The Perfect 5-Day Itinerary For An Amazing Oahu Vacation

Aloha, fellow travelers!

If you’re anything like me, you’ve probably dreamed of exploring the breathtaking island of Oahu. Trust me, I’ve been there many times with my boyfriend, and each visit leaves us longing for more. With its stunning beaches, lush rainforests, captivating sunsets, and exhilarating hikes – not to mention the mouth-watering cuisine – it’s no wonder we keep coming back!

I know firsthand how overwhelming it can be to plan a vacation that ticks all the boxes while still being time-efficient and stress-free. That’s where my extensive experience comes in handy: after countless trips to this Hawaiian paradise, I’ve perfected a 5-day Oahu itinerary that covers all the must-see spots (and even some hidden gems!).

Now let me tell you something about myself – I have spent a considerable amount of time researching and exploring every nook and cranny of this beautiful island. So when I say this itinerary is crafted with love and expertise, believe me!

As an avid traveler just like you who wants to make the most out of their precious vacation days on Oahu, rest assured that following my guide will help you hit all those amazing local spots without feeling overwhelmed or rushed.

Warning: You might find yourself making up wild stories just so your friends back home won’t think your trip was too good to be true!

So kick back, relax (we’re on island time now!), and let’s dive into our adventure-packed 5-day journey through Oahu!

Day 1: Exploring the urban Waikiki

Spend your first day exploring the surroundings of your hotel in Waikiki. There are many beautiful sand beaches and restaurants to visit. Don’t worry if you arrive way before check-in, because most places have parking and amenities.

1.    Stock up on some local sweets at the famous Leonard’s Bakery

Before unpacking, or heading to the beach, grab some amazing baked goods at Oahu’s famous Leonard’s Bakery. This place smells heavenly way before you enter, and they make the best-baked goods, perfect to store for later snacks, taking on a hike, or eating at the beach. You can choose from their perfectly made and tasty pies (like Lilikoi), donuts, muffins, cupcakes, or traditional Hawaiian malasadas.

If you haven’t had malasadas before, they are donut-like fluffy dough cakes filled with all kinds of fillings. At Leonard’s bakery try the custard, chocolate, and guava flavors. Or just grab some freshly baked chocolate macaroons and chocolate chip cookies. They have several food trucks all across Waikiki and Honolulu, so make multiple stops during your trip.

2. Duke Kahanamoku Beach in front of Hilton Hawaiian Village

First, visit this beautiful sandy beach and lagoon in front of the Hilton. It’s part of Waikiki beach, and open to the public. The water is crystal clear, calm, and perfect for an easy swim. Being in front of the Hilton it is also clean, well-kept, and maintained. The view from the beach is stunning and it’s a good place to watch the sunrise or sunset. If you are looking to sunbathe or read a book, this is the spot. Usually, it’s not crowded. On Friday nights they even have a 10 to 15-minute fireworks show that is top quality.

3. Honolulu Cookie Company Waikiki – The trademark pineapple cookie

While at Duke Kahanamoku Beach, stop in at the Honolulu Cookie Company located at the Hilton Hawaiian Village. They are recognizable because they make the trademark Hawaiian pineapple cookie perfect for a gift or snack. The shop is pretty and reminds me of a perfume shop, and the cookies are beautifully packed in small boxes and tins. Depending on when you visit they have special additional shortbread cookies for the holidays. Also try the year-round favorites like the Mango Macadamia, Dark Triple Chocolate Macadamia, Guava, and Mango Macadamia.

4. Kuhio Beach or (The Ponds)

This is a great and safe beach to visit in Waikiki because it has two huge cement walls fencing on either side. This makes the ocean calm and easy for swimming. The beach also has a great easy entrance into the water with a large shallow end. Even if you haven’t checked into your hotel yet, there are plenty of amenities here, so after your swim, you can change and freshen up. They have showers, bathrooms, and food vendors. There are also lifeguards on duty. It’s also less than half a mile from Morimoto Asia, so you can just walk over from the beach when it’s time for happy hour.

5. Happy Hour at Morimoto Asia – modern Japanese right on the beach

This is a great modern restaurant with happy hour specials every day between 5 pm and 7 pm. It’s the perfect place to stop by for a couple of drinks and snacks before dinner. It’s also close to Waikiki beach, so no matter where you are it’s within walking distance. The restaurant has an amazing view of the ocean and beach from its deck seating. The menu is high-end Japanese and they have a renowned top chef preparing it. Try the yakisoba, rock shrimp, and wagyu meatball sliders with delicious papaya slaw. They also have great wine choices, crafted cocktails, and imported beers. The happy hour menu is almost all at or under $10.00 each. Make reservations and make sure to ask for covered outside seating.

6.    Enjoy fine dining with an exclusive view at Orchids at Halekulani

Treat yourself on the first night to some of the best food, atmosphere, and views Waikiki has to offer. It’s located on the beach shore and has some of the most beautiful views, including an amazing sunset. The outside seating is well covered and the tables are spaced apart for comfort and privacy. The food is Hawaiian with a modern and fun twist. 

I highly recommend trying the lobster bisque, Hawaiian butterfish with mushrooms and fennel, or the octopus. Everything is fresh and the portions are nice. For dessert don’t miss out on the coconut cake. They also have a brunch buffet, and Afternoon tea with cake, scones, and great tea (there is a champagne afternoon tea option too).

Day 2: Head to the windward coast

The windward coast is famous for its natural beauty. It has some of the most beautiful forests and beaches in Hawaii. It’s also a much slower pace than the city center of Honolulu, so it’s a must for a day trip. Enjoy the best botanical garden, a beach in the middle of the ocean, and some great Polynesian culture while exploring.

1.    Byodo-In Temple – A beautiful Japanese Buddhist temple

Start your second day with a beautiful and peaceful walk through the Buddhist temple grounds. The Byodo-In Temple is located at the foot of the Ko’olau Mountains in the Valley of the Temples Memorial Park. It is surrounded by lavish green rainforests and misty mountains. While here, you will come across an abundant koi pond, turtles, peacocks, and swans that are home on the grounds.

Before entering to look around or meditate ring the large bell in front. It brings longevity and happiness (so don’t skip it!). And check out my favorite – the 18-foot-tall Lotus Buddha statue inside. There are many more small statues scattered around, so set aside at least an hour to walk the grounds. Enjoy some morning coffee or juice here, and you will love it.

2.    Grab food at Haleiwa Joe’s Haiku Gardens

This is a perfect stop between the temple and the Hoomaluhia Botanical Gardens. The restaurant is local, and unpretentious, and serves American seafood that is delicious. The restaurant has a great view of the lush rainforest and mountains making you feel like you are in the wild. There is even a small lake with a deck, perfect for exotic jungle pictures. There is no dress code, so sandy feet are also welcome. Best of all the portions here are very large, both for the food and the cocktails.  Recommend trying the crab legs, calamari, and fish of the day!

3.    Visit the picture-perfect Hoomaluhia Botanical Gardens

The gardens are a top destination on the windward side whether you love to hike or not. They have a drive-through park option that will take you 20 to 30 minutes, or you can spend hours walking around. The place is so beautiful it was made famous on Instagram with pictures of all the exotic plants.

Many of the plants are labeled and they cover over 400 acres of land. You won’t get lost because there is a downloadable map of the gardens. Around the trails, there is a manmade lake with picnic potential. This is a great place to rest, have a snack, and enjoy the swans and ducks. Stop by the visitor center before starting for any additional information and help. The staff is kind and friendly. This activity is free.

4.    Kaneohe Sandbar – Sand beach in the middle of the ocean

The sandbar is unique and exotic, so don’t skip over it – if the tide is low on your visit. Some people paddle out, but that is dangerous, and the best way to get out is with a 4-hour boat tour. The tour will assure you have all the equipment you need, they usually provide a BBQ lunch, and it’s a safe and dry place to leave your stuff.

The Kaneohe Sandbar is essentially a small sandy island to enjoy snorkeling and swimming. It’s surrounded by the ocean and the water gets from ankle deep to waist high. The sand is white and the water is crystal clear, which makes the experience tropical and exotic. This is a good activity for all ages. Just make sure to wear sun protection and a hat – there is no shade on this deserted island.

5.    Polynesian Cultural Center

You will want to take a tour of the Polynesian Cultural Center. You will get unlimited access to authentic island villages (6 of them) with lots of hands-on activities, music, and dance. They also have some great artwork and a canoe ride. There is also a nice lei, which makes a great souvenir. If you choose the Exclusive Ali’i Luau Package, after your exploration there is a tasty Alii Luau Buffet.

Here you can try some traditional food from the area including pork baked in an underground oven. There is also a Breath of Life show. Everything here is set among beautiful waterfalls and lush jungle forests. You can make it a whole day or just a couple of hours.

Day 3: Explore the adventurous North Shore

The North Shore is famous for its professional and world-famous surfing, but it’s also a great place for amateurs to try out some water sports, observe sea life, and take a great hike. The Dole Plantation is also located in the North and is definitely worth touring.

1.    Waimea Valley Trail – The cant miss waterfall hole for swimming

This is a great family spot or a trail for those not looking for a hard workout. The trail is paved and there is a great organization in the valley. At the entrance, there are usually hands-on activities for visitors including jewelry and art making, hula dancing, and other fun activities. You should opt for the 1.9-mile out-and-back trail which ends at Waimea falls and the swimming hole. The trail shouldn’t take you more than 20 minutes one way and is filled with exotic jungle views.

It ends at the Waimea waterfall and swimming hole. This is a good place to swim because there is a lifeguard and life vests are provided to all the visitors. They also have showers and bathrooms here, so you can change and freshen up before heading back. This is a great place to take some fun photos.

2.    Go snorkeling at Shark’s Cove – Tidal pools and exploring in the shallow end

Sharks Cove is a perfect place for snorkeling regardless of your experience level. There are both shallow and deep areas to explore full of sea life, coral, and tropical fish. Sharks Cove is part of the Pupukea Beach Park and most of the beach is made of lava making it perfect for crabs, starfish, and sea anemones. So there is plenty to see and enjoy on a nice walk, even if you don’t snorkel. This place usually isn’t crowded, so enjoy some quiet and reflection. The area is public, free and there is roadside parking available. Expect to spend here about 2 hours. No sharks to see!

3.    Observe the sea turtles at Laniakea Beach

Laniakea Beach is also known as Turtle beach. It’s famous for the large population of green turtles that live and sunbathe on the beach. If you haven’t spotted them up close on your trip yet, this place guarantees an encounter. You can spot them all year round, but the largest populations are usually here between May and October. The beach itself is great for swimming and has an easy entrance into the water. Don’t skip over having a nice swim here. This is a public beach, free for use without a capacity limit. It’s also not very crowded.

4.    Have some fun at the Dole plantation tours

You will really enjoy this tour. It’s an unexpected surprise well worth your time and money. They offer a customizable tour that can last for 30 minutes to many hours and have a friendly and helpful staff. Some of the tour options are the train ride and the world’s largest pineapple garden maze. On the garden tour, you can stroll through eight different gardens which include cocoa pods, coffee, and other exotic fruits.

They have a great restaurant too, so grab a meal while here. You can check out their menu online, or just show up to enjoy some teriyaki chicken plates, kalua pork plates, and pineapple chili bowls. Both kids and adults will love their famous Dole Soft Serve. My favorite is the chocolate-covered pineapple. At the very least you will enjoy 1 to 2 hours here.

5.    Go Shopping in the exotic district of Haleiwa

Haleiwa is a world popular surfer destination and the town reflects the unique Hawaiian surfing spirit. They have a fun and original outdoor shopping area that has many tourist-related shops, restaurants, drug stores, banks, bookstores, and more.

Polu Gallery, Wys Galleries, and Haleiwa Store Lots are just some of my favorite spots to visit. Also don’t miss out on the Matsumoto’s Store (here since 1951) surrounded by mom-and-pop stores selling jewelry, souvenirs, and clothes. If you are looking for original and one-of-a-kind pieces, this is the place to be. Stop by and grab some local food or head to the farmers market. Everything here is very local and authentic.

Day 4: A day of relaxation and romance

On every vacation, we must take some time to ourselves and with our partners. Hawaii is generally romantic and tropical, but these activities around Honolulu will make your romantic experience super special. Pamper yourselves with walks, massages, local wine, and a sunset boat ride complete with a luau.

1.    A morning walk at the shady Moanalua Gardens

This botanical garden and park are about 5 miles out from downtown Honolulu and stretch on about 24 acres of green lush land. A park is a perfect place for a morning walk, letting the children run around and play, or having some coffee and donuts before your day starts (The grass area is huge and well-kept).

There are benches under the trees for shade. This is a popular place for weddings due to the natural beauty and some hula competitions are held here. Also, you can enjoy the large monkey pod tree, koi pond, and many ducks. The park is surrounded by an urban area and small shops, so there are lots to see or stock up on snacks and drinks for the day. Overall, this is a peaceful, calm, and romantic place to enjoy.

2.    Indulge in the Lava Massage & Day Spa couples massage

Lava Massage & Day spa has the best setting and most professional masseuses on the island. It offers everything luxurious at reasonable prices and friendly service. For ultimate relaxation and romance, visit here. You will need to book ahead though. Whether you choose a single or couples massage, you will get the top experience.

For extra romance choose a couple’s massage packages like the full body massage and hot stones for 105 minutes. Another great couple’s choice is the COCO package. This is my favorite because it includes a full-body massage, a mini facial, and a Lilikoi sugar foot scrub. The entire place smells calming and soothing. The products used are high quality. Whatever you choose, you will leave feeling pampered.

3.    Drink up at the funky Winery Oeno – Beat Island Style Wine Tasting

The Oeno winery makes local natural wine and is the only winery on the island. You can spend some time enjoying the wine and food here with music, or try the Wine tasting. The wine tasting includes 6 different types of original wine made from watermelon, coconut, pineapple, and other exotic fruits.

All the ingredients are fermented and bottled from raw ingredients in Hawaii. During the wine tasting, you will have a friendly and knowledgeable host guiding you through the process. There are snack options with the wine including some made from scratch bread and garlic dip. Grab a couple of bottles to take home to your friends.

4.    The Pacific Star Sunset Buffet & Show Cruise abroad the Star of Honolulu

Don’t miss out on this high-quality cruise with a Luau show (Polynesian Journey show), a sunset ride, a dinner buffet, and an awesome bar.  The Star of Honolulu sails out of Honolulu Harbor and offers magnificent panoramic views of the sunset and Waikiki city lights from 4 floors of walk-around decks and a 60-foot-high observation deck. Here you can have some romantic privacy or mingle with other guests. They even have strolling musicians to take song requests.

If you do the Friday night cruise, you get to stay out an extra hour or so, and watch the Hilton Hotel fireworks right off the water. The prices are great, the boat is large and safe for kids. You even get to choose your dining experience from the buffet, casual, or deluxe options. Whatever you choose the menu is fresh and amazing. Some of my favorites include the baked Misoyaki BBQ Chicken, fish with coconut curry sauce, green tea tiramisu, and coconut cake.

Day 5: The hidden gems of Honolulu

Being the hub of Hawaii, Honolulu deserves more than one day of your time. It has many things to see, some commercial and some authentic and local. Make sure to make time for some hidden gems like the Bishop Museum, Hanauma Bay Nature Preserve, or Waikiki Starlight Luau at the Hilton.

1.    Hanauma Bay Nature Preserve – Best snorkeling experience in Oahu

Make sure to visit the Hanauma Bay Nature Preserve because it is home to the largest collection of live coral, tropical fish, and other sea creatures. There are over 400 types of tropical fish living here, making it the best place to snorkel and explore. Also, the water is crystal clear and turquoise. It’s a perfect place for all skill levels because there are shallow pools and deeper areas. It’s a great place to swim as well.

The park limits entrance to 1 thousand people per day, so reservations need to be made. You can make reservations ahead of time through the Honolulu parks & Recreation website. Working hours are from 6:45 am to 4 pm and parking fills up fast, so I recommend you get there first thing in the morning. The park has bathrooms, showers, and a small snack bar. You are allowed to bring your own food and non-alcoholic drinks, but make sure it’s a small cooler. Large ones are not allowed.

2.    Bishop Museum – the largest collection of Polynesian artifacts on Earth

This is a short stop (14 miles) after the Hanauma Bay Nature Preserve and a true treasure you shouldn’t miss on your vacation. They work from 9 am to 5 pm so plan your time, or book tickets online. Bishop Museum has the biggest collection of Polynesian artifacts on Earth and stretches out on 3 floors of a beautiful building (there is an elevator). This collection was started in the 1800s and has numerous exhibits including some of my favorites. Check out the Surfing in Hawai’i exhibit, tattoo exhibit (throughout time), modern street art, and the history of boats from ancient to modern centuries. There is an interactive program outside, so check ahead for activities at Flanders Lawn.

The museum also has a good-sized planetarium with multiple shows each day that last from 45 minutes to an hour. Take a look at both kid-friendly options and shows for adults. The two best shows in my opinion are the Ngā Tohunga Whakatere: The Navigators and Wayfinders (in collaboration with the Polynesian Voyaging Society). There are also night shows on the first Saturday of the month, so look into it. If you get hungry the café has fresh poke bowls, hot dogs, sandwiches, and veggie wraps.

3.    Grab all you need at The Ala Moana Centre – the biggest open-air mall

Make sure to pick up all the souvenirs and presents for your trip home while experiencing the largest open-air mall in the world. The Ala Moana Centre is filled with small local shops, big department stores, and many diverse restaurants. The mall has over 350 shops and restaurants altogether. In fact, it’s so big, there is a navigation application available for download.

The center often hosts daily events including live music and hula shows. Even if you are not looking to buy anything you can spend a good 2 to 3 hours just looking around. Here you can stop by the Honolulu cookie company (if you missed it at the Hayat) or the Diamond Head Chocolate Company which makes handmade chocolate gifts. My favorite place to grab lunch is Mama’s Spaghetti House and Shabuya (all-you-can-eat wagyu beef, seafood, and noodles). Han No Daidokoro is also great for Korean BBQ.

4.    Take an art tour at the Honolulu Museum of Art

Even if you are not an art fan, there is so much cool stuff to see here (less than 3 miles from Waikiki beach). The museum has over 50 thousand pieces on display at all times, and a huge collection of Asian art in all forms. They have sculptures, paintings, prints, and cloth work. It attracts some of the world’s famous artists and displays. You can take a guided tour through the displays or take your time and enjoy the space on your own.

You will experience Hawaiian art, and European and even Japanese woodwork. My favorite display is the beautiful prints from Japan and Islamic textiles. For those interested, they even offer art classes (fiber arts, ceramics, metal work, painting, prints, and more!) They have a wonderful Doris Duke Theater with films and a solid snack bar with a lunch and dinner menu. Make sure to book tickets online (they don’t work Monday through Wednesday).

5.    End with the most authentic Luau on the Island – Experience Nutridge  

This is not a high production setting, instead, it’s an intimate backyard-style BBQ or luau. The Nutridge Estate is located inside Pu’u Ualaka’a Wayside Park. Your experience will last a full 4 hours and include a walk through the rainforest, building an imu together (underground oven for roasting pig meat), and a sunset show.

They even have organized transportation both ways and one way for guests. For dinner, you can make special dietary requests ahead of time, but in general, there is shredded pork, lau lau, grilled chicken, rice, green salad, chocolate cake, and coconut jello. If you wish to partake in the whole process of the luau, in an intimate and local setting, this is the choice for you.


Oahu is an amazing vacation destination and the best in Hawaii. That’s why, no matter how much time you have, there is always more to experience and see. Make sure to follow this itinerary to get the best experience for a 5-day vacation.

Visiting these destinations will assure you get the best of everything, including some amazing beaches, hikes, museums, and waterfalls. Not to mention top shopping and restaurants.

Enjoy a sunset cruise with fireworks and exquisite food at The Pacific Star Sunset Buffet & Show Cruise abroad the star of Honolulu.

Have an intimate luau where you participate in each step at Experience Nutridge.

Swim with over 400 tropical fish species at Hanauma Bay Nature Preserve.

Or relax at Waikiki’s sandy beach known as Kuhio Beach.

I recommend following the entire itinerary for the best trip. But there are so many great ideas, you can also pick and choose.

Enjoy your trip and make the best of it!

Last Updated on April 6, 2023 by Brigitte