Driving along the Windward coast of Oʻahu feels like stepping into a postcard, a welcome escape from the usual city bustle. Summer is a fantastic time to explore this stretch, bringing back those carefree childhood memories. The journey from Waimānalo to Kahana Bay showcases the dramatic, carved beauty of the Koʻolau Range, with plenty of opportunities to stop and dip your toes into the clear, turquoise waters along the long sandy beaches.
A Scenic Drive Awaits
Starting your day early is key to truly appreciating the natural beauty here, a legacy of volcanic activity that began millions of years ago. It’s the perfect pace to soak it all in without the rush.
Sweet Starts and Serene Shores
A good way to kick off the day is with some delicious malasadas. You can find them at Agnes’ Portuguese Bake Shop, a food truck continuation of a beloved Kailua bakery. Sometimes, the veteran baker Non DeMello himself is there, serving up these warm, fried treats. It’s a sweet note to begin your explorations, especially if you pick some up near the Manuheali‘i brand store.
Instead of joining the crowds heading up Ka‘iwa Ridge, consider a more peaceful experience at Kaiona Beach Park in Waimānalo. This spot offers a much more tranquil atmosphere, perfect for avoiding the well-trodden paths and the endless stream of Instagrammers.
Where Can I Find Sweet Treats?
Grab some malasadas from Agnes’ Portuguese Bake Shop if you haven’t already. It’s a perfect grab-and-go option for a roadside snack as you drive.
They are a classic Hawaiian treat that’s worth seeking out at the start of your day.
Coastal Views and Historical Echoes
If you’ve packed those malasadas, you’ll want to find a picnic table with a view. Mānana Island, often called Rabbit Island, provides a striking backdrop. From there, a leisurely walk along the beach reveals local fishers, snorkelers preparing for a dip, and outrigger canoes waiting for their next practice session.
As you make your way back towards Kailua along Kalaniana‘ole Highway, you’ll pass horses grazing peacefully by the roadside. Keep an eye out for the sign marking Hūnānāniho, the original name for Waimānalo Bay Beach Park, also known as Sherwoods. This area recently underwent restoration, completed in 2021, and it’s a testament to preserving the area’s heritage.
What’s the Original Name of Sherwoods Beach?
Hūnānāniho is the original name for Waimānalo Bay Beach Park.
It’s interesting to see how places are named and renamed over time.
A Culinary Journey Through Kailua
Kailua offers a delightful array of breakfast options, whether you indulged in those early morning malasadas or are just starting your day. The neighborhood is known for its fantastic brunch and breakfast spots, catering to various tastes.
Pancake Paradise and Classic Comforts
For many, the name Cinnamon’s in Kailua is practically synonymous with pancakes. Their menu features a tempting variety, including guava chiffon, red velvet, and banana. It’s a great family spot where it’s easy for everyone to find something they love, with classics like eggs Benedict also being a popular choice.
If you’re looking for a more contemporary breakfast experience, Over Easy is a fantastic choice. Their Potato ‘n’ Eggs dish puts a unique spin on eggs Benedict, topping fluffy eggs with a creamy potato purée. The brunch bowl is another standout, combining soft-cooked eggs, avocado, a house-made tomato jam, yogurt, fresh greens, candied bacon, and crusty sourdough slices. It’s a hearty and flavorful start to any day.
What Are Some Unique Breakfast Dishes?
Try the Potato ‘n’ Eggs or the vibrant brunch bowl at Over Easy.
These dishes offer creative twists on classic morning meals.
For those who crave the cozy, old-school diner vibe, Times Coffee Shop on Hāmākua Drive is a must-visit. Don’t miss their fried rice, especially the vegetarian version. It’s also the perfect place to indulge in a classic loco moco, thanks to their delicious, in-house made hamburger patties.
Local Flavors and Hearty Portions
Another satisfying option, especially if your family enjoys savory dishes, is the kālua pig hash. This hearty meal combines tender kālua pork piled high on a bed of Okinawan sweet potatoes and fingerling potatoes, often served with lomi tomato. It’s a taste of authentic Hawaiian comfort food that’s perfect for a filling meal.
Where Can I Get Traditional Hawaiian Pork Hash?
Look for kālua pig hash at local diners and cafes.
It’s a robust dish featuring slow-cooked pork and island potatoes.
Shopping Treasures and Local Finds
After fueling up, it’s time to explore Kailua’s unique shops. Parking is convenient in the free lot behind Longs Drugs, making it easy to access the local boutiques and bookstores.
Book Havens and Vintage Finds
BookEnds is a beloved independent bookstore packed with a wide selection of local titles, budget-friendly finds, and bestsellers. It’s the kind of place where you can easily spend a good hour browsing through rows of books, discovering new authors or finding a nostalgic favorite.
For a bit of retail therapy with a local flair, Coco’s Trading Post offers a curated selection of made-in-Hawaiʻi decor, accessories, and clothing for all ages. (Note: The Kailua location of Coco’s Trading Post has since closed.)
A short walk across the street leads to the art of Nick Kuchar. His work, often inspired by vintage surf and travel themes, evokes a wonderful sense of nostalgia. You might find yourself drawn to his distinctive style, perhaps picking up a motel-style keychain as a unique souvenir.
What Kind of Art Is Available in Kailua?
You can find vintage-inspired surf and travel art.
Artists often capture a nostalgic and charming aesthetic.
Thrifting Adventures and Eco-Conscious Choices
While OG bowling alleys like Pali Lanes may be gone, a different kind of pastime has taken its place: thrifting! The sprawling Salvation Army store here is consistently a treasure trove of great finds. For those who enjoy digging for bargains, it’s a fantastic stop. The Goodwill Hawaiʻi store has also relocated from Kailua to Kāneʻohe, so be aware of that if you’re planning a thrift-shopping spree.
A short stroll will bring you to Protea Thrift, which now operates as a boutique focusing on secondhand clothing. They have specific days for buybacks if you’re looking to bring in items, typically Tuesdays, Thursdays, and Saturdays.
For a refreshing snack, head to Wilson Store for a shave ice. Ask for lemon peel bits as a topping – it adds a delightful tartness. It’s the perfect way to cool down before hopping back in the car towards Kāneʻohe.
Where Can I Buy Secondhand Clothes?
Protea Thrift has a boutique for pre-owned clothing.
It’s a great place to find unique fashion items.
Around a 20-minute drive away in Kāneʻohe, Masa & Joyce Okazuya offers a delightful range of light, handheld lunches. Their wasabi ‘ahi hand rolls, Spam musubi, and maki sushi are perfect for a quick bite. If you can resist their other delicious offerings like nishime, mac salad, or garlic chicken, you can even pack some in a cooler for later enjoyment.
Exploring Hidden Gardens and Local Bounty
Venturing a bit further opens up more opportunities for discovery, from tranquil gardens to vibrant local markets.
A Peaceful Garden Retreat
Just a short 3-mile drive leads to the Friendship Garden. This privately owned historic spot is a true hidden gem, welcoming the public during daylight hours. Established in 1927 as part of a planned multiethnic community called Kokokahi, meaning “one blood,” the 10-acre park embodies a spirit of harmonious living. Parking can be limited, so carpooling is a good idea. The peaceful, hour-long loop trail offers beautiful bay views, a serene bamboo grove, and a shady stone amphitheater, perfect for a quiet picnic or moment of reflection.
What Is the Friendship Garden?
It’s a historic 10-acre park focused on community harmony.
Visitors can enjoy scenic views and a bamboo grove on its trails.
Coastal Delights and Fresh Produce
A 15-minute drive brings you to K.Bay Bros. Fish & Ice, a great spot to pick up some protein-packed snacks for the road. Their kim chee shrimp, tako dynamite, and boiled peanuts are delicious choices. As you head up the coast towards Kahana Bay, notice the roadside fruit stands and flower farms, often accompanied by “Keep Country Country” signs, a common sentiment on the island.
Kahana Bay, part of Ahupuaʻa ʻO Kahana State Park, offers a stunning crescent-shaped beach with family-friendly waters perfect for a swim. Just down the road is the KualoaGrown Market, a fantastic place to discover homegrown products. You’ll find an array of items, from frozen shrimp and oysters to marinated teri beef, kalo, kohlrabi, and even beautiful bouquets of ginger and heliconia. It’s a wonderful opportunity to support local farmers and producers.
What Can I Buy at KualoaGrown Market?
You can find local produce, fresh and frozen seafood, and meats.
They also offer flowers and other farm-fresh goods.
Imagine shucking fresh Kualoa Ranch oysters right at the beach – a truly memorable island experience! It’s these kinds of simple pleasures that make a trip here so special. You can enjoy these local delicacies along with your other road trip treats.
Take-Home Hawaiian Favorites
To round off your culinary adventures, consider picking up some classic Hawaiian food for dinner. Waiāhole Poi Factory is a popular spot, but calling ahead or ordering online can save you time waiting in line. Their menu features traditional hand-pounded poi, flavorful lau lau (pork-filled bundles), squid or beef lūʻau, and sweet haupia for dessert. It’s the perfect way to share a taste of the islands with friends and family, whether you enjoy it as a picnic on the way home or back at your accommodation.
Where Can I Order Traditional Hawaiian Food?
Waiāhole Poi Factory offers classic dishes like poi and lau lau.
It’s recommended to order ahead to save time.
Exploring the Windward coast from Waimānalo to Kahana Bay is a journey filled with natural beauty, delicious food, and unique local experiences. It’s a part of Oʻahu that truly captures its spirit, offering a refreshing blend of relaxation and discovery. I hope you find as much joy in exploring it as I did.