Last spring my husband and I got married in St. Thomas with a small group of family and friends. Since that time, several of those friends, along with my husband’s parents, have been saying “we have to go back” (an inside joke from Lost) because vacationing together in the Caribbean was such a great time. As… View Article

Travel Diary: Grand Cayman Island

Location: Grand Cayman Island

Last spring my husband and I got married in St. Thomas with a small group of family and friends. Since that time, several of those friends, along with my husband’s parents, have been saying “we have to go back” (an inside joke from Lost) because vacationing together in the Caribbean was such a great time. As the weather descended into typically dismal temperatures in December, I made the decision to plan a trip with those friends and Curtis’ parents to the Caribbean this winter. After some poking around, I decided to give Grand Cayman Island a try, partially because it’s farther south in the Caribbean and we wanted to go in February, when the weather is crumbiest in Chicago.

We found a rental house using VRBO (a favorite of ours) that looked beautiful. It was situated on the North side of the island–far from the overly touristy and cruise-ship-heavy west side–and had a private pool, private beach, and a bathroom for each bedroom. We were sold. In all, there were six of us: myself, my husband Curtis, my “man of honor” and longtime best friend Brandon, Curtis’ best man Andrew, and Curtis’ parents Pat and Candy.

cayman island vrbo rentalcayman island sunset clouds

We flew out on a Saturday morning and landed by mid-afternoon after a short stop in Atlanta. The weather was a bit blustery–we found out on arrival that it was a bit colder than usual. After a brief stop at the liquor store (where much rum and mixers were purchased) and the grocery store (where many snacks and dinners to be made on the grill were procured) we made the 30-minute drive across the island to our rental house.

cayman island beach plum villa vrbo rental

The house was a dream–beautiful and airy with large rooms, a huge deck, a private pool, a set of private palapas, and a private beach. We would have been utterly in heaven had we not gotten unlucky with the weather. As it turns out, the north side of Grand Cayman Island can sometimes fall prey to wind storms. The weather was still warm, but the wind, at 25 – 35 miles an hour, made it feel chilly. We found on arrival that the pool wasn’t heated. Had there been no wind, this would have been fine. With the wind, it was a bit too chilly to spend much time in.

cayman island windy swimsuitcayman island brain coral

I found a sunny patch somewhat out of the wind on the side deck of the house, and enjoyed my first drink on the island–a Goombay Smash. We spent the first night unwinding, having some drinks, and exploring our beach. Brandon told me he liked “brain” coral, so I searched for the most brain shaped coral I could find.

cayman island sunset ocean
german flavor mambas

We had grilled salmon for dinner the first night, followed by Mambas for dessert. Brandon works for the German company Stork (you probably know them as the company that makes Worther’s Originals) and had brought along some of their more interesting German flavors. We ended up snacking on these throughout the trip.

cayman islands striped bikinicayman islands striped bikini
bikini Target (top, bottom)
black wide strap bikini bottoms Target
cateye sunglasses Target

The next morning I awoke with a stomachache–nothing too serious–but bad enough that I ended up sleeping most of the morning away. It was another windy day. The sun was out, so it was still relatively warm on our deck, but the wind was a nuissance. A quick look at the weather told us that we’d be dealing with wind storms this day and the next, then we’d have several gorgeous days mid-week, then we’d be back to a few breezier days at the end of the trip. But that said, the first few days were decidedly the worst. We made a plan to visit Rum Point, a bay on the north side of the island very close to us, that day and to explore Seven Mile Beach on the west side of the island the following day.

With that decision made, we suited up to head to Kaibo Beach Bar on Rum Point for some lunch.

cayman islands striped bikini
cayman islands striped bikinicayman islands striped bikini
kaibo beach bar cayman island rum pointcaybrew

We ordered a bucket of local beers at Kaibo, which had a nice relaxed beachy setting. Our waitress was very nice, and as it turned out, she was from France. We later discovered that almost everyone in the tourist industry on Grand Cayman was from another country and just spending some time working there. This was a bit different from what we were used to throughout the Caribbean. On most other islands we’ve been to, the people living and working there were actually from there. This might be because the Caymans weren’t actually settled until much later than most islands in the Caribbean.

kaibo beach bar
kaibo beach bar cayman island rum point white tip lager buckettwisted citrus kaibo beach bar
ceviche kaibo beach bar

Curtis ordered the ceviche for his lunch. I had a nice mahi mahi sandwich that I totally forgot to photograph before I wolfed it down. After my stomachache subsided my hunger came on strong.

kaibo beach bar cayman island rum point mudslidestarfish point cayman islands

There are several restaurants and beach bars on Rum Point, and they all have one thing in common: the mudslide. Apparently it’s a featured drink for all of them. Brandon and I each ordered one and were very happy with them.

starfish point beach cayman

After our lunch, we decided we wanted some active beach time. I asked our waitress where a nice local beach was on Rum Point and she pointed us in the direction of Starfish Point–a place mostly known to locals. It’s just a small beach at the end of an almost unmarked trail where starfish tend to congregate. We discovered on arrival that there have been fewer starfish there of late. We also discovered a giant party yacht docked not far from the beach. We found a spot that was somewhat far away from the yacht and the boys tossed around a football while I soaked in some late afternoon sun.

starfish point cayman islands volleyball

We brought a volleyball with us too, and we all ended up playing pepper in the water. Andrew was particularly good at this, though I have to say some of my old volleyball skills from high school definitely shone through.

sunset starfish pointcayman island conch
cayman islands palazzo pantscayman islands plazza pants porch
palazzo pants Popana
sleeveless top Banana Republic (similar)
bracelet Official Larimar Shop (c/o)

After we got back from Starfish Point we decided to bust out some of the Cuban Cigars we had purchased when we first arrived. I know that this isn’t a very common thing for a young lady like myself to enjoy, but I think cigars are great. I don’t smoke them regularly (trust me, I know the dangers of too much smoking) but on occasion they can be exactly what I want–like a cup of black coffee or a good scotch. Smoking a cigar in the Caribbean with a drink in hand is one of lifes many pleasures.

over the edge turtle entree

That night we decided to go to one of the restaurants in the area that had good reviews: Over the Edge. It was a relatively low key place–and pretty dark, as you can tell from the quality of these photos. I ordered a Cayman Lemonade (apparently lemonades are the drink of choice on Cayman Island much like Bahama Mamas are the drink of choice in the Bahamas) and quite enjoyed it. For dinner, I decided to go with something local and ordered the turtle steak entree. It came with a nice big salad and a tasty sauce, but I have to say I didn’t overly enjoy it. Turtle is just too tough a lean a meat to make into a good steak–it was very chewy. Brandon and Andrew both ordered fish and quite liked it, so I’d stick with that if you ever eat at Over the Edge.

over the edge rum cake dessert

Rum cake is one of my favorite desserts. In fact, my wedding cake was a set of rum cakes. During our stay on Cayman Island I had just about as much rum cake as a person could have. I ordered it for dessert at Over the Edge and it was enjoyable as always.

cayman island beach runcayman island

The next morning I woke up feeling great and started a morning ritual that I kept up for the rest of the trip: I went for a long run on the beach. The beaches in our area were a bit rocky and seaweed strewn, so it was lucky I brought my running shoes (I actually always run on the beach with shoes on–I don’t like the feeling of running barefoot). It was amazing how different the beaches were each morning depending on the tide. Some mornings I had huge expanses of sand to run on, others I was basically running in the grass at the edge of the beach, the water level was so high. Either way, I loved starting the day with a good endorphin-releasing workout, and the views along the beach were spectacular.

cayman island breakfast oceancayman island mimosa by the pool

After a nice breakfast of eggs and toast we broke out the champagne and made mimosas. We spent the morning relaxing by the pool–the winds were already down a bit–and listening to music on the bluetooth speaker Curtis brought.

cayman island smoking cuban cigar

We decided to break out the cigars again and we all sat together in the sun enjoying them and having a great time.

cayman island smoking cigars with the family
seven mile beach group cayman island selfie

Around mid-day we packed up and drove toward 7 Mile Beach. We stopped at a place called Ever-Glo for lunch as a bit of a joke. It looked like a place to get good jerk. It was kind of bizarre once inside though–I think it probably functions as more of a night club–but the food actually was quite good and seemed authentic. I had oxtail rice and beans.

After that, we soldiered on to the north side of 7 Mile Beach and parked at the public beach there. We walked for a while down the beach and eventually put down our towels near the Hilton. The boys played in the water and I went to the bar to grab some drinks (I had another Cayman Lemonade–delicious if overpriced).

seven mile beach group cayman island
sunset seven mile beach swimmingsunset seven mile beach

We spent the rest of the afteroon relaxing in the sun. Eventually we all went together to the Hilton for happy hour–a big thing on Cayman–and had a few half-priced beers. The crowd there reminded us of why we had wanted to stay on the far side of the island, though. There were too many tourists making pushy and entitled demands for drinks. Still, we had a good time and tried to befriend the harried bartenders.

cayman island tortuga rum cake box

On our way back we stopped to do a bit of shopping, including buying more rum, more cigars, and a rum cake. Tortuga cakes are made on Cayman and are pretty much what everyone served there. Brandon and I decided we had to pick up a box. You can see below how quickly it went, it was so delicious! I made the mistake of looking at the calories afterward, though. As it turns out, Tortuga Rum cakes are decidedly not a low-calorie food.

That night we had home grilled hamburgers. I fried up some bacon and carmelized some onions for topping while Curtis and his dad manned the grill. There were fantastic. Maybe it was something about our long day in the sun, but we all agreed they were just what we all had been wanting.

cayman island tortuga rum cake

After our big hamburger and rum cake dinner we were all feeling lazy, so we poked around Netflix, decided on Dodgeball (which I thought was surprisingly pretty good) and had a lazy evening in.

cayman island palms
cayman island coverupcayman island coverup
coverup H&M (similar)

The next day, Tuesday, was the day the weather broke. Early in the morning a rainstorm rolled through, dampening all of our spirits, but when it ended the weather turned gorgeous. We spent the rest of the day in the pool and in the ocean.

cayman island sunbathing
cayman island pink bikini pool bloody marycayman island

That’s Andrew’s hat chilling by the pool. And that’s a bloody Mary in my cup, in case you’re curious.

cayman island swimming in the north side ocean

That evening we had delicious steaks grilled by Curtis and his dad (seriously, they’re the masters of steaks) and another quiet evening in. The following day was much of the same: drinking, relaxing, and partying by the pool.

cayman island off the shoulder topcayman island palazzo pants
palazzo pants Popana
off the shoulder top Forever 21
sandals La Dolce Vita
sunglasses Target
bracelet Official Larimar Shop (c/o)
earrings Kenneth Jay Lane
lip Burt’s Bees (Niagara Overlook)

That night we decided to have dinner at Tukka, an Australian restaurant on the far east side of the island. I had read that they do a four course “walkabout” dinner on Wednesday night and was intrigued.

I put on this breezy, comfortable outfit for dinner. As I explained in the full outfit post, it’s important to keep your legs covered during the evening in the Caribbean to fend off sand fleas. The pants did a great job of that, while being comfortable, bright, and tropical. They were one of my favorite clothing items that I brought along on the trip.

cayman island off the shoulder top
cayman island larimar braceletcayman island palazzo pants
cayman island sunset
cayman island tukka walkabout dinner appetizer

Apologies in advance for the low quality of these photos–it was a very low-light dinner and we were using our phone cameras.

The setting at Tukka was phenomenal. The restaurant sits along a short cliff at the edge of the ocean, and nearly all of the seating was on a very long balcony overlooking the water. During our meal, we actually got to watch a shark swimming in the ocean.

The meal was no less fantastic. We all did the “walkabout” dinner, which was a four course Australian/Cayman meal. It started with a plate of three appetizers. From left to right: ceviche, an eggroll “cigar” (I can’t recall the filling), and a conch fritter. The conch fritter was probably my favorite, though they were all quite good.

tukka walkabout dinner appetizer conch balltukka walkabout dinner soup

After a refreshing palette cleansing soup, we had our entrees which we were all too excited about to photograph, apparently. I had an Australian fish, barramundi, which was excellent, and several of the boys had the lamb/beef skewer.

cayman island tukka walkabout dinner dessert

We finished the meal with one of the best desserts I’ve ever had. This is the plum pudding–which basically was a sticky pile of delicious chocolate cake–with a caramel sauce. I was in heaven.

cayman island docks ocean

I went for an extra long run the next morning after our big meal at Tukka and settled in for another relaxing pool day.

cayman island coffeecayman island lizard

These little lizards were all over the place on Grand Cayman.

cayman island swimming with a glass of wine for national drink wine day

As it turns out, it was National Drink Wine Day, so we decided we might as well partake. We even took our wine for a swim in the ocean. One of my favorite memories of the trip is chatting with Pat while floating on the waves, glass of wine in hand.

cayman island victorias secret colorblock bikinicayman island victorias secret colorblock bikini
colorblock bikini Victoria’s Secret (top, bottom)
surf sunglasses Target

This may be my favorite bikini I brought on the trip, largely because I love the colorblock trend so much, and because I love soft pink hues.

cayman island victorias secret colorblock bikini
cayman island victorias secret colorblock bikinicayman island victorias secret colorblock bikini
cayman island sunset palmscayman island rose
cayman island north side waves

The next day, Friday, was a bit windier again, so we decided to adventure out and have lunch at a small but highly recommended place, then go snorkeling on the south side of the island.

cayman island vivines kitchencayman island vivines kitchen

For lunch, we drove back over the east side of the island to try Vivin’s Kitchen. It was a tiny place–literally just two women running a kitchen out of their house. You eat at picnic tables in the back yard. We’d heard it was the most authentic food we could get, so we had to try it.

cayman island vivines kitchen beef soup mango juice lunch

Curtis ordered the oxtail soup, which was very savory and delicious, as an appetizer and I had a freshly squeezed mango juice, which was really quite good.

cayman island vivines kitchen chopped fish lunch

I ordered the chopped fish for my lunch–almost everyone else got fried fish. I enjoy a good many unhealthy things to eat, but fried food isn’t generally one of them, so I decided to save calories where I could. The chopped fish was interesting–good but not insanely good. It had a nice jerk seasoning on it. I particularly liked the rice and beans, which were flavored with coconut (Cayman style) and the varied vegetables on my plate, most of which I couldn’t identify. I love trying new things.

I did try a bite of Curtis’ fried fish and it was quite good, in case you’re curious. Candy ordered the fritters, thinking they were conch fritters. In reality they were just fried bread, which is a Cayman thing. Basically they tasted like unsweetened donuts, and were actually quite good.

cayman island tropical flowerscayman island palm leaves
cayman island wreck of the ten sailscayman island wreck of the ten sails

We played tourist on our drive down to Spott’s Beach–where we were headed for snorkeling. We stopped at the Wreck of the Ten Sails. Apparently a ship sank here sometime in the past. It wasn’t really worth stopping to see.

cayman island blow holescayman island blow holes

We also stopped at the Blow Holes–literally just rock formations that cause a lot of spay when the waves hit them. They were also not really worth stopping to see.

cayman island spotts beach

We had a great time at Spott’s beach–the water was calm and the wind wasn’t nearly as strong as it was on our side of the island. Curtis and Brandon went snorkeling and saw a few interesting things, including a pod of cuttlefish. Candy and I went for a walk along the beach and just drank in the sun and beautiful views.

cayman island chickens everywherecayman island sand mermaid

Here’s something you probably didn’t know: Grand Cayman has chickens running around it everywhere. Seriously, they’re like pigeons. Our neighbors at the beach had managed to open up a coconut from one of the palms, and when they weren’t looking a pair of chickens came to inspect their cache.

cayman island spotts beach
cayman island spotts beach
cayman island spotts beachcayman island smoothies at everglo

On our way back from Spott’s beach we stopped at Ever-Glo again. When we had lunch there Curtis discovered, from talking to a local, that the stand outside made great smoothies. The boys all wanted another one (I’m not that into smoothies, so I passed). They were quite good though–they had lots of fresh fruit and crushed peanuts as a secret ingredient.

cayman island sunset beachcayman island sunset beach drink
cayman island sunset

That night we had another quiet evening in. We made fajitas for dinner, polished off the rum cake, and watched The 40 Year Old Virgin (another movie I hadn’t seen, but I didn’t like it nearly as much as Dodgeball).

cayman island breakfast

The next morning dawned on our last full day on the island. We made as much of it as we could. We spent the day drinking by the pool again–listening to music and having a great time.

cayman island hermit crabcayman island hermit crab

Andrew spied this little hermit crab on the beach during the day. We tried not to disturb it while we snapped a few pictures.

cayman island pool selfie
cayman island docks
cayman island white tropical floral dresscayman island white tropical floral dress
dress Forever 21
bracelet Official Larimar Shop (c/o)
lip Burt’s Bees (Niagara Overlook)

For our last dinner on the island we decided to go to the Lighthouse. We had read rave reviews, and thought a nice dinner on our last night would be fun. I wore this white wrap dress I found at Forever 21 with a nice bright larimar cuff.

cayman island white tropical floral dress
cayman island photoshootcayman island white floral dress
cayman island photoshoot
cayman island sunset oceancayman island lighthouse menu
cayman island lighthouse julepcayman island lighthouse seafood platter

The Lighthouse has a gorgeous setting–you eat right out on a dock over the ocean. It was beautiful to watch and listen to the waves roll in all around us while we ate.

They’re known for their juleps, so I ordered their blueberry version. It was quite good. We ordered the house bread to abate our hunger while we waited for our food, and that was defiitely worth it as well.

Curtis and Andrew shared the house seafood special for dinner, pictured above.

cayman island lighthouse pirate pasta

I ordered the Pirate Pasta for dinner. It was a mixture of seafood–scallops, mussels, clams, shrimp, and lobster–in a nice sauce with linguine. It was sublime. I actually finished my plate–not something I usually do when I order pasta.

cayman island ocean
cayman island vrbo rental beach plum villa

We were sad to pack up the next morning. So sad, in fact, that after we had packed everything up we actually unpacked our swimsuits and sat in the pool until our 11 AM checkout time came. We smoked our last cigars, finished off the rum and beer, and drank in the amazing weather (of course the weather was beautiful on the day we left, ::sigh::). It was so hard to leave.

cayman island athleta dress
cayman island athleta dresscayman island athleta dress
dress Athleta
surf sunglasses Target
sandals La Dolce Vita
bangles Charming Charlie
ring Charming Charlie
clutch Etsy
cayman island tropical print purse
cayman island ironshore beercayman island chicken at kfc

We drove into Georgetown for some last minute shopping and lunch before our flight home. We actually saw some chickens hanging out direclty outside the KFC downtown and had a good laugh about it.

cayman island margaritaville georgetown

We had lunch at Margaritaville, which is not a place I would normally ever choose. On Sundays, though, nearly everything is closed on Grand Cayman so we had limited options. Margaritaville did have a nice balcony, though, and a menu with lots of options. It was actually a pretty nice experience, overall. We enjoyed watching the tourists from the cruise ship wander around, and the reuben was excellent.

cayman island margaritaville georgetown reuben
cayman island airport barcayman island airport

If you ever go to Grand Cayman Island, make sure to hit the airport bar on the roof of the aiport. It’s quite nice. They have a good drink menu, daily specials, and a nice viewing deck. I actually got to watch Pat and Candy’s plane take off while we waited for our flight.

All in all, we had a stellar time escaping the Chicago winter in Grand Cayman island, and I can’t wait for our next sojourn in the Caribbean.

cayman island airport

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4 Comments and Pingbacks for Travel Diary: Grand Cayman Island.

  1. Wow! Looks like an amazing trip. I love your bikinis and the coverup. Great job documenting.

    Traci on March 15, 2016   /   Reply
    • Thanks, Traci! I love to be able to relive a trip through the photos!

      Joules on March 15, 2016   /   Reply