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We recently traveled to Grand Cayman to shoot our Vacation Club campaign and completely fell in love with the island in the process! There’s something about Grand Cayman that immediately slows you down in the best possible way. Even with all the buzz and work behind the prep and photoshoot days, we still found ourselves often stopping and just admiring how incredible our surroundings were. Maybe it’s the crystal-clear water, the warm breeze coming off the ocean, or the fact that every sunset feels like a movie scene. Whatever it is, our few days on the island felt magical. We accomplished so many work goals and made so many amazing memories as a team, we really feel like the island life rubbed off on us – we hope it shows through in the collection!
If you’re planning a Cayman Islands trip with littles (or honestly just want a beautiful, relaxing getaway), here’s our personal guide to where we stayed, ate, explored, and everything we’d do again.
We stayed at Botanica’s Beach Cottage, and it honestly felt like the dreamiest little hidden gem. The home itself was incredibly aesthetic — every corner felt photo-worthy — but what made it extra special for us was the 4 bed bunkbed room. The kids had so much fun deciding which bed they wanted and climbing up and down the ladders, it was honestly an unexpected hit!
The cottage has private beach access literally steps from the back door, which made early morning walks and sunset swims so easy with kids. We spent downtime enjoying the hot tub, lounging on the porches, paddleboarding, and using the snorkeling gear that came with the house. There is a full kitchen and a washer/dryer, which is a must if you’re traveling with littles.
One unexpected highlight? The funny roosters wandering around the property that the kids became obsessed with. They of course were all named and practically pets by the end of the trip.
And because we were there for the photoshoot, we especially loved how naturally beautiful everything felt. It was the perfect backdrop for this campaign and completely brought our vision to life.
We’re not exaggerating when we say this, and it’s not just a marketing line… Sara really only packed Jammers for the girls for the whole trip! From splashing in the ocean (Weekend Swim collab), to beach-front dinners (hello new daywear styles!), to bunk bed storytime (so many cute prints to choose from), these three girls did not need any other clothes – they were all set. And of course Sara, our Founder, and Rachel, our Creative Director, had PJs picked out for each night. After getting to see everything in person, and lots of begging, we got them to choose a favorite: Sara loves matching with the girls in Indie Floral and Rachel is obsessed with Sea Blue Polka Dot.
We stayed directly off Cemetery Beach and honestly never felt the need to leave. It was quiet, calm, and felt more secluded than many of the bigger tourist beaches nearby. White sand beaches, turquoise water, warm sun–everything we needed!
What made it especially magical was the snorkeling. The water was unbelievably clear, and the kids were able to spot marine life right from the beach. Cemetery Beach is known for its calm atmosphere and reef snorkeling just offshore, making it one of Grand Cayman’s most beloved quieter beaches. Blakely even braved the paddleboard all on her own and crushed it as we cheered from shore.
Watching the kids explore an entirely new underwater world was one of our favorite parts of the trip. If you’re traveling with children and want a beach that feels beautiful but not overly crowded, this area was perfect for us.
This was one of our favorite spots for lunch and poolside lounging. The atmosphere feels playful and tropical in the best way, and the menu had such unique dishes that everyone found something they loved, even the kids.
It’s the kind of place where you can lose track of time, in the best way — especially with kids enjoying hopping between the pool and the table.
Tillie’s was hands-down one of the prettiest dinners of the trip. Beachfront dining, incredible ambiance, and genuinely one of the best dessert menus we’ve ever had.
Everything about it felt elevated without being stuffy, which is exactly our favorite kind of vacation dinner. We were able to watch the sun set right from our table and felt so lucky to be doing what we are doing with you all.
After enjoying beach cabanas, transitioning into dinner here was so easy and fun. It had that perfect kid-friendly beach club energy, and the pizza was genuinely so good. Definitely one of those places that feels effortless in the best way.
Coffee is an absolute necessity for the Jammer’s team. Before leaving for the trip we had already mapped out the coffee shops we would go to, just to make sure coffee would be secured every morning! Of course the house had a coffee machine, but we all know it’s more fun to go out!
Our favorite aesthetic, slower morning stop. Amazing coffee, pastries, and a little shopping all in one place. It felt curated and cozy — exactly the type of place we love finding while traveling.
A quicker grab-and-go option but still super cute and relaxed. Perfect for an easy coffee run before heading to the photoshoot.
One of the most special parts of this trip was getting to connect with local Cayman families during our shoot. We worked with the sweetest local mamas and their mini-me’s to be featured in the campaign alongside us, and it made the experience feel so much more meaningful. We got to introduce Jammers to a lot of mamas for the first time, got to see what kids thought of the new collection, and got the chance to further highlight the beauty of the Island, from the scenery to the people.
We also worked with a local Cayman photographer, Tanya Jane (@tanyajanephotography on Instagram), who helped bring the entire shoot to life. There’s something really special about collaborating with people who know the island so personally.
And one piece of advice we’ll absolutely stand by: book the family vacation photoshoot. The little moments end up becoming the ones you want to hold onto forever.
Especially if you’re traveling with kids. You’ll want the flexibility to explore the island, and taxis are really the main alternative since app-based ride-share services are unavailable.
Caymanians drive on the left side of the road, which definitely took us a minute coming from the U.S. There were a lot of funny moments of us triple checking with each other, “Wait… I’m supposed to be in the left lane, right?!”
If your kids love the ocean, this is such a fun place to explore underwater life right from shore. Cemetery Beach especially is known for snorkeling and marine life visibility. No appointment needed, just grab your gear and head to the beach!
Grand Cayman gave us the perfect mix of beauty, adventure, calm, and connection. We packed so much into four days and still left feeling like there was so much more to experience. The crystal-blue water, the slower pace, the incredible food, the warmth of the local community — it all made such an impression on us. Safe to say: this won’t be our last trip to Cayman!
Where should we shoot next??
