Destinations / Hawaii • USA

A Curated 10-Day Itinerary of Hawaii

April 1, 2020

Before you jet off to Hawaii for a glorious sun-soaked vacation, let me drop some essential wisdom on you.

Do NOT call it “shaved ice” unless you get some perverse pleasure from embarrassing yourself. It’s SHAVE ice. Only throw a shaka (you know, the hang loose sign) if you can pull it off without looking super awkward (I learned this the hard way 😓). The second largest ethnic group in Hawaii is Japanese so the cuisine is most authentic you can find outside of Japan. Car rental is crucial to get around, especially on the more remote islands like Kauai.

I also learned during my trip is that apparently my ethnically ambiguous Asian features look Polynesian. Totally useless information for you but…there you go.

On more than one occasion during my trip, locals would ask me “What island are you from?” Uh, Toronto…?

While I may not be ethnically Polynesian, I did consider relinquishing ties with wintery Canada if only to continue improving my tan. After I take you on a curated tour across 3 of the 8 main islands that make up the southeastern archipelago of Hawaii, you’ll understand why I’m so eager to trade city for island life.


8 Drool-Worthy Places To Eat In Oahu For Every Foodie
A Drool-Worthy Guide To Where To Eat in Hilo, Hawaii
➳ A Guide To Snorkelling with Manta Rays in Hawaii

Poipu Beach in Kauai


Duration: 10 Days

Day 1 – 4: The Big Island
Day 5 – 7: Kauai
Day 8 – 10: Oahu


Days 1 – 4: The Big Island

The Big Island was aptly named because, well, it’s BIG (that’s what she said)! Also confusingly known as the island of Hawaii, what it lacks in beach quality it makes up for in volcanoes. With active lava flow, it’s quite the sight to see landscapes covered in black volcanic rock.

Quick, refreshing dip in the natural pools at the Grand Naniola Doubletree Hilo


Where to Stay on The Big Island:

Kona Town is the part of the island to stay if you want to be close to all the action. Personally, I adored the charming grit and community of Hilo which is almost a 2 hour drive from Kona Airport. You’ll be close proximity to waterfalls, the Volcano National Park plus the nearby restaurants are BOMB— it was the best food I ate the entire trip.

The best bang for our budget-friendly buck (Hawaii is expensive!) was the Grand Naniola Hotel Hilo where we were welcomed with a warm cookie. The rooms were clean, the beds were super comfy and they had an idyllic little area with natural pools that you could swim in.

Natural pools on the Grand Naniola Doubletree property. Nice to cool off in!


Where to Eat on The Big Island:

+ Pau Hana Poke: Upon arrive to the Kona Airport, immediately drive 10-minutes south to this humble poke shop. Served with furikake sprinkled rice and your choice of sides (I got pickled onion and spicy crab salad), the classic shoyu ahi poke was my first taste of Hawaii and it was heaven! Firm yet melted in my mouth like butter.

Hawaii Itinerary Eat Pau Hana Poke

My first taste of Hawaii still in my clothes from the airplane….shoyu ahi…SO GOOD!!

+ Hawaiian Style Cafe Hilo: Enjoy casual vibes, friendly aloha spirit and monstrous servings of Hawaiian comfort food. Dig into a terrifying gigantic platter of loco moco—a local specialty of rice topped with spam or beef patties and a fried egg, drowning in thick, brown gravy. Why have I never heard of this before??!

Hawaii Itinerary Eat Hawaiian Style Cafe Hilo

Haupia pancakes, Da Big Mok Loco Moco and a side of mac salad

The must eat here? Fluffy haupia pancakes the size of a dinner plate smothered in thick coconut cream and toasted coconut flakes. Plan to take a nap post-meal.

+ Paul’s Place: Paul made us feel so at home in his cozy three-table cafe in Hilo (right by the farmer’s market), alternating between chatting with us about our travels and preparing the best breakfast we had on the entire island.

Hawaii Itinerary Eat Paul's Place

Naturally we ordered half of the daily menu – eggs benny, perfectly crispy, lightly sugar-dusted waffles and The Breakfast Caprese was a symphony of ripe cherry tomatoes, bacon, black olives, mozzarella and fresh basil.

+ Koji’s Lunch Stop: Before heading out for a day of exploring, grab a classic Hawaiian lunch plate consisting of a hot bar item (like the juicy shoyu chicken, yum!) with a scoop of mac salad and rice. So damn good for so damn cheap.

Hawaii Itinerary Eat Koji's Lunch Stop

Succulent shoyu chicken from Koji’s

+ Two Ladies Kitchen: Other than Japan, the best place to gorge on mochi is at this tiny family-run shop in Hilo.

Hawaii Itinerary Eat Two Ladies Kitchen mochi

Fill a box (or purchase a premade one) of soft-chewy rice cakes in a variety of flavours like lilikoi (passionfruit), peanut butter and Azuki with a whole, fresh strawberry! I was drooling over the indulgent butter mochi made with coconut milk.

+ Kula Shave Ice: Head to this spot right by the Hilo Farmer’s Market for a killer açai bowl.

Hawaii Itinerary Eat Kona Shave Ice Acai Bowl

Sip on a refreshing lilikoi iced tea or a Vietnamese iced coffee before digging into a dish of crunchy granola, hemp and chia seeds, shredded coconut, peanut butter, topped with juicy papaya and apple banana.

+ Poke n’ Stuff: Right next door to Kona Shave Ice, I grabbed a heaping scoop of ahi sesame shoyu poke from the sweetest woman. $4 for so much tuna!

Hawaii Itinerary Eat Vibes Cafe

+ Vibes Cafe and Health Bar: If your body is crying out for nourishment, this vegan and vegetarian cafe is your best bet. We noshed on avocado toast and an açai bowl before washing it down with lilikoi lemonade (lilikoi everything!!). The star of the meal was the daily pizza that was gooey with goat cheese, artichoke, pesto and mozzarella.

+ Moon and the Turtle: Trade your sand-covered beachwear for fancier attire and head to this farm-and-ocean-to-table haven that blends local ingredients with Asian flavours.

Hawaii Itinerary Eat Moon and the Turtle

We gorged the daily offerings — garlic butter ahi belly, Portuguese sausage puttanesca with fresh pappardelle and a massive bowl of truffle shiitake mushroom risotto that was so rich and fragrant that I dream about it to this day. Reservations are a must!

+ Suisan’s Fish Market: Browse the dizzying array of seafood so fresh that the fish are practically still flip-flopping about in their buckets! Sold by the pound, choose from a mouth-watering variety of poke from Ahi Mango Habanero to Wasabi Salmon King. You can get rice to go with your fish but I chose an extra pound of poke instead 😜

Hawaii Itinerary Eat Poke

Hawaii Itinerary Eat Suisan Fish Market

Feast at the picnic benches out front or take it to-go.

+ Umeke’s Fish and Grill: On the Kona side of the Big Island, hit up this spacious establishment for casual vibes, a cool beer and local favs like kalua pork with a side of mac salad and fresh poke.

+ Ululani’s Shave Ice: Referred to as “ice shave” on the Big Island, this refreshing Hawaiian treat is made by shaving a block of ice (duh) and drenched in flavoured syrups.

Hawaii Itinerary Eat Ululani's Shave ice

I got lychee, lilikoi and almond syrup with macadamia nut ice cream in the centre!

Ululani’s syrups are pure cane sugar and you can request macadamia nut ice cream in the centre because, why not!

Read: A Drool-Worthy Guide To Where To Eat in Hilo, Hawaii


What to Do on The Big Island:

+ Manta Ray Sunset Snorkel: This was the most MAGICAL experience I had in Hawaii and is the thing to do on the Big Island. Face down and snorkel up, you float holding on to a surfboard-shaped contraption with bright lights attached to the bottom to attract plankton.

Hawaii Itinerary Do Manta Ray Snorkel

If you’re lucky, massive, graceful manta rays swoop in within an inch of you, gulping plankton in their open maws while you exclaim “HOLY SHIT!” into your snorkel tube. Bucket list activity, people. I angst-ed over which company to go with and was very happy with Big Island Divers. They were professional and hilarious!

+ Snorkelling at Captain Cook Monument: Want a chance to dive into the ocean but not much of a beach bum? Grab some snorkel gear, a kayak or join a boat tour to Kealakekua Bay. Explore the sea life surrounding the monument where Captain Cook was killed for attempting to kidnap the Island of Hawaii’s monarch.

+ Waterfalls: Don’t go chasing waterfalls….unless you’re in Hilo. Start at Akaka Falls which is the furthest away from Hilo — a 20-minute drive — and soak up the lush surroundings on an easy 0.4 mile roundtrip hike.

Hawaii Itinerary Do waterfalls

Pe’epe’e Falls

Work your way back to town, dropping by Pe’epe’e and Rainbow Falls (very close to each other) for more waterfall-viewing action. If you have time, hit up the Botanical Gardens after the Akaka Falls.

+ Mauna Kea Observatory: Head to the summit of the Mauna Kea for some stellar star-gazing. The location, lack of pollution and the inky black sky provides the ideal viewing conditions. If you’re an astronomy buff, take a tour of the independent astronomical research facilities and large telescope observatories while you’re there.

+ Beaches: If your skin is in need of vitamin D, head to the sunnier side of the island, Kona. Sink your toes into the soft sand and turquoise waters at Manini’owali Beach or trek to the more secluded Makalawena Beach.

Hawaii Itinerary Do beach

Hawaii Itinerary Do beach

Punalu’u Black Sand Beach, black from all the volcanic rock that the island is known for

For potential sea turtle sightings, Kukio Beach or the Punalu’u Black Sand Beach are your best bets.

+ Coffee Plantation Tour: Kona coffee is not only famous across Hawaii but throughout the world. When you’re on the Kona side of the Big Island, make a pit stop at Greenwell Farms at some point between 9am and 4pm. They offer complimentary tours where you can learn about the cultivation process and pick up a bag of beans as a souvenir. If coffee isn’t your thing, mac nut and pineapple farm tours are also popular.


Days 5 – 7: kauai

Often called the wettest spot on Earth, Hawaii’s Garden Isle is lush, green and absolutely breathtaking. From the pristine beaches, tropical rainforests and dramatic cliffs to adrenaline-pumping activities that will literally take your breath away, the island has been the backdrop to movies from Jurassic Park to 50 First Dates to Skull Island.

After eating ourselves into floral-patterned muumuus (to camouflage the jiggly bits) on the Big Island, our focus for Kauai was less on eating and more on exploring as much of the verdant island as we could.


Where to Stay in Kauai:

Arguably the most picturesque part of Kauai to stay in the lush Princeville on the North Shore. Located on a bluff, not only is it near Hanalei Bay and some of the best restaurants on the island but you’ll be treated to expansive mountain views.

Impromptu photoshoot at the Makai Club Resort before heading to the beach

I stayed at the Makai Club Resort that had a really chill vibe and we appreciated the privacy of having our own little unit with a kitchen and living area to lounge around in. You also have nice surrounding foliage that’s perfect for impromptu photoshoots.

If you’re with a crew, the Surf Shack makes for stylish accommodations.

Surf Shack Kauai

Photo of Surf Shack via AirBnB

On the southern, sunnier side of the island is Poipu you’ll find resorts like the Grand Hyatt and Sheraton with easier access to beaches. But no matter where you stay on the island, you’ll be paying an arm and a leg!


Where to Eat in Kauai:

+ Aloha Juice Bar: Kick your day off with a fresh açai bowl loaded with crunchy granola and juicy chunks of fruit. Linger on a bench at this local hot spot or grab a real fruit smoothie and hit the road.

Hawaii Itinerary Eat Kauai Juice Co

+ Kauai Juice Co: Angst over a selection of kombucha in a range of inventive flavours like mango mint jalapeño and lilikoi lychee or opt for a cold pressed juice like the Starburst, a blend of strawberry, pineapple and orange.

Hawaii Itinerary Eat Kauai Juice Co

The nut milks were delicious and filling, perfect for breakfast on-the-go. Not only are you doing your body good but the bottles are refillable to help keep the island clean.

+ Hamura Saimin: After arriving at Lihue Airport, head to this nearby shop for a comforting bowl of saimin.

Hawaii Itinerary Eat Hamura Saimin

A favourite fast food of local Hawaiians, this noodle soup comes steaming with wontons, roast pork, green onions, egg and a fish cake. Snag a slice of lilikoi chiffon pie for dessert!

+ Ama: With high ceilings and an open concept design, we were lucky enough to be seated at the counter that offered an epic view of mountains beyond a cozy yard complete with a fire pit surrounded by Adirondack chairs.

Hawaii Itinerary Eat Ama ramen

Start the meal with brussel sprouts and fried chicken bao before moving on to a traditional ramen in soup or a brothless mazeman with pork belly and a sticky peanut sauce.

+ Bar Acuda: Right next to Ama you’ll find glowing lanterns, gently waving palm fronds and a farm-to-table menu featuring innovative tapas dishes. Serving undeniably delicious but small modest portions, I was obsessed with their local salad of crispy chickpeas, cucumber, avocado, crumbled feta, fresh herbs and a white balsamic vinaigrette. I’ve made it approximately 5x since returning home.

Hawaii Itinerary Eat Bar Acuda

Hawaii Itinerary Eat Bar Acuda

P.S. In case you’re dumb like me and didn’t notice, it’s Bar Acuda…like “baracuda” the fish 🤯

+ Tahiti Nuit: As Kauai’s oldest bar, this local haunt is infamous for their festive weekly luaus and live music. It’s the ideal spot to knock back some Mai Tais while you wait for your pizza to arrive, hold the pineapple. Or don’t. It is Hawaii after all!


What to Do in Kauai:

+ Kayak to Secret Waterfalls: Wake up early and make your way to the mouth of Wailua River and either rent a kayak or join a tour for a brisk paddle to the Secret Falls. Admire the impressive view of the falls and frolic in its invigorating waters before the journey back.

Hawaii Itinerary Kauai Na'Pali Coast

+ Helicopter Ride: You’ve taken to Kauai by land and by sea but what about my air? Hop in a helicopter and take off in search of panoramic, aerial views, including the stunning Na’Pali Coast. You’ll even see corners of the lush island that are inaccessible by foot!

+ Na’Pali Coast Boat Tour: For day of fresh air and unforgettable views, board a catamaran with Capt Andy’s for a tour of the Na’Pali Coast. Glide alongside playful pods of spinner dolphins and catch glimpses of elusive whales on the way to Kauai’s North Shore.

Hawaii Itinerary Kauai Na'Pali Coast snorkel

Hawaii Itinerary Kauai Na'Pali Coast

Hawaii Itinerary Kauai boat tour

Emerald cliffs that dip into lush valleys serve as an awe-inspiring backdrop while you snorkel with placid sea turtles in the Pacific Ocean.

+ Whale Watching: If you find yourself in Kauai between November through March, you’re in luck. Join a tour and scan the shorelines for sight of a majestic humpback whale leaping in the air or its massive tail and it dives down.

+ Haku Lei Workshop: Craft a (floral) crown fit for Hawaiian royalty by spending the afternoon at a workshop with The Lei Collective. Nimbly arrange fragrant blooms and greenery into a haku lei, also known as a lei po’o (lei meaning “flower garland” and po’o meaning “head”) for a hands-on experience learning about Polynesian culture.

Hawaii Itinerary Kauai Hanalei Bay

Hawaii Itinerary Kauai Hanalei Bay

+ Hanalei Bay: Stop at The Dolphin Fish Market to snatch up a selection of mouth-watering poke to-go before heading to Hanalei Bay for sunset. Grab a seat at the end of the pier and marvel at the 360 degree view of the bay awash in a golden glow as the sun dips below the surrounding mountains.

+ Mountain Tubing: Venture deep into the densely forested heart of Kauai with Kauai Backcountry Adventures to an old sugar plantation where they have exclusive access to the irrigation system that fed to the crops.

Hawaii Itinerary Kauai Backcountry

Hawaii Itinerary Kauai Backcountry Mountain Tubing

Strap on a head lamp, hop onto an inflated tube and take a thrilling and refreshing (see: cold AF) ride through narrow canals and several pitch black caves.

Hawaii Itinerary Kauai Backcountry Mountain Tubing

+ Queen’s Bath: As dangerous as it is beautiful, this unique tide pool in Princeville is surrounded by lava rock.  At the time of year we went (winter) we didn’t even want to risk being anywhere NEAR this beautiful site. If you do go, make sure to check surf reports beforehand and think twice before going for a swim.

+ Secret Beach: This 3,000 foot stretch of not-so secret beach — officially known as Kauapea Beach — can be found on the north shore of the island. It’s prized for being an idyllic and secluded hideaway to sunbathe in peace.

Hawaii Itinerary Kauai Secret Beach

Wear secure footwear because it’s a steep and somewhat treacherous climb down.

Read: 11 Epic Things To Do In Kauai, Hawaii’s Garden Island


Days 8 – 10: OAHU

While my work-weary body benefited from the sleepy, slow-paced Big Island and Kauai, the city girl in me was excited for the livelier rhythm of Oahu. Known as The Gathering Place, it is home to the historical Pearl Harbour and legendary Waikiki, beloved by surfers and shoppers alike.

Insta-worthy pool at Surfjack!


Where To Stay in Oahu:

Oahu is ripe for choice in terms of accommodations, the best hotels being on or near Waikiki Beach. Not only is everything is more accessible on this island but there are also way more Ubers available to get around.

Both the Moana Surfrider and The Royal Hawaiian are classic picks located a stone’s throw away from Waikiki Beach. Further inland on the store strip is the super cute Laylow Hotel, perfect for a wild girls trip or evening drinks.

Our room at Surfjack

In the heart of Waikiki, we stayed at the Surfjack Hotel and Swim Club. The style of this boutique hotel very glam beach house with vintage patterns mixed with modern lines. Take a dip in their IG-worthy pool, reminiscent of retro postcards with “Wish You Were Here” scrawled along the bottom or grab a cocktail in the lounge and enjoy their signature scent wafting in the air. They also have an on-site café and a restaurant, Mahina & Suns, that is headed by the same chef as Mud Hen Water.

But my absolute favourite thing to do was sit on my balcony and listen to the awesome nightly live performances with a balmy breeze. Performer Dustin Park remixed Craig David and I was obscenely excited.


Where to Eat in Oahu:

+ Piggy Smalls: First stop off the tarmac, I insisted that we beeline for this Vietnamese eatery in Honolulu.

Hawaii Itinerary Eat Honolulu Piggy Smalls

After parking our suitcases to the side, I sipped a traditional Vietnamese egg coffee before getting my grubby mitts on their popular brisket bánh mì with spicy hoisin sauce that you dip into a bowl of pho.

Hawaii Itinerary Eat Honolulu Piggy Smalls

We continued to dig in to the flavourful garlic, bacon and soy stir-fried ramen noodle topped with sunny eggs and their churro French toast. Everything. Was. Bomb.

+ Helena’s Hawaiian Food: If you want an authentic taste of Hawaiian cuisine, Helena’s is where it all started. Or at least it seems that way. Arrive early to snag a table and order a feast of traditional dishes – luau squid, pipikaula shortribs, kalua pig, poi and a scoop of mac salad (each!).

Please ignore the middle finger…my phone got wiped when I got back and I lost all of my delicious photos from Helena’s.

My personal favourite was the long rice chicken which is misleading since it’s actually a soupy glass noodle and NOT rice…

+ Fresh Catch: I used a moderately active morning of surfing to justify pigging out on 1.5lbs of glorious chunks of poke. By myself.

It’s low-key place in comparison to the well-known Ahi Assassins and Ono Seafood but Fresh Catch is a local fav and can’t be beat in terms of variety of flavours they offer. I was so overstimulated by the excess of choice that I ended up with a box of 4 (!!!) different kinds of ahi and ate every last melt-in-your-mouth bite.

+ Giovanni’s Shrimp Truck: Often, places that have excessively long lines turn out to be overrated but not this time. The popular scampi plate came with a generous pile of sautéed shrimp smothered in butter, lemon and garlic over rice. Legit AF.

Be prepared for garlic to seep out of your pores and to repel people with your pungent breath afterward #worthit #whoneedsfriends

+ Leonard’s Malasadas: Made to order, these fluffy, sugar-crusted Portuguese doughnuts are packed in a very Wes Anderson-esque pink box with Leonard’s scrawled across the top in retro font.

You can’t go wrong with the classic sugar malasada but the ones bursting with shockingly pink guava creme and rich haupia were heavenly, especially when devoured fresh and hot.

+ Mud Hen Water: Despite a Pinterest-worthy interior, savouring a meal of remixed Hawaiian specialties under twinkle lights on the patio will elevate your dining experience to dreamy heights.

Nosh on loaded baked bananas indigenous to Hawaii with curry butter or the hefty short ribs dish lightened with the tang of lime, stringy spigarello and grape tomatoes.

+ Coco Ichibanya Curryhouse: For those craving a comforting taste of Japan, order a plate of hearty, slightly sweet Japanese curry from this popular chain.

+ Musubi Cafe Iyasume: Originating from the Japanese onigiri, musubi is cheap, fresh and ideal to grab before heading out for a day in the sun.

Order the standard spam musubi atop rice still warm from the rice cooker and wrapped in nori or if you’re feeling adventurous, try variations with cheese, egg or my personal favourite — spicy cod roe.

+ Waiola Shave Ice: Hawaiians have very strong opinions on where the best shave ice on the island can be found. Waiola has been the biggest contender in Honolulu for decades, offering thousands of different flavour combinations on fine, soft ice.

Level up your cool treat with various toppings like lychee jelly or condensed milk.

Read: 8 Drool-Worthy Places To Eat in Oahu For Every Foodie


What to Do in Oahu:

+ Circle Island Tour: If you’re short on time, join a full day tour around the entirety of Oahu. From Hanauma Bay to North Shore to Waimea Valley, you’ll walk away without a FOMO hangover.

+ Kualoa Ranch: Spend an epic day of adventure roaming the 4,000-acre private nature reserve and cattle ranch where Jurassic Park was filmed. Board a bus for a jungle expedition or secure a helmet on your noggin before racing across the property on sturdy ATVs. Take in the sweeping landscapes and giant skeletal remains from of film sets and explore the remnants of war bunkers left over from WWII.

+ Take a Hike: If you want to work off the generous portions and heavy Hawaiian dishes, go on one of Oahu’s many hikes. Lanikai Pillbox Hike, also known as Kaiwa Ridge Trail is ranked as intermediate with a steady steep uphill climb and offers views of the Mokulua Islands, Kailua Beach, Lanikai Beach.

Plan on rising early to hike Diamond Head to beat the crowds and you’ll be rewarded with 360-degree vantage point.

Rainbow at Ala Moana Bowls. Good luck for a surfing lesson!

+ Surfing: You can’t go to Hawaii and not at least attempt to surf. Take a break from the bustling urban energy of the island and drive out to North Shore to check out the legendary beaches that make up the infamous Triple Crown of Surfing. Watch the pros carve up the surf, navigating intimidatingly massive waves.

At RV Sports surf shop! See what I mean about awkwardly throwing a shaka sign?

The last time I had surfed, I had a bad fall so I was quite nervous to go back in. Heading into the surf at Ala Moana Bowls, Uncle Roy of RV’s Ocean Sport literally took my by the hand and made me feel calm and safe, dropping life wisdom as we waited for good waves. His teachings, adjustments and encouragement set up a foundation for surfing that my previous education lacked.

And there you have it — 10 days, 3 islands, countless meals. I am now blind and as I work as a graphic designer, I have no been rendered useless from writing this extensive itinerary of Hawaii for you planning pleasure. Of course, there are tons more things to do, eat and see across the Big Island, Kauai and Oahu but this is what was notable to me. Since I’m the one writing it, my opinion is the only one that matters 😜

If you’re looking for more inspiration for where your next adventure should be, check out these other itineraries I’ve curated.

Keep your stalking game strong and follow me @teriaki if you aren’t already!