Hawaii Travel Guide | 7 Day Oahu, Hawaii Itinerary for First Timers

by | Mar 4, 2019 | Live Work Play Travel, USA Live Work Play | 17 comments

Aloha, welcome to Oahu, Hawaii. I have lost count of the number of times I have been to Hawaii, I just love the place! Why? Well, I just love the variety of things you can see and do in Hawaii. From spending lazy days on a beach or by a pool, learning to surf or snorkel, hiking through one of the many tropical rainforests and enjoying the fabulous local food and drinks. There are so many things to see and do in Hawaii for everyone. If you are planning your first ever trip to Oahu, Hawaii, here is my suggested 7 day Oahu, Hawaii itinerary for first timers. I have updated this November 2021.


A little about Hawaii


Hawaii is a state of the United States of America. The state of Hawaii consists of 137 islands with 7 being inhabited. Most first-time visitors to Hawaii spend their time on one or more of four islands. Oahu (the main Hawaiian island), Maui (the valley island), Hawaii (known as the big island) and/or Kuwai.

Oahu is the most popular of the islands for visitors, particularly first-timers to Hawaii. It is known as ‘the gathering place’ due to the number of people that live there. It also has the Daniel K. Inouye International Airport in Honolulu, the doorway to your Hawaiian adventure. Oahu is a great place to start your 7 day Hawaiian adventure. Because it provides visitors to her shores many things to do and see and a great taste of Hawaiian culture.


When to visit Hawaii


Anytime is a good time to visit Hawaii though if this is your first visit the seasons, accommodation price and crowds can influence your decision.

Hawaii’s climate is quite pleasant all year round. The dry season falling between April and October and the wet season from November to March. Many people visit during the summer months of June, July and August which fall during the dry season. The climate is usually hot and humid during this time. Many people visit as the weather is great and it is often school holidays, so expect a lot of people holidaying. Flights and accommodation can be more expensive over the summer months though, as well as during the high season, mid-December to mid-April. However, when you go can depend on when your holidays are. My dad always took holidays in May, so that is when we would go to Hawaii.


How to get to Hawaii


As the Hawaiian Islands are surrounded by water, you could cruise to Hawaii either on a cruise liner or your own boat. Most people arrive by air at the Daniel K. Inouye International Airport. Can I just say, the view landing and taking off can be spectacular. As the airport is near the shoreline, you are often treated to the sights of Waikiki and Diamond Head before you even step off the plane. For a great deal on an airfare and to book check out Hawaiian Airways.


Accommodation in Oahu


There is loads of accommodation on the island of Oahu, particularly in and around Honolulu, the capital and the famous Waikiki Beach. You are spoilt for choice with the range available catering to every budget. From hostels to 5-star hotels and everything in between, there will be something there for you. Most people stay in and around the Waikiki Beach area which has loads of accommodation available. Staying here also provides access to many of things you must see and do while in Hawaii. Some accommodation will have incredible views over the beach or the other way towards the mountains and over the Ala Wai Canal.

Most people stay in and around the Waikiki Beach area which has loads of accommodation available and provides access to many of things you must see and do while in Hawaii. If you are interested in a bed in a hostel then check out the Polynesian Hostel Beach Club or the Waikiki Beachside Hostel. Both offer dormitory style accommodation though the Polynesian Hostel Beach Club does have some private rooms. Both offer breakfast, free Wifi and are close to all the action in Waikiki and Honolulu.

If you are seeking a budget hotel in the Waikiki area I recommend the VIVE Hotel Waikiki. It is not right on the beach like some of the more expensive hotels, but it is only a 7 minute walk away.

For mid-range accommodation, a place I have stayed a number of times is the Hilton Hawaiian Village. It is right on the beach and has easy access to Waikiki Beach and has loads of amenities. You often see it in photos of Waikiki Beach. Another hotel I can recommend is the Ohana Waikiki East by Outrigger. Once again this facility has loads of amenities and is only a 3 minute walk to the beach.

If you are seeking some luxury during your 7 day stay in Hawaii you cannot go past the Royal Hawaiian. This historic pink hotel was constructed from 1927 and offers visitors all the luxury you need.

For longer holidays in Hawaii I have stayed in an apartment such as the Aqua Ohio Waikiki Studio Suites which is only 300m from the beach but I like it because it offers a kitchen in your room. This is a great way to help save money on meals as I simply get some basics like orange juice, milk, bread, etc. cause then I don’t need to go out for every meal.

If you want to stay in Downtown Honolulu there is the Pagoda Hotel and also the Ala Moana Hotel which are both close to the Ala Moana Shopping precinct and all the other sites to see in Downtown Honolulu. They are both a great base in Honolulu allowing you to be close to many of the things to see and do in Honolulu.

For other accommodation options in Honolulu and Waikiki check out HostelWorld if you want a bed in a hostel and Booking.com if you want a hotel room or apartment. And don’t forget travel insurance as you just never know what might happen. Without further ado, here is my suggested 7 day Hawaiian itinerary for your first visit to Oahu, Hawaii.


Day 1 – Waikiki Beach


Waikiki Beach with Diamond Head – what a view!!


Start your first day in Hawaii at Waikiki Beach. It is the most famous and recognised beach in Hawaii. It is a must visit on your Hawaiian itinerary particularly if it is your first time in Hawaii. This is a bustling hub of beaches, shops, restaurants and activities. Some people are quite happy to never leave Waikiki as there is so much to see and do there.

Waikiki Beach is a 2 mile stretch of white sand that has different sections to it. It begins with the Duke Kahanamaku Beach located near the Ala Moana channel and harbour and ends down near the bottom of Diamond Head. Each beach area offers something different. Fort DeRussy Beach Park has a beautiful grassy area with palm trees, shade and picnic tables while other beaches have plenty of waves for surfing and water activities. There are also lagoons with calm water for swimming. There are plenty of shacks where you can rent equipment like surfboards or book a canoe lesson.

Off the beach and Waikiki is a vibrant neighbourhood where you will find designer fashion stores along Kalkaua Avenue as well as souvenir shops and markets. It is abuzz after dark with waterside dining, hula shows and cocktail bars. Try a Mai Tai while listening to someone playing the eucalele. Every Friday night you can watch a firework display held over the water.

Other things to see and do in Waikiki on your first day could be to visit the Honolulu Zoo which is near Diamond Head or maybe the Aquarium.

End your day at a luau. There is no other cultural experience like a Hawaiian luau. A luau is more than just a party it is a feast with music and dance to celebrate an event. Most luaus include Hawaiian cuisine like Kalua pig cooked in an Emu (earth oven) or Poi (Taro) followed by Haupia (coconut pudding). As well as the food you will be treated to Hawaiian culture through authentic Hawaiian music, hula performers and fire dancers. Book your Hawaiian Luau here.


Day 2 – Diamond Head Climb & learn to surf


The view from the top of Diamond Head is spectacular


For day 2 of this 7 day Hawaiian itinerary I suggest visiting Diamond Head. After all, you cannot go to Hawaii and not see Diamond Head, it towers over Waikiki Beach. Formed around 300,000 years ago it is a saucer-shaped crater that is actually a volcano that has been dormant for 150,000 years! It got its name from some sailors who thought they could see glittering stones on it, hence the name Diamond Head.

Hike to the top of the crater, 560 feet above sea level, for magnificent views. The hike is only 0.8 miles but it is quite steep and narrow with many steps. The return trip can take 1.5-2 hours but that depends on how long it takes you to hike up and down and how long you spend at the top. If you don’t want to drive yourself there for the hike, you could take a tour that will drop you off in the Diamond Head car park and let you jump the que to enter. Don’t forget some water, wear sunscreen, light clothing and good walking shoes or runners.


Day 3 – Oahu Circle Island Tour


A great day out is to take a tour or drive yourself around the island of Oahu. I actually took a tour and I am so glad I did cause I learnt a lot of secrets about Hawaii from my tour guide that I would not have learnt if I drove myself. Check out tours here.


Plenty of places to stop on your circle island tour!


There are many places to visit as you drive around the island of Oahu. The best way to see and experience the beauty of Oahu is to drive. You cannot drive around the entire island, but you can drive around most of it. Just follow the main highways and you will see yourself enjoying the beaches, the lookouts and plenty of local produce stops. You can either rent a car or take a tour. Driving is very easy in Hawaii – just remember to drive on the right side of the road! If you prefer to be driven to all the best spots take a tour.

First stop on this circle island tour of Oahu could be the Nu’uanu Pali Lookout. Located a short 5-mile drive from Honolulu and Waikiki this lookout has some of the best views over Oahu. It is extremely windy here at the lookout. The wind can literally knock you off your feet so hold on to your hat.

Aside from the fantastic views and the wind, this is the site of one of King Kamehameha’s most gruesome victories. King Kamehameha was the king who united the Hawaiian Islands in 1795. I was told that it is windy because Kamehameha’s army pushed the opposition to the edge of the cliff faces. He told them if they didn’t join him they would be killed. Many of them jumped to their deaths causing the wind. About 100 years later around 500 human skulls were found at the base of the mountain.

From the lookout you could head to Hanauma Bay where you could snorkel and swim with the some 400 species of sea life that live in the reef there. It is only a quick stop here, if you stop at all, because I have a day allocated to spend at this beautiful spot on day 5 of this 7 day Hawaiian itinerary.

From Hanauma Bay drive around some beautiful coastal scenery with beautiful beaches and small islands off the coast such as Chinaman’s Hat. You could stop at the Polynesian Cultural Center, a Polynesian-themed theme park and discover how Polynesian people arrived in the Hawaiian Islands. You could come here at night on its own for a luau. I have heard the luau’s here are fantastic.

Kualoa Ranch could be a stop on your island tour. This is a 4000 acre private nature reserve and working cattle ranch and is a popular attraction due to the number of movies that have been filmed there. You could walk where the dinosaurs walked in Jurassic Park!

Surfing enthusiasts will love visiting the Oahu’s North Shore. Home to some famous surfing spots such as Sunset Beach, Banzai Pipeline and Waimea Beach. You could head in to the Waimea Valley and walk through a Hawaiian botanical garden of cultural and archaeological significance to visit the beautiful Waimea Waterfall where you could swim in the fresh water. Although there are plenty of places to stop for some lunch you could spoil yourself with a smorgasbord at the Turtle Bay Resort. Or if you need somewhere to stay on this part of the island, this resort could just be the place. Check out rates and availability here. I have stayed here a couple of times and enjoyed the ‘splurge’ and pampering I experienced. And the food is very good too!

There are a number of pineapple plantations you could visit on your tour around Oahu, including one of the most popular, Dole Plantation. You may remember one of Elvis Presley’s movies was set on a pineapple plantation in Hawaii! Learn how they grow the pineapples and try some of their products.

On your way back to Honolulu you could stop at the Punchbowl Crater. The Punchbowl Crater is an extinct volcanic tuff cone which is now the location of the National Memorial Cemetery of the Pacific. It serves as a memorial to honour all the men and women who served in the United States Armed Forces.

Head back to drop off the car. After such a long day you may want to get some dinner and have an early night! or not!


Day 4 – Pearl Harbour and Honolulu Historic District Walk &


Pearl Harbour is etched in history thanks to the Japanese who bombed the harbour on December 7, 1941. This bombing ultimately led to the United States into World War II. And on your first to Hawaii visiting Pearl Harbour is an extremely interesting and emotional experience. One I guarantee you shouldn’t miss. You can visit Pearl Harbour by taking public transport but it is far easier to book onto a tour. A tour will pick you up from your hotel, give you a historical rundown on the area and let you jump the queues to be taken out to the memorial. Plus there are many different tour options from spending 1 or 2 hours there to longer or to visiting other boats like Mighty Moe.Then, you will be dropped you back at your hotel. You can book onto tours here.

But to give you an idea of why you should visit Pearl Harbour. Many ships were sunk during the bombing of the harbour by the Japanese including the USS Arizona. 1,102 sailors lost their lives on the USS Arizona that day and they are entombed in the sunken hull. A floating memorial has been built over the USS Arizona which is a surreal experience to visit. It is quite eery walking over the sunken boat knowing so many souls are entombed below as you walk over the ship. You reach the memorial by small boat.

Tickets to visit the memorial are limited each day so definitely book a ticket in advance. This is something you definitely don’t want to miss out on. There are other attractions to visit at Pearl Harbour including USS Bowfin Submarine Museum and Park, the Battleship Missouri, known as Mighty Moe and the Pacific Aviation Museum.

After lunch, head into downtown Honolulu for a walk through the Honolulu Historic District Walk. This will give you a great insight in to a part of the Hawaiian History. A period when missionaries came to the islands to ‘tame the natives’ with religion.

One of the main places to visit on your walk is Iolani Palace. This was the official residence of King Kamehameha and is the only royal palace in the United States. In 1893 the monarchy was overthrown and the building was used as a capital building before being restored and opened as a museum in 1978. You are able to enter the palace and visit different rooms including the Throne Room, Grand Hall and the private suites of the King. Portraits of Hawaiian Royalty line the walls. You can take a guided or self-guided tour.

Near the palace is a statue of King Kamehameha. If you love the TV series Hawaii Five-O then you will recognise this statue and the rooms inside the palace where the show was filmed.

As you continue your walk visit the Mission Houses Museum. Here you can step back in time to when the missionaries first arrived in Hawaii, way back in the 1800’s. Some of the buildings are the oldest western-style buildings still standing in Hawaii, like the Mission House built in 1821.


Day 5 – Haunama Bay


Snorkel with the fish in Hanauma Bay


If you like swimming and snorkelling then spending time at the Hanauma Bay Nature Preserve should be high on your Hawaiian 7 day itinerary. Here, around 400 species of sea life live in the reef including turtles, fish, rays and more. It is quite easy to spend a day here, so that is what we are doing today.

Hanauma Bay is a 30-minute drive from Honolulu depending on the traffic that is. It is on the southeastern side of Oahu near Hawaii Kai and tucked into the sheltered side of Koko Head. The bay is essentially a flooded crater in the shape of a horse shoe. It is a far cry from the hustle and bustle of Waikiki and Honolulu. You can spend a quick half hour here (while on a circle island tour) or you could spend a whole day sitting on the beach or snorkelling.

Hanauma Bay is a major attraction with hoards of people coming to visit this marine ecosystem. In 2002 a Marine Education Centre was opened at the entrance of the bay. All visitors must watch a short video about the conservation of the bay before entering the beach.

The beach is reached by walking down a paved but steep path or you could pay to take the shuttle bus. There is also an admission fee. Hanauma Bay is closed on a Tuesday to allow the marine inhabitants a day to feed without interruption from visitors.

There are a number of ways to get to Hanauma Bay. You can take the local bus or visit it on a tour which is a great option as it includes transport to and from the bay plus your entrance and learning to snorkel. You can check out tours here. Or you could hire a car and drive yourself. From Honolulu take Kalanionaole Highway (H1 72) east from the city and then look for the signs to Hanauma Bay.

Don’t forget the sunscreen, your bathers, towel and a hat. You can rent snorkelling equipment on the beach and take lessons if you haven’t snorkelled before. After a long day in the sun and surf head back to your accommodation, wash up, and head out for dinner. Followed by a walk around the stores and alleyways, like everyone else! Or find a bar and enjoy a Blue Hawaii!


Day 6 – Ala Moana Shopping Centre


If in need of some retail therapy you can shop till you drop at The Ala Moana Center in Honolulu. Located just a short drive from Waikiki in Honolulu The Ala Moana Centre is Hawaii’s largest shopping centre and 7th largest in the United States. In fact it is the largest open-air shopping centre in the world. Home to some 350 merchants that include luxury brands, speciality stores and an array of local and international cuisine. You can easily spend a day or two here. Even if you aren’t a big shopper, it is the open air experience that you can enjoy – find a cafe, get a drink and sit and watch the shoppers go by!

If you do happen to get sick of shopping, then head across the road to the Ala Moana Beach for a dip in the water. And maybe end your day enjoying a drink and a meal at the Hana Koa Brewing Co, 962 Kawaiahao Street – only a few streets away.


Day 7 – Revisit your favourite Oahu, Hawaii spots


Day 7 on this 7 day Hawaiian itinerary is saved for you to revisit some of your favourite Oahu, Hawaii spots. Spend it down the beach, relaxing, surfing, swimming or snorkelling. Maybe do more shopping. Perhaps visit places that you drove past while on the circle tour such as the Punchbowl Crater! The choice is yours.


Extend your holiday on another Hawaiian Island


Extend your stay in Hawaii on another island


As mentioned, Hawaii is much more than just the island of Oahu. If you have the time you might want to visit some of the other islands. Each island has something to offer. Kauai is known as the Garden Isle. It has some incredible geological wonders to visit such as the Napali Coast. Here you are treated to lush green cliffs that plunge in to the sea. You could view these by boat or by helicopter. Spectacular is all I can say!

The island of Hawaii is known as the big island, cause it is the biggest of all the islands. One of the best things to do on this island is to visit the Hawaii Volcanoes National Park where you can get up close and personal with a volcano. There are self-guided drivings tours here you could take: The Crater Rim Drive Tour and/or the Chain of Craters Road. Each have unique things to see and you could even walk through a lava tube. Don’t forget a flash light! Or you might want to take a helicopter ride over the area to truly appreciate what you are seeing. Possibly visit Punalu’u Beach, known as Black Sand Beach. The black colour comes from lava fragments of the nearby volcano.

Maui is another one of the islands to visit. Where you could see the Haleakola National Park featuring an incredible summit that rises to above 10,000 feet above sea level. Or you could drive the Hana Highway which is an incredible 56-mile drive that takes you to incredible waterfalls and coastal areas on the island.

The best way to get between islands is by HawaiianAirways who have plenty of inter-island flights.


There are so many incredible things to see in Hawaii and most of them I have mentioned here in my Hawaii travel guide. Do ensure you make time to spend some lazing by the pool at your resort or on one of the many Waikiki beaches. If you want to be more active have a round of golf, learn to surf, go snorkelling or hiking through the rainforests. There are plenty of things to see and do in Hawaii for first timers. Aloha.


Thanks for sharing!

Useful Travel Resources for Your Next Adventure!


Accommodation: Where Will You Sleep Tonight? If you want a bed in a hostel dorm find a great deal with HostelWorld. I mostly stay in hotels now, Booking.com is my favourite site for booking hotels from budget to ‘I feel like splurging’. For something completely different I house and pet sitting through Trusted Housesitters – this has saved me thousands on accommodation, no joke!

Flights: I always head to Skyscanner first to find a cheap and flexible flight.

Car Rental: When I need to rent a car I turn to RentalCars.

Train Travel: I love riding the train rails and get the best value from Eurail and Interrail Passes. And Japan has a great one too – JapanRail Pass.

Bus Travel: Check out Busbud for bus tickets.

Pre-organised Tours: I’ve been on a few in my time with Contiki being my first and favourite. if you are 18-35 years of age you should check them out.

Jump-the-queue entrance tickets: I don’t enjoy standing in long queues which is why I book my entrance tickets and day trips in advance. My favourite website to book them in advance is GetYourGuide.

Travel Insurance. There are a number of reasons why travel insurance is important and I never travel without having bought a policy as you never know when something might happen. World Nomads is great for general travel insurance while SafetyWing is great digital nomads and long-term travellers.

Need something else? Check out my Resources page.


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Hi. Sharyn here, the face behind Live Work Play Travel. I’ve been travelling all my life thanks to my dad who worked for an airline. My aim with this blog is to help you work abroad or work online and travel the world.   Read more.


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  1. Shelley

    What a great & comprehensive article for a first timer to Oahu! It’s such a magical island. I’m pinning & saving this blog to send to anyone who’s planning for Hawaii travel.

  2. LindaJane

    Hawaii looks like an amazing place to visit. There are so many things to do and some great cultural experiences too. I’d love to go to a luau and explore the islands. This is a really helpful guide and I’m saving it for later.

  3. Samantha

    What a great guide! Can’t wait until I can visit Hawaii, looking incredible 🙂

    • Sharyn McCullum

      Hawaii is an incredible place to visit. It is my favourite holiday destination.

  4. Alma

    What a great first timers guide to Hawaii. On the other side of the world for me but would love to visit one day, so am saving this.

  5. sue

    Great post! I wish I’d had this when I first visited Oahu with my family a few years ago. I think I made it to many of these places but I did miss hiking up Diamond Head. There’s definitely plenty to go back for. Thanks for the inspiration!

  6. Lina

    Oh Hawaii is such a dream destination of mine! This is such a great guide which makes me wanna book a flight there right away!


    Does Ala Moana shopping center also sell designer stuff? One of my friends is shifting to Hawaii for work, and I coincidentally came across this article.

  8. Coralie

    Such an inviting and comprehensive guide! Reading this really makes me want to hop on a plane and visit.

    • Sharyn McCullum

      Good to hear the guide has inspired you. I feel like hopping on a plane to visit myself – once Australia opens its international borders.

  9. Lisa

    I assumed this post was about the Big Island since that’s technically “Hawaii” haha but it was fun to read about Oahu! I’ve been going to Hawaiian islands every year and love the diversity each one has to offer!

  10. Elena Pappalardo

    What a great first-timer guide. I have never been, so I found your insight useful and love all the spots you included!

  11. Jasmina

    This is such a great article. Hawaii are amazing destination.

    • Sharyn McCullum

      Hawaii is truly amazing. I love visiting. I want to retire there.

  12. Krista

    One of the first places I’d like to visit during a trip to Hawaii is Pearl Harbour as I’m a big fan of history. There are lots of other spots you’ve mentioned that look amazing too – thanks for the tips!

    • Sharyn McCullum

      Oahu is my favourite island. I love how you can get away from the crowds and then be in the hustle and bustle of Honolulu. It truly is an amazing place.


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