Oahu with Teenagers | Hawaii Vacation Itinerary

We spent 12 days on Oahu with teenagers. Here is our Hawaii vacation itinerary.

While this was my husband and I’s second visit, it was our kids first time vacationing in Hawaii.  For both of our visits we were blessed to have free places to stay.  So while I will be sharing all of the details from this trip and some of our trip 6 years ago, I cannot give accommodation suggestions.

With my first visit to the island we stayed on Schofield Barracks which is located in the central northern part of the island.  This time, with the kids we were just north of Honolulu on Aliamanu Military Reservation. This was more towards the middle southern part of the island. With different home bases each time, that did influence what activities we did on the trip. Traveling from one end of the island to the other takes about an hour.  This heavily depends on traffic, so try to coordinate travel around rush hour traffic and spots that have a lot of tourists.

We are an active family, so our itinerary is full of activities!  Our as my daughter referred to them “tasks.” We wanted to make the most of our time in Oahu, so we tried to pack in a full day.  Hubby and I are mid-forties, two kids in high school and one in college.

Day 1 (Thursday)

Travel

We flew via Southwest Airlines.  We do not fly very often.  This was our kids’ second time to fly.  Southwest provides snacks (nothing gluten free) and drinks in little cups.  The plane does have WiFi and texting available.  The free movies definitely made time go by faster, but make sure everything is fully charged – phone, tablet, airpods, or bring a portable charger! The most unique thing to me was that it is open seating, so none of us got to sit together! Hubby can’t remember what he picked when he bought tickets, but if you can get in loading group A or B then you will probably be able to sit two of your party together. If you are in the C loading group, which we were, then everyone is going to be split up.

Socializing with our host family

We got to our friend’s home around 3pm. We got settled in to our temporary accommodations and got to know our friend’s family. Korak and my hubby Matt were wrestling teammates at the University of Central Missouri. I dated Matt through college and was a wrestling manager for a couple years, so I also knew Korak. His wife also attended UCM but our paths never crossed.

Korak and his oldest son visited us in Centerville last year as they were looking at colleges in the midwest. That’s when we got the invitation to come to Hawaii!

Day 2 (Friday)

Makapu’u Lighthouse Trail

Makapu’u Lighthouse Trail is a nice paved trail with a parking lot. The trail is paved and a gradual incline with resting/lookout points along the way. During December to May this is a good place for whale sightings although we didn’t see any. At the third rest stop there is a path off of the paved trail that will take you down to some tide pools you can explore.  There is also a path to the beach when you first get on the paved trail.  It is very rocky at the water and there are also tide pools. This was the kids first time to touch the Pacific ocean off Oahu! 

It was very windy both times we did this hike. People wear anything from hiking gear to dresses and flip flops, so anything goes! There aren’t any restrooms on site. ALWAYS carry toilet paper with you.

Lan’ai Lookout & Halona Blowhole

These two short stops are on the way to our next stop.  Both have small parking lots but no restrooms. Our kids were less than thrilled with either stop.  The Blowhole is neat to see and there is a small beach next to it. A bunch of girls and couples were taking photos on the beach and a couple locals were spearfishing in wetsuits and snorkel gear.  

It was VERY windy and did not appear to be safe in the water at this location. Hubby and I did go to the beach the last time we were there, but didn’t with the kids. We did stop at the Lookout with the kids but we just drove by on our previous trip.

Brunch

Et. Al.

Et. Al. was a spontaneous restaurant stop that ended up being a great choice. It was on our way, had gluten free options and access to a public restroom.  It was even attached to a grocery store, so we also bought more bottles of water and a couple gluten free items to take to our friends house. Please note that all bread molds quickly in Hawaii, and the GF bread we purchased was moldy within days, so please refrigerate/freeze your baked GF goods!

My daughter absolutely loved the gluten free waffle!! 

Diamond Head Crater Trail

Post Covid, Diamond Head Crater Trail started requiring reservations, so be sure to make a reservation!  This trail does have a parking lot, restrooms, and picnic tables. It is also a paved path most of the way, but some of it is uneven terrain.  It can get steep and there are a lot of stairs.

Again some people walk the trail in flip flops.  You can stop as often as you need to although there aren’t many look out points until you get to the top.

Waikiki Beach

We learned the last trip that the best place to park when you visit Waikiki Beach is at the zoo.  So we parked at the zoo and headed down to the beach.  There happened to be a women’s pair beach volleyball tournament going on!

We brought 3 sets of snorkeling gear with us that I had purchased for the kids for Christmas.  I got two different sets just in case one of them was a dud, but both worked well.  HERE is one kind. HERE is another that sells as a pair. Then we borrowed a couple more sets from our friends.  We hadn’t purchased fins, as you float so well in the salt water, but we did end up borrowing some just in case the kids wanted to use them.

Hubby saw an octopus, but otherwise the snorkeling on Waikiki Beach was not very good.  While the boys were snorkeling a monk seal did swim up along the shore which I got on video.

After playing in the water a bit we walked the main drag at Waikiki before heading back.

We had intended on coming to Waikiki again for dinner at the famous Duke’s restaurant, but that didn’t happen. Hubby and I had eaten here on our previous trip. It just seems to be a place everyone goes, but I think it’s because most people stay in Honolulu. Another thing we did last time was visit the Waikiki Aquarium. It is right on the beach and a fun little visit to see jelly fish, octopus, and other tropical fish.

Dinner

Side Street Inn

Side Street Inn is a favorite dinner spot for our friends. Food is served family style, so we had about 8 different plates of food to try. Chicken Katsu was something new to us.  It’s basically like a pork tenderloin but instead of pork it is pounded/tenderized chicken with a Panko crust.

Gluten free was not marked on the menu, but the waitress seemed knowledgeable. Our daughter got edamame and ribeye steak.

Day 3 (Saturday)

Breakfast

Pu’uwai Aloha Bakery

My daughter found a designated gluten free bakery, so we made a stop and everyone grabbed a couple things.  It’s a tiny shop.  Everything we got was delicious, although we didn’t get everything we ordered in our bag.  Not sure if we paid for it or not, so pay attention if you are ordering a lot of things! Because they don’t have the best system down for bagging/totalling your purchases. The owner is super nice!

The owner also said she had been selling out, so I would be sure to go earlier in the morning when possible!

Hoʻomaluhia Botanical Garden

This was our first time at the Hoʻomaluhia botanical garden.  There are restrooms at the visitors center as well as around the gardens.  There are multiple parking lots throughout the park. You can pick up a map at the visitors center or scan a QR code if you have cellular service for a map of the trails.  All are well marked paths, short and easy to navigate.  You will hike one, drive to the next spot to hike another. We walked three trails and took lots of photos!  At the “end” of the garden is a spot with shelter houses and it seems a lot of people will get married here.

Many of the plants had name plates by them.  There were a few bodies of water in the garden.  Many koi and ducks to look at as well.

There were also campsites in the garden!  If you are a camper I think this would be a fun camping spot!

Bellows Field Beach Park

Bellows Field Beach Park is a military beach that is open to the public on Saturday and Sunday, but during the week is used for training purposes. This is our friend’s favorite beach! We met up with them for a packed lunch and to learn how to boogie board. You need a rash guard to boogie board!!  Raw belly’s and nipples if you don’t!!

We went out and bought rash guards because we knew we would be boogie boarding again! Something we did remember to bring from home was phone cases for the water. The cases allow you to keep your phones on you and dry. Yet you are still able to take photos! THESE are the ones we have.

After we spent the day on the beach we headed back to our friend’s house to relax, eat, and wait for our oldest to join us on vacation!

Day 4 (Sunday)

Kaneohe Sandbar

Our host got a pontoon boat for us to take out to a sandbar.  We saw our first sea turtle of the trip after we anchored on the sandbar.  The water was cool, it was cloudy and windy, so we didn’t stay very long.  When we got back to the dock you could see that there was a lot of rain coming down on the sandbar, so I think we left just in time!!

When it’s sunny, people pack coolers and lawn chairs and hang out all day on the sandbar!

Lunch

Maui Brewing Company Kailua

Hubby and I had eaten at Maui Brewing last time, but in Waikiki.  At this location you had to scan the menu and order online using a QR code. No gluten free options. So our daughter ordered a sandwich without the bun or side.

Lanikai Juice

We got smoothies and acai bowls here.  Delicious and right across the street from Maui Brewing.

Byodo-In Temple

We did not visit the temple six years ago but it was on our route this day.  Luckily they let our “kids” in as kids so it was much cheaper.  At full price I would not make the stop.  You can see the temple in photos and that is what you get in person.  There were baby pigs running around and koi fish.  You also can ring the “sacred bell.” There is a parking lot and restroom.

Manoa Falls

Manoa Falls is a muddy and wet hike.  We brought rain gear just for this hike although none of the kids wanted to use it.  Just know it can rain a lot here.  There is a parking lot, visitor center with restroom and a hose for cleaning off after the hike.

The main hike is rocked and a gradual incline with lots of stopping points and photo opportunities.  The waterfall is pretty tall with a light stream of water.  The pool at the bottom is no entry even though some sites I’ve been on show people at the waters edge and even in the water.

Near the falls is another trail that starts going up with stairs.  We had plenty of time, or so we thought, to do it.  We talked to a few people who were just coming back and they said it would probably take 1 hr. 30 minutes.  This trail was muddy, trees had fallen across the path, it’s one where sometimes you aren’t sure you are going the right way.  We did not have any cell service.  After climbing for about an hour we started getting nervous.  We didn’t know how much longer it would take to get to the top.  It was close to 5 and the park closes at 6. We weren’t exactly sure what that meant.  Would the road be closed and our vehicle stuck in the parking lot until the next day? Or maybe it just means the visitor center closes and they don’t allow anyone to enter the parking lot. Our daughter was sick of hiking, so we didn’t try to find out. Instead we turned around and headed back to the car.

Dinner

Mitches

Our youngest REALLY wanted sushi and not just rolls, so our friends gave us a few options.  We ended up at Mitches.  We had not made a reservation and got right in, but it seemed like they preferred reservations.  It is also a bring your own alcohol place as the table next to us brought in A LOT of alcohol!

Our youngest got some sushi and the rest of us shared a bunch of rolls.  It was all very good. They have huge platter options that would have been a good choice if more of us were going to eat sushi instead of just rolls.

Day 5 (Monday)

Breakfast

Cinnamon’s Restaurant Kailua

Cinnamon’s was one of our favorite breakfast restaurants the last time we were here, so we knew we wanted to bring the kids!  And boy did we luck out.  This day was there first day of them being open after being closed for a remodel and menu change.

The red velvet pancakes are absolutely amazing!! While they took cinnamon rolls of the menu, they added cinnamon roll pancakes.  Hubby got those.  No gluten free options, but the waitress did double check everything with the chef.  Our daughter got sides of eggs, bacon and sausage.

Kayak Excursion with Kailua Beach Adventures

We kayaked to the Mokes on our last trip and knew the kids would enjoy it.  It’s about 2 ½ miles to kayak to the islands and then the same coming back.  It had been so windy while we were there this time that I was very nervous about being able to kayak that far!  While it was designated an advanced day, it was not as bad as I had imagined.  The reef location really tamed the waves coming in.  However, getting onto the Mokes, my partner(Kash) and I capsized.  Of course it was caught on camera and you can watch it below.

A monk seal was sunbathing when we got there and Wedge Tailed Shearwaters are back after migrating all winter!  Read about these amazing birds and why them being back is such a big deal! Other than the animals we had the island to ourselves for most of the visit.

Checkout everyone plunging in the Queen’s bath…

We forgot that Kailua Beach Adventures give repeaters a discount, but that is something to ask about on any vacation! AND you have access to everything the day of your excursion. Think paddle boards, biking, etc.

We had two double kayaks and our oldest went on a single.  They provide lunch, take FREE photos, and provide a ton of knowledge. Gluten free lunch was a salad and by chance the chips were gluten free.

Not only did Kash and I capsize, we also knocked our guide, Mike, off his kayak.  We told him it would make a good story. 😉

They do have a retail space, showers, restrooms, etc. where you check in. The kids purchased a lot of bracelets, we bought some water shoes (similar to THESE), and I bought a pair of sandals I had been eyeing online.

Shopping | Walking around Kailua

Snack

Jamba

Jamba smoothies for the drive.  The kids wanted to go back, shower, and look nice for dinner. So, that’s what we did!

Dinner

Haleiwa Joe’s Kaneohe

Hubby and I had been to this restaurant at the north shore location.  In Kaneohe the Haleiwa Joe’s overlooked beautiful gardens and had a great atmosphere.  This restaurant does not do reservations and we had a 1 hour 45 minute wait.  You can walk the gardens while you wait.  There is also a bar where if you are lucky you can get a seat.  The rules do not allow you to stand or walk and drink.  So in order to order from the bar you have to have a chair, which I found to be a very odd rule.

Again the menu was not marked with gluten free items, but the waitress went and found out our options.  Our daughter got sirloin without the gravy and mashed potatoes.  EVERYONE loved the mashed potatoes and you can order them as a side! Our youngest wanted to eat lamb!

Day 6 (Tuesday)

Happy Birthday to our youngest!! Turning 15 in Hawaii!

Climb Works Zipline

Another repeat activity was riding ziplines at Climb Works North Shore.  We loved it when we did it and we knew the kids would too!  They do have restrooms, lockers, and a little snack bar when you check in. Once you start ziplining there are no restrooms.  They do take lots of photos, but you have to pay for them. We just took our phones with us using THESE.

Lunch

Right down the road is the Kahuku Sugar Mill. This is where the shaka was born.  We learned all about that on a bus tour we took on our first visit to the island. The statue of Hamana Kalili of Laie is surrounded by food trucks and dining.  There are so many options!

Hubby and I ate at Seven Brothers years ago, which is what the kids picked this time.  Their fryer was only used for potatoes, so our daughter was able to get a lettuce wrapped burger and the “fries” which were more like fried sliced potatoes. Hubby and I went over to a food truck, Da Bald Guy. It was delicious!

Shopping

We walked around some of the shops in Haleiwa with the intent of paddle boarding afterwards. However, paddle board rental at Blue Planet was for 2 hours and they closed at 5.  We were there at 4, so we decided to postpone paddle boarding.  Paddle boarding was one of my favorite things from our last trip.

While we were there, the kids jumped off the Rainbow bridge!

There is one main restroom in the middle of town and a few shops have their own restrooms if you ask for the key.

Shark’s Cove

Shark’s Cove was hands down our favorite place to snorkel on our last trip which was around the 4th of July. This trip was in March and our favorite spot was not accessible due to all of the waves.  There is a shallow tide pool where you can snorkel, so we tried that.  It had the best fish out of the places we snorkeled this trip.  No matter the water depth and wave height the water is not very accessible due to all of the lava rocks. If you have your water shoes, that would be helpful. While it was fun to be in the tide pools, the large waves can come over the wall and smash you into the rocks.

There are multiple small parking lots and restrooms/shower houses.

Dinner

Pounders

The majority of restaurants close at 8 or earlier.  The one place we found on our way home was Pounders which is located outside the Polynesian Cultural Center.  We had the Polynesian Center on our itinerary for another day, but were scheduled to eat at a Lua.  Pounders didn’t have gluten free marked on the menu, but they did have a few options, even a cauliflower crust pizza!!

Day 7 (Wednesday)

Waimanalo Beach

We spent the morning boogie boarding at the Waimanalo beach just south of Bellows Beach Park since it was closed for training.  The men of the family had a great time, but a reminder for lots of sunblock and a rash guard.

Lunch

Kono’s

One of our favorite places to eat on our last trip was Kono’s on the north shore.  Hubby drinks out of the coffee mug he bought there almost every morning (going on 6 years now). There happens to be multiple locations so we ate at Kono’s in Kailua.  Other than leaving off the bun, there were no gluten free options, so we got gluten free food from Down to Earth Organic & Natural, a nearby grocery store. Kono’s is a breakfast and lunch place, so be sure to go early.

Kailua Beach Park

Our kayak guide suggested that Kailua Beach Park would be better snorkeling than Shark’s Cove…it was NOT.  So, the boys played catch with a football while the rest of us laid in the sun and walked on the beach. This is a busy beach with parking, restrooms, and a shower house. In the morning it is common to see kite surfing.

Snack

Double Three

We got ice cream at Double Three and smoothies at Lanikai Juice for the drive. Double Three makes fresh soft waffle cones and adds very unique toppings.  Not gluten free, but the boys loved it!

Pink Pillbox Hike

The sun sets at about 6:45pm so we wanted to be starting our hike at 6.  There is no parking and no restrooms, you are just parking along the street. The Pink Pillbox Hike is just a dirt path that zigzags up a steep hill.  When you get to the top there are multiple pillboxes, one of which has been painted pink.  This is not a hike you want to do if you are scared of heights.

Sadly it was another cloudy day and we didn’t see a sunset.  We did see whales (video below) for the one and only time on this trip before it got dark!  While we were up there I let the boys do some flips.  See those HERE or watch below.  We also got to witness some kid spinning in a CYR wheel (video below).  I know that is a terrible description, so watch it HERE.

And the gnats/bugs were terrible at the top, so pack bug spray!

Day 8 (Thursday)

KoKo Head Trail

We got up extra early to get to KoKo Head Trail in the hopes of seeing the sunrise from the top!  But like most of the vacation it was cloudy, windy, & cool.  So we got to the top and depending on cloud location visibility was anywhere between a few feet to a few miles, but never a glimpse of the sun!

This trail is over 1,000 steps!!  A couple of our kids were dying, but they finished!!

This trail was in a lot better condition this trip than 6 years ago.  Thank you locals for maintaining this trail!

Breakfast

Leonard’s Bakery Truck/Moena Cafe

Leonard’s malasadas are a must!  A combination of a funnel cake and sugared doughnut.  We always go to the food truck at the KoKo Marina Center. Of course they aren’t gluten free, so after picking up some malasadas we went to Moena Cafe for some protein. They did not have any gluten free carbohydrate options.

Hanauma Bay

Hanauma Bay is another place that now requires reservations.  They only let you make reservations two days in advance and the tickets go quickly!  Both days we attempted it and they sold out in 10 minutes.

During Covid, because the bay was not used, the coral started growing back.  In order to help protect it they now limit the number of visitors. However it still seemed very packed!

They do allow a few walk-ins every day, so you could just risk it and show up! Listening to people around us on the beach they were successful, but also arrived at the opening time.

There is also a nice paved, gradual incline trail here.  We didn’t do it with the kids this trip, but did it on our last visit.

Lunch

Kona Brewing Co.

Kona Brewing Co. restaurant is back at the KoKo Marina and sits right on the water.  The menu was marked with gluten free items, but there wasn’t anything gluten free other than things that are naturally gluten free like fruit and salad.  Our daughter ended up ordering a sandwich with rice instead of a bun.

Dinner

We spent the rest of the day at our friend’s home. Laundry, socializing and our oldest was packing to head back.

Day 9 (Friday)

Took our oldest early to the airport.

Breakfast

Cinnamon’s Restaurant Kailua

Yes, we went AGAIN!! Both times we were able to get right in, but this can be a place with a long waitlist. I also popped into an antique shop that was across the parking lot.  Small, cute, but more like a flea market shop than an antique store.  You can check it out HERE.

Shopped Kailua

Hubby wanted to go back to a shop we visited earlier in the week to get a shirt and we need to waste a bit of time.

Polynesian Cultural Center

Hubby and I toured the Polynesian Cultural Center on our own years ago and did not go to the luau or evening show, Breath of Life.  With the kids we went all out and got a guide, ate at the luau and did the Breath of Life show. Our guide had an interesting life. The most unique thing was that he had TWELVE fingers!! He had an extra thumb on both hands, perfectly symmetrical. He mentioned hating it his entire life, but now (probably late teens/early twenties) he had come to embrace it.

Day 10 (Saturday)

Waimea Falls

Waimea Falls is a paid hike on pavement up to a waterfall.  The gardens on the way up are beautiful and you can spend a lot or a little time getting up to the waterfall. There are restrooms & snacks at the top. You must wear a life vest to get into the water at the bottom of the waterfall.  The life vests are passed out at the waterfall. There is also a spot where people stand next to the waterfall for pictures.  See what I’m talking about HERE or watch the video below.

Paddle Boarding

Blue Planet Adventure Co. rents boards and kayaks. Check their hours as we missed this activity earlier in the week, because it was too late in the day. We went back because it was one of my favorite activities from our last trip.  Allow two hours for this activity. You will ALWAYS see turtles here!  They are swimming and/or sunbathing on the river banks. Be sure to look because they can blend in and look like rocks! Our youngest even took some time to rope swing.  See a video of that HERE or watch below.

Lunch 

Stonefish Grill

Devan at Blue Planet suggested that we eat at Stonefish Grill instead of at Haleiwa Beach House.  I like the Beach House just for the views, but they weren’t actually serving meals in the afternoon when we were ready for a late lunch.  Be sure to check their hours! Stonefish Grill had been on my list of places to go a different night and it just didn’t work out to get there, so we went for lunch.  A couple appetizers were gluten free, but the menu overall is small. It was just ok.

Scoop of Paradise

We have visited Scoop of Paradise on both of our trips to Oahu! Whoever was working, was so nice and so busy all by herself! Homemade hard ice cream including gluten free options.  It was delicious!

Waimea Beach

The waves here were CRAZY!  This beach is right at the base of the Waimea Falls entrance. There is a parking lot and restrooms. A few people boogie boarding and body surfing, but the lifeguards were very adamant that if you didn’t have the right gear and/or weren’t a native, then you needed to stay along the shore. The boys did their best to do a little body surfing. See them in action below.

Dinner

We headed back so that we could watch the sunset and hang with our friends for the evening.

Day 11 (Sunday)

University of Hawaii

Our daughter thinks she may be interested in attending the University of Hawaii.  We figured while we were there we should take a tour! But it happened to be their spring break! Since we couldn’t schedule an official tour, we just walked around the campus.

Breakfast

Over Easy

We ate brunch at Over Easy with our friends.  You can call ahead 30 minutes to get your name on the waitlist.  The menu seemed a little unique/specialized, but all of the food we got was amazing!!  No gluten free options, so our daughter loaded up on protein.

Bellow’s Beach

We went boogie boarding to end our vacation at Bellow’s Beach.  This was the first sunburns the kids and hubby got on vacation as well!  Not the best feeling for a day of traveling on the plane. Sunblock and a hat are a must with a UV of 9!!

Dinner

We only ate at local places, mainly mom & pop shops, our whole vacation.  However, our last meal was Dominos and they did have gluten free pizza!

Day 12 (Monday)

Travel

Flying Southwest…

Other Things To Note…

Note for gluten free needs – I normally rely on my daughter to use her findgluten app.  HOWEVER, after one Google search I found out that Maui Mike’s Fire-Roasted Chicken (multiple Oahu locations) has a gluten free dedicated fryer!!

Hubby and I did eat here our first visit (our daughter had not been diagnosed at this point) and it is delicious!  So definitely a place to stop if you have Celiacs!

A couple of things we did our first visit to Oahu that we didn’t do this time…Pearl Harbor and Hi5 Tours Hawaii. Considering my husband is a Social Studies teacher I was surprised we didn’t go back to Pearl Harbor with the kids. But in the end we had to pick and choose our activities and this did not make the list. We did get to see it every day from afar.

We did schedule a tour with Hi5 Tours, but it would have just been our family on the tour. Since we had our own vehicle and did this exact tour last time, we knew that we could just drive the kids to our favorite spots on our own. We ended up canceling this reservation and got a full refund. Yanni was our tour guide last time and he was the person my husband talked to about our cancelation! The island tour is highly recommended!

Ask Away

Be sure to comment below if you have any questions about our Hawaii vacation activities! The kids had an absolute amazing time and unlike some of the vacations we took when they were little, THIS one they won’t forget!!