We have started a tradition in my family that our kids get to pick a 16th birthday trip. My oldest son is named Cayman. Where else is he going to pick, but the Cayman Islands! Despite his name, none of us had ever been to the islands. Since we were all scuba certified, it was a perfect choice for spring break 2022. What I didn’t prepare for was the adventure we would have just getting there!
Nightmare at the Airport
We pulled ourselves out of bed in the middle of the night for our 5:20 am flight. I thought we allowed plenty of time for our early morning flight. What we didn’t factor was labor shortages (thanks Covid) with economy parking bus drivers. It felt like one of those nightmares you have the day before a big trip, but unfortunately this was our reality. We called dispatch multiple times; they kept saying someone was on the way and we kept believing them. One bus came and completely skip our stop because they were full. A driver finally picked us up after over an hour waiting and the race was on.
The airport was in complete spring break chaos. My family has TSA pre-check and we can normally roll through the check in process quickly. Since our final destination was international, we had to show passports in person before getting a boarding pass.
Note – I have traveled internationally several times recently. Every other airline allows you to upload/verify your passport and travel documents via their app. Southwest Airline’s app at the time of this writing still doesn’t electronically verify for international travel.
We couldn’t check in via the electronic kiosks that scan passports. We were not within the check-in time for an international flight (even though our first leg was domestic). Our only hope was the ticket agent who was diligently trying to help. He quickly got us checked in, tagged our bags and started printing our boarding passes when the system “kicked us out” of the flight. After that happened two more times, he checked with his supervisor. Apparently the supervisor was behind the scenes pulling us off the flight. Even though we had time to check bags, get through security and board, he decided that was the day to take a hard line on the published check in time for international destinations.
Devastation
We were devastated. At the time of our booking there was one flight a week to Grand Cayman on Southwest. We had no way to get to Fort Lauderdale and make our connection. Imagine your kids dreaming about and planning their special 16th birthday trip for years and having it disintegrate in front of your eyes.
Frustrated by his supervisor’s decision, our ticket agent immediately tried to help us to find alternative solutions. He found one flight Southwest added the next day between Fort Lauderdale and Grand Cayman. But, there were no flight options (on any airline) to get to Fort Lauderdale. We were not ready to give up. We pulled up Google Maps. It showed a 21 hour drive (without stops) to Fort Lauderdale. We decided to go for it! We took the bus over to the car rental center to start our driving adventure.
Road trip to Grand Cayman?
Now we had a new plan and path to get to Grand Cayman, but it was not a done deal. We factored 21 hours of driving plus an hour time change to Eastern time. What we did not factor was:
- Car rental center didn’t open until 6 AM and was also short staffed
- Wreck on I-70 shutting down the interstate causing a two-hour delay
- That night was “spring forward” for daylight savings time so another hour gone
- Our pre-travel Covid tests were no longer going to be within 24 hours of our travel
We got the last car available at the car rental center; car shortages were still an issue due to Covid. After loading into our Jeep Compass (not recommended for a cross country trip), we were off.
Our kids were troopers. We traded off one adult driving in 4 hour shifts with one kid in the front keeping us company. We stopped only for gas and quick bathroom breaks. The best meal we had all day was a subway sandwich (to-go) attached to a gas station. We drove across Missouri (saw the arch), Illinois, corner of Kentucky, across Tennessee (went by the Grand Ole Opry). It was dark by the time we hit the Smokey Mountains and then through Atlanta. All along the way we were checking flights in St. Louis, Nashville, Atlanta, but nothing was available. By the time we hit Orlando we stopped trying to find flights and knew we would just drive it the rest of the way.
Another Road Block
We followed storms the whole drive, but thankfully had clear skies and dry roads. I took the 12 AM – 4 AM driving shift and was ready to switch out and let Tim drive us the rest of the way. When I woke Tim up for his shift he was sick to his stomach – too much gas station food. He felt bad enough that was ready to call it for the night. We were so close, I wasn’t ready to give up. Cayman had his learner’s permit, but we were not going to have our 15 year old drive a rental car at 3 AM out of state! I had to step up or give up.
Not my finest moment, but I went into the gas station and loaded up on Skittles and Frappuccino. This combo jolted me back awake enough to drive us the rest of the way. At one point Cayman expressed concern that my hands were shaking. I had to explain it was from the caffeine and sugar my body wasn’t use to!
Finally, we made it! We pulled into the car rental center, but we had no time to waste, we were still not home free.
More Covid Challenges
I had tried to call Southwest Airlines multiple times throughout the day/night to try to verify our Covid test would still be valid. I never got a clear answer. When we got to the counter and tried to check in, we were turned away because our Covid tests were now 36 hours old! Luckily, I had made appointments at the Covid testing center in the Fort Lauderdale airport just in case. We were again racing the clock. We mustered up the final push of energy after our all night cross country drive to run between terminals to get our Covid tests. After our tests, ran back to the ticket counter and waited for our results. We got our negative email results with about 10 minutes to spare!
After all of the rush, our flight was delayed! We didn’t mind, we were checked in and ready and were able to sit down and relax. We missed the first day of our trip in Grand Cayman. But, our over night road trip across country created a different kind of memory that we can now laugh about as a family. If nothing else, Cayman can say we did everything in our power to give him his 16th birthday trip!
Pre-Trip Planning
Where to Stay
When most people say they are going to the “Cayman Islands” they really mean Grand Cayman. Cayman Brac and Little Cayman are also part of the island chain. These are smaller less travelled islands that are known for scuba diving. For us, Grand Cayman had everything we wanted in one package; great beaches, scuba diving, shopping and restaurants without additional travel hassle.
On Grand Cayman, seven-mile beach is the most popular area to stay between Georgetown and West Bay. If you don’t plan to get a car, you want to be in the heart of seven-mile beach so you have restaurants and activities within walking distance. If you want to get away from the crowds, you may want to avoid seven-mile beach, although the crowds aren’t bad and it is family friendly even during spring break.
We knew we wanted easy access to marinas and activities, but we didn’t want to be in a bunch of traffic or crowds. We stayed at Discovery Point Club on the far north end of seven-mile beach close to West Bay. For us it was a perfect location where we could get a two bedroom condo with a kitchen, amazing beach, and quick drivable access to marinas and restaurants.
As you go further north in the West Bay area there are more coral formations off the beach for snorkel opportunities. From Discovery Point we could walk and swim to amazing snorkeling. If you want to ensure nothing but soft sand as far as you walk in the water (and don’t care about snorkeling from your lodging), you might want to stay a little further south on seven-mile beach. As the snorkeling gets better, so does the chance of rock/coral washing in.
What to Expect
Grand Cayman is expensive! Going spring break and staying on seven-mile beach, we knew we were paying a premium. If you go off season and stay on the North or East end, you could do it cheaper; but if you are looking for a low-cost trip you should look elsewhere. One thing that is affordable on the islands is diving, especially for shore diving. You can even find some dive friendly hotels that do packaged dive trips if that is your focus.
Grand Cayman is laid back and family friendly. You don’t have to worry about wild spring break crowds. It was a great introduction to traveling internationally for my kids. They speak English and most places take both the US dollar or Cayman Islands (CI) dollar. The island is safe and the people are friendly. It was a learning curve to drive on the left side of the road, but the roads are well maintained and they even help tourists by painting large arrows on the road to follow. I do recommend renting a car as there are a lot of things to see across the island. If you are in the middle of seven-mile beach you could get away with not having one if you don’t want to explore around.
One note about mosquitos – no one warned me that Cayman Islands is covered in them. It really wasn’t an issue except at dusk, but they came out quick. Our condo left bug spray out at the tables for guests to use and we did! We tried to watch the sunset from our beach chairs and couldn’t do it without bug spray.
Check out this link for more info on what to expect in Grand Cayman.
Travel Requirements
The Cayman Islands were hit hard with Covid. By March 2022 life was pretty much back to normal in the US, but the Cayman Islands were just reopening to visitors. We had a lot of hoops to jump through applying for traveler certificates, obtaining required travelers’ insurance with Covid coverage, submitting vaccination records, and video proctored pre-travel Covid tests. It was a lot even for someone like me. Luckily, those requirements have been dropped. It is always a good idea to verify any specific entry requirements to a different country, you can check out the Cayman Islands specific travel requirements from the US here.
Cruise Ships & Wind
If you plan your trip around anything – you need to plan around cruise ships and wind!
Cruise Ships
We went Grand Cayman at a very unique time when it had just reopened to tourists post-Covid, but it had not yet reopened to cruise ships. So essentially it felt like we had the island to ourselves. Cruise ships can come in and drop off thousands of people in Georgetown for a day of excursions. Popular areas such as Stingray City and the shopping districts will be crowded with people. Do yourself a favor and look at the cruise schedules and plan your trip around it. On days with the highest number of people coming on cruises, don’t try to drive across the island and do all the touristy things – these are great beach days!
Wind
Wind can be an issue with water activities in Grand Cayman (diving, snorkeling, stingray city, bio-luminance bay, etc.). Plan your water activities early in the week so you have flexibility to reschedule if wind/weather is not favorable. Boat operators will cancel for high wind so you don’t want to wait to do these things on your last day of vacation. You can look up wind forecasts here and potentially make last minute adjustments to your itinerary.
Day 1 – I don’t want to talk about it
Missed our flight out of Kansas City, epic overnight cross-country road trip to get to Fort Lauderdale (see above)! We had originally planned to arrive this day (Saturday) and get groceries because most places in Grand Cayman are closed on Sundays (including grocery stores).
Day 2 – Worth the Hassle
We finally arrived in Grand Cayman! After picking up our car and having a quick driving tutorial, we found our condo at Discovery Point. Walking in and seeing the view made all the trouble to get there worth it. It was beautiful. The condo was perfect for our family of four (we could have slept six with the pull out couch).
We started with a nap, but then were ready to start our vacation! The first night we made the short drive to West Bay for dinner at Tukka West. The menu was an interesting blend of Australia and Caribbean flavors. The food was delicious with a table on the dock overlooking the bay. We watched the boats and kite surfers while finally enjoying a meal that wasn’t from a gas station or airport.
Day 3 – Blue Iguanas
This was our day to explore the island. We hopped in our rental car and started driving. We went to Georgetown, drove through Bodden Town and over to Queens Elizabeth Botanic Park.
My family doesn’t get overly excited about botanicals, but the main event was seeing the endangered Blue Iguanas. Unfortunately, I didn’t realize the limited days/hours the Iguana Conservation was open. Luckily, we were able to do a self-guided tour through the botanical garden and spotted several of the Blue Iguanas on our own. If seeing and learning about the iguanas is important to you, go when the conservation is open. Even with the self-guided tour, we thought it was worth the visit for something different to do on a windy day.
We wanted to explore Crystal Caves and Rum Point, but these areas were still not reopened/recovered from Covid. We ended up just doing some shopping and back to the condo for some beach time.
Shopping
If you are looking for a detailed review of the shopping districts you are not going to get it here! I am not a great shopper. Grand Cayman is apparently known for high end tax free shopping on jewelry and luxury items. Our shopping consisted of buying a few t-shirts and some scuba gear.
Our favorite t-shirt shop and dive shop were in a little strip mall with Chicken!Chicken! I recommend stopping here for a quick, affordable meal (go with the jerk chicken if you can handle some spice). We then cooled off with some gelato from Gelato & Co in Camara Bay.
Camara Bay is a shopping area with a bunch of outdoor restaurants overlooking the bay. The “bay” here is where multiple water channels converge from the open bay. It is a unique area worth checking out.
Note – We originally we planned to dive this day, but it was way too windy. We were able to pivot plans and do inland activities. See note about wind in planning section above.
Day 4 – Let’s Go Diving!
Finally, a diving day! Our first dive was the USS Kittiwake Shipwreck. We went with Deep Blue Divers, dive shop licensed to give guided tours to certified divers through the 251 ft. long / 5 level ship. It was amazing, but disorientating! The ship was knocked over several years ago by a hurricane and now sits on the ocean floor at a 45 degree angle. Even when you cognitively know the ship is at an angle, it is hard to orientate yourself while going through it.
We were able to explore through multiple levels of the ship (following our guide very closely) and even pose for a few pictures. Typically, you can’t enter a shipwreck without a specialty certification for cave diving/wreck diving. This is a unique dive site that even open water certified divers can experience with a guide. If you are a diver, I highly recommend putting this site on your list.
Our second site dive site was a short boat ride away to the North Aquarium. Our dive followed a reef full of ocean life including stingrays, flounder and lionfish. Lionfish are beautiful, but invasive to the area and destructive, so those licensed are encouraged to spearfish them. If you are not into diving or spearfishing, you can do your part by ordering lionfish off of local menus!
After our dive we just wanted some carbs! The Brooklyn Pizza in Camara Bay was a great post dive lunch before our afternoon on the beach.
Day 5 – Stingray City & Starfish Point
Grand Cayman is known for Stingray City. If you have not experienced it, you should. We booked an ecotour through George’s Water Sports. I would highly recommend this tour, it was a great experience. We stopped at Stingray City, Starfish Point, snorkeling, lunch in Kaibo and the mangroves. Stingray City can get busy especially when there are a lot of cruise ship passengers on excursions (see note above about checking cruise ship schedules). The water is clear and about waist deep at Stingray City. Your guides will help instruct you how to handle and feed the stingrays if you want to.
Starfish Point
We really enjoyed the stop at Starfish Point. If you are staying on the North side of the island (or if you want to drive over there), you could visit this location on your own. I liked having a guide here to learn more about the starfish and understanding how to protect them.
Note: If you go to Starfish Point on your own (or don’t listen to your guide), do NOT hold a starfish up out of the water; they will die. Also please use reef safe sunscreen.
The tour we booked originally planned to stop for lunch at Rum Point, but again Covid had caused the restaurant there to close. The alternative location at Kaibo just couldn’t handle the demand. Although the food was good, the wait wasn’t worth it. The final “stop” was really just a boat ride through the canals of mangroves.
Bio-luminance Bay
Note that George’s Water Sports and several other companies offer trips to the bio-luminance bay. If you are staying close to Rum Point you can likely just go visit this bay yourself. The ability to see the bio-luminance is dependent on the moon cycle, so if that is important to you check out the lunar calendar before you book your trip! Unfortunately, the moon was too bright for us to go to the bio-luminance bay.
Spott’s Beach
We still had some energy in the afternoon and decided to go explore east of Georgetown to Spott’s Beach. Of all the places we went, this was the most disappointing. Spott’s Beach is a public beach where we had heard turtles were often spotted. Turtles like sea grass, so it was not surprising that this area had a ton of sea grass. Unfortunately, there was so much sea grass and the water was so rough (the area is not as protected from wind as the seven-mile beach area) we didn’t even want to get in the water. As we walked along the beach it was dirty and at one point we spotted a used syringe. That is when we packed it up and headed back to our beautiful beach on seven-mile for the evening.
Day 6 – Shore Diving
Thursday morning we did a shore dive to Devil’s Grotto with Eden Rock Diving Center. I love shore diving! This was the first shore dive I have ever done except at a lake which is not the same. It was so easy to just put on our gear, head over to the ladder and get in like it was a swimming pool. Shore diving is also so much more affordable.
Devil’s Grotto was an amazing site right by the cruise ship terminal. If you are ever on a day excursion from a cruise ship you could literally walk to this location and dive this site. We got a quick briefing from the shop and went out as a family of four without a divemaster. Typically, we always have a divemaster with us and do a follow the leader type dive; so we actually had to use some navigation skills on this one!
There were fun swim through openings in the reef that was teeming with large and small life. Tarpon, barracuda, lionfish, parrotfish and lots of colorful fish I can’t identify. But the swim through portions of the reef were unique and beautiful. My navigation was challenged a little with the swim through portions, but we surfaced pretty close to where we intended at the end of the dive. There are options to snorkel this site as well for non-divers. There is a second site, Eden Rock, at this location, but we decided to just do a single dive this day.
Georgetown
Since we were in the heart of Georgetown we decided to go ahead and walk around the shops / restaurants like you would when you were getting off a cruise ship. Again, we went shortly before cruise ships resumed coming to the island post-Covid, so there was a bustle of activity to try to get shops fixed up and reopened. Honestly, we were unimpressed by the touristy t-shirt shops and expensive jewelry stores geared toward cruise ship passengers. We decided get out of the heart of Georgetown and have lunch at Sunshine Grill. Sunshine Grill is a little pool site restaurant in the middle of Sunshine Resort. It was one of the most affordable places we ate with really good food. This is a great low-key place to grab a meal – breakfast lunch or dinner. I wished we had time to eat here more than once.
Snorkel at Cemetery Beach
Cemetery Beach is another public beach that was within walking distance of our condo. There is literally a cemetery where the parking area is, hence the name. If you are a strong swimmer and it is a calm day, I would recommend snorkeling here. There is a reef with coral and beautiful sea life, but it is about 60 yards out (straight out from the cemetery). My older son and I did this and it was great, but I will have to say between our swim/walk up to Cemetery Beach and the swim out to the reef (after our morning of diving), we were tired! I wouldn’t do this with young kids or mediocre swimmers unless you have a kayak or something to help with the swim.
After our day in the water we got cleaned up for a nice dinner at the Cracked Conch. Cracked Conch is a higher end type of place. Although the food was good, the attached Macabuca restaurant was even more our style . . . .so we went there the next day (see Day 7).
Note – if you are wanting to visit the Cayman Turtle Center it is right across the street from Macabuca. The Turtle Center gets great reviews, but since we have seen turtles in the wild while snorkeling and scuba diving, we passed on this activity.
Note – West Bay is also the location of a town called “Hell.” Again, we chose to pass on this, but some people get a kick out of sending a post card from Hell or getting a picture with the welcome to Hell sign.
Day 7 – Let’s Dive Again
We decided to pack in one more shore dive with Sun Divers at Macabuca. There is nothing better than an oceanside restaurant that has a dive shop and site right there! Where else can you get that? We literally dove, and then sat at a table for lunch. You can also snorkel this site.
We dove a site called Turtle Reef. It is a mini wall dive that was very easy to navigate down the reef and back. Although we didn’t see any turtles, there was quite a variety of fish including tarpon, stingray, spotted trunkfish and fount parrot fish. The variety of coral was also quite impressive. For me personally, I was more impressed with unique dive sites at Kittiwake and Devil’s Grotto, Sun Diver’s location can’t be beat. The entry was easy and beautiful right on the restaurant deck. I was able to exit the water and immediately have a fruity umbrella drink in my hand! Macabuca is casual with amazing food, unbeatable view and a relaxed outdoor environment. It is worth going to if you decide to dive/snorkel there or not.
We had to spend a few hours in the afternoon finding the Covid testing center to get our negative results and paperwork for re-entry in the US. Hopefully that requirement never comes back! After that we spent our last afternoon enjoying the beach before our final dinner out at West Bay at Calypso Grill.
Day 8 – Travel Day
I am happy to report that our travel day home went as planned.
Laura, your blog is really enjoyable! Thanks for taking the time and trouble to help others enjoy your adventures.