If you’re looking for the perfect destination for a beach and city vacation—look no further than Oahu, Hawaii. Oahu is the perfect blend of upbeat city atmosphere and laid-back surfer vibes—all on one island! It’s fun, beautiful, and not to mention, there are tons of unique places to eat.
The truth is, there are too many things to do on Oahu to possibly fit into one week. You could be here on vacation for months and never get bored! However, for your convenience, I’ve narrowed down the best things to do in Oahu to a handy five-day itinerary for Oahu you can easily replicate.
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Oahu Itinerary Day 1 – Waikiki
Since you just arrived in Honolulu yesterday, spend today exploring your home base for the week—Waikiki! Here’s a brief overview of how to spend your first day in Waikiki on this itinerary for Oahu, but check out this complete guide to Waikiki to discover more activities, attractions, and places to stay in Waikiki.
Basalt Waikiki
The first stop on your five-day itinerary for Oahu is a hearty breakfast at Basalt Waikiki. This restaurant is located in Duke’s Lane Marketplace, a small collection of coffee shops, bakeries, restaurants, and a grocery store! I ordered the French Toast crusted with coconut and macadamia nuts, and it was amazing.
Waikiki Beach
Next, spend the late morning and early afternoon at Waikiki Beach, one of the most popular beaches in the United States! You can take surfing lessons, go on an outrigger canoe ride, embark on a sunset catamaran cruise, rent boogie boards or a SUP to take out into the ocean, or simply relax on the beach with a cocktail admiring the crystal blue waters. If you look in the distance, you can see Diamond Head Crater—one of the best hikes on Oahu!
Banan
Once you’ve spent enough time in the sun, it’s time for a refreshing treat at Banan, located just off Waikiki Beach between the Outrigger Waikiki Beach Resort and Cheesecake Factory. Banan serves delicious soft-serve ice cream made from bananas (hence the name). I ordered the Chunkadelic — banana ice cream topped with dark chocolate, granola, shaved coconut, honey, and Banan’s house-made macadamia nut honey butter —yum!
Kalakaua Avenue
Next, venture out to Kalakaua Avenue — the shopping hub of Waikiki, where you’ll also find most of the high-end resorts. You’ll find everything on this shopping stretch, from worldwide brands and luxury chains to souvenir shops and local stores. Be sure to check out both of the outdoor shopping centers, International Marketplace and Royal Hawaiian Center.
While you’re on Kalakaua Avenue, be sure to do some resort hopping to see some of the most beautiful and iconic hotels in Waikiki. These hotels are destinations and attractions in and of themselves! You won’t want to miss stopping at the Royal Hawaiian, Moana Surfrider, and Hilton Hawaiian Village.
Ainahau Triangle
After venturing down Kalakaua Avenue, make your way over to the Ainahau Triangle. It’s a lush, green park that features tons of Hawaiian plants and flowers, like banyan trees and plumeria flowers. Plus, the Ainahau Triangle is a beautiful place to watch the sunset that’s lesser-known than the beaches in Waikiki.
Duke’s Waikiki
The final stop on the first day of this itinerary for Oahu is dinner at Duke’s Waikiki — one of the top places to eat in Oahu.
Duke’s is an iconic restaurant located in the lobby of the Outrigger Waikiki Beach Resort. It offers spectacular views of Waikiki Beach, tiki vibes, and a surf ‘n’ turf menu. I highly recommend making a reservation to avoid waiting several hours for a table, or visiting late afternoon during happy hour for a shorter wait. I ordered the Coconut Shrimp and Lava Flow cocktail, and both were fantastic! I also love the fish tacos at Duke’s — we eat here every time we visit Hawaii!
Oahu Itinerary Day 2 – Kailua & Kaneohe
Today on this itinerary for Oahu, you’ll explore Oahu’s Windward Coast, located about 15–20 miles from Waikiki. You’ll need to rent a car for the next three days of this Oahu itinerary. We got our rental car through National Car Rental, located in the Hilton Hawaiian Village, and we had a great experience. National is by far our favorite car rental company!
Lanikai Pillbox Hike
After fueling up with a filling breakfast at Over Easy, drive to Lanikai Beach — one of the best things to do on Oahu for free. You won’t be lounging at the beach yet, though. First, you have to conquer the Lanikai Pillbox Hike!
Since the entrance to the hike is located in a neighborhood, I recommend using public parking at Lanikai Beach. It’s a short walk to the entrance of the hike, and it’s a hassle to find street parking. The Lanikai Pillbox Hike is a rocky and steep 1.8-mile trail that offers spectacular views of Lanikai Beach, the Ko’olau Mountain Range, and Oahu’s Windward Coast. This hike gets its name from the two military pillboxes located at the end of the trail. They were used as observation stations during World War II in the 1940s. Now, they’re a perfect photo opportunity!
Lanikai Beach
Now, it’s time to take a dip in the refreshing ocean you just saw from the top of the mountain — Lanikai Beach!
Lanikai Beach is considered to be the most beautiful of Oahu’s beaches (and it’s easy to see why!). The turquoise blue waters and pillowy white sand will give you plenty of tropical island vibes. Even though I’m wearing my snorkel gear in this photo, this wasn’t the best snorkeling spot. It’s a beautiful place to swim, but after an hour or so of snorkeling, we only managed to see one sea turtle and a few fish. The best snorkeling spots on the island are Hanauma Bay and Shark’s Cove.
Island Snow
After the beach, head to Island Snow for the best shave ice you’ll eat on Oahu. They have all-natural, locally made flavors that are amazing. Plus, every shave ice comes with a scoop of macadamia nut ice cream at the bottom. Enough said, right? Stop here for “lunch” today since we’ll be having an early dinner soon!
Ho’omaluhia Botanical Gardens
Ready to soak in Hawaii’s natural beauty — that’s not on a beach?
If so, visit Ho’omaluhia Botanical Gardens in Kaneohe for 400 acres of dramatic mountain views, breathtaking scenery, and tropical plants from around the world, including the Philippines, Malaysia, America, India, Sri Lanka, Hawaii, Polynesia, and Africa! And the best part? Ho’omaluhia Gardens is completely free to visit. They are open from 9 AM – 4 PM daily. I recommend arriving no later than 2:30 – 3 PM to have plenty of time to explore this gorgeous botanical garden.
Haleiwa Joe’s
Haleiwa Joe’s in Kaneohe is an open-air restaurant that overlooks a tropical garden and the Ko‘olau Mountains. Eating dinner here is one of the best things to do on Oahu, and actually, it was one of my favorite experiences of our entire trip!
The restaurant is just a short three-mile drive from the Ho’omaluhia Botanical Gardens, which is perfect because you’ll want to arrive at least 15 minutes before the restaurant opens to avoid a three-hour wait. Yes, it’s that popular! We arrived at about 4:15 PM and were seated immediately. We asked the waitress for a table near the balcony to overlook the gardens, and she was happy to accommodate our request.
I recommend ordering a Mai Tai and anything from the surf ‘n’ turf menu — but really, the best meal at Haleiwa Joe’s is the feast for your eyes. And that’s saying something, because the food is fantastic! After your meal, walk down to the gardens to explore until the sunset. If there’s a wait time when you arrive, use the time to explore the gardens before your meal!
Oahu Itinerary Day 3 – Honolulu & Leeward Coast
On the third day of your itinerary for Oahu, you’ll be taking full advantage of the car and driving all around the island!
Breakfast at Leonard’s Bakery
Good morning! After stopping for coffee, drive to Leonard’s Bakery for breakfast (namely, malasadas). Malasadas are Portuguese doughnuts that are crispy on the outside, fluffy on the inside, dusted with granulated sugar (& sometimes cinnamon), and served piping hot! At Leonard’s Bakery, you can order malasada puffs — malasadas stuffed with delicious tropical flavored custards, like coconut, macadamia, guava, pineapple, or mango.
Leonard’s Bakery has been serving the island of Oahu fresh, hot malasadas since 1953, and it’s one of the most popular bakeries on the island. If you’re like me, you’ll love the retro flair of the shop and the bright pink boxes the malasadas are served in.
Pearl Harbor National Memorial
If you’re a history-lover like me, you can’t miss the chance to pay your respects at the Pearl Harbor National Memorial in Honolulu, Hawaii. The Pearl Harbor National Memorial commemorates the Japanese attack on the U.S. Pacific Fleet on December 7th, 1941. This catastrophic event ended the life of 2,403 American citizens and military personnel, sunk or damaged 18 U.S. warships, and launched the United States into World War II.
Pearl Harbor is one of the best things to do on Oahu for cheap — you can visit the USS Arizona Memorial, Remembrance Circle, Road to War Museum, and Attack Gallery Museum for free. You can tour the USS Missouri Battleship and USS Bowfin Submarine and Museum for an additional fee. You can also purchase a tour of Pearl Harbor that includes other activities and transportation, like this popular Pearl Harbor and Honolulu City Tour.
Tour Disney’s Aulani Resort
After stopping for lunch at Monkeypod Kitchen, we visited Disney’s Aulani Resort to explore, shop, and eat a Dole Whip (of course). If you’re a Disney fan, it’s worth stopping at the resort if you’re not staying there — it’s beautiful, and it’s a small slice of Disney magic on the island!
However, if you’re not interested in visiting the Aulani Resort, here are some other ways to spend your afternoon that fit well into this itinerary for Oahu:
- Dole Plantation — The location where Dole Pineapples are grown, and Dole Whip is made!
- Waimea Botanical Garden — Beautiful tropical garden with a waterfall
- Hanauma Bay — One of the best places to snorkel on Oahu
- Downtown Honolulu — The city’s capital, featuring Chinatown and the Ala Moana Center
- Koko Head Crater — One of Oahu’s most challenging hikes with remarkable views!
- Polynesian Cultural Center — Location highlighting Polynesian culture with luaus, live shows, tours, and more
- Kualoa Ranch — The filming location of “Jurassic Park” with outdoor adventures like ziplining, horseback rides, ATV rides, and film tours
Attend a Luau
To end the third night of your itinerary for Oahu, enjoy an oceanfront luau for fantastic food and entertainment wrapped up in one evening! We attended the Ka Moana Luau at Sea Life Park, and we had an amazing time! I loved learning the dances, customs, and cultural differences of the Polynesian cultures in Hawaii, Tahiti, Papua New Guinea, and others countries across the Pacific Ocean during the evening.
Other luaus to consider include Toa Luau on the North Shore, Germaine’s Luau on the Leeward Coast, Paradise Cove Luau on the Leeward Coast, Chief’s Luau at Wet ‘N’ Wild Hawaii, and Diamond Head Luau in Waikiki.
Oahu Itinerary Day 4 – North Shore
During the fourth day of your itinerary for Oahu, you’ll travel across the island to the North Shore — famous for its killer waves, laid-back lifestyle, and the traditional “island” vibes you’d expect when visiting Hawaii! You can read my blog about how to spend a day on the North Shore for a more in-depth look at the following items on today’s itinerary.
Breakfast at Haleiwa Bowls
First, start your day at Hale’iwa Bowls — a small kiosk on the North Shore that serves delicious acai bowls! This local stand uses local fruits, coconut, honey, and other local products to build to serve fresh and delicious bowls. I ordered the Blue Majik Bowl, and my sister ordered the Hapa Acai Bowl — both are pictured below (and both were delicious!).
Snorkel at Shark’s Cove
After breakfast, head to Shark’s Cove for an incredible snorkeling experience. Shark’s Cove is a small, rocky bay where you can spot tons of aquatic life, including triggerfish, butterflyfish, parrotfish, needlefish, trumpetfish, and sea turtles (but no sharks, don’t worry!). Don’t forget to check the current before your snorkel, watch out for the jagged rocks, and always wear reef-safe sunscreen. And the best part? Snorkeling at Shark’s Cove is free, so bring your own snorkel gear!
Explore Haleiwa
After your snorkeling adventure, head to Haleiwa — the hub of art and culture for the North Shore. Here, you can go shopping for local goods and souvenirs, grab a Breakfast Bomber from Kono’s Northshore (they are so tasty!), or snap a photo at the Colette Miller Wings mural, located on the Anahulu Shave Ice building.
Spot Sea Turtles at Laniakea Beach
Looking for the best place to spot a sea turtle during your trip to Oahu? Look no further than Laniakea Beach, located just north along the coast of Haleiwa. Typically, the sea turtles emerge in the afternoon, which is why it’s best to save this stop for later in the day. Plus, it’s a beautiful place to watch the sun sink below the horizon!
Matsumoto’s Shave Ice
Before you drive home, stop at Matsumoto’s Shave Ice for an iconic treat — they’ve been serving shave ice to the island of Oahu since 1951! With over 30 flavors, you’ll be able to mix and match to create a delicious, refreshing treat. I ordered a coconut, pina colada, and guava shaved ice with sweetened condensed milk. It was a fun way to end a memorable day on the North Shore! And the prices are really reasonable too, making it one of the best cheap eats on Oahu.
Grab Dinner on the North Shore or in Waikiki
Since many places on the North Shore close early, we decided to drive back to Waikiki for dinner. We went to Maui Brewing Company, just across the street from the Outrigger Waikiki Beach Resort. It offers a fun, upbeat atmosphere, and it’s a great place to try a local Hawaiian brew. You’ll also want to return your car tonight. You’ll be spending your last day in Waikiki!
Oahu Itinerary Day 5 – Waikiki
It’s your last day in Hawaii — cue the tears. But don’t be sad for too long because you still have one final day planned for your itinerary for Oahu, and it’s filled with plenty of fun things to do!
Hike Diamond Head Summit Trail
After stopping for breakfast at Knot’s Coffee Roasters, head to Diamond Head State Monument to hike the Diamond Head Summit Trail! This trail is just a short 2.2-mile (eight-minute) drive from Waikiki Beach. I’d recommend biking or driving to the mountain (basically anything but walking) to spare your feet for the rest of the day.
The views from the top of the Diamond Head are absolutely breathtaking! You’ll be able to see Waikiki Beach, Honolulu, and even the Windward Coast from the top of the volcanic cone. The hike is pretty short, only 1.8 miles, and the trail is well-paved. Diamond Head costs $10 per car or $5 per walk-in, but the cost is worth it. Diamond Head State Monument is closed on Wednesdays. However, the park is open the other six days of the week from 6 AM – 4 PM!
Snorkel at Queen’s Beach
After your morning hike, head down to Queen’s Beach for the afternoon. Queen’s Beach is the best place in Waikiki to snorkel, and while the marine life isn’t as abundant as it is at Shark’s Cove, it’s still a fun way to spend the afternoon! If you’ve already had enough snorkeling at Shark’s Cove yesterday, you can also use this afternoon to check out the Honolulu Zoo, the Waikiki Aquarium, or any of these best things to do in Waikiki.
Dinner at SKY Waikiki
The final stop on your itinerary for Oahu is a sunset dinner at SKY Waikiki — a seafood and cocktail bar. This fabulous restaurant is located on the 19th floor of the Waikiki Business Plaza and offers phenomenal views of Waikiki Beach and the surrounding city once the sun goes down. Try the Mai Tai and Garlic Lemon Shrimp — both were amazing! (or grab something from the raw bar, like oysters or scallops).
Say Goodbye to Hawaii
Sadly, your time in Oahu has come to a close. If you’re following this itinerary for Oahu, I recommend flying out early the next morning. If you’re flying back to the mainland, you’ll lose several hours coming back, so I recommend getting an early start to make up for “lost” time on the flight home.
FAQs – How to Spend Five Days in Oahu
Where is Oahu?
Oahu is one of eight small islands that make up the state of Hawaii. It is located in the Pacific Ocean and is nearly 2,000 miles away from the mainland. Oahu is the most densely populated Hawaiian island, with nearly one million people living there. It is home to Hawaii’s capital city, Honolulu, and the popular neighborhood of Waikiki.
How do I get to Oahu?
Honolulu International Airport (HNL) is the main airport serving the island of Oahu. Once you arrive at the airport, you’ll be only a 30-minute drive from Waikiki Beach and a 15-minute drive from Downtown Honolulu.
Where should I stay in Oahu?
There are plenty of cheap hotels and luxury resorts in Oahu. However, the majority of hotels are in Waikiki (which is where I recommend staying if you’re following this itinerary). Popular beachfront hotels in Waikiki include the Royal Hawaiian, Outrigger Waikiki Beach Resort, Moana Surfrider, and Hilton Hawaiian Village.
Do I need to rent a car in Oahu?
The short answer? Yes, you need to rent a car in Oahu to explore all that the island has to offer — not renting a car is one of the biggest mistakes to avoid when traveling to Hawaii! However, you don’t need to have a vehicle for every day of the trip if you’re staying in Waikiki. We rented a car for three out of five days of our trip, and we felt that was the perfect amount of time to explore the attractions outside of Waikiki.
Plan a Memorable Trip to Hawaii with this 5-Day Itinerary for Oahu
There’s no doubt that you’ll make tons of fun memories in Hawaii following this jam-packed five-day itinerary for Oahu! With so many fun things to do, you’re guaranteed to have a wonderful time. Which of the days on this itinerary for Oahu sounds the most fun to you?
Save This 5-Day Itinerary for Oahu for Your Hawaiian Vacation
Read More
Did you love reading this 5-Day Itinerary for Oahu? Check out these other posts about Oahu to help you plan your trip to the Aloha State:
- Perfect Oahu North Shore Day Trip Itinerary for First Timers
- Ultimate List of Things to Do in Waikiki (+ Hotels & Restaurants)
- 34 Free or Cheap Things to Do in Oahu (Under $10!)
- 26 Delicious Places to Eat & Drink in Oahu, Hawaii
- 16 Best Resorts on Oahu for a Luxurious Beachfront Vacation
- Is Oahu in Honolulu? The Difference Between Oahu, Honolulu & Waikiki
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