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Looking to pack in a ton of fun on your trip to Oahu? Don’t worry, I’ve got you covered! As on-the-go travelers, we don’t like to waste a second of fun. Here’s our 5-day itinerary for our trip to Oahu! We stayed in Waikiki, so assume the driving distances are from the city. It was a super special trip we took with a bunch of trips for our bachelorette/bachelor party and we had a blast! This is a great itinerary for large groups, families, and couples alike!
Day 1
Morning/Afternoon
We’re based in California so the flight out to Oahu isn’t too bad. It’s anywhere between 5.5 to 6 hours. Long enough to feel like you’re traveling very far away, yet short enough to not get too stir-crazy. Also, since there is a 3-hour time difference, you gain three hours of sunlight when you land. It makes the day feel super long, which is awesome! I love landing in a new place and feeling like I have a whole day ahead of me.
Whether you choose to land in the morning or closer to the evening, I recommend staying in Waikiki if it’s your first time on the island. It’s about a 20-minute drive from the airport and many of the restaurants stay open til late!
I would also recommend renting a car during your trip, it makes getting around the island super easy and convenient. We rented our car from Enterprise and it was a seamless pick-up. Depending on what terminal you land in, you may need to take a shuttle bus. Regardless, there are plenty of kind people around to help you out!
If you’ve landed earlier in the day, I recommend checking-in to your stay, freshening up, and throwing on your vacation gear. Always wear your bathing suit underneath your clothes, you never know when you’ll jump into the ocean!
Spend the day exploring Waikiki. This is a very lively part of Oahu. It’s super walkable and has so many stores and restaurants to explore. It’s super family-friendly and there is a beach nearby!
Evening
If you’ve landed in the evening, grab your rental car and head to your stay. Freshen up and go out to grab a bite to eat! Waikiki is full of different restaurants that stay open late. Personally, we really loved Sam’s Kitchen for a quick bite of food. We also walked to Long’s Pharmacy to grab some water and sunscreen before turning in for the night.
Day 2
Morning
Rise and shine! It’s your first full day in Oahu! Wake up early and grab the famous acai bowls and Island Coffee from Vintage Island Coffee. It’s a great way to get a taste of refreshing island flavors first thing in the morning. The line may look long, but don’t be intimidated. It moves quickly and they have their service down to a science. Everything we tried was super yummy so you can’t go wrong. They even have vegan options if that’s your jam!
Once you’re done with your breakfast, take your time to walk around Waikiki if you didn’t get the chance to do so the day before. There are so many cute little shops to check out! A lot of the stores have exclusive Oahu gear, as well. The Stussy store and Lululemon stores are always packed with people trying to get some special gear.
Afternoon
After a few hours of exploring the city, sit down for lunch at Ginza Bairin. They’re known for their thick-cut katsu and endless refills of delicious miso soup and cabbage salad. They are quite popular so make sure you call a few days/a week in advance to make a reservation! The restaurant was super accommodating and the food was to die for. They have great drinks on their menu, too.
Once you’re stuffed with all that delicious food, walk back to your hotel to take a quick break and change into your swimsuit! You’re going snorkeling! Depending on where you stay, it may be a further walk to Pink Sails Snorkeling, but after the katsu meal, it may be warranted before jumping into the ocean.
Make sure you bring a bag to store all your goods, it can get a little bumpy. We signed up for our snorkeling tour via Get Your Guide but there are so many other ways you can get in contact with the tour. They have a ton of tours throughout the day but make sure to book in advance so they don’t run out of space for you and your group!
After two hours of enjoying the incredible views and wildlife, you’ll return back to shore. At this point, take a lovely stroll back to your hotel and stop by an ABC Mart on your way. Grab a yummy lilikoi drink and maybe some shrimp chips to enjoy and tide you over until dinner.
Evening
After a long day out and about, take a nice shower and rest up before dinner. It always feels like heaven to sink into that hotel bed after being active day. Take your time getting ready, you’re on island time after all!
If you’re looking for an amazing view with dinner, head over to RumFire. It has the most amazing views of Diamond Head and the sunset from the outdoor patio is unbeatable. It does get quite crowded around dinnertime so make sure to call ahead to reserve a table! The food is standard American. It was pretty decent but if I were to go back, I’d probably only do appetizers to share and a few rounds of drinks.
If you decide to go the appetizer and drink route, you can pop by Aloha Melt and grab a yummy grilled cheese to top off the night!
After you fill up on fuel, end your first night dancing beneath the stars. SKY Waikiki is a rooftop club that plays super fun music and welcomes patrons of all ages. If you’re just looking to dance and have a good time, it’s a fun spot to stop by! Dress code is pretty mixed so you can feel free to be dressed to the nines or be in shorts and a cute top!
Day 3
Morning
Today is going to be packed with adventure so make sure you got a good night’s sleep or have coffee ready first thing in the morning! Your first stop is going to be Moena cafe for the most delicious Short Rib Loco Moco. The meat is so tender, it falls off the bone! Moena cafe is quite popular in Oahu so make sure you get their early or be ready to wait.
Since we were running a bit late to our UTV tour at Kualoa Ranch, we decided to put our orders for take-out and walk around while we waited. Since we were out there on a Saturday morning, there was a cute craft market going on around the parking lot that featured local goods. Another great thing about putting in a to-go order is that you get to walk just across the way to grab some of Leonard’s famous Malasadas. It’s the perfect sweet treat to what is to be your savory dish.
At Leonard’s, get once of each to share or just stick with your favorite. The Malasadas come out piping hot and they’re perfect to enjoy right by the truck. Even if there’s a long line, the staff has their service down to a tee so you won’t be waiting too long!
Although we went to Moena’s specifically for the Short Rib loco moco, there is an array of delectable-looking dishes. I’d like to go back and get a taste of some of their special pancakes! Since we had a little bit of time before we had to head into our car for our UTV tour, we found a few tables to eat our meal just a walk away. It was the perfect breakfast for a fun afternoon!
Afternoon
When going to Oahu, you cannot miss the iconic Kualoa Ranch. It is home to dozens of iconic movies and amazing history. Additionally, it has one of the most beautiful landscape you will ever lay your eyes on. The tour guides are super friendly and it’s incredibly fun to zip around on the UTV cars. You do need to hold a valid driver’s license in order to drive, but it’s equally as fun to be a passenger! You can read more about my Kualoa Ranch tour here and check out the tour I booked through Get Your Guide.
After 2 hours of zipping around, we were dropped back off at our start point. You do get quite dusty so remember to wear something you’re okay with getting a little dirty! After browsing the photos they took for us and hitting a quick bathroom break, we were off to our next activity –Hanalei Beach!
Hanalei Beach was about an hour drive from where the UTV tour was, but it fit into our timeframe the best. Feel free to break it up into another day if you want to spend more time exploring the area! We found it to be the perfect combination of activities–something adventerous and something more relaxing.
On our way to the beach, we passed by a Foodland and knew we had to stop for snack before hitting the beach. If you’ve never been to a Foodland before, it is glorious! Foodland is a locally owned and operated grocery store in Oahu that features some of the most amazing food. It is home to some of the BEST poke and local snacks. Before you spend the rest of your day laying on the beach, grab a few tubs of poke, some chips, and a few other fun snacks to enjoy by the water. Your stomach will thank you after hours of floating around in the beautiful ocean.
Hanalei Beach was about a 10-minute drive from the beach. The parking lot is medium-sized but fills up very quickly. There are always people coming and going so be patient and you will find a spot.
Once you’re parked, grab your goods and find a spot to post up. It’s generous coastline provides enough space for everyone to lay out and I love that there are outdoor showers to rinse off in before you leave. Enjoy the calm waters and relax until you’re ready to leave for home.
Evening
After a super busy day popping around the island of Oahu, get home, take a shower, and give yourself time to relax. Once you’re feeling refreshed, decide what kind of night you want to have. If you want to have a more relaxing night, walk around Waikiki and grab a bite to eat at whatever strikes your fancy.
If you feel like going out, make a reservation at Tanaka of Tokyo. It’s a teppanyaki spot that can accommodate large groups. We went with a group of 12 and it was no problem. It was super fun to watch the chef’s cook and the food was great! It was definitely a Benihana-style experience, which some may find a little womp womp, but we loved it! It’s definitely a great spot for families and big groups alike!
And if you’ve still got some energy left in you, head right next door to Buho Cocina y Cantina to dance the night away!
Day 4
Morning
When you’re in Oahu, you have to make the most of every day! Today is hike day! Arguably, the best way to see Oahu’s landscape is by hiking. The beautiful trails take you far up so you can get a bird’s eye view of the gorgeous island.
Before you go on your hike, hit up b patisserie. This amazing pastry shop originates from San Francisco but it’s Waikiki branch mixes in some signature Hawaii style. Come hungry and ready to share because you’re going to want to taste a little bit of everything.
I highly recommend the Seasonal Kouign Amann (it was POG flavored when I went), the pineapple coconut almost croissant, the black sesame Kouign Amann, and whatever other Oahu exclusive they have! Their savory pastries are also out of this world so grab a few of those while you’re at it. And of course, you can’t miss out on their coffee! Their beans are out of this world so don’t forget to grab a drink before you go. The line can look intimidating, but it is well worth the wait!
Now that you’ve got your morning pastries, you’ve got to grab your lunch. With another long day ahead you, it’s important to stock up on food and snacks. Stop by Iyasume Musubi to grab an assortment of their different musubis and bento boxes for the beach after the hike. Trust me, you’ll thank me later!
Afternoon
The Lanakei Pillbox hike is about a 35 minute drive from Waikiki. It’s not too far but the parking is a tad atrocious. Since the start of the hike is located in a residential area, it can be quite hard to find parking. As you drive through the neighborhood, just remember to be mindful of the residence. Also, be patient! People are coming in and out so you’re bound to find something. Also, once you park, you can keep your car there all day–you’ll hop to the beach after your hike so it ends up being worth it.
Once you’ve found parking, make your way to the trail head. It’s about a 2 hour roundtrip hike –mostly because you’ll want to stay at the top of the hike to take in the beautiful sights. The hike can be slippery in places so make sure your shoes have traction on them! This hike is quite doable for most hiking levels, just make sure you go slow and steady when you feel unsure.
When you get to the top of the hike, you’ll see some of the most stunning views of Oahu. It truly feels like a Window’s screensaver. Sit on one of the “pillbox” bunkers and enjoy the views. And don’t forget to take a ton of pictures, too!
Once you’ve gotten back down from your hike, stop by the car to change into your swimsuit and grab your snacks. It’s beach time! The beach is quite narrow but the further north you walk, the more space there seems to be. Grab a spot, get comfy, and jump into the beautiful water! There is quite the bit of coral so just make sure to watch your feet.
Once you’ve got your fill of beach time, it’s time for a refreshing treat. Drive back towards Waikiki and to the refreshing Waoli shave ice. The flavor combinations are endless and super fun! Pro tip, add mochi and a scoop of ice cream to your bowl. We loved it so much, we went back for seconds! It was the perfect sweet treat after a long day out hiking and laying out at the beach.
Evening
You’re tired after a long day but, you must make the most of your last night! Shower off the day and head over to a local favorite –Rainbow Dine-in. It’s an iconic establishment and no trip to Oahu is complete without it.
Although there’s a ton to eat, my recommendation would be the Mahi Mahi Plate and Chili Tots. I know what you must be thinking…chili tots?? Yes, Chili Tots! It’s a local favorite and honestly, one of the most amazing combinations of food I’ve had in a while.
After digging into your meal, check out the 7-11 right next door. It’s not the biggest but it does have all of the local favorites. We walked around for quite some time grabbing all the fun snacks we can’t find in the US. Even if you don’t get anything, it’s a great place to browse before heading back for the night.
Day 5
Morning
Depending on what time your flight leaves, you can squeeze in a bit more fun before you leave Oahu!
Spend the morning grabbing amazing coffee at Arvo Coffee and browsing their cute store. There are a ton of local goods sourced from companies right on the island. It’s one of those adorable stores that carries all the small, cool brands. I don’t know about you, but I’m a sucker for a store like that!
After you finish browsing, take to the streets and walk to Waikiki beach. Since it’s still quite early, the streets are a little quieter and so is the beach. Take a seat, enjoy your drink, and soak in the last bits of Oahu before you leave.
Once you’ve finished your coffee, head over to Iyasume Musubi to grab a few snacks for the airplane. This will be your second time going so you can try all the things you missed out on your first go! After you’ve grabbed the musubi, grab yourself your last poke lunch at Maguro Bros and head back to your room to eat, pack your last minute items, and head to the airport.
Although the trip was short, I hope you had the best time ever. The itinerary is packed but I promise you’ll feel leaving satisfied yet excited to come back to see more of Oahu!
