Island Time: Hawaii Travel Diary

Tuesday, September 6, 2016

sunset over Kapolei

When I was little, we never traveled or took family trips- save for an hour drive to Canada, or a Florida wedding trip that I can't remember. My parents would always say "next year," when I brought up how my classmates were always in Disneyland and then repeating the phrase for the years that followed. We've recently started traveling a bit more and let me tell you, Montgomery family vacations are something straight out of a movie. I'm talking National Lampoon's Vacation meets Home Alone meets Good Luck Charlie, It's Christmas! and basically every horribly dysfunctional family vacation movie to ever exist. This was our third year in Hawaii so we knew all the ins and outs... but just because we were well seasoned did not mean it was all smooth sailing.


This was our third year in Honolulu and our second time staying at the Outrigger Waikiki Resort. If you are planning a trip soon, this is such a great place to stay! The staff is so accommodating and friendly, and they even remembered us from our previous trip which was very cool! A true example of Hawaiian hospitality. The beach is literally in your backyard as you walk straight out the back of the lobby and you're at the ocean. Not only is it an oceanfront hotel, but it is within walking distance of tons of shopping and restaurants and all of Waikiki's nightlife. There are also free trolleys for hotel guests that can take you all around the island. No car rentals are needed when you're staying here! Our days were spent tanning and relaxing by the pool, then jumping in when we got too hot. When the tropical rain would hit, we'd spend our time warming up in the hot tub. The beach was just steps away from the pool, so when laying around would get boring, we'd just run down the sand and swim on the beach. We stayed at the Outrigger for seven nights and then went on to Kapolei.

Waikiki Beach at night

hot tub at Outrigger 
poolside smoothies
sunrise on Waikiki Beach

The last 4 days of our trip were spent in Kapolei at the Disney Aulani Resort. We stayed in a one of the hotel's luxury 2 bedroom villa complete with a full kitchen, washer and dryer, and basically every amenity you'll need. The villa was like an apartment which made it feel a lot more homey than a crammed hotel room. Aulani is packed with so many different things to do so you can't really get bored. There are multiple pools and hot tubs, and even adult zones which were typically pretty empty. That was nice for when you didn't want to be in an overcrowded pool of kiddos. There was even a private beach just steps away from the resort. There were outdoor movies, waterslides, gift shops, bars and poolside services (the Pina Coladas were to die for), and so much more. We basically lived off of Dole Whip soft serve and fries. Aulani is very family and kid oriented but it is still fun for older teens and adults. There is always something to do and everyone should get the chance to act like a kid again for a little bit. I definitely would recommend staying here at least once in your lifetime.

the fam with Mickey
girls x Goofy
sunset behind Aulani infinity hot tub
overlooking Ko Olina Lagoon
Aulani lazy river caves


During this trip, I did a lot of things I didn't think I would ever do. One of the biggest things being paragliding. My aunt's husband is actually the VP of the Hawaii Paragliding Association, as well as a tandem instructor, so we were lucky enough to get to go when we wanted and for no cost. Now those of you who know me know that heights are one of my biggest fears. I'm even too afraid to go on the ferris wheel at the fair, yet here I was, over 1,000 ft in the air flying over the ocean and doing spins and tricks over Makapu'u.

view from the air

I've recently been getting into hiking, and lucky for me, my aunt lives in Hawaii and agreed to be our tour guide for a day. She took us to tons of private beaches, secret local favorite spots, and all the "touristy" places that you could only get to by car since we didn't have one at the hotel. We did an easy hike with her up to the Makapu'u Point Lighthouse, and the next day my family and I hiked Diamonhead which is supposed to be easy, but I swear I died about 4 times. Then again, there were five cute Australian guys behind Akela and I, so we pushed ourselves so that we wouldn't look weak in front of them.... no greater motivation than a cute boy am I right ladies?!

hiking Makap'u
on top of Diamonhead
If you're in Honolulu and you like acai, you should definitley check out Banan Bowls. We walked to the food truck location at the base of Diamonhead. It was a bit of a walk and I definitely was more sweaty than I'd like to admit, but it was so yummy and so worth it. Plus, can we talk about the boys who work there??? Actually the cutest boys I have ever seen in all of my twenty years on Earth.

Banan Bowls!

Before we left to Aulani, we spent the day in my aunt's neighborhood. She lives in a private community on a marina and they have a clubhouse type of thing with a private pool and decks. She reserved it for the day so we had the whole place to ourselves which was really cool. I even went paddle boarding for the first time (I fell off instantly but who's keeping track). See what I mean about trying new things on this trip? We also went boating on the marina and tubing which was so fun and scary and crazy and my aunt says she'll never look at the boat the same way without remembering us all screaming and flying around and laughing.

view of the marina from my aunt's deck
koko isle
koko isle
koko isle
koko isle
lounging at koko isle


With the adventurous memories comes the dysfunctional-- which in all actuality were just as good. We took our best friend Sav on the trip with us so she got to witness the mess firsthand and even add to the chaos. When we were staying at the Outrigger, Sav and Akela shared the bed and I shared the pullout couch with my 9 year old sister Bella. THAT WAS THE WORST!! When I say she moves a lot in her sleep, I mean she moves A LOT in her sleep. I woke up with a foot in my ribs and a butt in my face on so many different occasions I kid you not. 

There were nights when we were hungry but didn't want to walk far and somehow ended up in Denny's. Even on vacation, you still find a way to end up there at 1am. There was one time we walked to a little grocery store and bought so much candy that the man working the register kept going, "ohh sweet tooth!" and we laughed the whole way back to the hotel. 

We bartered with old women at the flea market, spent way too much money on clothes and shopping, ran when we thought creepy men were following us at night,,, and yes, Sav ran for the first time in months and it was horrible and so funny and embarrassing and amazing. We got in stupid fights, watched funny youtube videos, and laughed too hard at stupid things. Akela probably nearly peed her pants a few times. 

There was one time we were drinking rum punch and I yelled out how I needed some "LIQUID..... BRAVERY!!!" fully thinking that was the correct phrase. Sav broke half her toenail off and I got so sunburnt I was actually a human lobster. 

Once in Aulani, we lost my little brother and searched for an hour only to find him floating down the lazy river so carefree and unaware that my dad had given his description to half the lifeguards. While my parents were looking for him, we were in our villa where Bella walked into the room with a towel on her head and the hotel robe on making us all crack up, and my other brother jumped through the wall and sliced his toe open. Told you we were dysfunctional.

There were a lot of dad jokes, little arguments and lots of hangriness. We got separated in the airport multiple times, Sav always had to go through extra security and nearly got stripped searched at one point. My brother forget he had pens in his bag and on the screen at security they showed up as "bullets" so they stopped us all for having "ammunition." You can't take us anywhere, I'm telling you.

Sav, Akela, and I basically lived off of Kona Mochas from Island Vintage Coffee and candy from ABC stores. There was a lot of snapchatting and taking "hoe pics" of each other. Most of our conversations this trip consisted of comparing nipples and talking about poop. There really are no boundaries when it comes to best friends on vacay. At one point I even flashed the hotel rooms across from our balcony and made Sav record me. From running in the halls to handstands in the elevators to sitting on the hotel washers and nearly denting them in and overusing the pineapple emoji... it was certainly a trip to remember.

We also survived a 'hurricane'??? No big deal or anything, we're just pretty awesome.

one too many Dole Whips

look mom, I'm famous!

Waikiki at night
outrigger pool
lush face masks for our sunburnt noses
brandy x aerosmith
outrigger lanai 
first night in the hotel
halfway to HI
leaving SEA
flying home
a rainy welcoming home

There are tons of things that happened and a lot of funny family moments that I know I'm forgetting but believe me when I say that our family trips are no joke. Waikiki- you are awesome but next year I think we'll bring the Montgomery storm to Maui for a change.

As amazing as Hawaii is, I am so happy to be home in my own bed with my puppies and Seattle rain. The leaves are changing colors and I've been consuming an alarming amount of tea. Fall is my absolute favorite time of the year and I'm excited to blog fall fashion, recipes, and even some DIY projects this season.

Thanks for reading!
Malia x