The Ultimate 5-Day Oahu Itinerary for First-Time Visitors
Aloha, and welcome to Oahu, the “Gathering Place” of Hawaii! If you’re planning your first visit to this stunning island, you’re in for an unforgettable adventure with this 5-day Oahu itinerary.
Oahu is known to be one of the best holiday spots in Hawaii, and it is for good reason. There’s something on this island for everyone. Whether you’re traveling with a group of friends, as a family or a couple, you’ll find an array of activities and sights to visit to keep you busy.
A couple years ago we spent just over a week on the island, exploring some of Oahu’s top attractions and eating some delicious local food along the way. From world-famous beaches to historical landmarks, Oahu offers a perfect blend of natural beauty, cultural richness, and thrilling activities. In this ultimate 5-day Oahu itinerary, i’ll guide you through the must-see attractions and provide tips to help you make the most of your trip.
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5-day Oahu Itinerary Overview
- Diamond Head, Waikiki Beach, Sunset Cruise
- Pearl Harbour, Kalakaua Avenue
- North Shore, Dole Plantation, Polynesian Cultural Centre
- Hanauma Bay, Halona Blowhole, Makapuʻu Lighthouse Trail, Waimānalo, Lanikai and Kailua Beach
- Downton Honolulu, Shopping
Oahu Itinerary
This 5 day Oahu itinerary is specifically designed to include some of the top attractions in Oahu. You can mix and match and change things around to suit your needs.
It’s important to understand the basic geography of the island so you know exactly where to base yourself and plan your attractions accordingly.
The first thing you need to know when visiting Hawaii is that it’s not just one island. Hawaii is made up of many islands, Oahu is the most visited by tourists. It’s home to the majority of Hawaii’s population and offers a multitude of activities and attractions.
The island of Oahu is made up of five regions: Honolulu, the Windward Coast, Central Oahu, the Leeward Coast, and the North Shore. While most visitors spend the majority of their time in Honolulu and Waikiki, there are hidden treasures throughout the island; from the surfer culture of Haleiwa and the North Shore to the Makapuu Lighthouse on the island’s southeast tip and the lush valleys and scenic panoramas of the Windward Coast.
Oahu Itinerary Travel Guide – Know Before You Go
- English and Hawaiian are the two languages in Hawaii. However, English is pretty much spoken throughout the country.
- The official currency is the US Dollar. All major credit cards are widely accepted at major tourist destinations.
- Driving is on the right-hand side of the road. You will need to present a valid driving license, along with photographic identification, at the time of rental. You must also have a valid credit card (not a debit card) as the car hire company will need your card to authorize a security deposit payment.
- Tipping is very much part of the culture in Hawaii. Tips of between 15-20% are expected for all bar and restaurant services and about the same percentage should be applied to taxi fares. Hotel porters who assist with bag carrying also expect a tip. So, it is important to have some low denomination notes for this purpose.
- Hawaiian food is a blend of Asian, Polynesian, Hawaiian, and American influences. As Hawaii is a tropical destination, you can also enjoy a variety of fresh, locally grown fruit.
- American plugs and voltage are very different from other parts of the world. Depending on where you are traveling from, an adapter is a must if you’re planning on taking electronic devices to Hawaii.
- It’s important to always pack for hiking, the beach, and snorkeling (plus a change of clothes) when you are on the move in Hawaii. Carry plenty of drinking water, snacks, a hat, and most importantly sunscreen.
Best time to visit Oahu, Hawaii
This really depends on what you’re looking for in your vacation, but generally, the most favorable times are from April to June and September to mid December.
During these months, the weather is warm but not overwhelmingly hot, and the crowds tend to be smaller since it’s outside of the peak tourist season (winter holidays and summer). You’ll get pleasant temperatures, fewer tourists at popular spots, and great rates on accommodations.
Winter (December to March) is the peak season due to the holidays, with great surf conditions on the North Shore for those into big-wave riding. However, it also means more crowds and higher prices. On the other hand, summer (June to August) attracts families, especially with school breaks, so you can expect busier beaches and attractions, plus warmer, sunnier weather.
So, if you’re looking for a balance of great weather, fewer crowds, and more affordable prices, visiting in late spring or early fall is ideal.
Getting to Oahu
Reaching Oahu is easy with frequent flights from the mainland United States, international locations, and neighboring Hawaiian islands. Most visitors arrive at Honolulu International Airport (Daniel K. Inouye International Airport), a bustling hub that connects you to paradise.
- Flight Tip: Book early to get the best deals, especially during peak travel seasons.
- Pro Tip: Opt for a window seat to enjoy spectacular views of Oahu’s coastline during your descent.
Once you land, you’ll be greeted with a warm aloha spirit that sets the tone for your Hawaiian adventure. Before heading out, consider grabbing a refreshing Hawaiian shave ice or a cup of 100% Kona coffee at one of the airport kiosks to kick off your vacation.
Transport in Oahu
While public transportation is available on the island, renting a car is the best way to explore Oahu’s diverse attractions at your own pace.
Renting a Car
Oahu’s attractions are spread out, and a car provides flexibility and convenience. I highly recommend this option!
Tips:
- Book your rental in advance, especially during peak travel seasons.
- Choose a smaller vehicle to navigate narrow roads and for easier parking.
- Make sure your rental includes GPS or download offline maps to stay on track.
Renting a car also allows you to uncover hidden gems, such as scenic lookout points and lesser-known beaches, that are inaccessible via public transport.
I highly recommend using RentalCars.com so you can compare prices.
Alternatives to a Car
- Public Bus (TheBus): Affordable but time-consuming. TheBus is an option for budget-conscious travelers who aren’t in a rush.
- Shuttle Services: Great for airport transfers and specific attractions. Some shuttles also offer guided tours.
- Ridesharing: Apps like Uber and Lyft are available, but costs can add up quickly. Use them sparingly for short trips or nights out.
The Ultimate 5 day Oahu Itinerary for First Time Visitors
This Oahu itinerary assumes you arrive in Oahu the afternoon or night before your 5 days in Oahu begins. Once you arrive, pick up your rental car and check into your accommodation, the real fun begins!
Make sure to check out my post on Places To Visit in Oahu.
Day 1: Hike Diamond Head, relax on Waikiki beach and catch a sunset cruise
Morning: Diamond Head
Begin your day with an exhilarating hike to the top of Diamond Head Crater, an iconic Oahu landmark. The 1.6-mile round-trip trail rewards you with panoramic views of Waikiki and the Pacific Ocean. This is a very popular hike in Waikiki so it’s best to start early in the morning to walk up the mountain before the heat and humidity get the better of you. It will be one of the most crowded hikes you’ll do, but no matter when you begin the hike, there’s no such thing as beating the crowd with this one.
The hike contains many stairs but you’ll be rewarded with stunning views of Waikiki and Honolulu. The gates open at 6am and so the earlier the better!
Reservations are required hike Diamond Head and may be made up to 30 days in advance. Admission is $5 per person and parking is $10 per vehicle.
- Tips:
- Arrive early to beat the heat and crowds.
- Bring water and sunscreen for the hike.
- Wear comfortable, closed-toe shoes suitable for rocky terrain.
Ready to cool off? Up next, head to Waikiki Beach!
Afternoon: Spend the afternoon relaxing at Waikiki Beach
Make your way to Waikiki after your hike, grab a bite at one of the local establishments before you head to the beach to relax and cool off for the afternoon. You can sunbath, swim, surf or even take a paddle boarding lesson.
Where to Eat: For a mid-afternoon treat, grab a poke bowl from a local joint like Ono Seafood or Da Hawaiian Poke Co.
Evening – Sunset Cruise Dinner
Wrap up your first day with a beautiful sunset cruise. This sunset cruise sets sail from Waikiki Beach on a stunning catamaran where you can enjoy breathtaking sunset views over Leahi (Diamond Head) .
What to Bring: A light jacket, as it can get breezy on the water.
Day 2: Immerse yourself in history at Pearl Harbour National Memorial, Kalakaua Avenue
Morning: Pearl Harbor National Memorial
Start your morning with a visit to the historic Pearl Harbor National Memorial. Pearl Harbor, is one of the most iconic and historically significant sites in the United States. It serves as a living monument to those who lost their lives and the resilience of a nation during a time of conflict. You can book this indepth tour here.
Visiting this historic site offers a unique blend of reflection, education, and inspiration, drawing millions of visitors annually to explore its museums, memorials, and exhibitions.
There is no shortage of things to do at Pearl Harbor. Start your journey at the Pearl Harbor Visitor Center, where you can learn about the attack through interactive exhibits. The main attraction at Pearl Harbour is the USS Arizona Memorial, accessed by a short boat ride, which floats above the sunken battleship.
History enthusiasts will enjoy touring the Battleship Missouri Memorial, often called “Mighty Mo,” the site of Japan’s World War II surrender. Don’t miss the Pacific Aviation Museum for an immersive look at wartime aviation and the USS Bowfin Submarine Museum & Park.
Getting to Pearl Harbor is easy, with several transportation options, including public buses, private shuttles, and car rentals from Honolulu, just 10 miles away. A visit to Pearl Harbor is a compelling experience, offering both somber reflection and a profound appreciation for history.
Tips:
- The USS Arizona Memorial is free, but reservations for the ferry from the visitor center are strongly recommended. You can do so online up to a month ahead of time.
- Arrive early to avoid crowds.
- Allocate at least half a day to fully explore the site.
Evening: Explore Kalakaua Avenue
After a long day exploring one of the most significant sites in history, head back to your accommodation to freshen up.
Take a stroll along Kalakaua Avenue to explore shops, restaurants, and street performers. Don’t miss the bronze statue of Duke Kahanamoku, the father of modern surfing, which serves as an Instagram-worthy landmark.
Stop by the International Market Place, a shopping mall built around a huge 160 year old banyan tree. The open air centre is a great place to do a bit of shopping. You can also head to Royal Hawaiian Centre and check out some shops there.
If you are looking for some places to have dinner, check out Oahu Mexican Grill (OMG), which is a great spot in Waikiki for a quick meal.
Day 3: North Shore Adventures
Start day 3 nice and early so you beat the traffic to get to the North Shore. Make sure you have a big breakfast before you get on the road.
A day trip from Waikiki to the North Shore of Oahu offers an authentic and laid-back contrast to the hustle and bustle of the city. The journey takes about 45 minutes to an hour, depending on traffic, and you’ll quickly notice the scenery shift from urban to lush, tropical landscapes as you head north.
Once you arrive, the North Shore is a surf haven, home to world-famous beaches and a relaxed vibe that’s perfect for a day of exploration. Along the way, you’ll come across small trucks selling fresh fruit or shaved ice. Indulge in delicious tropical fruit or get some shaved ice to cool down.
Morning: North Shore Exploration
Before we get to the beaches, we’ll make a pit stop along the way at the famous Dole Plantation. This iconic spot is where you can learn about the history of Hawaii’s pineapple industry, take a walk through the world’s largest maze, or enjoy a sweet treat like their famous Dole Whip, a refreshing pineapple soft-serve that’s perfect after a day in the sun.
As you drive along the coastline, be sure to stop for a bite at Giovanni’s Shrimp Truck, famous for its garlic shrimp plates that have become a must-try for any North Shore visitor. Alternatively, you can check out the many food trucks serving local specialties like poke bowls, plate lunches, and shave ice. You can grab some delicious garlic shrimp and head to the tables across the road.
Next make your way to the charming town of Haleiwa, home to boutique shops, art galleries, and food trucks. Make sure to try Matsumoto Shave Ice, a local favorite.
Afternoon: North Shore Beaches
Now, there are plenty of beautiful beaches on Oahu’s North Shore, and if you are only making a day trip, you won’t be able to get through them all. So, here’s my suggestion for some of the beaches you can visit.
Start by visiting Laniakea Beach. It’s beautiful but parking here can be a challenge. You’ll find green sea turtles basking in the sun so make sure you have your camera ready to go. Next, you’ll head to Waimea Bay, one of the most iconic beaches on the North Shore. The bay is perfect for a swim during the calmer summer months, but it also attracts big-wave surfers in winter. If you’re into surfing, you can either watch pros catch massive waves or, if you’re adventurous, take a lesson from one of the local surf schools.
Another beach famous for its waves is the Banzai Pipeline (Ehukai Beach), renowned for its massive and powerfwinter,es, especially during the winter months, attracting surfers from all over the world. You can take a walk along the beach or sit on the sand and watch the pros tackle the waves.
Next up is Sunset Beach Park, one of the prettiest in the area. The waves are gentle enough for swimming in the summer, but in the winter they can reach 30 feet. It’s a beach spot to catch a sunset.
The North Shore’s beaches are known for their beauty, but they also offer a peaceful contrast to the more crowded beaches of Waikiki.
Other North Shore Beaches
If you have more time on your hands or are staying on the North Shore, you may want to visit some of the other beaches in the area. Here’s a list of notable beaches you can explore on the North Shore:
- Haleiwa Beach Park – A family-friendly beach with calmer waters, perfect for swimming and picnicking. It’s located near the historic town of Haleiwa, with plenty of dining and shopping options nearby.
- Alii Beach Park – A smaller beach that offers gentle surf, making it a great spot for beginner surfers or those who want to relax and enjoy the ocean.
- Kuilima Cove – Known for its calm waters, Kuilima Cove is ideal for swimming, snorkeling, and families with young kids. It’s located near the Turtle Bay Resort.
- Shark’s Cove – A popular spot for snorkeling, Shark’s Cove offers clear waters and abundant marine life. It’s part of the Pupukea Marine Life Conservation District, so it’s a great place to see colorful fish and corals.
- Pupukea Beach – A scenic, quieter beach with tide pools and good snorkeling opportunities. It’s not as crowded as some of the other North Shore beaches, making it a nice spot to unwind.
- Mokuleia Beach – A less crowded beach with golden sands, great for long walks and picnics. The waves here are usually calmer, making it suitable for swimming and relaxing.
- Kahuku Beach – A hidden gem on the North Shore, Kahuku Beach is known for its peaceful vibe, with excellent opportunities for fishing and a secluded atmosphere.
These beaches offer a wide variety of activities, from surfing and snorkelling to relaxing by the water, and each one has its own unique charm. Whether you’re an avid surfer or someone just looking to enjoy the scenery, the North Shore beaches have something for everyone!
Evening: Polynesian Cultural Center
Finish your day on the North Shore at the Polynesian Cultural Center, a place where you can immerse yourself in the diverse cultures of the Pacific Islands. The center offers a variety of activities throughout the day, from interactive exhibits to traditional performances. Don’t miss the evening luau and the spectacular Ha: Breath of Life show, which showcases Polynesian music, dance, and storytelling, providing a perfect end to your North Shore adventure.
With its stunning beaches, laid-back atmosphere, delicious food, and rich cultural experiences, a day on the North Shore offers a refreshing escape from the busy streets of Waikiki.
Day 4: East Oahu and Beyond
Morning: Hanauma Bay
Located on the southeastern coast, Hanauma Bay National Preserve is a stunning marine embayment and is one of the most popular things to do on Oahu. You’ll need to plan you day beforehand to ensure you have a great visit.
Known for its vibrant coral reefs and crystal-clear waters, Hanauma Bay is one of the island’s most popular destinations for snorkeling. I absolutely loved the snorkeling here; you can see so many turtles here.
It’s best to visit Hanauma Bay in the morning, just after it opens and before it gets overly crowded. I cannot stress enough but GET THERE EARLY! It’s a popular spot for both tourists and locals. Weekdays are also generally less busy than the weekends. The park is Wednesday to Sunday, from 6.45 am to 1.30 pm. So plan your visit accordingly.
Pack yourself a nice picnic, take your snorkelling gear, togs and reef safe sunscreen and enjoy the morning at this beautiful spot.
Important tips for visiting Hanauma Bay
- Make Reservations ahead of time: You will need to book an entry slot ahead of your visit. You can do this upto 2 days prior to your visit.
- Snorkeling Gear: You can rent snorkeling gear on-site, but it’s a good idea to bring your own if possible, as rentals can sometimes be in high demand. Don’t forget to bring reef-safe sunscreen to protect the delicate marine life.
- Marine Life Respect: Don’t touch the coral or disturb the marine life.
- Admission Fees: There’s an entry fee to Hanauma Bay, which helps fund conservation efforts. As of 2025, it’s approximately $25 per person. Children and residents of Oahu can often get discounted or free entry, but check the official website for the latest updates.
- Environmental Education: Before you enter the water, you’ll be required to watch a short video about the history of Hanauma Bay and its conservation efforts. This is an essential part of your visit, ensuring you understand the rules and respect the environment.
- ARRIVE EARLY!
Afternoon: Scenic drive along the windward coast
After a morning of swimming and snorkelling you’ll make your way to Halona Blowhole, not far from Hanauma Bay. Parking here can be tricky, but there’s someone always leaving at some point so be patient.
This blowhole puts up quite the show as the water shoots up through the blowhole.
Take a leisurely drive along the Windward Coast, stopping at picturesque points like Makapu‘u Lookout and Waimanalo Beach, known for its powdery white sand and turquoise waters.
The Makapu’u Point Lighthouse Trail is a fairly easy paved trail, but it’s uphill all the way without any shade. So it can fell very hot. You’ll be rewarded with amazing views of the ocean.
Less than 10 minutes from the lighthouse, you’ll find the beautiful Waimanalo Beach Park. It’s where you’ll find a lot of the locals. It’s much quieter than Lanikai or Kailau.
If you keep going further up north, you’ll find yourself at the beautiful Lanikai Beach. Spend sometime relaxing at the beach. Your last stop before you head back to Waikiki will be Kailau Beach Park. We absolutely love beaches so didn’t mind making stops along the way and spending sometime at each of the beach. You could very well pick one or two of these beaches to visit.
Its roughly about a 40-minute drive back to Waikiki from here. You can stop by Waiolo Shave Ice on the way back if you are looking for a refreshing treat.
Evening: Dinner at Waikiki
You’ll be really tired after a long day out and about. So, this evening will be nice and relaxing. Freshen up and head out for a nice dinner before you call it a night.
Day 5: Honolulu
Morning: Explore Honolulu
Start your day in Honolulu with a visit to the iconic Diamond Head State Monument. Arrive early to avoid the heat and take a hike to the top, where you’ll be rewarded with panoramic views of the city and the Pacific Ocean. After descending, head to the nearby Kapiolani Park for a peaceful stroll or a light breakfast at one of the local cafés. From there, make your way to the Honolulu Museum of Art, where you can explore Hawaiian and Asian art collections in a serene setting.
Afternoon: More of Honolulu
After your morning adventures, head to the Iolani Palace. It’s a beautiful and historic landmark where you can learn about Hawaii’s monarchy and its royal legacy. The palace offers guided tours that provide an in-depth look at Hawaiian history and culture. After exploring the palace, stroll around the nearby King Street and check out the charming shops and local cafés. If you’re in the mood for some outdoor fun, take a short trip to Manoa Falls. The short hike through lush tropical rainforest leads to a stunning 150-foot waterfall, perfect for a refreshing mid-afternoon escape into nature.
Evening: Final beach stroll and dinner
As the day winds down, make your way back to Waikiki Beach, where the golden hour provides the perfect lighting for a relaxing stroll along the shore. Watch as the soft waves and stunning sunset create an idyllic atmosphere.
For dinner, treat yourself to a meal at one of the beachfront restaurants, such as Duke’s Waikiki, known for its fresh seafood and island-inspired dishes. After your meal, take one last walk along the beach, with the city lights twinkling in the distance, and enjoy the serene sounds of the ocean while you reminisce on your perfect 5 days in Oahu.
Final Thoughts
And that’s it for my 5-day Oahu itinerary. Oahu is a destination that offers something for everyone, from history buffs and adventure seekers to beach lovers and foodies.
This 5-day Oahu itinerary captures the island’s highlights, ensuring you experience its beauty, culture, and charm. This itinerary works equally well if you want to base yourself in Honolulu or if you prefer to spend a couple of nights on the Windward or North shores. Feel free to move things around to suit your preferences and schedules.
Whether it’s your first visit or one of many, Oahu’s magic will leave you yearning for more. So pack your bags, plan your trip, and get ready to say Aloha to paradise!
Happy Travels!
More time in Oahu
- Visit Honolulu Zoo
- Kualoa Ranch
- Koko Crater Trail
Where to stay on Oahu
Oahu, Hawaii, is a diverse island offering a variety of accommodations, ranging from budget-friendly options to luxurious resorts. Here’s an overview of key areas in Oahu, with a breakdown of accommodation options at different price points:
1. Waikiki (Honolulu)
Waikiki is Oahu’s most famous and bustling area, known for its vibrant nightlife, shopping, dining, and beautiful beaches.
- Budget:
- Mid-range:
- Luxury:
2. North Shore
The North Shore is known for its world-class surf breaks, laid-back vibe, and natural beauty. It’s ideal for those seeking more peace and quiet.
- Mid Range
- Luxury:
3. Ko Olina
Located on the western coast of Oahu, Ko Olina is more relaxed and quieter, offering resorts and lagoons, perfect for families or those looking to unwind.
- Mid -Range:
- Aulani, A Disney Resort & Spa
- Ko Olina Beach Villas Resort
- Luxury:
4. Kailua
Kailua, on the windward side of the island, offers a quieter, local vibe with gorgeous beaches like Kailua Beach and Lanikai Beach.
- Budget:
- Mid-range:
5. East Oahu (Hanauma Bay, Diamond Head)
East Oahu is known for its stunning natural beauty, beaches, and trails, perfect for nature lovers and hikers.
- Luxury:
This breakdown of accommodations by price point should give you a great starting point when choosing where to stay on Oahu, depending on your budget and preferred area!
What to eat in Oahu
Oahu’s food scene is a melting pot of Hawaiian, Asian, and international influences, offering a culinary journey you won’t want to miss. Here are some must-try dishes and where to find them:
- Poke Bowls: Fresh, marinated raw fish served over rice. Try it at Ono Seafood or Fresh Catch.
- Kalua Pig: Slow-roasted pork, often served at luaus. Check out Helena’s Hawaiian Food for authentic flavors.
- Garlic Shrimp: A North Shore specialty, with Giovanni’s Shrimp Truck being the most famous spot.
- Plate Lunch: A hearty meal featuring rice, macaroni salad, and your choice of protein. L&L Hawaiian Barbecue is a popular chain.
- Shave Ice: A refreshing treat with flavored syrups and toppings. Matsumoto Shave Ice is iconic, but Waiola Shave Ice is equally worth a visit.
- Malasadas: Portuguese-style doughnuts, best enjoyed at Leonard’s Bakery.
- Acai Bowls: A healthy breakfast or snack loaded with fruits and granola. Visit Island Vintage Coffee for some of the best on the island.
Don’t forget to pair your meals with local beverages like Hawaiian sun juices or a Kona Brewing Company beer!
Tips for this 5 day Oahu itinerary
- Travel during low seasons (mid-April to mid-June and mid-September to mid-December): This will definitely save you money on accommodation among other things on the island.
- You can visit discount grocery stores or ABC stores which have everything from clothing, food, and drinks to basic necessities.
- Plan Ahead: Popular attractions like Pearl Harbor and Hanauma Bay require reservations. Also book accommodation well in advance to ensure you are getting the best deals.
- Pack Light: Casual, breathable clothing and comfortable shoes are essential.
- Stay Sun-Safe: Bring reef-safe sunscreen, sunglasses, and a wide-brimmed hat.
- Respect Local Culture: Learn a few Hawaiian words and adhere to island etiquette, like removing shoes before entering homes.
- Be Environmentally Conscious: Dispose of trash properly, avoid stepping on coral, and use reusable water bottles.
- Budget for Activities: Many attractions have entry fees, so plan your budget accordingly.
- Check Weather Reports: Conditions can vary, especially during winter when some beaches may have strong currents.
Note: The information here is updated the best we can at the time of writing this article. Please check attractions, activities, and transport before your trip as things tend to change from time to time.
