming hot and their Acai bowls are to die for.
  • ​​Benihana Japanese Steakhouse: After a full day at work conferences, we were exhausted with jet lag so we made our way to Benihana which is conveniently located inside of the Hilton Hawaiian Village.
  • Dukes Waikiki: This laid-back beachfront restaurant is walkable from the Hilton Hawaiian Village. Make reservations! The beach vibes and sunset views are hard to beat and so are their refreshing cocktails. We enjoyed fresh fish tacos and macadamia nut crusted chicken by the tiki torch lights after a long day of exploring the island.
  • Giovanni’s Food Truck: This is the North Shore road-trip find I mentioned above. Try out their famous garlic-shrimp … but be warned, ‘must-love-garlic!’




And just like that, we were off to the island of Maui! Conveniently a quick < 45 minute flight on Hawaiian Airlines, you can hop island-to-island in no time.   We chose to stay at Maui Seaside Hotel in Kailua for our first part of our time in Maui and we went through Expedia to rent a convertible for this stretch of the trip. 


Beautiful pit stop views along the Road to Hana

After two nights at Maui Seaside Hotel, we moved to a different part of the island, Lahaina. Here we stayed at Aston Maui Kaanapali Villas Highly recommend. It was great getting to base ourselves in two different cities during our time on the island. Our first stay was mostly based around our Road to Hana drive and our Haleakala Summit sunrise.  As always, it is nearly impossible to pick ‘favorites’ but with so much to do and so little time, I would recommend the highlights below.

Fresh Coconut Ice Cream along the Road to Hana

Cruising around and the best way to see the Road to Hana on Maui


  • The Road to Hana: One of the most scenic road in the islands. A full-day (or two) is what you will want to give yourself for this famous Hawaiian road trip. Road-trip, it was a 12-hour drive.  The best suggestion I can give is (1) leave VERY early in the morning  and (2) take.your.time. If you are rushing, you will miss so much of the beauty passing you by. There are pit-stops along the way such as a colorful shack that advertises their homemade coconut ice cream or the fresh farmers market set up outside of the health center. Every curve brings about a new wonder; think cascading waterfalls, Jurassic Park style mountains, black sand beaches, red sand beaches and rainbows. 

Exploring the black sand beaches along the coast of Maui

  • Check-out favorite pit-stops below. 
    • ​Black Sand Beach or “Wai’anapanapa State Park”
      • Red Sand Beach or “Kaihalulu” 
      • Paia Town – Where we started our journey. Paia has a hippie-surfer town vibe dating back to the 1970s. I fell in love with all of the coffee shops, yoga studios and other eclectic boutiques. 
      • Twin Falls at Mile Marker #2
      • Wailua Falls at Mile Marker #45
      • Ohe’o Gulch, also known asSeven Sacred Pools“: Located in the Haleakala National Park. This is a must-see. It cost ~ $10 per car to get into the park but it is good for 3-days. There are various hikes at this area. Located at Mile Marker #42
      • Back side of Haleakala: leading you through ‘upcountry’ and a complete change of scenery as you make your way back to your starting point

Red Sand beach on Maui

The black beach on the island of Maui Hawaii

  • Sunrise at the Mt. Haleakala summit: This calls for an EARLY wake-up call… more like middle-of-the-night wake up call. We woke up at 2:30AM and we were on the road by 3:00AM heading to Mt. Haleakala summit. After debating the night before, we decided to take the risk despite the ‘weather hot line’ saying it was 50/50% rain and cloud cover, which was not encouraging.  The drive up was easy. We took blankets from our motel .. but note-to-self should have brought gloves and hand warmers. We blasted heat along the way with our convertible top down allowing a perfect view of the stars  in the black sky above. Around 4:30 AM, we arrived at the summit, ate our leftover pizza from dinner and motel coffee as we waited for time to pass. At 6:07 AM, we were outside of the car, fully bundled up and watching as the colors in the sky began to change and the sun peaked over the top of the cloud cover. Absolutely no rain and perfect cloud cover … the sunrise was PERFECT. There are no words to describe this experience . If you can make the trek up the crater and the weather cooperates, this is a must-do activity during your time in Maui. 

Swimming with Turtles in Maui

  • Snorkeling at Napili Bay: Another one of our many highlights of the trip was snorkeling with the turtles. Napili Bay was one of the spots we had our best luck and saw a ton of large, beautiful, sea-turtles. Such beautiful creatures and what a treat to swim within inches of their side. 

Spouting water hole on the island of Oahu


Seafood. Acai Bowls. Vegetarian Friendly. You name it, you can find it in Maui.
Enjoying morning coffee on our Holo Holo Charters boat trip in Kauai

We absolutely LOVED all of our food finds around the island.. so much that it is tough to bring favorites but here are just a few of best spots!

  • Mama’s Fish House: Oh.My.Goodness. I can’t say enough good things about the charming, (very popular), waterfront restaurant. Watch the sunset surrounded by tiki lights and a sky full of colors as you sip on one of their specialty cocktails ( we opted for our take on a traditional Mai-Tai ). Make reservations*, months in advance.. this place fills up quick. AND lastly, try out their King Crab Stuffed Mahi Mahi… Unreal. This place is great even for those who do not like seafood. They have delicious vegetarian options and the staff is very accommodating.
  • Flatbreadin Paia: Hip little pizza shop in downtown Paia: We tried out their veggie vegan pizza and ate it all up after our long day on the road to Hana.
  • Night cap (or scoop) at Paia Gelato (‘Ono Gelato’): located right down the road from ‘Flatbread’, their Peanut Butter Sea Salt Carmel Graham flavor is to die for.
  • Hula Grill: Lovely atmosphere right on the beach.. tiki lights and a live band in the evenings. Try out their ‘Poke’ ahi-tuna tacos alongside a Mai Tai ( if you aren’t sick of Mai Tais by this point )









  • Aqua Beach Resort in Lihue:  great location, good restaurant, beautiful scenery and beach access right out your hotel room.
  • Yoga on the Beach with Anya in Kauai: Kick off your day with yoga on the beach … truly… yoga with your toes in the crashing waves as the sun comes up.
  • Checkout the Kilauea Lighthouse 
  • Kalalau Trail: All together, this is an 11 mile trail that goes from Ke’e Beach to Kalalau Beach  along the Na Pali coast. This hike is not for the faint-hearted. We only made it a little over 2 miles one-way but during those 2 miles, we were amazed with unforgettable  cliffside and valley views.
  • Jump on in to Queens Bath during low-tide before sunset
  • Watch the sunset from St. Regis Kauai

Sunsets at the St Regis Kauai

  • Holo-Holo Charters: Highly recommend the Niihau + Na Pali Super Tour; Kick your day off with a continental breakfast as you sail along the breathtaking Na Pali coast… the staff will point out hidden waterfalls, valleys and sea caves along the way. Beware- Lots of sea-sick folks on our trip… We used patches and had no issue but if you have ANY tendency to feel sick in the open sea, take the appropriate measures so you can fully enjoy your day!  The tour takes you from the Na Pali coast over to the “Forbidden Island” of Niihau. At Niihau, you will be able to snorkel or just float and relax as you take in the beauty of this uninhabited island. On your way back to the main island, they serve up a deli-style buffet lunch along with local Hawaiian beer and wine.

  • Blue Hawaiian Helicopter Tour: Seeing the island by foot, sea and air, was one of our best decisions we made. The island has so much to offer and the landscape of the Na Pali coast should be appreciated from all different perspectives. We had a great experience with Blue Hawaiian Helicopters and we were able to dip into the Waimea canyon, get close to cascading waterfalls in the mountains, and watch over the Na Pali coastline all while getting a history lesson on the island.

  • Explore the town of Poipu : Go to Poipu beach to lounge around for the day or explore all of the restaurants and shops that the town has to offer.

Beginning the hike along the Napili Coast in Kauai

Hiking along the Napili Coast Kauai


  • Hippie Cafe: One of our favorite spots. The acai bowls are delicious. and don’t miss out on their ‘ Chocolate Coffee Kiss ‘, a healthy morning treat to start your day consisting of Maca, Coffee & dark chocolate.
  • Wishing Well: Mmmmm… the best shaved ice. ( one of many ). A colorful spot on the north side of the island. They also have a wide variety of acai bowls (do you notice a trend here?!) Try out your favorite shaved ice flavor with coconut ice cream on the bottom.
  • The Beach House: Make reservations. Somewhat fancy. Hard-to-beat views… Even if you don’t eat or drink there, it is the perfect spot to watch the sunset
  • Java Kai: Think fresh-brewed coffee, healthy breakfast and a laid-back Kauai vibe

A cute healthy vegetarian restaurant in Maui


Panoramic Views from the top of Koko Head Trail
Panoramic Views from the top of Koko Head Trail
Sunrise views above the clouds at the peak of Mt Haleakala

For more USA travel inspiration full of beautiful hikes, scenic foods and delicious food; check out my guide to Havasu Falls, Zion National Park in Utah and Vermont.