This first edition of our Grand Cayman Cruising Guide – Sailing & Activities was written during Winter 2019. We sailed down to Grand Cayman during the Christmas/New Year’s Holiday and stayed four months. Here you will find all of our favorite activities during our stay, in a daily log format. Our hope is that you decide to sail to Grand Cayman and can use this guide to plan your own activities.

Grand Cayman in the Winter

Pilar spent the Winter of 2019 in Grand Cayman. We visited several times to get away from the cold rain in North Carolina. Cayman is our tropical paradise. Having visited numerous times before on our Diving adventures, we knew the island well. This time, viewing things from our boat, we got quite a different perspective on things.

We docked in Cayman Islands Yacht Club in West Bay, on the Seven Mile Beach side of the North Sound for 4 months. We arrived January 3 (my birthday!) and while the boat stayed through April 22, we flew back and forth a few times to spend some time in beautiful, friendly, warm, sunny, safe Grand Cayman.

February 14 – 18: Girls Trip

On this trip, I had invited 2 friends to join me, Laura and Erica. Thursday, we arrived, rented a car, stopped at Tortuga rum company for some chocolate run cake and a couple free shots. Then we headed to the boat and enjoyed a relaxing kickoff lunch at Bacaro, a restaurant on-site at the marina. Dining out in Cayman tends to take a while, so 2 hours later, we headed to the grocery store to get provisions at the CostULess which is much like a Costco. Our first night, we had small bites and cocktails out on the veranda. Yes, we left our husbands alone on Valentines’ Day – funny they didn’t seem to mind too much.

Grand Cayman Island Tour

Friday, we did our all-day tour around the island. We headed towards East end and traveled the half way road over to Rum Point. We stayed the day, got our dose of Vitamin D sunshine, snorkeled, read, and napped. Then we traveled to the far East End so we could see the entire island.

We passed Morritt’s, Ocean Frontiers, stopped at the Blow Hole, then made our way back to Pilar. We were expecting a lot of traffic from Kaboo, a festival that was occurring right across from Cayman Islands Yacht Club, but we were lucky to arrive around 630 when traffic was lighter. Dinner on the boat was fresh grilled Wahoo.

Saturday, we enjoyed a lazy day on the boat. Walked the piers, walked around the Yacht Club water’s edge and scored some more fresh Wahoo from a neighboring fishing boat that had been cleaning them to sell to area restaurants. Dinner that night was sautéed Corvina.

Grand Cayman Water Fun

Sunday, we journeyed over to Stingray City and stood on the sandbar while we touched, fed and petted the Stingrays. Our tour guide called them Puppies. Stingray City came to be when local fisherman would stop there on their way back to clean their catch and threw their scraps overboard attracting the Stingrays. Today, there are over 60 Stingrays that call that area home – from fully matured (4-foot-wide) to babies.

After Stingray City, we stopped at a snorkel spot rightfully called the Aquarium with so many varieties of fish. Then back to the boat for a quick lunch before heading out to Seven Mile Beach for the rest of the day.

West End Grand Cayman Attractions

Monday we visited Hell, a unique geological formation created by salt and lime deposits over 24 million years, called that because the locals believed the place was similar to Hell’s landscape.

Then we were off to the Turtle Centre, where we learned about the turtle farming (sustainable), and the turtles they release to the wild every year. Then, one last visit to the boat to gather luggage, and off to lunch at DaFish Shack and the airport to drop off my friends.

Tuesday was boat cleaning day for me. It rained a little, which worked out fine for rinsing.

Wednesday was boat repair and provisioning day to prepare for Stephen’s arrival.

February 20 – 25: “Just Us” Trip

Stephen arrived Wednesday night and quickly got onto “island time”. We had an amazing dinner at Bacaro and enjoyed an evening on our dock.

Thursday, we left the dock by 10 AM to begin our sailing adventures.

First stop was Stingray City, where Stephen got to enjoy the Stingrays up close. This was quite different than our past diving experiences, where we tried to only watch the stingrays from a safe distance.

Grand Cayman’s Starfish Point, Rum Point & Bio Bay

Second stop was Starfish Point, an area famous for its 8” diameter starfish. We walked the beach, spotted starfish, and swam in the warm waters. After dinner we ventured out to see the bioluminescence in the nearby Bio Bay.

Bio Bay is an area of water that literally glows when it is stirred up in the dark. There are microorganisms in the water that generate an electric current every time they are moved. We could see jelly fish moving in the water creating the glow, fish swimming glowed, seagrass moving glowed, basically everything in the water glowed when moved. It is in a water area by Rum Point between Sand Point Rd and Water Cay Rd.

If you go, just follow the locals in and the further you go towards the end of the bay, the brighter the bioluminescence gets. Feel free to swim in it, or just move the water with your hands or paddle. It was the most brilliant bio-luminescence either of us had ever experienced. You could see it in our boat’s wake and by using a paddle to move the water. You could even see it as fish moved in the water. We stayed anchored for the night at Starfish Point in our beautiful spot. Totally alone.

Friday, we did some boat work in the AM, followed by lunch at Kaibo, a popular beach restaurant. We then sailed to Harbour House Marina to see about some propane fills (they had none) and a few boat parts. Then we were off to snorkel in the North Sound Reef – stingray, all kinds of juvenile fish, parrotfish, yellowtail jacks and more. We stayed anchored for the night. Totally alone.

Georgetown Snorkeling

Saturday, we headed around the northwest point of the island to Georgetown. We moored at Eden Rock, and took our propane tank to Home Gas for refills. Tried to get a cab, however after waiting for too long, we decided to do the 20-minute walk. When we were close a super friendly person saw us walking and offered to give us a lift back to our boat after the refills. As I said, the people in Cayman are so completely hospitable and pride themselves on it.

After returning to the boat, we snorkeled Eden Rock – schools of Blue Tang, Bait Balls, Tarpon and these interesting translucent electrified jelly fish with black dots on them that we had never seen before. Then we sailed south and were planning on anchoring between Pedro’s Point and Prospect Point, however the waves were 10 ft rollers and we decided to turn back. After trying several anchor spots, which all turned out to be too wavy, we returned to Eden rock and stayed the night there.
North Sound

Sunday, we headed back to North Sound. We anchored near Barker Cay and Sander’s Rock. This is hard to find on a regular map, so use your charts. We snorkeled around the rock and were treated to watching a school of squid, thousands of tiny fish, yellow tail, pipefish, striped grunts and more. Then we enjoyed our last views of North Sound reef from Pilar’s front deck.

Before dinner, we headed back in to our dock at Cayman Islands Yacht Club. Stephen directed while Dawn actually drove the boat for the first time all the way through the channel and made it 4 feet from the dock where Stephen took over to complete backing it in place. Once we were secure, we enjoyed our last night in Cayman.

Monday, we cleaned the boat, prepared it for another 3 weeks without us, and headed to the airport.

March 20 – 26: Sailing with the Chinnis’

Our first yacht guests down in BVI were Pauline and Bill Chinnis. So, we asked them to join us as repeat customers for a week in Cayman. We arrived Wednesday morning, lunched at Sunshine Grill, provisioned, and left the dock at 6 pm. Our plan was to sail to Little Cayman, since we had a North wind, which is very rare. However, as luck would have it, we did not have enough wind, and decided that we did not want to motor sail all the way there. So, we anchored outside Governor’s cut for the evening.

Circumnavigate Grand Cayman

Thursday AM, we decided to sail around Grand Cayman – again, the North wind made this trip more possible than ordinarily. We sailed easterly along the north side of the island, then sailed south along the east end, stopped at an East End beach to snorkel and do a beach walk, then sailed down to the Pedro’s Pinnacles mooring ball by Spott’s Beach and Pedro St James by the gorgeous cliffs.

Friday, Bill and Stephen decided to finish cleaning the hull with the Brownie hookah. All went went well except they discovered that our zincs were really bad. So, we spent the afternoon trying to get parts. Dinghied in to the beach, where we caught a cab and rode into Georgetown for the parts. Dined at Da Fish Shack. We were also strategically waiting for the wind to turn. Even cruise boats were anchoring in Spott’s Bay because it was too dangerous to try to get into Georgetown.

Saturday, Bill and Stephen fixed the zincs, then we left the mooring ball with nothing but sail! No engines! We sailed towards Georgetown, down 7 Mile beach and then along the north tip of the island where we entered Governor’s Cut and docked at Starfish Point. We snorkeled to shore to see the Starfish, then enjoyed happy hour on the veranda, followed by local grilled porkchops for dinner, with wilted spinach with tomato, red pepper, and avocado.

Then we treated Bill and Pauline to Bio Bay. After returning to our boat, we then did a little people watching as a party boat barge came by around 9 pm and partied til 11. We enjoyed our last anchorage in Starfish Point Saturday night.

Sunday, we tried to head to Stingray city, however the waves were too choppy to anchor and enjoy that safely, so we headed back to the dock and spend the day doing projects, resting and exploring the local beach. Dinner that night out at Bacaro – a wonderful small plates restaurant at CIYC.

Camana Bay

Monday, last day for fun! We head over to Stingray City and have much better luck with the waves. We fed them some leftover bait Stephen had. Then after lunch, we sail over to Camana Bay for some sightseeing, shopping and enjoying the Observation Tower views of the entire bay area. Coincidently, a memory came back to Stephen and I as we looked over the canal. We had been to Camana Bay before about 5 years ago and dreamed of boating down the canal to Camana Bay. That dream just came true.

Our last dinner Monday night was at Morgan’s Seafood Restaurant.

Tuesday, we cleaned the boat and headed home. Next time we would return to Cayman would be to sail Pilar home to Charleston, SC.

Grand Cayman Customs Clearance

Clearing in was fairly simple. We headed to the Georgetown Port Authority, and cleared in just an hour. No guns, no spearguns, paperwork ready, no hassle.

Clearing out was a bit more confusing. We had crew coming in different days, and you can only clear out 24 hours in advance. So, 3 of us cleared out on Sunday at the Georgetown Customs office (different than the Port Authority), with a pre-clearance notification on our Monday arrival. But our Monday crew arrival still had to clear in at airport, then head to Customs office downtown to clear out. Additionally, clearing people out was easier than clearing the boat.

Boats are allowed 30 days automatically, but then must be renewed for additional time. Since our boat had been there about 4 months, we had emailed paperwork in for that extension, as well as mailed it. But we never heard back from anyone. Phone calls would not connect as the phone system prevented us from actually getting through to a person. The Port official was none too pleased with us, however in the end, he was very helpful and accommodating and made it all work out just fine.

If you want assistance navigating this, please send us an email, so you can avoid doing it wrong!
Grand Cayman Scuba Diving

Since we used to Scuba Dive Cayman a LOT, here’s a few videos in previous years. If you are interested in scuba while you are there, go to Dive365Cayman and you will be able to see all the great spots and get details on diving there. This also includes snorkeling spots.