14-Day Hawaii Travel Itinerary: Kauai, Oahu, and Maui
My recent two-week vacation to the Hawaii islands, a review of the things I did, and a breakdown of my travel itinerary so that you can replicate the same trip.
- Days 1-4: Kauai - The Garden Isle
- Days 5-9: Oahu - Vibrant City & Stunning Nature
- Days 10-14: Maui - Tropical Luxury & Adventure
Buckle up—this isn’t your average travel guide. I’m about to take you through a two-week Hawaii travel itinerary that's brutal honesty, snark, and the advice you need to actually enjoy it.
Kauai – The Garden Isle (Days 1-4)
Where I Stayed
Grand Hyatt Kauai Resort & Spa – Because You Deserve to Feel Like Royalty
Look, I didn’t fly all the way to Hawaii to stay in some sad roadside motel with a questionable "ocean view" (aka a parking lot and a sliver of blue between buildings). The Grand Hyatt Kauai is THE SPOT. It’s got lagoon-style pools, waterfalls, lazy rivers, and enough tropical vibes to make you feel like you’re starring in your own episode of ‘White Lotus’ (minus the drama and murder, hopefully).
I found a great deal on Booking.com (because I’m not made of money), and let me tell you—waking up to the sound of waves, sipping coffee on the balcony, and pretending I live here permanently? Absolute goals.
Why Stay Here?
- It’s straight-up paradise – If Kauai itself isn’t already stealing your heart, this resort will.
- Insane pools – Yes, plural. If you don’t love a lazy river, we can’t be friends.
- Steps from Shipwreck Beach – Not the best for swimming (rip currents love to humble tourists), but perfect for sunrise views.
- Feels secluded but still close to everything – Because no one comes to Kauai to be in a crowded city.
Nearby Attractions:
- Waimea Canyon ("The Grand Canyon of the Pacific") – Nature flexing hard.
- Nā Pali Coast Boat Tour – You’ve seen the Instagram pics, now go live them.
- Wailua Falls – The kind of waterfall that makes you rethink your entire life’s purpose.
- Poipu Beach – Snorkeling, turtles, and a solid chance of seeing a Hawaiian monk seal napping in the sun.
Some of the Things I Did (And You Should Too, Unless You Hate Fun)
The Tea on These Experiences
Kalalau Trail – Nature, But Make It Brutal
Everyone hypes up the Kalalau Trail, and for good reason—it’s STUNNING. Lush cliffs, insane ocean views, the kind of scenery that makes you question why you don’t just quit your job and move to Hawaii.
BUT.
It’s also not for the weak. Slippery mud? Check. Steep cliffs? Double check. The possibility of falling to your doom? Yep. If you’re doing just the first 2-mile stretch to Hanakāpī‘ai Beach, it’s doable, but if you go all the way to Kalalau, you better be ready for a hardcore, life-changing trek.
Would I do it again? Absolutely. But not without good hiking shoes, an early start, and a reality check on my fitness level.
Helicopter Tour Over Nā Pali Coast – Take My Money
If there’s one thing you should splurge on, it’s this. Seeing the Nā Pali Coast from above? Unreal. Like Jurassic Park, but without the risk of getting eaten.
Pro tips:
- Doors-off tours are next-level (unless you’re afraid of heights—then, uh, maybe reconsider).
- Book early – These sell out faster than you can say "aloha."
- Take motion sickness meds – You’ll thank me later.
Kayaking the Wailua River – A Workout Disguised as Fun
Kayaking sounds peaceful until you realize you’re paddling for your life against the current. But the jungle vibes? Worth it. You’ll end up at Secret Falls, a gorgeous hidden waterfall where you can cool off.
Would I do it again? Yes. Would my arms agree? Probably not.
Snorkeling at Tunnels Beach – VIP Access to the Turtle Club
This place? Turtle central. I popped my head in the water and immediately locked eyes with the chillest sea turtle I’ve ever met. We bonded. We vibed. We were basically best friends for a solid minute before he swam away, unimpressed by my existence.
Best part? The coral formations are next-level, and the water is so clear it feels like swimming in an aquarium. Bring reef-safe sunscreen unless you want bad karma from the ocean gods.
Sunset at Hanalei Bay – A Free Show
If there’s a more perfect way to end a day, I haven’t found it. The sun melts into the ocean, the sky goes full fire emoji, and you realize this is one of those core memories you’ll never shut up about. 10/10, would sunset again.
Eating Everything in Sight – No Shame
Hawaiian food slaps. Hard. If you leave Kauai without eating at least:
- Poke from a random roadside shop – Trust the locals, not Yelp.
- Shave ice (preferably from Wailua Shave Ice) – Life-changing.
- Loco moco – Rice, hamburger patty, egg, and gravy. A heart attack, but make it delicious.
- Malasadas from a food truck – Deep-fried, sugary, and worth every calorie.
Final Thoughts on Kauai
If you love nature, adventure, and feeling like you accidentally walked into a postcard, Kauai is your place. It’s quieter than Oahu, more rugged than Maui, and packed with jaw-dropping scenery at every turn.
The only downside?
The rain can be unpredictable (it’s what makes everything so lush), and things aren’t cheap (welcome to Hawaii). But if you’re not afraid to get a little muddy, do some hiking, and eat your weight in poke, you’ll love every second.
Alright, let’s leave Kauai’s lush, chill vibes behind and jump straight into Oahu (Days 5-9)—where paradise meets crowds, overpriced cocktails, and some undeniably amazing experiences.
Oahu – Iconic Beaches, Big City Vibes & Epic Adventures (Days 5-9)
Where to Stay
Halekulani – Because Waikiki Hotels Are a Gamble, and This One Actually Delivers
Here’s the thing about Waikiki: it’s beautiful, it’s lively, and it’s also where every tourist and their cousin decides to stay. So if I’m going to stay in the middle of it all, I at least want a hotel that doesn’t feel like I’m trapped in a chaotic theme park. Enter Halekulani.
This place is old-school luxury done right. No tacky luau decor, no loud pool parties—just serene oceanfront views, top-tier service, and an infinity pool where you can sip a mai tai in peace. The kind of hotel where you half-expect James Bond to be chilling at the bar.
Why Stay Here?
- Best ocean views in Waikiki – If I’m paying to be here, I want the view, not some concrete jungle backdrop.
- Not overly touristy – Unlike some nearby resorts, this one keeps it classy.
- Insanely good food – House Without a Key (their restaurant) serves up next-level Hawaiian eats with live music at sunset.
Nearby Attractions:
- Diamond Head Hike – Because who doesn’t love sweating at sunrise?
- Pearl Harbor – Heavy but essential history.
- Hanauma Bay – Snorkeling heaven (if you get there early).
- Lanikai Beach – A 10/10 beach without the chaos of Waikiki.
Some of the Things I Did (And You Should Too, Unless You Hate Fun)
The Tea on These Experiences
Diamond Head Hike – Sunrise Beauty, Leg Day Pain
Everyone says "hike Diamond Head at sunrise!" so I did. And yes, the views are unreal—you’ll see Waikiki glowing golden in the morning light, and it’s one of those "oh wow, I’m really in Hawaii" moments.
BUT—it’s also steep, crowded, and involves a ton of stairs. If you hate cardio, maybe just Google the views and call it a day.
Pro tips:
- Get there before 6 AM if you want to beat the crowds.
- Bring water unless you enjoy paying $5 for a bottle at the top.
- The last staircase is brutal—prepare for pain.
Would I do it again? Absolutely. But maybe not before coffee next time.
Pearl Harbor – A Heavy but Powerful Must-See
You can’t come to Oahu and not visit Pearl Harbor. It’s one of those places that hits you hard in the feels. The USS Arizona Memorial is particularly moving—you’re literally standing over the sunken ship where so many sailors remain.
Worth it? 100%. Just be ready for a more somber experience.
Things to know:
- Get tickets in advance – This place sells out fast.
- Go early to beat the crowds – Do you sense a theme here?
- Respect the space – This isn’t just a tourist attraction; it’s a memorial.
Hanauma Bay – The Snorkeling is Unreal, If You Time It Right
Hanauma Bay is basically Finding Nemo IRL. Crystal-clear water, tons of tropical fish, and even a chance to spot a sea turtle if you’re lucky.
BUT.
- It gets PACKED – If you show up at noon, enjoy fighting for space in the water.
- They now require reservations – Don’t just roll up expecting to get in.
- The reef is fragile—wear reef-safe sunscreen (or risk getting side-eyed by eco-conscious locals).
Was it worth waking up early for? Absolutely.
Lanikai Beach – Waikiki, But Without the Chaos
Listen, Waikiki is cool, but Lanikai Beach is next-level. White sand, electric blue water, and NO high-rise hotels ruining the vibe.
The only problem? Parking is a nightmare. So unless you enjoy the thrill of circling residential streets like a shark looking for a spot, I recommend Ubering.
Would I rather spend all my beach time here instead of Waikiki? Yes. Yes, I would.
North Shore Road Trip – Shrimp Trucks, Giant Waves, and Peak Hawaii Energy
Driving up to the North Shore is mandatory. This is where you get less touristy, more local, more surf vibes.
What to do:
- Eat at Giovanni’s Shrimp Truck – Garlicky, buttery heaven.
- Check out Sunset Beach – In winter, the waves here are INSANE.
- Stop at the Dole Plantation – Pineapple soft serve, aka Dole Whip, aka happiness in a cup.
North Shore is the laid-back, chill Hawaii you dream about.
Drinking My Way Through Honolulu – Mai Tais & Food Comas
Oahu has killer food and drinks, and I did my best to try everything.
Best eats & drinks:
- 🍹 Mai Tai at Duke’s Waikiki – Classic. Also, very strong.
- 🍛 Spam musubi from a hole-in-the-wall shop – Don’t knock it till you try it.
- 🍜 Garlic shrimp on the North Shore – Worth the mess.
- 🍣 Omakase sushi at Sushi Sho – Pricey, but chefs kiss.
Would I come back just to eat? Yes.
Final Thoughts on Oahu
Oahu is the perfect mix of adventure and city life—you get stunning beaches, great hikes, and a food scene that will ruin all other food for you.
The downside? Waikiki can feel touristy and chaotic, but if you know where to go (aka Lanikai, North Shore, and local spots), you’ll get the best of both worlds.
Next Stop: Maui (Days 10-14)
Alright, we’ve tackled Kauai’s jungle paradise and Oahu’s mix of city chaos and beach bliss—now it’s time for Maui (Days 10-14), where the sunsets are too perfect.
Maui – Luxury, Adventure & The Best Damn Sunrises (Days 10-14)
Where to Stay
The Ritz-Carlton, Kapalua – Because If I’m Going Broke, I’m Doing It in Style
Look, Maui is bougie AF, and if you’re gonna do it, do it right. I wanted something secluded, scenic, and far from the tourist madness of Lahaina’s main drag. Enter The Ritz-Carlton, Kapalua.
It’s tucked away in lush, green paradise, has pools straight out of a dream, and a spa that basically erases all stress from existence. And don’t even get me started on the ocean views—I spent an embarrassing amount of time just staring at the waves, questioning my life choices.
Why Stay Here?
- Kapalua is peaceful – No crowds, just endless nature and postcard-worthy beaches.
- Rooms with a view – No “partial ocean view” scams here, just pure, unfiltered paradise.
- Close to top Maui spots – You’re right near Honolua Bay for snorkeling and the start of the Road to Hana.
Nearby Attractions:
- Haleakalā Sunrise – The literal peak of the trip.
- Road to Hana – Because I love risking motion sickness for waterfalls.
- Snorkeling at Molokini Crater – The fish here are fancier than I am.
- Ka’anapali Beach – Good vibes, great snorkeling, mild sunburn risk.
Some of the Things I Did (And You Should Too, Unless You Like Being Bored)
The Tea on These Experiences
Haleakalā Sunrise – Worth the 3 AM Wake-Up Call
You know what’s fun? Dragging yourself out of bed at an ungodly hour, driving up a volcano in pitch darkness, and freezing your butt off at 10,000 feet.
You know what’s MORE fun? Watching the sun rise above the clouds and realizing you just witnessed something so unreal, it looks like it was CGI’d by nature itself.
Pro tips:
- Get your permit early – The National Park Service loves red tape. Book your sunrise spot in advance.
- Dress WARM – You’re on a freaking volcano, not a beach. It’s COLD. Like, “Why did I come to Hawaii for this?” cold.
- Bring coffee – Or just accept your fate as a sleep-deprived zombie.
Would I do it again? Absolutely. But I’d also bring a blanket next time.
Road to Hana – The Ultimate “Are We There Yet?” Drive
This drive is BOTH the most beautiful and maddening thing you will ever experience. Imagine:
- Endless waterfalls – Some you hike to, some you just admire from the car because you’re too lazy.
- One-lane bridges & hairpin turns – Hope you like playing "chicken" with oncoming cars.
- Breathtaking views – Every 10 minutes, you’ll pull over for another "Wow, is this real life?" moment.
Would I recommend it? Yes, but ONLY if you’re okay with winding roads and possibly wanting to throw up.
Snorkeling at Molokini Crater – Next-Level Underwater Views
Snorkeling here felt like I accidentally teleported into an aquarium. Crystal-clear water, bright coral, and SO MANY fish just casually minding their business.
Best part? No sharks. Worst part? Trying to gracefully get back on the boat without looking like a drowned cat.
Pro tips:
- Morning tours = calmer water.
- Reef-safe sunscreen or the ocean gods will judge you.
- If you can’t swim, stick to the floaties. No shame.
Ka’anapali Beach – Classic Maui, Minus the Overcrowding
If Waikiki is the Vegas of beaches, Ka’anapali is the chill cousin who does yoga and drinks green juice.
The snorkeling near Black Rock is phenomenal, the sand is soft AF, and you actually have room to breathe.
Would I swap my life for a permanent beach bum existence here? 100%.
Eating My Way Through Maui – The Real MVP of This Trip
I didn’t just eat in Maui. I committed.
- 🍍 Fresh pineapple straight from the farm – Shockingly better than supermarket pineapple.
- 🥥 Coconut shave ice from Ululani’s – I would trade my soul for another cup.
- 🥩 Loco Moco from Kihei Caffe – Rice, beef patty, egg, and gravy? Heart attack in a bowl, but worth it.
- 🍰 Hula Pie at Duke’s – Imagine a giant Oreo ice cream cake and then make it Hawaiian.
Would I return to Maui just for the food? Don’t test me.
Final Thoughts on Maui
Maui is the perfect balance of adventure and luxury. You can hike up a volcano at dawn, snorkel in a crater by noon, and sip cocktails by an infinity pool at sunset. It’s THAT good.
The downside?
- It’s expensive (Hawaii tax is real).
- The Road to Hana will test your patience and stomach.
- You might actually cry when it’s time to leave.
14-Day Hawaii Travel Itinerary Recap:
- Kauai (Days 1-4): Lush, wild, and waterfall heaven.
- Oahu (Days 5-9): Beaches, city chaos, and legendary food.
- Maui (Days 10-14): Luxury, adventure, and the best damn sunrise you’ll ever see.
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