We spent Thanksgiving weekend in Grand Cayman, meeting my friend and her husband for a few days of sunshine, good food and plenty of time by the water. Sometimes that’s exactly the kind of holiday you need.
We stayed at the Grand Cayman Marriott Resort, just a short walk from Seven Mile Beach, which proved to be an excellent base for a long weekend. The island was busier than usual as it was hosting a college basketball championship, but despite the extra visitors, everything still felt easy to navigate.
First Impressions
One of the first things that struck me about Grand Cayman was how modern everything felt. In many ways, it reminded me of an extension of South Florida. The roads were well maintained, the infrastructure was excellent and it felt incredibly safe and easy to explore.
George Town, the island’s capital, is a popular cruise ship port, and you’ll notice plenty of luxury jewellery stores, banks and waterfront shopping areas reflecting that.
One thing I wasn’t expecting was the chickens. They seemed to be everywhere – from outside the airport to beach clubs and even wandering around Seven Mile Beach with tiny chicks following behind them. It quickly became one of those quirky little details that made the destination memorable.
We booked our airport transportation through Expedia and also found Ubers reasonably easy to get while we were in Grand Cayman.
A Relaxing Thanksgiving Weekend
Our plan wasn’t to fill every day with activities. Instead, we spent most of our time doing exactly what we’d come for – swimming, reading, enjoying long lunches and catching up with good friends.
November turned out to be a lovely time to visit. The temperatures were warm enough for swimming every day without the intense heat and humidity of the Caribbean summer. The Marriott had excellent facilities, and we found ourselves alternating between the beach and the pool throughout the day.
Our friends had one of the ground-floor rooms opening directly onto the pool deck, which became the perfect spot for afternoon drinks before heading out for dinner. One morning I joined a yoga class by the pool, while my daughter happily spent time making bracelets as part of the children’s activity programme.
It’s always a good sign when everyone finds something they enjoy.
Thanksgiving Lunch
For Thanksgiving we booked lunch at Grand Old House, one of Grand Cayman’s best-known waterfront restaurants.
They were serving a traditional Thanksgiving menu complete with turkey and cranberry sauce, making it a fun way to celebrate while still enjoying a Caribbean setting.
Great Food and New Friends
One evening we had dinner at Lobster Pot Restaurant & Wine Bar, which ended up being one of the highlights of the trip.
Earlier that day we’d met a lovely couple from New Jersey while relaxing on the beach. One conversation led to another, and before long they were joining us for dinner.
It’s funny how that always seems to happen on holiday. At home we can go weeks without making new friends, yet somehow when you’re sitting on a beach with a cocktail in hand, conversations come naturally and complete strangers can end up feeling like people you’ve known for years.
Some of my favourite travel memories have come from those completely unplanned encounters.
Stingray City and Starfish Point
Our one big excursion was a boat trip visiting some of Grand Cayman’s most famous attractions.
We stopped at Stingray City, where you can stand in shallow, crystal-clear water surrounded by southern stingrays, before continuing to Starfish Point, where bright orange starfish rest in the calm shallows. Both stops were well worth doing and are among the island’s signature experiences.
The rest of the trip was intentionally low-key, with piña coladas by the pool, swims in the ocean and plenty of time doing very little at all.
Seven Mile Beach
One thing I found fascinating was watching the daily rhythm of Seven Mile Beach. Whenever a cruise ship arrived, large groups of passengers would make their way to the beach, hire loungers and enjoy a few hours in the sun before disappearing almost as quickly as they had arrived to head back to the ship.
By late afternoon, the beach would feel noticeably quieter again. It was interesting to watch the island shift between busy and peaceful throughout the day.
Final Thoughts
Grand Cayman is one of the easiest Caribbean destinations I’ve visited. It’s clean, modern and incredibly easy to navigate, making it a great choice if you’re looking for a relaxing beach holiday without too much planning.
If you’re searching for colourful fishing villages, rugged coastlines or a more traditional Caribbean atmosphere, other islands may offer more of that experience. But if your idea of a holiday is comfortable resorts, excellent restaurants, beautiful beaches and simply spending quality time with family or friends, Grand Cayman does that exceptionally well.
I’d happily return.
Mrs Globetrotter Tips
Best for: Couples, families, friends and anyone looking for an easy Caribbean getaway.
When we visited: November (Thanksgiving weekend).
Don’t miss: Stingray City, Starfish Point, Seven Mile Beach and lunch at Grand Old House.
Worth knowing: Cruise ships bring large numbers of visitors during the day, particularly around George Town and Seven Mile Beach, but things become much quieter later in the afternoon.
Would I return? Yes. It’s one of the easiest Caribbean islands to visit and a great option for a relaxing long weekend.
