Taste of Hawaii , Island Food crawl (Day #1)

urbanappetitela
Apr 8
10 min read

Hawaii is a paradise not just for its stunning beaches and breathtaking landscapes but also for its incredible food scene. During our trip, we set out on the ultimate food crawl across the island, indulging in everything from local favorites to world-famous treats. From hidden gems to must-visit hotspots, we made sure to taste our way through the best that Oahu has to offer.

Now, come along with us as we eat our way around the island—one bite at a time! 🌺🍍🌊

A Sweet Escape to the Dole Plantation – Oahu, Hawaii

A visit to Oahu wouldn't be complete without a stop at the Dole Plantation, a place bursting with tropical charm and, of course, the world-famous Dole Whip. Nestled in the heart of the island, this historic plantation offers a mix of rich history, scenic beauty, and delicious pineapple-inspired treats that make for a fun and refreshing excursion.

A Taste of the Iconic Dole Whip

The Dole Whip is legendary, and rightfully so. This soft-serve pineapple treat is the ultimate tropical indulgence—light, airy, and bursting with the naturally sweet and slightly tangy flavor of fresh pineapples. The texture is unbelievably smooth, almost like a pineapple cloud melting on your tongue. It’s the perfect cool-down treat after exploring the plantation grounds, and trust us, one cup might not be enough!

For those looking to elevate the experience, the Dole Whip Float is a must-try—creamy pineapple soft serve swirled into a cup of fresh pineapple juice, making for the ultimate sweet and refreshing combination. Every spoonful tastes like a Hawaiian summer in the best way possible.

Exploring the Plantation by Train

Aside from the treats, one of the highlights of our visit was hopping aboard the

Pineapple Express Train Tour. This charming train ride takes guests on a leisurely journey through the sprawling pineapple fields, lush tropical landscapes, and even past scenic views of the Waianae Mountains. As we rolled through the plantation, we got a fascinating glimpse into Hawaii’s pineapple-growing history, learning about how James Dole turned this land into one of the largest pineapple farms in the world.

The ride is both relaxing and educational, making it a great experience for all ages. It’s the perfect way to take in the plantation’s beauty while getting a fun history lesson along the way.

Final Thoughts

Whether you’re a first-time visitor or a returning guest, the Dole Plantation remains a must-visit for anyone exploring Oahu. Between the creamy Dole Whip, the scenic train ride, and the laid-back island vibes, it’s a stop that offers both a sweet and cultural experience. If you’re looking for a fun, family-friendly activity that gives you a taste of Hawaii’s history and flavors, this is definitely the place to be.

Urban Appetite’s Take: You don’t come to the Dole Plantation just for the sights—you come for the legendary Dole Whip. Cool, creamy, and refreshing, it’s a non-negotiable Hawaiian treat. A must do on your trip to Oahu. 🍍✨

Address: 64-1550 Kamehameha Hwy, Wahiawa, HI 96786

Jenny’s Shrimp Truck – A Hidden Gem in Oahu’s North Shore

After cooling off with a refreshing Dole Whip at the Dole Plantation, we continued our island food crawl and made our way to the North Shore, an area famous for its surf culture, scenic coastline, and, of course, its incredible food trucks. Tucked away in this laid-back neighborhood, Jenny’s Shrimp Truck is a small, charming roadside eatery serving up some of the best garlic shrimp on the island.

Ambiance & Experience

Jenny’s Shrimp Truck is a quaint little food truck that truly embodies the spirit of North Shore—simple, welcoming, and full of aloha. It's located just off the main road, making it easy to miss if you aren’t looking for it, but trust us, it’s worth finding. Quick tip: parking can be tricky, so we recommend parking at the gas station next door to avoid the crowds.

What really made our visit special was the hospitality. The owners were super sweet and welcoming, and to our surprise, they even offered us free drinks to complement our meal. It’s these little moments of kindness that make finding local gems like this even more rewarding.

The Food – A Garlic Lover’s Dream

We came for one thing: their famous Garlic Shrimp Plate, and let’s just say, it exceeded expectations. The plate came loaded with:

Plump, juicy shrimp, generously coated in a buttery garlic sauce that packed a bold punch of flavor. Every bite was a perfect blend of rich, garlicky goodness with just the right amount of seasoning.
A side of fluffy, seasoned white rice, perfect for soaking up that irresistible sauce.
A fresh local salad, adding a crisp and refreshing contrast to the rich shrimp.
A sweet, juicy slice of pineapple, the perfect palate cleanser to balance out the meal.

Each bite transported us to pure island bliss. The shrimp were cooked to perfection—buttery, garlicky, and bursting with flavor. The garlic wasn’t overpowering but rather complemented the natural sweetness of the shrimp. Combined with the fluffy rice and refreshing salad, it was a well-balanced and satisfying dish that truly hit the spot.

Final Thoughts

Jenny’s Shrimp Truck is a must-visit for anyone venturing to the North Shore. It’s a hidden gem off the beaten path, but if you’re looking for authentic, mouthwatering local eats, this is the place to be. The welcoming hospitality, incredible food, and laid-back island vibes make this spot an unforgettable part of our Hawaiian food crawl.

If you're looking to experience some of the best shrimp on the island, make sure to add Jenny’s Shrimp Truck to your list. Now, let’s keep this adventure going—onto our next food stop! 🍤🌴✨

Address: 66-532 Kamehameha Hwy Haleiwa, HI 96712

Seven Brothers – More Than a Meal, a True Taste of Ohana

As our North Shore food adventure continued, we found ourselves at Seven Brothers, a beloved family-owned restaurant that has become a staple in Oahu’s dining scene. Nestled in the laid-back, surf-friendly community, this charming spot radiates a relaxed, beachy vibe with a boho-chic aesthetic that perfectly embodies island life.

The Story Behind Seven Brothers

More than just a burger joint, Seven Brothers is a true family legacy. The restaurant was born out of a love story—when a Samoan surfer and a California girl fell in love, built a life together, and raised seven sons who would eventually open this restaurant. Starting as a small “hole in the wall” in Kahuku back in 2009, Seven Brothers quickly grew into a local favorite, known for their flavor-packed burgers, loaded fries, and welcoming Ohana spirit.

The staff here fully embodies the meaning of Ohana. From the moment we walked in, we were greeted with warm smiles, friendly conversation, and expert recommendations to help us choose the perfect burger. It felt less like a restaurant and more like being welcomed into someone’s home—where good food and good company come together.

The Food – Bold Flavors & Irresistible Combinations

We ordered The Spencer Burger, a fiery and flavorful creation that perfectly balances crispy, smoky, spicy, and creamy elements.

🍔 Spencer Burger – Bringing the Heat

A thick, juicy beef patty, grilled to perfection and packed with flavor.
Topped with a crispy onion ring that added the perfect crunch.
Savory bacon paired beautifully with melty Swiss cheese.
The heat from the jalapeños added a nice spicy kick without overpowering the burger.
Finished with their signature Spencer sauce, a creamy, tangy, and slightly sweet house-made dressing that brought everything together.

This burger was nothing short of amazing. The flavors were bold, balanced, and insanely satisfying, making it one of the best burgers we’ve had on the island.

🍟 Paniolo Fry – A Flavor Explosion in Every Bite

A mountain of crispy fries loaded with grilled pineapple, caramelized onions, melted cheese, BBQ sauce, and house sauce.
Topped off with two perfectly golden homemade onion rings.
The combination of sweet, smoky, tangy, and savory flavors made this an absolute must-try.

Every bite of these fries was an explosion of textures and flavors—crunchy, cheesy, saucy, and just a little sweet from the caramelized pineapple. This was the ultimate side dish, and we’re still dreaming about it.

Final Thoughts

Seven Brothers isn’t just a place to grab a meal—it’s an experience, a legacy, and a taste of true island hospitality. The food is bursting with bold flavors, the atmosphere is laid-back and inviting, and the people here make you feel like family.

If you’re exploring the North Shore and craving a truly unforgettable burger experience, Seven Brothers is an absolute must-visit. The flavors, the vibes, and the sense of community make this one of the best food spots we’ve hit on the island so far.

Address: 66-197 Kamehameha Hwy Haliewa, HI 96712

Now, let’s keep this food crawl going—who’s hungry for our next stop? 🍔🌊✨

Matsumoto Shave Ice – A Legendary Taste of Hawaiian Tradition

After indulging in savory bites around Oahu, we decided to switch things up and dive into something sweet, refreshing, and iconic—Hawaiian shave ice. Our next stop was Matsumoto Shave Ice, a North Shore institution that has been serving up Hawaii’s most famous shave ice for decades.

A Brief History – The Legacy of Matsumoto

Located in Haleiwa, Matsumoto Shave Ice has been a beloved local treasure since 1951. What started as a small family-run grocery store quickly evolved into one of Hawaii’s most popular shave ice destinations, attracting locals and tourists alike. Known for their ultra-fine, fluffy ice and homemade syrups, this spot has kept its traditions alive while bringing in new generations of shave ice lovers.

The Atmosphere – A True North Shore Vibe

The ambiance at Matsumoto is everything you’d hope for in a classic Hawaiian beach town spot. It’s a grab-and-go style location, but the energy here is laid-back, fun, and totally gives off that surfer beach vibe. The decor is nostalgic, colorful, and filled with vintage Hawaii vacation memorabilia, making it feel like a scene straight out of an old-school island postcard.

And the experience doesn’t stop after getting your shave ice! Once you have your icy treat in hand, you can wander through their charming Hawaiian-style gift shop. It’s filled with adorable souvenirs, t-shirts, mugs, and local trinkets—perfect for bringing a little piece of Hawaii back home.

The Process – Three Steps to Shave Ice Perfection

At Matsumoto, getting your shave ice is an experience in itself. It’s a simple three-step process that lets you customize your treat just the way you like it.

1. Pick Your Size – Choose from small or large (but let’s be real, go big or go home!).

2. Add Your Toppings – They offer ice cream, mochi, azuki beans, condensed milk, and more to take your shave ice to the next level.

3. Choose Your Flavors – With over 30 flavors, the combinations are endless. You can pick up to three different syrups to mix and match your perfect icy creation.

Our Order – The Classic Rainbow Shave Ice

🌈 Rainbow Shave Ice

A beautiful blend of strawberry, lemon, and blue pineapple syrup, creating a vibrant, picture-perfect treat.
The flavors are bright, fruity, and nostalgic, reminiscent of summer days and tropical island vibes.
We topped ours with condensed milk (Urban Appetite Tip: Always add condensed milk—it’s a game-changer!) which gave the shave ice a sweet, creamy finish.

The texture of the ice was so light and fluffy that it melted instantly in our mouths, making each spoonful an absolute refreshing delight. The mix of flavors was sweet, tangy, and tropical, perfectly balancing each other out without being overpowering.

Final Thoughts

Matsumoto Shave Ice is more than just a dessert—it’s a Hawaiian experience. From its rich history to its delicious flavors to its cute, homey gift shop, it’s easy to see why this spot is a must-visit on the North Shore. Whether you’re a first-timer or a longtime fan, you can’t leave Oahu without trying a bowl of this legendary shave ice.

Now, let’s keep going on this Hawaiin island food crawl —who’s ready for the next bite? 🍧🌺✨

Address: 66-111 Kamehameha Hwy #605, Haleiwa, HI 96712

Haleiwa Joe’s – A Stunning Dining Experience in Kaneohe

After indulging in an array of local island bites throughout the day, we decided to end our night on a more refined note at one of Oahu’s most breathtaking dining destinations—Haleiwa Joe’s Seafood Grill. Nestled in the lush, tropical mountains of Kaneohe, this restaurant feels like a hidden paradise, offering sweeping views, fresh island flavors, and an upscale yet welcoming atmosphere.

Getting There – A Hidden Gem in the Mountains

Haleiwa Joe’s has two locations, one in Haleiwa on the North Shore and one in Kaneohe on the Windward side, which is the location we visited. Tucked deep into a residential neighborhood, this spot isn’t the easiest to find, but trust us—it’s worth the journey. From the parking lot, you follow a short path down to the entrance, where you’re immediately greeted by lush greenery, the sounds of nature, and the anticipation of an unforgettable meal.

One of the most incredible features of this location is its stunning, panoramic view of a private tropical garden and koi pond below, all framed by the dramatic volcanic mountains surrounding the restaurant. To fully soak in the ambiance, we highly recommend arriving early for dinner and requesting a table by the window—it’s the perfect way to set the mood for a dreamy Hawaiian evening.

The Menu – A Fusion of Island and Steakhouse Classics

Haleiwa Joe’s is well known for its fresh seafood and perfectly cooked steaks, blending high-end meats and fish with a signature local twist. We decided to go all in and order some of their most popular dishes.

🥩 Prime Rib – The Star of the Show

If you come to Haleiwa Joe’s, the Prime Rib is an absolute must. This massive, tender cut of meat is slow-roasted to perfection, served with a rich au jus and a side of horseradish cream sauce that adds the perfect tangy kick. The meat itself is incredibly juicy, melt-in-your-mouth tender, and bursting with flavor. Accompanying the prime rib is a generous helping of their homemade garlic mashed potatoes, which are buttery, creamy, and seasoned just right, along with a mix of local island vegetables that bring a fresh and vibrant contrast to the plate.

🥗 Wedge Salad – A Crisp and Flavorful Starter

We also opted for the Wedge Salad, a refreshing and hearty dish featuring crisp iceberg lettuce topped with smoky bacon, chopped egg, diced tomatoes, and crispy fried shallots, all drizzled with a creamy and tangy bleu cheese dressing. The combination of crunchy textures, salty bites of bacon, and the cool creaminess of the dressing made this a fantastic way to start our meal.

Final Thoughts – A Must-Visit for Food and Views

Haleiwa Joe’s is so much more than just a restaurant—it’s an experience. From the breathtaking views and serene ambiance to the flavor-packed dishes that blend fine dining with island soul, it’s easily one of the top dining spots in Oahu. Whether you're celebrating a special occasion or just looking for an unforgettable meal, this spot should definitely be on your list.

Urban Appetite Tip: Make sure to arrive early to snag a spot with the best views and call ahead for reservations since this place fills up quickly.