Can we go back now please???? There’s just something about spring break that makes you crave sunshine, salty air, and a full week with your favorite people. After a long stretch of winter and ice storms and snow and chilly temps mixed with busy schedules, we packed up the crew and headed south for a week in the Cayman Islands—and it was EXACTLY the reset we all needed. We had gone skiing last year, so we decided it was definitely time to go somewhere warm + tropical this go-around!
I had been to Grand Cayman before, but only on a brief visit on a family cruise years ago… but we had heard AMAZING things about this place and decided to try somewhere new and add a new stamp to our passports, too. This trip was extra special because we got to spend it with dear family friends which meant double the kids, double the laughter, and lots of quality time together. Our home for the week was the most incredible oceanfront villa in Rum Point called Olympus, and truly the setting couldn’t have been more perfect for a laid-back island getaway where all we wanted to do was eat + drink, relax and unwind and spend time taking in all the island had to offer.
Here’s a high level play-by-play + overall recap of our week in Grand Cayman as it seems many of you are considering looking at taking a trip there soon, too:
Day 1 | Travel Day + Villa Life
Our alarms went off way before the sun with a 6:40AM flight out of Nashville, but the early wake-up felt worth it knowing we were headed somewhere warm and we were officially on vacation. We connected through Orlando before landing in Grand Cayman just before lunchtime… there’s nothing like that first moment stepping off the plane and feeling the warm Caribbean air—it instantly flips the switch into out-of-office mode.
We headed straight to Rum Point where we would be staying for the week, and I’m not exaggerating when I say the house took our breath away. The villa sits right on the water with the most beautiful views of the reef-protected ocean, and the entire main living area opens up with floor-to-ceiling sliding doors to a huge terrace and pool. It was one of those homes where indoor and outdoor living blend together so seamlessly that you forget where one ends and the other begins.
The kids immediately claimed the pool and sandy backyard as their territory while the adults unpacked, settled in, and took it all in. That evening we had dinner at the villa prepared by Chef Carlos, and after a long travel day it was the most relaxing way to start the trip. The kids played outside while we enjoyed a slow dinner together—good food, lots of laughter, and the perfect kick-off to the week.
P.S. I cannot say enough great things about Olympus = the house is super fresh + modern with every amenity you could imagine = it’s situated on the quiet part of the island which is exactly what we were looking for. Our house manager, Steve, made sure everything was well stocked all week and checked in with us daily on any specific requests, etc.
Day 2 | Settling Into Island Time
Our first full day was intentionally slow, which is exactly how we like to start a vacation. We woke up to sunshine pouring through the windows and ocean views in every direction. And of course hot coffee because we had hit up Kirk Market when we arrived… think Fresh Market/Whole Foods on an island = a great place to stock up on everything you need!!
Most of the day was spent exactly how spring break should be spent—pool time, swimsuits all day, snacks whenever you want them, and plenty of exploring around the beach right outside the house with snorkeling right outside in the ocean. The kids went back and forth between the sand and the pool nonstop while we soaked up the sunshine and lounged + leisured! My favorite kind of days that don’t require much planning but end up being some of the sweetest memories.
That night, we loaded up in the van [PRO TIP | rent a car as it’s easy to get around the island… just be prepared to drive on the wrong side of the road!] and headed to dinner at a local eatery Kaibo. The most gorgeous beach club restaurant with love music, incredible local seafood fare and great atmosphere with picturesque views for days! And Carson may have had a little run-in with her favorite football coach, Josh Heupel = GO VOLS…
Day 3 | Island Adventures + Dinner at Tillies
Another beautiful island day meant more time outside enjoying the water and the slow pace of vacation life. We hopped in the van and decided today was the day to hit up some of the most iconic and well-known snorkeling spots on the island… and when I tell you how amazing it was, let’s just say we swam with sea turtles, lots of incredible fish and wildlife and took in some FABULOUS scenery as well!
PRO TIP | For great snorkeling and public access, check out Cemetery Reef, Starfish Point, Spotts Beach, Rum Point, Coral Gardens and Kittiwake Shipwreck!
That evening we headed to Seven Mile Beach for dinner at Tillies, and the setting was just gorgeous. Palm trees, ocean views, and the prettiest sunset made it feel like one of those nights you want to bottle up and keep forever. It was fun getting everyone dressed up just a little after a day in swimsuits, and the food was absolutely delicious!! Great people watching, a stellar beach setup, fabulous drinks and food everyone will enjoy…
Day 4 | All the Island Adventures
By this point we had fully settled into the rhythm of the week—slow mornings with coffee in hand watching the sunrise [my absolute favorite part of the day], long afternoons outside [reading a great book and playing Tidal Ball], and evenings gathered around the table.
The kids had completely claimed the backyard and spent hours relaxing by the pool, using the kayaks to head out into the ocean and snorkeling right off the shore! One of my favorite things about the house was how easy it made everything feel. No schedules, no rushing—just time together and catching up on plenty of R&R…
Day 5 | Stingray City + Bioluminescent Bay
This was one of the most memorable days of the entire trip and one that I was personally counting down to! We spent the morning lounging around the house… sleeping in a bit [8AM for me = and yes, that’s as late as I can sleep in on vacation] = then in the late afternoon we headed over to Kaibo Docks where we met the crew from Crazy Crab Cayman for a private boat charter. Our first stop was the famous Stingray City sandbar in the North Sound where you can swim with the stingrays, and it was every bit as magical as everyone says. The water is unbelievably clear and the stingrays glide right up to you—it’s such a unique experience and the kids were completely fascinated [adults too of course!!]… we LOVED having a charter to ourselves… that way we could take our time to swim and interact and enjoy the views without having to feel rushed! HIGHLY recommend our crew too…
From there, we headed to Rum Point for an al fresco dinner beachside = a great way to unwind, sip on their mango mojitos, indulge in their homemade pizzas thar were delish and spend some time enjoying a slower pace before our nighttime activity…
After sunset we headed to the Bioluminescent Bay, which honestly felt like something out of a movie. As the boat moved through the narrow and shallow bay, we got the chance to jump in and swim with millions of tiny plankton that lit up around us, glowing in the dark. It’s one of those natural wonders that’s hard to describe but absolutely unforgettable and something we will never forget!! Absolutely recommend doing both of these activities because they are super family friendly and a great experience that’s unique to Grand Cayman.
Day 6 | Exploring + Dinner Out
More sunshine, more pool time, and lots of soaking up our last few full days on the island.
That evening we headed into George Town for dinner at Grand Old House, which sits right on the water and was such a fun spot for a night out. Be sure to request a table outside on the patio so you can take in the scenery + sunset… we also got a tour of this old plantation venue, which made it all the more special! And if you’ve got someone at home that loves cigars, be sure to check out their master cigar roller that is there each night = such a fun souvenir to bring home! A super special and fancy dinner out with family + friends recapping so many highlights from our trip 🙂
Day 7 | One Last Island Night
Our final full day always sneaks up faster than you expect = whish just means it’s time to plan another trip!! We spent the last day doing all of our favorite things one more time—swimming, relaxing outside, more snorkel time by the house and soaking up every last bit of sunshine. That evening Chef Carlos returned to the villa for another dinner at home, which felt like the perfect way to close out the week! Plus, there’s something really special about ending a trip gathered around the table with the people you’ve spent the week making memories with.
All in all, our first time as a family in Grand Cayman was everything we could have imagined AND more… easy to get to with minimal travel time, the best views + scenery, happy island locals who made us feel quite at home throughout our stay, gorgeous accommodations that we’d absolutely stay at again and of course lots of sun, seafood and surf = we left with full hearts AND a camera roll full of memories!
This trip was the perfect mix of relaxation, adventure, and time with dear friends—exactly what spring break should be! The Cayman Islands completely stole our hearts, and something tells me we’ll be dreaming about those ocean views for a long time…
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