A Week in Ko Olina: Sun, Style, and So Much Gratitude
October 2025
When my bestie Justine told me earlier this year that she wanted to my family and me to celebrate her 40th birthday in Hawaii, I told her we’d love to be there. I just wasn’t sure I could make it work with school, concerts, and life. I also told her I needed to wait and see if I got invited to LTK Con before committing, since both trips fell around the same time.
When I didn’t get the invite, it felt like a sign that I was meant to be in Hawaii instead. We booked the trip, packed our bags, and went all in on celebrating her big 4-0. And honestly, I’m so glad we did. It ended up being one of those experiences that fills you up in every possible way.
This trip wasn’t about fancy outfits or perfect photos. It was about friendship, family, and a whole lot of laughter. I’m still in awe of how seamlessly it all came together and how special it felt to be part of something so personal.
Thursday: Poolside and Birthday Dinner
We arrived in Oahu late Wednesday night and checked into the Beach Villas at Ko Olina. Justine had everything planned and waiting for us, right down to the details. When we walked into our condo, there was a gift bag on the bed filled with the sweetest welcome gifts: matching pajamas, Hawaiian chocolates, a “Justine’s 40th Birthday Crew” t-shirt, and a perfectly packed travel kit full of every little thing you might forget.
Matching pajamas and unfiltered joy before celebrating our girl Justine’s big 4-0. Proof that comfort really is a love language.
Thursday morning started with Chick-fil-A breakfast on Justine’s lanai and hours by the pool with Isla. The day was all about relaxing and soaking it in. Later that night, we walked to 808 Craft House for Justine’s birthday dinner. Her family joined us, there were three cakes (coconut, ube, and passion fruit), and it was such a joyful evening. We ended the night with night swimming under the Hawaiian sky.
Vibe: Comfortable, ready to land in paradise.
Aerie sweatshirt cardigan layered over a white tee, Amazon pants, and gold Birkenstock Arizonas. Traveled with my BEIS carry-on and Mini Weekender bag.
Vibe: Easy, feminine, and ready to celebrate.
Oversized cream shirt and lace maxi skirt, both from Aerie, layered over cream Athleta biker shorts. Gold Birkenstock Arizonas and my Amazon crossbody finished it off.
Friday: Breakfast, Waterpark, and Monkeypod
We started the day early with breakfast at Eggs ‘N Things. I finally got my macadamia nut pancakes with bacon jalapeño fried rice on the side. Heaven. Then we spent the rest of the day at Wet ‘n’ Wild. Justine had rented a cabana and stocked it with drinks and snacks from Costco, because that’s who she is, always thinking ahead and taking care of everyone.
After a quick change, Brant and I joined a group for happy hour at Monkeypod. I tried the famous Mai Tai with the honey lilikoi foam top, and it was hands down the best one I’ve ever had. We shared poke tacos and pizza, and I laughed so hard my stomach hurt. Back at the condo that night, I made margaritas for everyone. It was one of those easy, happy nights that you want to bottle up and keep.
Vibe: Sun-soaked and joy-filled.
My outfit that day was simple: a brown Amazon tee, black cutoff Madewell denim shorts, and Archies flip-flops.
Saturday: Snorkeling with Turtles and Beach Day
Saturday started early with our family’s snorkel excursion out of Waikiki. It was a two-hour trip with about an hour in the water, and we saw turtles, stingrays, and schools of tropical fish. It was beautiful, chaotic, and a little overwhelming — there were moments when it felt like a party both above and below the surface, but when my son asked to head back to the boat, I was secretly relieved for the quiet. Watching the rest of the group from the deck while he sat drying in the sun was one of those unexpected calm-in-the-chaos moments that I’ll remember.
After the boat ride, we grabbed lunch at a local fish market (crab-cake salad for me, chowder because I couldn’t resist) and headed back to Ko Olina for one last afternoon at the lagoon with everyone. We stayed until sunset before packing up for our red-eye home.
Vibe: Cozy, grateful, and wishing I’d booked one more night.
Banana Republic Factory sweatshirt and barrel leg sweatpants, gold Birkenstock Arizonas, and my BEIS carry-on with the Mini Weekender.
The Takeaway?
This trip reminded me that the best vacations aren’t about the itinerary or the outfits. They’re about the people. I’m so grateful for Justine, for her kindness, her generosity, and for including us in something so special. Watching her turn 40 surrounded by the people she loves most felt like a gift in itself.
Traveling with friends changed how I want to vacation moving forward. It took the pressure off. The kids had friends to hang with, the adults had each other, and everything just felt easy.
If I could go back tomorrow, I would. Same condo, same people, same everything.
