First Time In Hawaii One Week Itinerary

Aloha friends, my sister and I visited Hawaii for the first time and we had an amazing time. I did a ton of research on what to do, what to eat and where to stay on Oahu beforehand and wanted to share what we did while visiting the islands – including what we thought was worth it – and what wasn’t. Sharing my first time in Hawaii one week itinerary

Let me preface this post by saying that my sister and I are pretty adventurous and active vacationers. We prefer to have activities to do that keep us busy most of the days with bouts of relaxation/chill built in. This is definitely was not a chill on the beach for a week trip but we did do some of that.

We flew Southwest Airlines from Salt Lake City (where my sister lives) with a stop in Oakland, CA on a Tuesday. Total flight time was about 6.5 hours with 5 hours being the leg from California to the islands. The flight was not overly crowded and basically, each row got the middle seat free, which was really nice. Our trip was the first week in September after school has started and the busy tourist season on the islands has slowed down. I’m so glad we went during this time. This is obviously a popular time for honeymooners and anniversary trips. Those were the majority of people we ran into at various activities. Also, saw quite a few solo travelers and friend groups.


We stayed at the Aston Waikiki Circle Hotel on the island of Oahu in the popular tourist area of Waikiki.


It’s a circular hotel right on Kalakaua Avenue (which is the main road with all the beaches, shops and eateries in Waikiki) only footsteps from the beach as you can see here. It cost about $1800 for the full week’s stay including amenities fees, parking fees and a room upgrade.

If you’re not a person who is really picky about hotel rooms, this is totally a great place. We hardly spent any time in the hotel and mainly wanted to get a beachfront hotel for our first time in Hawaii to wake up and fall asleep to the sights and sounds of the ocean. Totally worth it. The hotel is older and it shows but not in a bad way. The rooms were small but clean and the staff was super helpful. It’s not a luxury hotel by any means but it’s a fun spot and I would totally stay there again.

Pros: Unique hotel. Centrally located (you can walk to everything in Waikiki). Footsteps from the beach. Great view of the beach even with at 75% ocean view. Have free beach towels you can borrow daily along with first-come, first-serve floaties and other beach equipment. Popular breakfast spot in the lobby of the hotel and your room key gets you 10% off.

Cons: Booked a specific room online and at check in was given the option to upgrade to a 75% ocean view for $10/day or a 100% ocean view for $35/day extra. Outdated rooms and amenities. Shower is very small. Super limited parking spaces – during a busier time of year there might be an issue.


Tuesday was our travel day to the islands and we arrived around 1:30pm local time. Administrative things ate up most of the day. We picked up our rental car, checked into the hotel, soaking in the amazing views, walking around by the hotel to scope out what was around us and eating a late lunch/early dinner.

We ate at burger shop on Kalakaua Avenue, Cheeseburger in Paradise, and it was really good. About $16 bucks for a burger and fries. Also, tried our very first Mai Tai’s of the trip here. FYI: These were the best we had of all the places we went. $6 during happy hour!

It was pretty late in the day by then so we just wandered around the main avenue and eventually picked a spot along the beach and watched the first sunset of our trip. It was just as beautiful as imagined.

Then we pretty much turned in for the night because we were super tired from a full day of travel.


Up and at’em early Wednesday morning to seize the day. We didn’t intentionally plan this, but most of our activities were scheduled toward the end of the trip so the first day or so we didn’t have a tight agenda with tours or appointments anywhere. In hindsight, it kind of made our vacation start out slow but it’s just the way trying to book the tours worked out.

Enjoyed a morning coffee out on our balcony watching surfers catch waves and then headed off to Pearl Harbor.

Enjoyed this amazing Acai Bowl from Tucker & Bevvy. It was awesome. 10/10 recommend especially if you want a healthy and filling meal to kick off or end a long day of fun.

Pearl Harbor

Really enjoyed soaking in all the history and touring Pearl Harbor National Memorial.

If this is in your plans, make sure you a lot about half a day out here and apply sunscreen. We both got a little bit of sun because we didn’t anticipate being outside for so long but we were. Also, be sure that you don’t bring any bags or backpacks with you (especially if you don’t drive) they are not allowed in the memorial because it is a military installation. They have lockers to rent but they were pretty pricey.

Bring your military ID, if you’re a military family because you will really benefit from the price of admissions for the different attractions here.

The USS Arizona is the most popular for visitors and something we definitely wanted to see. It’s highly encouraged that you purchase tickets for this online in advance, especially during busy season. You take a boat ride out to the memorial and unfortunately during our visit this was shut down due to a safety issue with the dock so we were only able to see the memorial from afar.

However, we enjoyed all the other attractions at the National Memorial (all of which have separate costs associated with them – FYI).

These photos were taken on the USS Bowfin, a WWII submarine and really cool to tour. We really liked it. It’s an audio tour that automatically speaks when you enter different areas of the submarine and tells you what you are seeing and how the sub operated.

Would not recommend it if you’re claustrophobic. It’s very tight quarters, made even tighter with people milling about. Also, tall friends, you’re going to need to duck in few areas and maneuver through different portals. 🙂

From the USS Bowfin you’ll take a free shuttle to the other attractions, the USS Battleship Missouri and the Aviation Museum.

We got off the shuttle at the battleship and walked around for a bit but ultimately chose not to tour the battleship because we’ve toured quite a few battleships in our day.

We did opt-in for the Aviation Museum and had a really great time there. We met a fantastic volunteer who shared a lot of historical information about the planes in the museum, the stories about their mission and crew. We also got to see some behind-the scenes spots that were really interesting and made our experience even more enjoyable.

Dole Plantation

After Pearl Harbor we drove out to Dole Plantation, we ate lunch and had some of the famous Dole Whip.

This was one of the activities that we were excited about but kind of fell flat. We had different expectations about what we would be able to see and do here. They have a few attractions there including a train and a maze but mostly it’s a big store. I was hoping to see pineapples being used in all these creative ways and/or see how they’re harvested.

The food, in my opinion, was pretty overpriced and not very tasty. Also, this was when we first noticed how big the portions are in Hawaii. Neither of us finished our food and could have definitely got by sharing something. This ended up being a common theme through the rest of our vacation – so definitely keep this in mind if you’re not big eaters – you can probably share.

We honestly ate and left. The wait for the train was 2 hours in the sun and we didn’t really have any interest in getting lost in the world’s largest maze. There is no admission to visit but the attractions have admission fees.

Spent the rest of the day at the beach near our hotel. We purchased these floaties for $5 at the ABC store and they were the best investment. So relaxing to float and enjoy the sunshine. Doubles as a pillow for laying on the beach.

I have very fair skin that burns easily so most of my swimwear included rash guards for sun protection. These are the sunscreen brands that I used on the trip: For body: Banana Boat Sport, Sun Bum Face: Supergoop Glowscreen, Supergood Unseen Sunscreen.

A lot of the beaches off Kalakaua Avenue, including the one in front of the Aston Waikiki Circle Hotel have breakers that create a safe swimming or floating space for all. You still get to feel the motion of the waves without being crashed with them or knocked over.

After Hours

We went on a long journey to find the highly rated Mai Tai Bar right on Waikiki Beach and it took quite a while to find it. It is on the back side of the Royal Hawaiian Hotel (which is STUNNING) but it’s only really accessible on foot. Ended up making it there about an hour before it closed. Got to listen to a little live music but it was really overrated and overpriced, in my opinion.

Also, went to a place called Cuckoo Coconuts, an old school Tiki Bar, and it was SUCH a fun place. 10/10 recommend. It’s such a cool vibe. Super great live music. Keep in mind it is a loud place so you won’t be able to chat much. Tried their Pina Colada in the pineapple and it was super.


Picked up McDonald’s breakfast and hit the road early Thursday to the North Shore and Jurassic Valley – you will recognize the scenery from many popular Hollywood movies. Locally known as Kualoa Ranch.

In hindsight, I wish we would have scheduled more time on the North Shore in our first time in Hawaii one week itinerary. It is beautiful and untouched. It is such a different feel from the busy city of Waikiki. The beaches are different, the ecosystem is different, everything is different. This part of the island definitely looks like what you think Hawaii looks like.

There are TONS of tours and activities at the ranch for all different adventure levels. Book early or you might not be able to fit it into your schedule. We really wanted to do the ziplining but there were no openings available during our stay – so that was a bummer. We ended up doing a 1-hour ATV Raptor Tour.

The tour was very fun and we got to see a lot of filming locations from Jurassic Park, 50 First Dates, and other movies. Learned a lot about the history of the island and the property as well.

TIP: Don’t wear white or any clothes/hats that you are fond of. These ATV’s do not have shields on them and you will leave the tour covered in dirt. They have outdoor sinks but no paper towels or dryers. Highly recommend bringing a change of clothes and/or wipes of some kind to clean up, especially if you plan to do other activities afterward. I’m serious, our faces and arms were covered in a thick, visible layer of dirt. We went straight back to the hotel to shower and change.

p.s. I had to trash my hat and my shirt because the dirt would not come out upon washing when I got home.

We took a long route back to the hotel to see more of the North Shore and then spent the rest of the day lounging on the beach with the new beach umbrella that we purchased for ~$30 at the local ABC.

Funny Story

My sister and I are not experts or regular beachgoers so the two of us trying to install this beach umbrella was quite humourous. It is not a simple as it seems. There is an art and a strategy to a sturdy beach umbrella. While we were stumbling around with this umbrella, just sticking it in the sand like the inexperienced beach umbrella people we are, a couple down the beach was enjoying our struggle. A husband and wife were watching us try to get this umbrella to stay and not blow away. Eventually, the wife took pity on us and sent her husband to help us. It was then – that we learned the art of beach umbrellas. He told us that he was quite enjoying us trying to figure it out and was keen on seeing if we were going to figure it out on our own but his wife insisted that he come and help us. Thank goodness. We gave her a little wave of thanks and he helped us dig a hole in the sand about 6 inches, twist and pound the umbrella stake into the deep sand with a rock, then pack and pile the sand around the base for a secure umbrella experience. It was quite funny and we were thankful for their help!

We also popped by Walmart to grab some on-the-go cereal, crackers, milk, goldfish, 2 gallons of water and a few other snacks. The rest of our trip featured tours/bookings at 8 am so we knew we wouldn’t have time for breakfast in the morning so we grabbed some supplies to tide us over. Highly recommend if you want to save a few bucks and not be pressed for time/starving while you’re out on your activities.


Friday was our most packed activity day starting around 8 am and ending well after 10 pm.

Try Scuba Diving

We were up early Friday morning to go try Scuba Diving. We booked with Try Scuba Diving. Super friendly, patient, and experienced divers. They really make you feel comfortable with the skills.

My own apprehensions prevented me from completing the Scuba Diving experience but my sister went through the whole thing. Breathing out of your mouth is a lot harder, mentally at least, than it seems. Still 100% recommend trying it out if you’re interested. I’ll probably give it another go, another time but it just wasn’t meant to be this time around.

My sister loved the experience and is looking into more opportunities to dive further. You start out on the beach and then walk into a breaker-protected cove. You’ll practice with the gear. Get comfortable breathing underwater. Then slowly swim out of the cove to a reef just beyond and dive about 15 feet down.

The one thing we noticed here is that the dive experience was advertised as 8-10 am but we were finished a little after 9 am. So that was a little misleading. We expected the whole experience to be the full length of time but really we think the additional time is built in for people to get used to the gear, practice, and get comfortable. Since my sister’s group caught on quickly, they were back quicker.

Be sure to bring cash to tip your instructor. Some of them have Venmo or CashApp but cash is still best.

Hike Diamond Head

Diamond Head is one of the most popular hikes in Oahu with a beautiful view of the island and blue water. You can see the whole island essentially.

It’s a moderate hike that took about an hour and a half to complete. The first 3/4 of the hike is a pathway and dirt trail. After that you will have to climb 90-ish stairs. The first set is completely open to the elements. Then there is a steeper set of yellow stairs (pictured below) followed by a pretty long tunnel, then a spiral staircase, that puts you at the top of Diamond Head. Your legs will be jello.

It was a pretty heavily trafficked hike. We went mid-morning about 11 am and were back by 1:30 pm or so.

TIP: Don’t drive there, unless you’re going first thing in the morning. Take the bus or get dropped off by a ride share. They have a mega small parking lot. We made it to the lot only to be turned away and sent back down the volcano to look for other parking (which there basically is none). It also costs $10 bucks to park there. We got super lucky that there was a single spot at a nearby park with a trail that led back the 0.5 mile hike back up to the entrance.

Yes, it’s a half a mile walk uphill to the entrance then you have to buy hiking tickets for $5 per person. There is someone that checks your tickets at the entrance to the trail.

It was a really fun, easy hike and great exercise to break up the day. Definitely recommend.

Chief’s Luau

Since it is our first time in Hawaii, a luau was a must. Strongly recommend booking this early in your trip planning so you can go to the luau of your choosing. We wanted to go to a different luau but unfortunately, there were no spots open on the day we were looking to attend. We ended up going to Chief’s Luau.

No matter which one you choose to attend on the island. It is not a budget experience. It was very pricey but it was part of the experience we wanted to have.

We paid for transportation, a tour bus, which picked us up at a spot near our hotel about an hour prior to the check in. Our guide on the tour bus was a true gem. We were stuck in traffic and she shared a lot of information about Polynesia, Hawaii, and the different cultures.

This was one of those things that I’m glad we did and the performance was fun but everything else was kind of blah. If you attend this luau, you only need the basic package. There are so few differences between the Paradise and Royal Experiences. Your tickets include alcoholic beverages, which are very small and weak. Super disappointing for the price. They have larger drinks in pineapples or tiki glasses for $20/$30 bucks each and they are also super weak drinks and aren’t worth the extra money.

There is a lot of waiting around before dinner is actually served then you’ll be released table by table to pick up your plated dinner. It’s a pretty tasty offering and it was nice to try some traditional Hawaiian fare and flavors.

The show itself was about 45 minutes. The Chief was really funny and a great host. The performances were awesome and fun to watch. Of course, the fire dancing is the best and last performance of the evening. It’s about a 5 hour experience all-in-all including driving to and back from the venue which is in a different part of the island.


Got to sleep in a little this day then went on a hike to Manoa Falls which is located near a residential neighborhood near Waikiki. You are transported to the Hawaiian jungle and it is just a breathtakingly scenic hike. Parking is $7 and there were no issues finding spots. It’s a quick hike so people are coming and going pretty regularly.

TIP: Wear appropriate shoes for hiking. The whole trail is loose rocks. It is slick and muddy.

The hike is super easy and chill. The temperature under the canopy is amazing. It also misted rain on and off the entire hike (hence why the trail is slippery and muddy). The whole hike took about 1 hour and 20 minutes there and back.

The waterfall is pretty. Also, would not recommend doing what these folks are doing and getting in the pool at the bottom of the falls. It’s not allowed and there are reports of bacteria in the water. Just saying, swim at your own risk.

FYI: I feel like it’s always a good idea to look up any hikes you’re interested in taking on the All Trails App. Just to see what people are saying about their experience and make your own judgment call.


Parasailing was one of the highlights of the trip for us. It was such a fun experience. It wasn’t what we expected but so much better.

We booked through Hawaiin Parasail. Great experience all around. Wear your bathing suit because you will get wet. I read that you can do the whole thing dry but essentially that was pretty much debunked, not to mention it was a cool, refreshing experience to get a dunk in the ocean.

I mentioned earlier that the experience wasn’t what I expected, I meant that it was such a calm and smooth takeoff and landing. You would think you’d be jolted into the sky by the parachute but it’s a smooth glide up and back.

You will need to pay an additional $30 if you want them to shoot pictures of you. Totally worth it if you see our smiles here. You can pay to go up at different heights but it seemed to me everyone went up the same height. 10/10 would recommend. This would be fun for the whole family. The views are incredible and it’s so peaceful and quiet while you’re sailing.


Sunday is for snorkeling during my first time in Hawaii one week itinerary.


We booked a tour with Oahu Turtle Canyon Catamaran Snorkle Cruises. Loved everything about the captain and crew. Another highlight of the trip.

First, you’ll take a 10-15 minute boat ride to the snorkel spot. You’ll be a little surprised where it is but it does not disappoint. FYI – this is a busy spot and there will be more than one tour there so be prepared for crowded waters.

Highly recommend wearing a rash guard of some kind to protect your skin from the sun while snorkeling and get plenty of sunscreen on your backside.

The tour provided everything from life vests to snorkel gear. If I had to do it again, I would have bought and brought my own snorkel mask – just so I know where it’s been. You can buy them everywhere on the island for cheap.

As mentioned earlier, the tour is pretty crowded so once you get in the water I’d try and separate from the crowd a little or you’ll just be in a pile and see butts and fins, no fish or turtles. LOL

We saw a ton of turtles, beautiful fish, and coral. It was an awesome experience. You spend about 40-45 minutes in the water so you really get a lot of time to see all the marine life.

You’ll get drinks (alcoholic and non-alcoholic) and snacks on the boat when you return as you sail back to the marina.


Monday we spent catching up on all the zzzz’s, shopping for souvenirs and gifts to bring back with us, and relaxing on the beach for our last day in Hawaii. It was an amazing trip. There were a few things that we wanted to do but just didn’t get around to doing like taking a surf lesson, standup paddleboarding, kayaking to the Mokula Islands, spending more time on the North Shore, ziplining, Shark Cage Diving, Whale watching (out of season). So all the more reason to go back again.


It was an all day travel day back to the mainland. A little under 5 hours back to the Oakland airport and then my sister headed back to Salt Lake and I flew home to Houston.

This is what we did for our first time in Hawaii one week itinerary. Hope you enjoyed the trip and gained some useful information for your trip to the Oahu Hawaii. Aloha!


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