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Team Jilly’s 30 Day Hawaiian Weekend

Aloha loves! As most of you would have figured out by watching my Instagram stories last week, myself and Team Jilly were all in Hawaii, while we were only there for 3 days, ultimately it felt like 30!! This isn’t because there were seven of us sharing two bathrooms lol but because we knew we were only there for such a short period of time that we jammed as much stuff into these three days that we possibly could.

A good 2 weeks prior to our trip to Hawaii I spent a few solid hours researching things to do and places to eat and while my long itinerary totally overwhelmed the girls (LOL!!!), I knew it would pay off in the end and keep us organized, on time and smiling the whole way through … and that’s exactly what it did! After I assured the girls that the early morning photo shoots and multiple reservations weren’t set in stone and everything was flexible, all of their excitement came flooding back in and the countdown to our first ever Team Jilly retreat was underway!!

We ended up deciding to drive to Vancouver from Kelowna as we had to get a few things done in Vancouver on the way back so we had a full vehicle on the way there and took off from YVR on a smooth sailing flight all the way to Honolulu thanks to WestJet!! Ps. If you haven’t tried flying WestJet Plus I totally suggest giving it a try … especially on longer flights, it’s worth it. Not convinced? Free wine. There, did that do it?? LOL!! We just may have indulged in a few mini bottles as we excitedly counted down the hours until landing. Lol. Team Jilly at its finest.

Jillian Harris A Week In My Closet

We landed in Oahu around 10pm, grabbed a minivan and made our way to the beautiful Moana Surfrider Resort , we got lei’d, dropped off our bags, and immediately made our way to the Beach Bar for a Mai Tai (Ps. If you’re planning on visiting the Moana Surfrider, we recommend the 1944 Mai Tai from the menu … it’s delish and potent … lol!!), after a couple of drinks and some much needed veggie burgers we headed back to our room to catch some z’s.

Thankfully the time difference was on our side, seen as how we are three hours ahead here in BC most of us had trouble sleeping in and were up between 5:30 – 6:30 every morning … this was perfect according to my itinerary … LOL!! Alright, let’s take a look at what our three days looked like!

Jillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii Recap

Day 1

Even though we were all bagged from our full day of travelling the night before, that didn’t stop us from getting up at the crack of dawn and hitting the beautiful beach for an early morning photo shoot. The lighting was so perfect and the beach was so beautiful that we couldn’t resist. We spent about an hour here before we headed off to our first breakfast at the Moana Surfrider Beach House. We started off with a round of water, coffee (kinda needed that after hour 5-hour sleep lol) and delicious guava mimosas!! Mmmm … I could go for one of those bad boys right now!! After breakfast, we didn’t waste time tossing our swimsuits on and making our way down to the beach where we lounged, caught up with each other and soaked up some sun!

Jillian Harris Honolulu Hawaii Recap-Jillian Harris Honolulu Hawaii Recap

My Dress | Tori’s Dress

After we got nice and toasty (don’t worry, we used sunscreen) we headed back up to the room and freshened up to head out for lunch at one of my favourite spots, Bills!! The last time Shay and I were in Honolulu we went their TWICE and we were only there for 2 days (that’s how good it is). So I was SURE to include this on our itinerary for the girls to experience. They have the BEST drinks in Honolulu (hands down!) and their food is fresh and local and unreal! We (I speak for all of us lol!!) totally LOVED their Watermelon Spritz and Bloody Mary’s!! YUM!!

After lunch, we did a little shopping because what’s better than shopping while you’re a little buzzed?! YOU GET A T-SHIRT … AND YOUUUU GET A T-SHIRT … lol. Ok, maybe that was a bad idea. But it was fun! We then headed back to our rooms to get ready for dinner! I had made us a reservation at House Without a Key because so many of you recommended it! When we got there they had live music which we enjoyed all while sippin wine and digging into our tasty meals! While everything was amazing here I would suggest skipping the appetizers as they were pretty pricey for small portions! By the end of dinner, it was a debate whether or not we were going to head out for a nightcap before bed … but the majority of the vote was to hit the sheets so back to the resort we went!

Day 2

This was another early day! As soon as we got up we grabbed a coffee and hit the road! Our plan was to tour around Oahu and make pit stops at a few beaches to snag some fun photos along the way. We kicked off this tour by stopping in at the local organic market … just kidding … it was Whole Foods … LOL!! You can’t keep me away from this place! We loaded up on snacks for the day … some sparkling rosé (yessss … they sell it there) and of course, what road trip is complete without some Mochi Ice Cream?! As Tori and Tyler were indulging in these they immediately had a lightbulb go off and thought about how freakin’ great these treats are for kids!!! NO MESS ice cream sandwiches (kinda lol)!!!! Hallelujah!

Jillian Harris Honolulu Hawaii Recap

Dress | Hat (Similar) | Watch | Bag

Our first stop (after trusty Whole Foods) was Hanauma Bay!! Tori and I hadn’t been back here since 1986, so we were pretty excited to see how much it hadn’t changed … us on the other hand, we are about 2″ taller and a little bit wiser now. LOL!! If you’ve never been to Hanauma Bay, you have to check it out, it’s soooo beautiful but look out … the tropical fish like to nibble your toes … it freaked most of us out, other than Kaitlin … she got a kick out of it. LOL.

Jillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii Recap

My Swimsuit Top | My Swimsuit Bottoms | WatchSunglasses | Tori’s Swimsuit (Similar)

After Hanauma Bay, we stopped by the Byodo-In Temple which is a stunning (and peaceful) Buddhist temple! This was a nice change of scene and was so cool to see!!! After the temple, our stomachs were GROWLING so we decided to hit up a food truck and that’s when the  Shrimp Shak appeared! Apparently, it’s one of Food Network’s “Unique Eats” … LOL! Welp, their food was damn good and we were totally stuffed when we left, so that was a win in our books … and tmmies!

We ended the day at Sunset Beach with a can of sparkling rose and lots of laughs … along with a heated debate whether there are more grains of sand or cups of water on earth … this debate lasted all day and carried on to the night (thanks, Shay …) where it was determined thanks to Google and some crazy mathematics by Mackenzie that there are (apparently … even though I STILL don’t believe it) more cups of water to grains of sand on Earth. LOL.

Jillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii Recap

That night we decided to go casual for dinner and ate at the restaurant called Dukes which was right next door to our hotel. We ordered up some drinks and I decided on the Steak Street Tacos for dinner but I tweaked them a bit so they were meatless by substituting the steak with black beans and they were freakin’ DELISH!!!

Day 3

This was our last day and we wanted to make the most of it but we also wanted to just relax and chill out so we had a light breakfast and spent the morning chilling out in the cabanas at the Moana on the beach … we then thought it was a great idea to get a few double Pina Coladas … whose idea was that anyway?! LOL.

IMG_0166Jillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii Recap

My Swimsuit | Shay’s Swimsuit | Hat (Similar)

Later that afternoon we all headed to the Moana Lani Spa to get pampered before our last dinner … there’s really nothing like salt scrubs and massages to wrap up an amazing day … plus they have these amazing reclining chairs that are so ridiculously comfortable … we lounged in those for a bit before showering up, packing, and getting ready for our last meal! Once our bags were packed and we were all sorted we headed down to the Moana’s Beachhouse restaurant … we had a little bit of wine, unwound, mentally prepared to check out and devoured our meals!!

Jillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii RecapJillian Harris Honolulu Hawaii Recap

photo credit

We took the red-eye from Hawaii to Vancouver and we all fell asleep INSTANTLY (me, before takeoff) lol. It was a short trip but we packed so much into those three days that we were totally bagged by the end of it!! LOL! The fine folks at WestJet got us safely into Vancouver that following morning and thanks to a super smooth flight we were able to snag about 5 hours of shut-eye in! LOL.

My goodness, I am seriously so thankful that we were all able to take some time to just relax and catch up with one another, it was certainly needed!!

If you’re looking to head to Hawaii for a quick getaway and would like to know HOW in the world we crammed all of this into a short period of time here is our itinerary from our trip … it might come in helpful!


  • 9:20 PM – Arrive. Get car. Make our way to the hotel. Check-in.
  • 10:30 PM – Drinks in the lobby. Settle into our rooms.


  • 5 AM – Wake up. Get ready.
  • 6 AM  – Photoshoot on the beach.
  • 7 AM  – Breakfast at Veranda Beach House
  • 8:30 AM – Back to room to get ready for the beach
  • 9:30 -12:00 – Beach & chill!
  • 12:30 PM – Lunch at Bills
  • 2 PM – Walk around Honolulu, do a little shopping
  • 5 PM – Head back to room to get ready for dinner
  • 6:30 – Sunset dinner and drinks at House Without A Key


  • 6:30 AM  – Wake up. Get ready
  • 7 AM – Get coffee and breakfast 
  • 8 AM –  Tour the ISLAND!
  • 6 PM – Arrive back at hotel. Get ready
  • 8 PM – Dinner and drinks


  • 7:30 – AM Wake up
  • 8 AM – Grab coffee and breakfast
  • 10 AM – Head down to beach and relax in cabanas
  • 1 PM  – Lunch
  • 3 PM – Spa Treatments
  • 5:30 PM – Departure Dinner at Moana Beach House 
  • 8 PM  – Leave hotel to catch flight

Oh, before I forget, below are some more of our dresses that we wore when we were in Hawaii!! Click on the images below to get additional details of each item!!

Hawaii … Team Jilly hopes to see you again sometime soon … but until then …



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Leave a Reply

  1. It sounds like it was a quick but amazing trip! I’m definitely bookmarking the places you recommended. Curious if WestJet sponsored your trip? It kind of reads that way but I didn’t see a disclosure so I wasn’t sure. Thanks for sharing!

  2. You guys are all absolutely adorable individually and an absolute dynamic team collectively.

    Jillian your honesty in all your posts simply makes you perfect.

    Thank you for always being your authentic self 🙂


  3. Love Hawaii and Love you! I might have to get myself the two piece white bathingsuit for our trip to Hawaii. Moana Beach House looks beautiful.

    Thank you for the itenary, you all got alot done in such a short period of time. 🙂

    Michele xo

  4. Loved this post! I’m looking for a short getaway to take my husband away for his 40th bday this year and this might be a great option! Also I totally just bought that baby blue swimsuit Jillian is wearing even though it’s almost October lol!! Thanks for sharing!

  5. Looks like a wonderful trip! I am in love with the blue one piece swimsuit!! Is it a suit you would highly recommend? Thanks

    1. I love it too but I did have to get it tailored a bit as the straps were too long, once it fit better it was amazing!! XOXO

  6. I’m always looking for cute one piece swimsuits. Love these! I live on Oahu so it was fun to see what you decided to do here.

  7. I have to ask…how many swimsuits did you bring?!?! My husband and I are going to Australia for 3 weeks over Christmas to spend the holidays with his parents and travel around a bit. He always thinks I pack too much! ?

  8. JILLIAN how do your bangs look so perfect ALL OF THE TIME even when you’re on the beach?! Bangs look so cute but are always the ultimate struggle! Would love a post on them!

    PS keep being amazing at everything, you’re the best!

  9. Jillian,
    Do you recommend the Moana Surfrider or Fairmont Kea Lani?? Going with our 4 year old son, spending the last five days at Aluani… But where do we stay the first 5 days?? Seriously can’t decide!!! Help! 🙂

  10. Would you say you prefer Weilea area over Kaanapali?
    My husband and I are travelling in february and have heard mixed reviews.

  11. Thank you for sharing your trip. Hawaii for us western Canadians is a dream. I am checking out all the places you mentioned. Thanks for posting all the places.
    Merry Christmas to you and your team for making these past 12 days so awesome.

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