Road Trippin’ Around the Island!

What would you do with a full day in Cayman, all to yourself? On my last trip to Grand Cayman, I ended up with just that, a full day to myself (with no pre-made plans) and all of Cayman set out before me to explore. Faced with endless options, an urge to explore and the inability to pick “just one” I decided to take a road trip around the island. My hope? To travel the entire perimeter of the island (where possible) and see what all I could do and enjoy in one day’s time.

First I had to pick where to start. Pull up a map of Grand Cayman, and you’ll see that Barker’s National Park caps the northeast point of West Bay. This was the perfect point to start my expedition. I headed that way with an explorer’s heart and nothing more than Google maps pulled up on my phone.

Barker’s National Park

I entered the park, and was glad the rental I was driving was an SUV. You could get by on some of the park’s gravel roads with a car, but I felt much better riding higher with an SUV. It was bumpy, but well worth the seclusion, nature and peacefulness found while wondering throughout.

While driving through the park mangrove waterways were almost always present on either side of the road. I neared an iguana in the road, and as it spotted me it made a comical b-line for the mangrove waters. It ran alternating the exaggerated slapping of each foot on the ground and then dove very quickly into the water. I was also lucky to spot a jellyfish swimming along one of the waterways. With no other vehicles in sight, I stopped the car and watched it swim along for a bit.

I didn’t pass a single vehicle on the road as I drove through the park, but I did pass some 4 wheelers! They were all together and a part of a cool new tour that ATV Cayman offers through Barker’s. Lucky for me they passed just when I needed some advice from another human. There was a large puddle across the road, and not knowing how deep or sandy it was, I was tentative to cross through it. I rolled down my window and asked the ATV guide at the back of the group if I was good to cross over. He said I’d be in good shape as long as I stayed over to the right (keeping half the vehicle out of the puddle on dry land available). He gave me the confidence to carry on, and on we both went in our separate ways.

On the last stretch of the Barker’s exploration, I found the beach. It’s worth a trip to the park just to see its natural beauty. Grape trees, pines and other trees covered the landscape and white sand led out to turquoise waters. There was turtle grass in the shallow waters, so not as great for swimming as Seven Mile Beach, but it would make a great picnic spot. I did pass a couple of parked vehicles on the beach as I exited the park which looked like locals likely soaking up the serenity. I also passed a group riding into the park on horses (another popular activity that leads to Barker’s Beach).

Lunch at Macabuca

From Barker’s I took the outer most road through West Bay and headed towards my favorite island bar for lunch—Macabuca. On the way, I passed by sweet West Bay homes and spotted some beautiful trees with orange blossoms in bloom. Walking into Macabuca, I was greeted with its ever present laid back vibes. Kenny Chesney tunes were floating in the air, as I pulled up a chair at the bar. I placed an order of coconut ceviche and a coke and kicked back for few while I waited. After I polished off the ceviche, I enjoyed a chat with a local West Bay resident and then hit the road again.

Pit-Stops at CCC, Island Naturals Cafe & Cathy Church’s

I headed towards Seven Mile Beach and with CCC being on my perimeter route I had to make a stop for good measure. I grabbed a selfie with the bright red turtle, and took a couple of photos of the beach which looked incredible as always.

With a full day of driving and exploring still ahead, I decided to grab some caffeine at a coffee shop I had been wanting to try. Island Naturals Cafe is located in a strip mall along the Seven Mile Beach corridor accompanied next door by sister retail shops of the same name (the downstairs retail shop selling health products and the upstairs a gift shop). I ordered a vanilla breve to go and hopped back in my trusty SUV. Next stop unknown.

Continuing my perimeter route of the island I passed through George Town. Shortly after I spotted a sign for Cathy Churches Photo Centre (located at Sunset House). With spontaneity in full swing I pulled into the Sunset House parking lot, and went inside to browse. Cathy Church is a renowned underwater, diving photographer. I was excited to see her work, and lo and behold she was there! It was lovely to get a chance to talk to her and enjoy her energetic banter with visitors. Aside from Church’s amazing photo displays the Centre also sells and rents all kind of underwater camera equipment and resources. I found a book recommended by Nancy Snowden in our recent snorkeling tips post and picked up my own copy: Reef Fish Identification by Paul Humann.

Road Side Stops for Mangoes, Beach Views & Art

Traveling from the photo centre to the East End, opportunities for stops were plentiful. I had a mission on this stretch of the trip. I wanted to find farm fresh mangoes, and Lisa (our property manager) had told me two places to look. She said that there was a produce seller that often setup near the Spott’s cruise terminal and another that setup where Frank Sound Road meets Bodden Town Road. Spott’s came first and Lisa was right on the money. I found a produce stand and I found mangoes! Here I got East Indian Mangoes.

On my way to the second fruit stand, I pulled over at Governor Russell Beach to take 5 and appreciate the beautiful day. I love the public beaches that dot the coast. They almost always have a pavilion or two painted in happy colors. This beach was small, and right on the road, but nature was still in full bloom. Palm trees, purple bay hops and pines surrounded the setting. There were also a few really neat fossilized rocks.

Back on the road, I made another game-time decision to pop back into a dreamy art studio my husband and I found in 2019. With just a sign that says “Art” and an arrow at the start of a winding gravel road we didn’t know what waited for us at the end. Our curiosity was peaked and well rewarded with Kay Smith’s lovely art studio (incredible beach views included). This time I knew exactly where I was going and had a nice visit with Kay plus go to say hello to my favorite painting again, Modern Girl—Kay’s updated version of Girl with a Pearl Earring. The subject is very reminiscent of the original except she has additional piercings and earrings.

Bookending the art shop with another produce stand stop, this time I found Willie’s Farm Stand and many varieties of mangoes!

A Special Menu Item at Eagle Rays

Entering East End I was on another mission: find Eagle Ray’s Bar and Grill and try their Lion Fish Tacos! Lion fish are an invasive, prolific species in the Cayman waters, and Eagle Ray’s is one of the few restaurants that’s serving them up. Choosing this item off the menu is a very sustainable choice. I wanted to see if they were any good. I’m happy to report that they were delicious! Plus they had tiny fries on top. How can you go wrong with that?

Incredible Island Flora & Peaceful Drive Time

From the East End I slingshotted around the island to the North Side. This stretch of the island is very quiet and peaceful. After spotting a few more of the “orange flowered trees” that were in blossom across the island I decided the next time I saw one I was going to pull over and have a little photoshoot. And that I did. The next tree I spotted was at the edge of a residential property on the road. I took several photos of the gorgeous tree, and then a man from inside the house waved a big friendly “hello” as I walked back to my car. I was “caught” and we both laughed. Lisa later informed me that these trees are poinciana trees and that they bloom every summer in Cayman.

Chasing the Sunset to Starfish Point

As I headed toward the North Side the sun began to get lower and teased that sunset was near. Driving as close to the perimeter of the island as I could I was getting to enjoy peeks of it dancing on the ocean through trees and clearings. By the time, I was nearing the north point of the North Side I was essentially chasing the sun. I wanted to find the best place to watch it set. I could see it as I drove and was calibrating where I needed to be for a good view. I chased it and ended up at Starfish Point.Only when I parked I could no longer see it. I walked the path through the pines (no one else in sight) and out to the edge of Starfish Point.

To my initial surprise I found several people at the end of the path there for the exact same reason, to watch the sunset. Most had boated to this shore point, and a couple others looked as if they had walked there, too. We all enjoyed an incredible sunset together, and I quickly understood why so many gathered at this point to watch it.

After the sun retired below the horizon I headed back to my car, walking back by the starfish beach. I waded into the water and found a couple 5 pointed friends holding down the fort and the beach’s namesake. It was a joy to see them in the first light of twilight, and there I decided today had been a very good day.

Night Cap at Czech Inn Grill

I hopped back in the car at Starfish Point and headed home to Christopher Columbus Condos. On the way back I pulled over for a “night cap” at Czech Inn Grill. Since I was driving that night cap consisted of a caprese salad and a coke. I enjoyed the banter of the barkeep (whom I think was likely the owner) and the others at the bar.

Towards the end, I was joined by a young woman who had just finished her serving shift at Welly’s. We had a nice chat. I asked for my check and discovered that while Czech Inn Grill will let you pay with a credit card, one can only tip in cash. Fresh out of cash (all spent at the produce stands) the bartender told me, “no worries, next time”. But I hate not tipping, so I racked my brain to think if there was anything else I could leave. “Do you like mangoes?” I asked the bartender. “Love them.” he responded.

I went to the car and grabbed a couple of the East Indian mangoes acquired from my day of adventure and passed them over the bar to him. He gave them a smell (a trick I’ll use next time) and delighted with what he smelled he told me which one he thought was best. It was definitely the first time I tipped in mangoes, and I don’t plan to make a habit of tipping in fruit, but this will remain a happy Cayman memory.

I arrived back at Christopher Columbus Condos around 9:00 p.m. very satisfied with my day of adventure. Looking back on it now, I cannot wait to do another “perimeter” road trip—next time with my husband or a friend along for the ride. There are hundreds if not thousands of different ways to do this trip. If not solo, I’ll definitely add a snorkeling and swim stop. I think I’ve found a new Cayman tradition. Next time you’re in Cayman, take a roadtrip and let us know where it takes you and what you discover!