Experience Oahu with Beautiful Beaches, Great Food and Incredible Adventures

Oahu has everything you could want in a Hawaiian getaway—beautiful beaches, amazing food, scenic hikes, and a rich history that makes the islands so special. There are so many things to do here – You can relax with a mai tai on the beach or explore waterfalls, coastal views, and hidden local gems. This five-day itinerary will help you make the most of your trip.

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If you like the freedom to go where you want, when you want, renting a car is the way to go. Waikiki is easy to walk, and Honolulu has public transportation, but some of Oahu’s best spots—like tucked-away beaches, quiet hiking trails, and the famous North Shore food trucks—are much easier to get to when you have your own car.

Booking a couple of excursions is an easy way to explore Oahu without the stress of planning, while still having time to enjoy the island on your own. Check out my top excursion picks here!

If you’d rather skip the planning, I can put together a custom Hawaiian vacation package with luxury hotels, private tours, and even inter-island flights. That way, all you have to do is show up and enjoy. Keep reading for a full itinerary, plus details on the best all-inclusive Hawaiian vacation packages at the end.

Ready to book or want to talk through the options?

Where to Stay in Oahu

Our Top Hotel Choices Are

Turtle Bay Resort
Halekulani

Choosing where to stay in Oahu comes down to the kind of Hawaiian vacation you’re looking for. Do you want to be in the heart of Waikiki, where you can step outside your hotel and be surrounded by restaurants, shopping, and nightlife? Or would you rather wake up to the sound of waves on the North Shore, far from the crowds? No matter what kind of trip you’re planning, Oahu has amazing hotels and resorts to choose from. Here are our top 3 hotels picks. See our full list of places to stay here.

Halekulani

It’s a luxury resort, but not in an over-the-top way—it’s elegant, peaceful, and has some of the best service on the island. The beachfront dining at House Without A Key is incredible! The food is amazing, it features live Hawaiian music, and a has a perfect sunset view. The pool overlooks the ocean, the spa treatments are next-level, and the location puts you just steps from Waikiki Beach. If you want a high-end experience with a relaxing, refined feel, Halekulani is a fantastic choice.

Prince Waikiki

Perfect if you want a beautiful oceanfront hotel but don’t necessarily want to stay in the busiest part of Waikiki. Every room has stunning floor-to-ceiling ocean views, and the infinity pool is one of the best in Honolulu. The on-site sushi restaurant is amazing, and the overall vibe of the hotel is calm, modern, and upscale. You’re still close enough to Waikiki Beach to enjoy everything, but when you’re ready to escape the crowds, you have a peaceful retreat waiting for you.

Turtle Bay Resort, now part of The Ritz-Carlton family

I love this resort because it is on a quiet part of the island and I love how many activities the resort has so that you don’t have to go very far to do amazing things!

This is the ultimate North Shore getaway. If you love wide-open spaces, quiet beaches, and exploring nature, this resort is a dream come true. It sits on 1,300 acres of gorgeous coastline, with access to hiking trails, horseback riding, and some of the best surf spots on the island. The rooms have been beautifully renovated, and there are incredible oceanfront restaurants, a world-class spa, and even a chance to spot sea turtles right on the beach. If you want to experience a different side of Oahu, away from the hustle of Waikiki, this is the place to be.

Day 1 | North Shore – Waterfalls, Shrimp Trucks & Boutique Shopping

Oahu’s North Shore is famous for it’s laid-back surf towns, incredible local food, and some of the most beautiful beaches on the island. It’s the perfect spot to spend your first day on the island exploring, eating, and relaxing.

Start your morning in Haleʻiwa, a charming little town full of surf shops, cute boutiques, and great coffee. Grab a coffee from Island Vintage Coffee – my favorite is the Island Latte! Then take a short stroll through the historic streets before heading to Waimea Valley. This botanical garden is home to tropical plants, ancient Hawaiian cultural sites, and a paved walking path that leads to a beautiful waterfall where you can take a swim. Be aware that this garden does have an entrance fee but for me it was totally worth it!

For lunch, head to The Shrimp Shack in Kahuku, famous for its garlic butter shrimp! Don’t miss out on grabbing a banana lumpia too—a crispy, deep-fried banana roll that’s warm, gooey, and totally addicting.

After lunch, head back to Haleʻiwa for some shopping. This cute town has local shops that have everything from handmade Hawaiian jewelry to surf-inspired art and fun souvenirs.

This is the perfect day to wear my Olukai flip-flops —my favorite flip flop brand. I think I have 5 different pairs in all different colors! They are super comfortable for walking around all day.

After exploring Hale’iwa make your way to Sunset Beach, one of the most famous surf spots in the world. In the winter, the waves here are massive, and you’ll probably see pro surfers taking on swells over 30 feet high. In the summer, the water is calm and crystal clear, making it perfect for swimming and snorkeling. No matter which season you visit, it’s an amazing place to watch the sunset.

Day 2 | Windward Oahu – Temples, Hidden Beaches & Coastal Hikes

Oahu’s Windward Coast has lush green mountains, quiet beaches, and relaxed pace, it’s the perfect place to slow down and soak in a different side of the island. Far less crowded than Waikiki, this area has stunning views, hidden gems, and that laid-back vibe.

Start your morning in Kailua with breakfast at Cinnamon’s and get the Guava Chiffon Pancakes. They’re light, fluffy, and amazing—definitely worth the hype. After breakfast, stop by Manoa Chocolate Factory and take the factory tour ($25 a person tour fee). It takes you through the factory to show you how Hawaiian-grown cacao is turned into rich, handcrafted chocolate. The best part? You get to sample as much as you want!

Next, head to Byodo-In Temple, a peaceful retreat in the Koʻolau Mountains. This beautiful Buddhist temple is surrounded by koi ponds, lush gardens, and a towering sacred bell you can ring for good luck. It’s the kind of place that instantly makes you feel more relaxed, and it’s a great spot to take photos or just sit and enjoy the stillness. The temple has an entrance fee of $7 and they do ask you to be respectful of where you are.

Afterward, drive over to Bellows Beach, a stunning stretch of white sand and crystal-clear water. Since it’s on military land, it’s only open to the public on weekend. It is an amazing beach but if you can only visit on a weekday, Waimanalo Beach is just down the road and just as beautiful.

Make sure your sunscreen is reef safe and the sun can sneak up on you, so I like to have a hat and sunglasses with me to help protect me from the sun.

After the beach, head to the Makapuʻu Lighthouse Trail for an easy sunset hike with beautiful ocean views. This two-mile paved path takes you along the cliffs, with waves crashing below. The best part is if you’re visiting between December and March, you can often spot whales! I love whale watching, so this path is a favorite of mine! Once you are done spotting whales, take a short drive over to the Leonard’s Malasadamobile. This food truck has amazing malasadas – warm, pillowy Portuguese doughnuts that are fried to perfection and coated in sugar. Stick with the classic sugar-dusted malasada, or go for one of the filled varieties like haupia (coconut) or custard. Or like me you can get one of each!!

Day 3 | Waterfalls, Ko Olina Lagoons, and Hawaiian Monk Seals

Today starts with a little adventure and then slowing things down for a relaxing afternoon by the water. You’ll start your day with a jungle waterfall hike, unwind at Ko Olina’s gorgeous lagoons, and end the day with a scenic coastal walk where you just might spot a Hawaiian monk seal.

First stop—coffee, of course! Morning Brew in Kailua is a great local spot with amazing Hawaiian-grown coffee and an awesome breakfast menu. The iced coconut Thai latte is my my favorite, and their breakfast burritos are filling without being too heavy—perfect for a morning hike.

Next, head to Lulumahu Falls, one of Oahu’s most beautiful hidden waterfalls. This 1.6-mile hike takes you through a bamboo forest, across small streams, and up a winding trail before opening up to a stunning 50-foot waterfall. The hike can get muddy, so wearing water shoes or sturdy hiking sandals will make things a lot easier.

Since the trail is on state land, you’ll need to grab a Hawai‘i State Na Ala Hele permit ahead of time, which you can get online here.

After your hike, it’s time to relax at Ko Olina, a resort area on the west side of the island. The calm, man-made lagoons are perfect for floating, swimming, or just stretching out on the soft sand. If you love snorkeling, the clear waters here are great for spotting tropical fish close to shore.

Lunch at Monkeypod Kitchen is a must – Their fresh fish tacos are delicious, and you should definitely get the Monkeypod Mai Tai. It’s topped with honey-lilikoi foam and I think is one of the best on the island. It’s a great place to hang out for a bit with their open-air seating and live music.

For a day of walking and shopping, I love this bag to carry all of my essentials and it’s light enough to not hurt my back!

After lunch and relaxing at the lagoons, take a drive up to Kaʻena Point, a rugged coastal area on Oahu. This wild coastline is home to nesting seabirds, tide pools, and, if you’re lucky, Hawaiian monk seals! The walking path is easy and scenic, with waves crashing against the cliffs and incredible ocean views.

After your wildlife spotting walk at Ka’ena Point, head back to Ko Olina to catch the sunset. Take a stroll along the lagoons, grab a tropical drink at one of the beachfront lounges, or just sit on the sand and watch as the sky lights up in shades of pink and orange.

Day 4 | Coffee, Hawaiian History, and Oceanfront Dining

Today is full of shopping, learning about Hawaiian history, and eating some delicious food. You’ll start the morning with fresh island coffee, explore Hawaii’s royal past, wander through a colorful arts district, and end the day with a seafood dinner by the water.

First things first—coffee! Green World Coffee Farm in Wahiawa is one of those places that smells amazing before you even walk through the door. This small, family-owned coffee farm is so great! It has rows of coffee trees, a cute shop filled with locally roasted beans, and free tastings of their coffee. You can a stroll through the fields and sip on your latte before heading into the city.

Next, make your way to downtown Honolulu to visit Iolani Palace, the only royal palace in the United States. Walking through this beautifully restored landmark feels like stepping back in time. You’ll see the grand throne room, intricate koa wood staircases, and even the private chambers where Queen Liliʻuokalani was held under house arrest. It’s an eye-opening glimpse into Hawaii’s royal history, and a must-visit if you want to understand the history of the islands.

For lunch stop by The Pig and the Lady This is a family-run restaurant that serves Vietnamese inspired dishes and is very popular, so come prepared to wait a bit. I love the French dip Bahnh Mi and it is only served for lunch or take out at dinner time. It’s closed on Sunday & Monday so be sure to visit on one of the days it is open.

After lunch, spend the afternoon exploring Kakaʻako, one of Honolulu’s trendiest neighborhoods. This artsy district is covered in colorful street murals, and has tons of great boutiques, coffee shops, and hidden gems. While you are there you should stop by Butterfly Ice Cream for a scoop of lilikoi cheesecake!

After a day of shopping, head to Nico’s Pier 38 for a relaxing dinner by the water. This casual seafood spot serves some of the freshest fish on the island, caught daily by local fishermen. The seared ahi plate is amazing but you can’t go wrong with a poke bowl or a catch-of-the-day special either. Get a table outside, to enjoy the ocean breeze and the beautiful Hawaiian sunset.

Day 5: Scenic Drives, Movie Sites, and Waikiki Beach Time

Your last day on Oahu you will be enjoying the island’s stunning scenery, spotting a few famous movie locations, and squeezing in one more beach day before heading home. The perfect way to end an amazing trip.

Start the morning with a drive to Ho’omaluhia Botanical Garden, one of the most breathtaking spots on the island. With towering palm trees, green mountains, and walking trails, this place is like a hidden paradise. Take your time driving through, stopping at scenic lookouts to snap some photos and just soak it all in. Make sure you obey all of the signage along the road through the gardens – there are places where stopping your car to take pictures is prohibited.

Next, head to Kualoa Ranch, THE SPOT for movie lovers and anyone who wants to see Oahu’s wilder side. Their movie sites tour takes you through the valleys and cliffs where Jurassic Park, Jumanji, 50 First Dates, and so many other Hollywood films were shot. Even if you’re not into movies, the views here are absolutely unreal—you’ll feel like you’ve stepped into a postcard.

Make sure you book in advance and plan on arriving an hour before your tour begins.

After your tour, head back to Waikiki for one last beach day. Enjoy a good book stretched out on the sand, float in the warm turquoise water, or just relax and take in the view of Diamond Head in the distance. If you’re up for one last bit of fun, rent a paddleboard or take a surf lesson to make the most of your time in the water.

For your final dinner, House Without A Key at Halekulani is an incredible way to spend your last night on the island. With tables right by the beach, live Hawaiian music, and some of the best mai tais on the island, it’s the perfect spot to watch the sunset while having an amazing meal. Order some fresh seafood, sip a cocktail, and enjoy the warm island breeze.

Best Hawaiian Vacation Packages for a Stress-Free Trip

Planning a trip to Hawaii should be exciting, not stressful. If you’d rather skip the endless research and just enjoy an unforgettable getaway, I can help you customize the perfect Hawaiian vacation package. From creating the Best Hawaiian vacation packages for couples to all inclusive Hawaiian island-hopping adventures or a relaxing cruise with stunning views, I can arrange and personalize these experiences to create a trip designed just for you.

Customized Private Tours | A Luxury Hawaiian Vacation, Your Way

If you want to experience Oahu without the stress of planning, a private luxury tour is the way to go. From breathtaking hikes and incredible food to world-class relaxation, everything is tailored just for you, with your own private excursions to experience everything without a big group.

Your trip starts with a warm Hawaiian lei greeting at the airport before a private transfer to Halekulani, one of Waikiki’s most stunning oceanfront hotels. Wake up to beach views, sip your morning coffee on the balcony, and enjoy the day at your own pace.

Adventure lovers can hike Diamond Head for panoramic views of Waikiki or wander through the lush trails of Manoa Falls, where you’ll find a stunning jungle waterfall. If you’re more in the mood to relax, Waimea Valley Botanical Gardens offers a peaceful stroll through tropical landscapes with a refreshing waterfall swim at the end.

A vacation is a big investment, so make sure it’s protected with travel insurance. I personally use Arch RoamRight and highly recommend them, but no matter which company you choose, having coverage gives you peace of mind for your trip!

Food is a can be a big part of your vacation, and your driver will take you to some of Oahu’s best local spots. Spend an afternoon on the North Shore sampling fresh seafood, like garlic shrimp and island treats, like chocolate haupia. When you are in Honolulu you can make reservations for lunch at The Pig and The Lady, known for its pho French dip and Laotian fried chicken.

Afternoons can be as active or as laid-back as you want. Relax at Halekulani’s beautiful oceanfront pool, take a private surf lesson, or take a drive along the island’s scenic coastline. You can end your day with a romantic dinner at La Mer, where fresh seafood, ocean breezes, and Waikiki’s golden sunset make for the perfect evening.

This tour is the best Hawaiian package for couples, honeymooners, or anyone looking for a luxury, stress-free Hawaiian vacation. Want to add a sunset sail, a helicopter tour, or a private beach day? Every detail can be customized to make sure your trip is exactly how you want it. If you are ready to start planning, schedule a complimentary consultation with me today!

Small Group Tour | 3-Island Hawaiian Vacation

Why visit just one island when you can experience three? This small group tour takes you on a 10-day adventure through Oahu, Maui, and Kauai, with a knowledgeable guide by your side the entire time. With all the planning handled for you, there’s no need to worry about flights, hotels, or activities—just relax and enjoy every moment.

You’ll stay at beautiful oceanfront resorts like the Moana Surfrider in Waikiki, Westin Maui, and Grand Hyatt Kauai—each offering stunning views, excellent service, and the perfect place to relax after a day of exploring. Every detail is arranged, including inter-island flights, daily breakfast, and guided sightseeing tours, so you can focus on enjoying your trip.

Your trip will include things like a sunset cocktail cruise, a traditional Hawaiian luau, and exploring some of Hawaii’s most breathtaking landscapes, like Maui’s Road to Hana and Kauai’s Napali Coast. Since your are traveling with a small group, you’ll enjoy a more personal guided experience while still having some free time to explore on your own.

This tour is perfect for travelers who want to see multiple islands without the hassle of planning, while also having a dedicated guide. If you’d like to add a private excursion or a little extra adventure, I can customize the trip to make it your dream vacation.

Norwegian Pride of America Cruise | The ONLY Interisland Cruise

If you want to visit multiple Hawaiian islands without the hassle of packing, unpacking, and catching flights, this seven-night cruise is the perfect way to do it. As the only interisland cruise in Hawaii, it takes you to Oahu, Maui, Kauai, and the Big Island, with overnight stays in Maui and Kauai so you have extra time to explore.

Spend your days snorkeling in Molokini Crater, hiking Waimea Canyon, or watching the sunrise over Haleakalā. In between adventures, relax on board with all-inclusive dining, live entertainment, and private balcony suites where you can wake up to incredible ocean views.

This is a great option for anyone who wants to experience an all inclusive Hawaiian vacation while exploring multiple islands. If you’d like to add private excursions or special experiences, I can help customize the trip to make it exactly what you’re looking for. Just unpack once, sit back, and enjoy the ultimate island-hopping vacation.

Which Hawaiian Vacation Style is Right for You?

If you love the freedom to explore, renting a car and following this five-day itinerary lets you see Oahu at your own pace. If you want to see multiple islands, stay in luxury hotels, and have every detail handled for you, a Hawaiian vacation package is the way to go.

However you choose to experience Hawaii, Oahu has the perfect mix of adventure, relaxation, and rich culture. Let’s start planning your dream Hawaiian vacation—reach out today, and I’ll help make it unforgettable!

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