More Details! Our Oahu, Hawaii Anniversary Trip

So how did we decide on Hawaii as the destination for our 10 year anniversary? It actually wasn’t our first, 2nd, or 3rd choice. Originally, it wasn’t even on the list! Only because I didn’t think it would be remotely affordable, and I assumed traveling there would be a huge pain. I was partially right about all of that, but mostly wrong.

I always figured we’d go somewhere in Mexico or the Caribbean, or maybe even the Florida Keys. I also always figured I wouldn’t be pregnant for this trip. And I never knew to expect the Zika outbreak. Once all those original choices were ruled out because of the combination of my unexpected pregnancy and Zika, I thought the only option would be something like Seattle or Vermont. I mean, not bad choices, but so different than what we had in mind.


After poking around on Expedia, I realized that the travel time to those places up north was actually the same as the direct flight from Dallas to Honolulu (8ish hours) for about the same price. I booked this back in August, so I don’t know if that holds true all year. We decided to use Expedia to book our flights and hotel, and wound up with 4 nights at the Outrigger in Waikiki.

While it was only for 4 nights, the vacation felt much longer because we arrived by 12:30 Thursday afternoon, and we didn’t fly out until 8 pm on Monday night. Yeah… I’ll get to that overnight flight in a little bit.

Where We Stayed

Okay- the hotel. Ugh. I want so badly to give it a glowing review because so many people seem to love it, but I really don’t think we’d chose to stay there again, at least not unless we could afford to upgrade significantly. I kinda feel like we were given the “Expedia” room- the one furthest from the good views, closest to the noise of the street and the AC system, maybe with the worst and most uncomfortable bed they have to offer.

To be fair, I never asked them to move us, but I really felt like it would have fallen on deaf ears because I can’t say the staff was all that warm and welcoming – except for the valets, they were great.

A photo posted by Jill Krause (@babyrabies) on

It’s not a bad hotel. It’s in a great location as far as Waikiki goes. The beach is amazing. The restaurants there are wonderful, but I really disliked that there wasn’t anywhere to sit that felt cool and comfortable in the AC at the 2 of the 3 we tried (Duke’s and Hula Grill), and there was a strong sewage smell coming from the back of the kitchen that leads out to the walkway along the side that takes you to the beach.

If we did stay there again, it would only be if we could afford a room with a better view/higher floor, assuming they put (much) better beds in those rooms.

What We Did

At first, I thought we’d just book a bunch of tours. It’s not hard to find plenty that will pick you up at your Waikiki hotel for free or a minimal charge. Once I started adding up the cost of all of those, though, I realized it wouldn’t be much more to just rent a car, even including the cost of parking at the hotel ($35/night), especially after pricing out airport transfers. We used Travelocity to book a week long car rental, and wound up getting a “triple upgrade” to a Jeep Patriot, for about $175.

I. Am. So. Glad. We would have been miserable stuck on a bunch of tour busses with people we didn’t know. We wound up loving the freedom of being able to drive wherever whenever. We only booked one “tour” but it was a totally different experience than most.

I will have a whole separate post on this soon, including some free digital downloads of photos (!!), but I think one of the best things we did was book an Epic Sunrise tour with Oahu Photography Tours. We booked it for the first morning we were there. The 5:30 am pickup time scared me, but wound up being perfect since that was 10:30 am Texas time and we’d been wide awake since 3.  Again, so much more on this to come, here’s just one of the pictures I got of that gorgeous sunrise.


Did I mention that I lived on Oahu from kinder-4th grade? Oh yeah. I guess that influenced our trip a bit. We tried to get on base where I used to live- Pearl City Peninsula- but since we didn’t have base passes or military IDs we were denied entry. I did get to see my old elementary school (Lehua Elem), though! And while we were out that way, of course, we visited the USS Arizona Memorial at Pearl Harbor.

Our extremely early wakeup worked to our benefit here, too. The memorial opens at 7 am, and since tickets are on a first come basis, I imagine it gets really crazy later in the day. We wound up only having to wait about 30 minutes to get on the 9:30 am tour.


After that, we drove up to the North Shore for lunch, and just to check out the waves. We fell in love with the sweet town of Haleiwa! We decided to book a surf lesson for Scott out there the next day, and thought a long, scenic drive around the island back to Waikiki sounded like a great way to spend the rest of the afternoon. It was lovely for about 30 minutes. The other 2 hours were pretty brutal, considering how many times we had to stop for me to pee.


Scott’s early morning surfing lesson with Uncle Bryan’s Sunset Suratt Surf School was one of the highlights of the trip. Scott was up on his board, catching waves within 30 minutes. And there was a photographer there who got some fantastic shots that were available for digital download for only $25 (including the one above).


Meanwhile, I got to watch from the shore, and they kindly provided me a beach chair and plenty of water. Can’t say enough kind things about them!


Can we take a minute to discuss my favorite bathing suit probably of all time, and definitely while pregnant? If you haven’t found @KortniJeane on Instagram yet, run there and follow them (or check out their site here). They have the cutest suits for all body types, and when I saw they had maternity bottoms, I instantly fell in love.

I paired it with this SwimZip top for trips to the beach (size L, not maternity, but definitely big and forgiving enough).


Okay, back to places we went. The last day we were there, we booked a Movie Site tour at Kualoa ranch. We saw some cool spots where Lost was filmed, and Jurassic park, along with a lot of other TV shows and movies. I wasn’t really there for that as much as I wanted up close access to photograph the gorgeous mountains and foliage there.


I do regret that we didn’t eat lunch there. Scott wasn’t impressed with the “cafeteria” atmosphere, so we wound up back in Waikiki and had to settle for a crappy cheeseburger place. That leads me to…

Where We Ate

Of course, we ate at our hotel at both Duke’s and Hula Grill. And yes, we did have a slice of Hula Pie (ordered to go and ate on the beach because it wasn’t worth waiting 45 minutes for a table).

Other than that, we had no idea where we would go before we got there, but I relied heavily on the Trip Advisor app, and it didn’t steer us wrong. I would just check to see what was around us at the moment, and read the reviews.

Our official anniversary dinner was at the Hau Tree Lanai, just down the street from our hotel. Great food (high prices), great service, great view of the sunset and the beach.

A photo posted by Jill Krause (@babyrabies) on

When we got to the North Shore, the reviews for KONO’s were too good to ignore. I had the pork plate. So yum!


The food did not disappoint, and was a great price, but I think Scott could have done without all the wild chickens pecking around our feet. Ha!


Also in Haleiwa, we had coffee and lattes from Coffee Gallery, and we discovered Island Vintage Coffee, which had THE BEST breakfast I’ve ever had in my life. It was so good, we had it again back at their Waikiki location the next day.

A photo posted by Jill Krause (@babyrabies) on

We ate at a couple other places, but nothing worth noting. We were pretty disappointed that the AC was broken during our reservation at Top Of Waikiki. It’s an enclosed space and they can’t open windows. We didn’t even make it all the way around because we ate so fast just to get out of there. It’s not an inexpensive place, and I wish we would have just gone elsewhere.

What We Would & Wouldn’t Do Different

Overall, we had an amazing time and don’t regret much, but if we are fortunate enough to make it out there again, I think we’d do things a little differently. For starters, we’d probably rent a house closer to the North Shore, especially if we’re able to bring our kids. We’d plan to stock up on lots of local produce and meat and cook most meals there.

We would definitely sign everyone who’s old enough up for more surfing lessons with Uncle Bryan! That was the only part of our trip that made me wish our kids were there. It would have been a joy to watch Kendall give it a try.

We’d make Waikiki a day trip, but wouldn’t spend most of our time down there.

A photo posted by Jill Krause (@babyrabies) on

I’d like to say we would definitely not book the overnight flight home, but it’s possible my extreme dislike of that situation was colored by being nearly 8 months pregnant. I can say, FOR SURE, I wouldn’t do that again while gestating. BUT, a Hawaii trip while pregnant (travel to there aside) can be enjoyable. In case you were wondering.


50 Things to Do Before You Deliver: The First Time Moms Pregnancy Guide
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