If I could snap my fingers and be magically transported anywhere, it’d probably be smack dab in the middle of Oahu. Seriously, Oahu has it all. This beautiful island blends beauty, adventure, and a vibrant city energy— a glorious combination!
In Waikiki, you’ll salivate over fresh island coffee, musubi on the go, and sunset cocktails. You’ll spend the second half of your trip on the island’s iconic North Shore where you’ll dine out on North Shore bakeries, incredible hikes, and coastal drives.
Use this City Girl’s Guide to plan the most epic 6-day trip to Oahu, using both Waikiki and North Shore as home base.
Day 1: Waikiki
Itinerary
Breakfast at Kona Coffee Purveyors
Drive out to Manoa Falls & hike to the waterfall
Visit the Kaiwi State Scenic Shoreline
Back in Waikiki, eat Musubi for lunch
Sunset drinks at House Without A KeyDinner at Roy’s Waikiki
Breakfast at Kona Coffee Purveyors: Start your morning in Waikiki with some of the best coffee on the island at Kona Coffee Purveyors.
Drive out to Manoa Falls & hike to the waterfall: Just a short drive from Waikiki, this trail leads you to the stunning 150-foot Manoa Falls waterfall. The hike is about 1.6 miles round trip and takes you through tropical rainforest scenery and bamboo forests.
Visit the Kaiwi State Scenic Shoreline: The Kaiwi State Scenic Shoreline is one of the best places on Oahu for dramatic ocean views and rugged cliffs.
Lunch: Back in Waikiki, eat Musubi: Back in Waikiki, grab a musubi— Hawaii’s staple grab-and-go snack. You’ll find musubi at convenience stores and local spots all over Waikiki. For lunch, grab a bunch of different flavors and have your life changed.
Sunset drinks at House Without A Key: Set right on the ocean at the beautiful Halekulani Hotel, House Without A Key is the perfect place to catch the sunset. Enjoy your tropical cocktail to the sounds of live music and hula dancing.
Dinner at Roy’s Waikiki: End your day with Hawaiian fusion at Roy’s, one of my favorite Oahu restaurants, because of its menu filled with fresh island ingredients. It’s upscale without feeling stuffy and perfect for a memorable first-night dinner.
Day 2: Waikiki
Itinerary
Hike Diamond Head first thing in the morning
Explore & shop up & down Waikiki Beach
Take a Sunset Sail Cruise
Dinner at Wasabi Bistro
Drinks & dessert at Duke’s Waikiki
Hike Diamond Head first thing in the morning: Start your day early with one of Oahu’s most famous hikes. The Diamond Head trail takes you through a 1.6 miles journey through a volcanic crater and indescribable panoramic views of the Pacific.
Explore & shop up & down Waikiki Beach: After your hike, spend the late morning and afternoon soaking up the more fabulous side of Waikiki. Pop into shops along Kalākaua Avenue, enjoy the people-watching, and stock up on souvenirs.
Take a Sunset Sail Cruise: Head out on the water for a sunset sail along the Waikiki coastline. I recommend booking the Holokai Catamaran for a relaxing, breezy, and unforgettable time seeing the island from the ocean.
Dinner at Wasabi Bistro: Wasabi Bistro is a local favorite for fresh sushi. It’s a cozy, low-key spot that’s perfect after a long day exploring the island.
Drinks & dessert at Duke’s Waikiki: Duke’s is a beachfront restaurant and bar that’s basically a Waikiki rite of passage. Grab a cocktail and don’t skip their famous Hula Pie, aka a massive ice cream dessert with lots and lots of chocolate.
Day 3: North Shore
Oahu’s North Shore is the coolest place on Earth. With its 17-mile stretch along the island’s northern coastline, it captures the heart of the aloha spirit and offers a glimpse into the iconic surf lifestyle. For the second part of your trip, you’ll transition over to the North Shore. I recommend booking one of the many epic Airbnb’s available by North Shore’s beautiful beach.
Itinerary
Drive the scenic Kamehameha Highway to the North Shore
Stop at Dole Plantation for Dole Whip
Drive to Laie Point Lookout
Lunch at Waialua Bakery
Explore & shop your way through Haleiwa Town
Dinner at Mayas Tapas & Wine
Drive the scenic Kamehameha Highway to the North Shore: The journey to the North Shore from Waikiki is one of the most beautiful drives I’ve experienced. Start your day cruising the Kamehameha Highway with the windows down, as you wind along the mountainous coastline.
Stop at Dole Plantation for Dole Whip: Stop at Dole Plantation, home to world-famous Dole Whip, aka heaven in a cup.
Drive to Laie Point Lookout: Laie Point is a lesser-known lookout point on Oahu’s northeastern coast. I drove about 25 minutes out here one morning while staying on North Shore and it was one of the most jaw-dropping sights I’d seen on the island. One of the best things about Laie Point is how peaceful it is. Unlike some of the more famous spots on Oahu, Laie Point doesn’t see many tourists, so it remains calm and off-the-beaten path.
Lunch at Waialua Bakery: Locally owned bakery with various fresh sandwiches, acai bowls, and salads. Perfect for a healthy, yet hearty, lunch.
Explore & shop your way through Haleiwa Town: Step into Haleiwa, North Shore’s colorful coastal “downtown.” Here, the air smells like the ocean, and the town is painted in shades of beachy blues and sunset pinks. I could spend an entire day browsing the local boutiques, surf shops, and art galleries, and eating everything in sight.
Haleiwa Town might be small, but the shopping packs a punch. I vintage shopped like an absolute maniac (ask my overweight luggage). I loved shopping at Lilikoi Rock: Island Jewelry and Vintage and Velzy Vintage.
I also loved visiting SoHa Living, a homeware boutique that has incredibly unique pieces. The store is filled with trinkets that are totally unnecessary in everyday life, but because they’re from Hawaii (!!!!!), it is entirely desperate and vital that you purchase them. SoHa Living also has locations in Waikiki Beach.As for art,Greenwoom Haleiwa is a local gallery selling affordable prints and merchandise that allow you to take a creative slice of Hawaii home with you.
Dinner at Maya’s Tapas & Wine: This tapas restaurant was recommended by our Airbnb Host and it turned out to be one of my favorite meals on the island. A+ date night, A+ patatas bravas.
Day 3: North Shore
Itinerary
Breakfast at Kono’s North Shore
Snorkel Sharks Cove
Visit Waimea Valley & its 45-foot waterfall
Watch the sunset on Sunset Beach
Drinks at Turtle Bay ResortOrder Seven Brothers for dinner
Breakfast at Kono’s North Shore: Groovy breakfast joint serving massive burritos and classic comfort dishes.
Snorkel Sharks Cove: For those interested in underwater exploration, Sharks Cove is where you should go for snorkeling. Don’t worry—there aren’t any actual sharks here (despite the name). The cove is made of crystal-clear water where you can peek at coral formations and tons of marine life.
Sharks Cove is a very popular spot and gets crowded with families and picnickers enjoying the cove. Snorkeling here is best during the summer when the waters are calm. I also recommended wearing water shoes for this activity, as the ocean floor is extremely rocky and the water is pretty shallow, making it hard to swim.
Visit Waimea Valley & its 45-foot waterfall: Waimea Valley is a lush, green paradise that feels like you’ve stepped into another world—an ancient one, where nature and Hawaiian history come alive. I’d heard about Waimea Valley mostly for its famed waterfall, but it’s so much more than that. This is where you get a sense of the island’s rich botanical life and a glimpse into the valley’s spiritual significance.
Once you reach the end of the trail, you’ll hear the sound of rushing water before you see it, and then it opens up to a beautiful 45-foot waterfall plunging into a pool below. The best part? You can actually swim here! After the humid walk over, taking a dip in the cool (actually freezing), fresh water is like hitting the reset button.
Watch the sunset on Sunset Beach: As the name suggests, Sunset Beach is the place to watch the dreamiest sunsets on the island.
Drinks at Turtle Bay Resort: Turtle Bay is the only resort on North Shore and it’s seriously so f*cking fabulous. I want to move in, like, yesterday. I recommend visiting for an overpriced cocktail that will eventually pain you when it’s time to pay the bill. It’s all for the experience. Do not linger for dinner or appetizers— sip on your sunset cocktail before enjoying a guaranteed better meal at a local North Shore restaurant.
Day 5: North Shore
Itinerary
Breakfast at Ted’s Bakery
Drive to Kaʻaʻawa Valley and spend the day touring Kualoa Ranch
Back in Haleiwa, have lunch at Poke for the People
Vintage shop in HaleiwaDinner at Haleiwa Joe’s
Breakfast at Ted’s Bakery: Casual North Shore eatery with awesome breakfast sandwiches, lunch plates, and dessert.
Drive to Kaʻaʻawa Valley and spend the day touring Kualoa Ranch: Spend the day exploring one of Oahu’s most breathtaking natural areas at Kualoa Ranch, a 4,000-acre private nature reserve. This ranch is famous as a filming location for movies and shows like Jurassic Park and Lost. Choose from activities like ATV tours, horseback riding, ziplining, or a Hollywood movie sites tour.
Back in Haleiwa, have lunch at Poke for the People: Fresh poke spot known for its high-quality fish and variety of sides
Vintage shop in Haleiwa: Haleiwa Town might be small, but the shopping packs a punch. I vintage shopped like an absolute maniac (ask my overweight luggage). I loved shopping at Lilikoi Rock: Island Jewelry and Vintage and Velzy Vintage.
Dinner at Haleiwa Joe’s: Lively hangout spot great for happy hour drinks and bar bites.
Day 6: North Shore
Itinerary
Breakfast at HI Pie
Ziplining at Climb Works Keana Farms
Lunch at Giovanni’s Shrimp Truck & Fasay Thai Wagon
Turtle watching on Laniakea Beach
Happy hour at Jorge’s Mexican Restaurant & BarDinner at Haleiwa Beach House
Breakfast at HI Pie: Small coffee shop with insanely delicious dessert (try the cookie dough cheesecake, trust me).
Ziplining at Climb Works Keana Farms: Adrenaline junkie? Climbs Works has 8 ziplines for you to glide above North Shore’s coastline, mountains, and valleys. As you move through the course, your guides will provide insights into the local crops, Hawaiian culture, and the island’s environmental conservation efforts. If you’re craving an adrenaline rush and want to experience Oahu’s North Shore from a totally new perspective, then Climb Works Keana Farms is the place to go.
Lunch at Giovanni’s Shrimp Truck & Fasay Thai Wagon: Giovanni’s Shrimp Truck is a popular shrimp truck known for its classic shrimp meal. Right next door is Fasay Thai Wagon, an affordable Thai food truck with generous portions.
Turtle watching on Laniakea Beach: Laniakea Beach on the North Shore is one of the best places on Oahu to spot Hawaiian green sea turtles resting on the sand.
Happy hour at Jorge’s Mexican Restaurant & Bar: Recommended by friends on the island, this North Shore hot spot serves Mexican with an island twist.
Dinner at Haleiwa Beach House: An upscale version of Haleiwa Joe’s with a slightly elevated menu and ocean views.
