Driving on the wrong side of the road only got me a couple of times. Those times were apparently worth yelling about from the backseat but we survived. I was the only one old enough to drive the rental car so I appointed my son as official navigator and the role reversal was not lost on me. More than once I was on the receiving end of a sincere (or sometimes joking) “Wow! Good job Mom” from my offspring. The same words I have said to them approximately ten thousand times. We celebrated every successful arrival like we’d accomplished something truly remarkable. We had. Don’t let anyone tell you otherwise.
We flew Delta and thanks to our Delta Amex card, Comfort Plus upgrades were waiting for us at the gate — a particular win for my son who is 6’4” and has legitimate opinions about legroom. The flight was smooth and we landed hungry, which meant one thing: get to the place, change into suits, and eat immediately.
Our Airbnb on Seven Mile Beach was what I can only describe as a secret gem. $2,200 total for the trip — four of us, two spacious bedrooms, stunning Caribbean views from the balcony, a pool and hot tub, beach chairs and umbrellas provided, a protected swimming bay with reefs just offshore, and an on-site restaurant and swim-up bar. It had every amenity of a resort at a fraction of the price. My college kids were a little skeptical of the Airbnb idea. They were not skeptical by day two.
We dropped our bags, changed, and descended on the on-site restaurant immediately — tropical drinks (the legal drinking age is 18), jerk pork sandwiches, a platter of nachos, all devoured. Then we hit the beach. The water on Seven Mile Beach hits all the different notes of blue, including my fave shade of turquoise. So blue, so clear, so calm. The kids found shells and rocks. The sunset from our balcony that evening was stunning.
Dinner that night was a quick trip back out onto the wrong side of the road (we were getting used to it, I think) to a nearby grocery store — breakfast essentials, lots of fresh fruit, and fresh burritos from the deli for the kids. Practical. Efficient. Exactly how we’ve always traveled. We save on the small things so we can splurge on the meaningful ones.
Day Two: Beach, Books, and Heritage Kitchen
The next morning my daughter and I were up early. Coffee first, then straight to the beach where we parked ourselves in the provided lounge chairs and didn’t move for hours. When my sons eventually emerged they brought us drinks from the swim-up bar without being asked, which I’m choosing to take as evidence that we raised them well. I read an entire book that had been sitting on my nightstand for months. It was exactly what the doctor ordered.
That evening we drove to Heritage Kitchen for dinner and a completely different view of the sunset. The food was homemade and authentic and we ordered things we’d never had before — conch fritters that became an immediate favorite, purple coleslaw that was as vibrant as it looked, coconut garlic curry shrimp that was deeply flavorful, and fresh hand squeezed juices my boys couldn’t get enough of. Six roosters roamed the grounds and eventually settled into the big tree nearby, keeping us thoroughly entertained while we waited. Heritage Kitchen is a place you stumble into and know it’s the real deal. Go. Just go.
Day Three: Captain Hank, Stingrays, and Starfish
Day three was our private boat tour with Captain Hank. He took us to snorkel spots where we saw large stingrays, vibrant fish, and a friendly sea turtle that seemed entirely unbothered by our presence. Stingray City was the highlight — a large sandbar where completely wild stingrays gather, and where you can feed them squid, hold them, and yes, give them a kiss. They are treated humanely and well and seemed genuinely unbothered — possibly even enjoying the snuggles. Our final stop was Starfish Point, where we waded in shallow water surrounded by more starfish than I’ve ever seen in one place. You can handle them gently but it is illegal to take them out of the water even for a moment — worth knowing before you visit.
We were hungry and tired by the end of the tour and stopped at Pepper’s Bar and Grill for a late lunch that we absolutely devoured. We kept noticing throughout the trip how fresh and healthy everything tasted — Grand Cayman takes its food seriously.
That evening we found Casa 43 Mexican Kitchen and Tequila Bar — packed, loud, full of character, just the vibe you hope to uncover on a trip. Followed by gelato at the Camana Bay (also worth checking out) which felt like exactly the right ending to that kind of day.
Day Four: One More Beach Day and the Bioluminescent Bay
Our last full day was intentionally slow. More beach. Another book finished — yes, two books in one trip, no I’m not sorry. Resting up for the evening excursion to the bioluminescent bay.
It was about a thirty minute boat ride to a bay that is, surprisingly, man-made, and also the reason Starfish Point exists. Beautiful homes lined the water, many of them also on Airbnb — something to consider for a future trip. The guides recommended wetsuits — not for the cold but because the silt at the bottom, in just three to four feet of water, will make you itchy. But the moment you disturb the water and watch it light up that impossible blue — like pixie dust, like fireworks, like something that simply shouldn’t be real — it’s worth every bit of the logistics. Truly surreal. One of those things you have to see to believe and still don’t quite believe after you’ve seen it.
We ended the night with gluten free pizza at a charming boutique hotel nearby — delicious, which was a happy surprise — and headed back to pack.
Last Morning: Turtles, Timing, and the Gift Shop
The next morning we stopped at the Cayman Turtle Centre on the way to the airport. A perfect final hour on the island — we learned more than we expected, loved every minute of it, watched in awe as these enormous creatures swam and ate, and had a surprisingly good lunch at the facility that kept us well fed and perfectly on schedule for our flight.
At the airport I did what I always do: found the gift shop and looked for the local coins. I’m not a souvenir person — tchotchkes aren’t my thing, and unless something truly special finds me in a place, I’d rather not bring home just more stuff. But the native currency fits that bill (pun intended) perfectly. It’s small, meaningful, and specific to exactly where you were. And I think about the fact that paper and coin money won’t exist forever — someday these will be artifacts from a world that moved on without them. A polished “penny” from somewhere that changed you a little.
So I bought a bag of peanut M&Ms — partly to get Caymanian change, partly because it’s a four hour flight and peanut M&Ms are never a bad idea. Double duty. That’s just efficient travel.
When I pulled them out on the plane my daughter looked at me like I’d produced them from thin air. “Where did those come from?” Fair question. The answer was: the gift shop, where I’d paid in cash (US Dollars) specifically to collect the change. She has known me her whole life and still gave me a little eye roll with a laugh.
While we waited to board, a frazzled mom and dad nearby were doing their heroic best to contain two small children who were tired, cranky, and convinced that every object within eyeline belonged to them. My daughter and I exchanged an amused look — no words needed. I glanced over at my three college kids, calm and self-sufficient and patiently waiting to board our flight and felt something settle in my chest.
Some seasons are behind me.
Not all of that is bad. Not even close.
Practical Details:
• Where we stayed: Seven Mile Beach — search Airbnb for the area, filter for pool and beach access. Ours was called Condo-Sunset Cove and Osbert was our host. Total: $2,200 for 4 people
• Private boat tour: Ask for Captain Hank from All aboard charters • Don’t miss: Heritage Kitchen, Stingray City, Starfish Point, Bioluminescent Bay (we toured with Six Senses Cayman Adventures), Cayman Turtle Centre
• Eat at: Heritage Kitchen, Pepper’s Bar and Grill, Casa 43 Mexican Kitchen and Tequila Bar, Lazy Lizard Bar & Grill (on the condo property)
• Gluten free travelers: Grand Cayman is remarkably accommodating — we never felt like an afterthought
• Driving: You will be fine. Commit to the roundabouts. Ignore the backseat.
P.S. Since you asked (and even if you didn’t) here are the two books I finally read on this trip. A beach vacation and an unread book are basically a moral obligation and these were great beach reads!
• The Surrogate Mother by Frieda McFadden —https://amzn.to/4niTL9Q
• A Long Time Coming by Meghan Quinn — https://amzn.to/4tQv3jw
