A Trip to the Cayman Islands: Rum and Revelation in the West Bay
Because skiing has gotten so douchey lately, I decided to forgo my annual ski trips this past winter and go somewhere warm. I had long wanted to plan some travel to the Cayman Islands. One of the driving factors in choosing this Caribbean hideaway was the fact that it’s so easy to take a flight to the Cayman Islands from LAX. They even have direct flights. Not knowing much about Cayman, I quickly realized that everything I learned about it from movies in the 90s was a damn lie.
Hollywood painted it as a sunny hideout for shady money — offshore accounts, quiet wire transfers, and sweaty white collars trying to stay one step ahead of extradition. If you saw John Grisham’s The Firm, you remember Tom Cruise sprinting through alleys in his power suit, dodging the IRS, FBI and Mafia hit men. That version of Grand Cayman is long gone — if it ever existed at all.
Travel to The Cayman Islands
Today’s Cayman Islands are a different kind of escape. A British Overseas Territory with the third-highest standard of living in the Western Hemisphere, this place is safe, clean, and refreshingly un-sleazy. No one’s trying to hustle you with shell necklaces or timeshares every 10 feet. There’s no hustle at all, really — just an island pace, a mix of Caribbean charm and British order, where people say good morning and mean it. I’m not even sure I saw a bank, let alone an investment banker.
Soon as we stepped out of the airport I knew our trip to the Cayman Islands was going to be different from the Caribbean vacations I have taken in the past. The Grand Cayman airport (GRR) was small, well organized and super clean. When you stepped outside you didn’t get mobbed by drivers trying to extort you into their black car. In fact, nobody paid attention to us at all. You simply walk outside and grab one of the many taxis that are politely waiting in line. How refreshing.
We had little interest in visiting Georgetown, the capital, where cruise ships dump thousands of people into jewelry stores and Margaritaville gift shops. Instead, we pointed our compass toward West Bay, where fanny pack nation rarely wanders. We used IHG points to book a stay at the Holiday Inn Resort Grand Cayman — which, let me be clear, is not your standard roadside Holiday Inn with waffle machines, floral bed covers and an army of children.
How Is The Holiday Inn Resort in Grand Cayman?
This hotel is a low-key gem, quietly owned by a real estate outfit in Chicago. The Holiday Inn Resort Grand Cayman is immaculate and sits on the bay side of Grand Cayman next to a golf course with its own private stretch of sea and a calming pier. The crowd was a curious blend — hotel guests, timeshare owners, and folks like us, burning through points and expectations. What we found was a tranquil haven that grew on us with every sunset. Travelers and retirees, mostly from the Northeast, gathered at the casual open-air restaurant each evening and it seemed many knew each other from annual trips to Cayman. It was always a nice welcome home after spending each day exploring Grand Cayman. Note: there is no beach, it’s a rocky coastline.
Day 1–3: Seven Mile Beach Mornings and Bonny Moon Bliss
Every morning started with a ride. The resort had cruiser bikes to rent — simple, reliable, and perfect for what we needed. After a quick morning workout or swim we pedaled our bikes 1.5 miles west to the ocean side of the island – Seven Mile Beach. This iconic ribbon of white sand and turquoise water has put Cayman on the map for beach vacation seekers.
Once a desolate stretch of coral rock and sea grape trees, Seven Mile Beach began booming in the ‘60s when the first hotels were constructed. Today it’s lined with resorts, beach bars, and beach clubs but there is space. It’s not like Cancun where 10 resorts line a one mile stretch of sand. Cayman has done a great job of protecting the beach from development with many parks & public beach access. Most resorts sit across the street from the beach.
Acting on a tip from our taxi driver, we posted up in front of Bonny Moon, a wonderful bohemian beach club tucked in beside a public beach and the fancy Hotel Indigo. The public access guarantees a great mix of locals and travelers enjoying free spirited cocktails in bikinis and boardshorts, while downtempo beats complete the vibe. The decor is driftwood meets disco, with old record albums from the 70s lining the walls. They have a bar, restaurant, beach club and excellent service. There was always a lively crowd, but never crowded. We quickly realized that March is one of the best times to travel to the Cayman Islands.
Bonny Moon was named after one of the few female pirates (Anne Bonny) who was the lover and partner in crime of the infamous pirate Calico Jack in the early 1700s. Jack was a flamboyant pirate swaggering through the Mediterranean, with two women pirates at his side, sword drawn like a middle finger to the Crown. He wasn’t the best or the brightest pirate and was captured during a half-hearted fight against the British Navy after a night of heavy drinking. He was tried & hung in 1720 in Jamaica at the age of 37. Anne Bonny was spared and many people believe her father paid for her release and subsequent return home to Charleston, South Carolina.
The ocean in Cayman is so clear and blue it feels like someone adjusted the saturation on your eyeballs. We’d post up for hours, alternating between swims, sand naps and Caybrews – the local beer. Our only real decision being where to eat dinner that night. It was the kind of vibe that makes you forget what day it is, and we did, because we hit repeat for the first three days.
Day 4: The Long Bike Ride to Macabuca
Now completely immersed in Cayman sun & surf, looking more like the locals, it was time for some adventure. Acting on a tip from our driver, we changed up our usual bike ride to the beach and pedaled past Bonny Moon heading north, several miles deeper into West Bay. It was a long, sweaty ride on a busy road with little to no shoulder. Our destination was the legendary Macabuca Tiki Bar. Now this place deserves a moment.
Macabuca isn’t some polished beach club built for influencers. It’s a rustic, open-air watering hole perched on a rocky bluff — a dive bar in the truest and most literal sense. Originally just a hangout for scuba divers exploring the nearby reef, Macabuca grew organically over the years, eventually sprouting into two restaurants: the laid-back ocean tiki bar and the more upscale Cracked Conch which sits above it.
Divers still come here to rinse off salt and tell stories, and there’s a ladder off the edge if you want to join them or just take a quick dip in between rum punches. Macabuca’s bar is a beautiful kind of chaos. It’s like Hemingway’s tackle box exploded and someone built a tiki shrine around the wreckage. License plates from dive trucks and Rust Belt relics hang like dog tags in a museum of lost maritime battles. There’s a fan mounted sideways on a wood crate from Cakebread Cellars like it’s trying to cool down the ghost of Blackbeard. Above it all, a fiberglass tuna sails through the rafters next to a life ring, like a sacred sea god watching over his rum-soaked parishioners.
This isn’t curated island chic. This is hard earned clutter — organic design that happens when you serve good booze to good people for many years and never once pretend to be something you’re not. This was the Cayman we began to seek out: low-key, unbothered, and a little bit weird.
Day 5: Rum Point, Scooters, and Local Lightning
We returned to the our hotel oasis that evening and were pleasantly surprised to see and hear live music in the poolside restaurant. A local gal was playing acoustic guitar and singing – perfect! A relaxing swim and dinner at the hotel bar quickly ensued; a great finish to an amazing, long day exploring the West Bay.
The next morning, adventure was calling again. Like Leo in the movie The Beach – it was time for us to check out the “other side of the island”. So spooky.
Having been on the island for four days now, it was definitely time to get on a boat. Passing on the sting ray tours and glass bottom boats was not difficult. We will leave that for Fanny Pack Nation. We opted instead to have lunch in Camana Bay, a short cab ride from our hotel. Camana Bay is a harborside retail district, basically an outdoor mall with apartments on top. It’s very non-aesthetically pleasing for an exotic trip to the Cayman Islands – but they have a ferry dock! Our destination was Rum Point, about 10 miles across the bay.
After our bougie lunch in Camana, we picked up some roadies and headed to the ferry dock. Gangster, I know. It reminded me of the many times I took the Falmouth ferry to Martha’s Vineyard in my twenties. We would hit the local packy, find a sneaky place to ditch our car, then sprint to the ferry just before final boarding with a case of Red, White & Blue under our arms.
The name Rum Point suggests a lush, exciting story of piracy, trading & booze, but history is not sure any of that ever happened here. What we found was more of a desolate and tranquil outpost, much like Gay Head on the Vineyard or Sconset on Nantucket. We were headed for what we thought was the only establishment in Rum Point, Kaibo a self proclaimed luxury beach club. The word luxury concerned me all day.
As soon as our boat entered the small harbor, I thought – this is going to be a long couple hours until the next ferry arrives. There is nothing nearby, just a wannabe luxury beach club, that looked – not-all-that. Then local’s lightning struck us again.
A rustic man with a salt-and-pepper beard, drinking rum out of bottle slides over, his voice low like he’s sharing a dirty secret. ‘You wanna know the real Rum Point?’ he says, flicking a thumb toward the horizon. ‘Get off the boat, and head down the road about a mile, there is a better spot no one talks about’.
And just like that, we walked straight thru Kaibo from the beach and out the front door. There’s something in the way locals talk—an insider’s code, a warning against the packaged paradise and filtered life that reeks of authenticity. That is the reason I made very loose plans when planning travel to the Cayman Islands. We were honored to have passed his cool test to receive such a recommendation and started walking down the road.
I will leave the rest of that day to your own imagination and discovery – something more travel writers should do to protect cool spots from being sanitized.
Final Days: Tranquil to Luxe and Back to Tranquil
For the final stretch, we leveled up — cashed in points for a suite at the Indigo Hotel, one of the crown jewels of Seven Mile Beach. The property is like any waterfront luxury hotel – its really nice. But luxury always has a price these days.
We were given towels and escorted to our poolside lounge chairs – yes, escorted. We jumped in to cool off then sat in our chairs. After less than one minute of listening to screaming kids, we looked at each other and nodded. Without a word, we got up and left the paw patrol of privilege, crossed the street and walked down the dirt path to our beloved Bonny Moon. The scene was blissful and the vibes right where we left them.
Final Thoughts
Our trip to the Cayman Islands surprised us a bit — not with flash, but with ease and discovery. It was an extremely pleasant trip. No sales pitches. No scams. No litter. Just bikes, beaches, boats, and hidden gems. A safe, clean, hassle-free island where you can actually relax and meet some very cool people if you choose the right path. And that direct flight to Cayman from LAX didn’t hurt, either.
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