48 Hours in Cayman Islands | Top 5 Recommendations

1. Book your stay in advance. 

As anyone who reads my posts knows, I love to be spontaneous. Because of this, I was taken aback by how strict the Cayman Islands government is with not having prearranged travel accommodations. I am probably in the one percentile, but I generally don’t book my stay until I get an opportunity to explore the area. Yes, you could say that is what research prior to going to the airport is for, but the discovery of the attractions (breweries, museums, beaches, architecture, etc.) has always been much more appeasing to me as opposed to immediately going to the hotel to drop my belongings off after landing at the airport. This time around, I was forced to leave my passport at Border Control, walk over to the Tourism area and make a reservation at a Holiday Inn before they let me proceed onto my adventures in the Cayman Islands. Like I said, this advice probably won’t be that helpful to many of you, but be sure to have your accommodations in place before traveling here.

2. Budget for pricey transportation and food.

The taxis are fairly expensive on the island, but I had no interest in driving on the opposite side of the road or trying to find my car in a parking lot with several beachgoers. I paid the $30.00 from the airport to Cypress Pointe. There are also a number of public busses that serve the area that are a little more affordable if you’re just going up the street. But, the weather is gorgeous here so it didn’t bother me to walk from place to place—although if you are walking several miles, be sure to bring some water because the blistering heat can be overwhelming.

3. Don’t skip the city!

When I got into the city, there was a parade on the main strip. Reggae music was blasting, people were clapping their hands and stomping their feet, the sun was beaming and everyone was just in a joyous mood. As much as I wanted to go to Seven Mile Beach right away, I was tempted to stand on the sidelines and watch the floats pass by and everyone in the parade high-five the crowd as they danced to the Caribbean beats.

4. Seven Mile beach is a great spot during the day and at night.

Later that afternoon, I got out my sandals and walked over to the beach and stopped at a bar. The sun was glistening and there were several people laying in lawn chairs while other locals got in their fitness by running against the wave’s splashes from the beautiful blue Caribbean with liberating tunes playing in the background. Paradise. I enjoyed some of the local beers (White Tip Lager) and devoured some of their delicate Caribbean Jerk and rice. It is fairly pricey on the island, with just a beer and meal costing you nearly $25.00.

There are several public areas on the beach, but there are also restricted areas across the seven miles of the beach. There is also a popular beach nightlife spot (Calico Jack’s) that partygoers go throughout the day. I would say there were definitely more nightlife opportunities on this island compared to other places I’ve been in the Caribbean. However during the daytime, you can’t sit in the lawn chairs on the beach unless you pay $5.

5. Snorkeling and swimming with the stingrays is a must-do.

The highlight of the trip was making a reservation through Captain Marvin’s and heading to Sting Ray City. For $45.00, a bus takes you out the boating dock and the two crew members lead you onto the beautiful crystal clear Caribbean Sea. The first stop was at Coral Gardens and we parked in the middle of the sea isolated from all worries. Stress-free, relaxed, and in awe I looked out into the vast sea and grinned knowing that I was in for a treat with this being my first time snorkeling. I put on my gear, jumped into the sea, and immediately put my head under water. It was as if I had stuck my head into a real-life aquarium as various fish swam past me and I swam around the coral reefs to avoid disturbing them from human touch. The next stop was at Barrier Reef where we got another opportunity to snorkel. This is area on the edge of the North Sound — where we got to maze in between more coals, make friends with additional species of fish, and watch in awe as the majestic waves crashed along the surrounding barrier of the Sound. It was almost as if we were on a beach watching the waves come up to the sand, but instead we were far from shore in the middle of the Caribbean Sea. It was jaw dropping!

The best for last — Stingray City.  We pulled up to an area where there were five other boats tied up near each other enjoying the beautiful Saturday afternoon at a sand bar. Our tour group parked about forty feet away from the other boats as the crew members threw squid into the gigantic swimming pool to attract the string rays. The water was about two feet deep and it was so unbelievably clear. I have not seen anything like it before. We jumped off the boat as stingrays created their own parade coming towards us. Everyone let out a shriek in excitement as the very docile and unique looking creatures swiftly swayed their bodies across us just to say hello. Everyone took turns taking pictures as stingrays maneuvered onto our shoulders. We also proceeded in kissing the stingrays as it provides you with seven years of prosperity. Before we took off, we fed the stingrays squid from our hands, it was interesting to learn that their eyes and mouths are on opposite sides of their bodies.

The Cayman Islands is a perfect vacation spot and I can’t wait to go back. The next thing to do on my checklist is to go further north and tour the Turtle Farm.


About the author

As an employee for a world-class airline, Matt is able to travel the world via free standby flights. Originally from Wisconsin, Matt now lives in the Logan Square neighborhood of Chicago and loves the Green Bay Packers. He's TravelSages' expert on how to navigate the top experiences a city has to offer in a limited time, on a limited budget.

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