My Hawaiian Escape with the Girls

ALOHA!!!! I hope all of you had an AMAZING time over the holidays with friends and family!! Now that the holidays are behind us I can finally catch up on some of the recaps I owe you! I thought I would kick things off this year with a recap of our girl’s trip to HAWAII!!

I knew I wanted to kick off my 40th birthday celebrations with a girls-only trip and what better way to celebrate the big 4-0 than a trip to MAUI?! I know … I’m still in shock that all of us were able to sneak away (although we did sneak in a little work each morning with our coffee and Bailey’s in hand!). Let me start from the beginning and take you along on a little trip down memory lane!

We flew out on Saturday, December 7th and it was quite the morning for us girls! We were up at the crack of dawn (well, some of us were … Tori accidentally slept through her alarm! LOL!) … 3am to be exact and we were at the airport shortly after with smiles on our faces and luggage in tow! Even though it was a SUPER early morning with little shut-eye the previous night (too excited to sleep!) we were eager and ready to get GOING and before we knew it we were all aboard our WestJet flight to MAUI!!

All 9 of us girls were sitting together on our flight and I’m sure you can well imagine what that was like! Lots of photos were being snapped, excited giggles were filling the cabin and the coffee was flowing … well, until the drink cart rolled around! LOL! Needless to say, we were all pretty excited to get away for a much-needed vacay!

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Day 1

WE MADE IT!!! Time to hunker down for the week at the GORGEOUS Fairmont Kea Lani. I was so excited to stay here as you all know just how much I love it but also because most of the girls on the trip had never stayed here before so I couldn’t WAIT to show them around!!

When we got to the Fairmont Kea Lani our villas were being prepared for us so we dropped off our luggage and did what any group of girls would do …. WE WENT SHOPPING! LOL! I know, it seems a bit crazy to arrive at a beautiful hotel like The Fairmont Kea Lani and then take off shopping but we wanted to get it out of our system early and the shops were only a hop, skip, and a jump away.

Once we got back from our little shopping adventure we quickly hit the pool before we had to get showered up for our very first dinner at Monkeypod! I’ve said this before, and I’ll say it again, the food and (especially!!) the Mai Tai’s at MonkeyPod are SOOO delish! It was the perfect way to kickstart our trip!

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Day 2

On our second day in Maui, we made sure to spend a good portion of the day relaxing on the beach! We had the most amazing setup, beach chairs for everyone and umbrellas for the perfect amount of shade! We made sure to take it easy during the day because we had a big night ahead of us … we were headed to the Old Lahaina Lu’au later that evening!

If you haven’t been to the Old Lahaina Lu’ua before I would 100% suggest adding this to your bucket list! Every time we come to Maui we try to make it part of our trip. It’s entertaining for the ENTIRE family! I mean, does it really get any better than great food, delicious drinks, and an AMAZING beachfront show?! I don’t think so!

We also had Natalie from Flytographer join us throughout our trip in Maui, we met her here at the Old Lahaina Lu’au then she came to the Fairmont Kea Lani the next day for a quick sunset beach session and even came along with us on our Trilogy Boat Tour to snap gorgeous photos along the way so we could share our journey with you. If you have a vacation coming up and would like to book Flytographer to capture your special moments feel free to us code JILLY50 for $50.oo towards a photoshoot purchase or gift card!

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Day 3

On the third day of our Hawaiian escape, we lounged poolside for the ENTIRE day … we got into our SummerSalt bathing suits, loaded up on our favourite Coola Sunscreen, worked on our tans, snacked, sipped on some Pina Colada’s and Mai Tai’s and just enjoyed every second of it. Once we wrapped at the pool we slowly made our way back to the villas to lounge in our Smash + Tess robes and shower up before we met up with Natalie from Flytographer so capture some sunset photos on the beach!

After our fun photoshoot on the beach, we settled in for the most memorable dinner of the trip! A Chef from the Fairmont Kea Lani came to our villa and barbequed a delicious plant-based dinner for us while we were serenaded by the sweetest acoustic ukelele player. It was a total dream and it all took place right in front of our villa as we watched the sun disappear and the shooting stars come out (no word of a lie!).

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Day 4

Our second last day in paradise was spent exploring the waters of Maui via the EPIC Sail Trilogy snorkeling tour. This was by far the BEST way to wrap up our vacation with each other. We lounged on the stunning Trilogy sailing catamaran and tossed on our snorkeling gear to see what we could come across in the beautiful water. Well, this trip certainly did not disappoint as we saw plenty of vibrant fish and even a REEF SHARK!!! It was so amazing!!!

Once we were finished snorkeling we climbed back on board and sipped on delicious drinks as dolphins cruised by our boat and whales put on a show for us. It was one of those “pinch me” moments that none of us will ever forget. I mean, one thing we certainly won’t forget is Kaitlin screaming in excitement every time she saw even the SMALLEST glimpse of a whale, it made our whole day!

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Photo Credit: Natalie from Flytographer

Day 5

Sigh. Day 5. It was the last day of our trip and it was so bittersweet. We were all sad to see our incredible trip come to an end but we made so many lasting memories along the way. We spent our last few hours poolside then packed up our bags and ended our trip with a delicious dinner at Ko Restaurant at the Fairmont Kea Lani before we made our way back to Canada!

I hope you enjoyed following along with our Hawaiian adventures! Next up will be my Disneyland recap! Stay tuned for my tips and favourite memories!

Leave a Reply

  1. Hi jilly,

    What was that store called in Maui where you found the cute and reasonably priced dresses (it was in your stories). This trip looks absolutely amazing!! xx

  2. I spent my 50th in NYC with my girl friends. It truly was a trip to remember.
    What a great way to celebrate your milestone day and the girls in your life.
    Looking forward to more of your adventures! Happy Birthday!!

  3. Your trip looked amazing! I followed it the entire time on your IG stories LOL. We went to Oahu in November and it was absolutely amazing – I definitely recommend it!! It’s a beautiful Island with sooooooo much to see and EAT 🙂

    Thanks so much for sharing! Love you and your family so much – your posts and content make me happy 🙂

  4. Loved the flytography photo shoots, any chance you can let us know where you got the puffy sleeve longer dress from?

  5. Hey Jillie!

    This trip looked so amazing! What was the name of that shop where you and the girls found the cute/affordable summer dresses in Maui – I remember you talking about this in your stories.

    Thanks! xx

  6. Thank you for the memories love your holiday in Maui. I am so glad you had a great time you deserve it. ❤️☀️🤗

  7. OMG that vlog was so fun!!! I’m not sure but the best part might be the grumpy lady in the Monkey Pod!!🤣 And that Villa was to die for…Happy Birthday to you 🥂, 40 isn’t all that bad especially when you do it up like you did!

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