10 Insider Tips for the Best Luxury Vacation in the Cayman Islands

If you’re planning to visit the Cayman Islands for the first time, perhaps for a destination wedding or a romantic getaway over a long weekend, you’ve got questions. When is the best time to visit? Where’s the best place to stay? What are the must-do activities and the best secret places for a wonderful meal? We’ve done the work, and we’ve got answers. Here’s our report from an insider with tips on the best first luxury vacation trip to the Cayman Islands, including when to go, where to stay, top restaurants and things to do (plus the real story on what to skip).

our insider itinerary series

Insider Itinerary is an occasional series here at Dandelion Chandelier that shines a light on the best places to see, stay, and dine in some of the hottest travel destinations worldwide. Our far-flung correspondents are sharing their inside tips on how to best experience their chosen cities, especially if you’re visiting for the first time. Consider it your local luxury GPS. You’re welcome!

We began this series with Cape Town. Since then, we’ve shared insider itineraries for Ljubljana, Reykjavik, Copenhagen, Oslo, Stockholm, Porto, Zurich, Bermuda, Nantucket and East Hampton, among others. Next up? Our friend and colleague Kevin Dallas shares the inside scoop on the Cayman Islands (along with some help from his colleagues who live there full-time). Full disclosure: our Founder & CEO is on the board of NT Butterfield & Son, a consumer bank and trust company doing business in the Cayman Islands.

insider itinerary for the best first luxury vacation trip to the Cayman Islands

1. Why the Cayman Islands? Why should we go?

Cayman is changing.  Not only is the economy booming, but visitors to Grand Cayman will find a tourism product that is increasingly geared towards the needs of luxury travelers.

The Cayman Islands Government’s decision not to build port facilities for mega-ships means the islands are increasingly off the cruise industry’s itineraries – by 2024, Cayman day visitors will be less than half what they were in 2019.  Instead, a slew of new, and newly renovated, hotels, restaurants and attractions await the visitors arriving by air who are taking their place.

2. How long is the ideal first visit?

Getting to the Cayman Islands is easy, making a long weekend trip possible from just about anywhere in the United States or Canada.  Grand Cayman is just 90 minutes from Miami, and Cayman Airways and U.S. carriers offer direct flights from most major east coast and southern gateway cities.

In addition, Cayman Airways commenced non-stop year-round service from LAX in November 2022.  Outside the winter peak season, some routes operate weekly, but visitors don’t need to worry about running out of things to do – or places to eat – for stay that long.

3. What hotel(s) do you recommend? Or should we rent an apartment/house/villa?

You can’t go wrong with the Ritz Carlton, Grand Cayman. It reopened to visitors in 2022 after a $50 million refit.  The hotel is situated right in the middle of the famous Seven Mile Beach and includes a wealth of amenities, including the island’s best (9 hole) golf course.

For visitors seeking something more boutique, the design-oriented Palm Heights hotel is just down the beach.  The all-suite hotel has only 50 rooms and is intended to invoke the aesthetic of a 1970s Caribbean mansion and is filled with collectible design pieces like Mario Bellini sofas, Ingo Maurer lights and an Ettore Sottsass rug.  The hotel has become the ‘it’ place for Caymanian residents, who flock to the hotel’s Tillies restaurant on the beach for brunch.

4. What are the 5 most important “must see” sights – natural wonders, museums and the like?

Top Must-See Areas in the Cayman Islands: Stingray City

While it’s ‘touristy’, no trip to the Cayman Islands is complete without a visit to Stingray City, the islands’ number one tourist attraction.

Accessible only by boat (private charters available!), this sandbar is a gathering point for wild stingrays, who love to engage with human visitors. Environmentally aware travelers need not worry, the marine environment is carefully managed, and the animals are on a strict and regulated diet.

Top Must-See Areas in the Cayman Islands: the Cayman Turtle Farm

Located in the West Bay of Grand Cayman, the Cayman Turtle Farm is a popular stop for travelers with younger children.  If you’re going to visit, I’d recommend a day when there are no cruise ships visiting.

Top Must-See Areas in the Cayman Islands: Rum Point and Cayman Kai

Rum Point & Cayman Kai, located on the tip of Grand Cayman’s north side, is a bit of a drive but worth it for the laidback vibe and sandy beaches with shallow water at Rum Point itself and nearby Starfish Point.  The namesake restaurant popular with tourists is currently closed for redevelopment, but locals prefer nearby Kaibo – with live music and entertainment – at Cayman Kai anyway.

Top Must-See Areas in the Cayman Islands: the National Gallery of the Cayman Islands

Located just outside of Camana Bay, the National Gallery of the Cayman Islands is an ideal activity for a rainy day, but is worth a stop regardless.

The 9,000 square foot gallery space built in 1996 is home to both revolving exhibitions and the museum’s permanent collection, showcasing the rich cultural history of Cayman and the vibrant contemporary local art scene.

Top Must-See Areas in the Cayman Islands: Cayman Brac or Little Cayman

Lastly, visitors staying more than a few days should venture off Grand Cayman to one of the less developed Sister Islands of Cayman Brac or Little Cayman where you’ll find true wilderness and, if it interests you, great diving.  There are no ferries the islands, but Cayman Airways operates regular daily services.

5. Is there good shopping? If so, where?

While George Town is the historic heart of the Cayman Islands and the seat of the government, it’s been displaced as the hub of commercial activity by nearby Camana Bay. Connected directly to Seven Mile Beach by a parkland overpass, this 600+ acre mixed use development was designed to be walkable, with shady courtyards and pedestrian friendly streets. It’s the perfect place to enjoy some retail therapy, with a mix of local stores and top international brands, including POLO Ralph Lauren, Prada, Gucci, Michael Kors, Lacoste and more.

6. Which restaurants do you love?

The Brasserie, unassumingly in an office park on the outskirts of George Town, is a little off the tourist track, but is one of the best meals I’ve had on the islands. Grand Cayman’s original farm-to-table restaurant, Brasserie’s menu emphasizes what is in season and local fishermen are bringing to shore.

Luca is an upscale Italian restaurant with Caribbean influences located in the Caribbean Club, right in the center of Seven Mile Beach. Always busy, and very popular with both residents and visitors, the menu is an electric mix of sushi and more traditional Italian. The pasta (including gluten free options) is made on site – I’d recommend the pappardelle with braised beef short rib.

For the ambiance alone, Grand Old House is worth a visit. On the waterfront in George Town, as the name implies, the restaurant is a converted colonial ‘great house’. The menu changes daily, and the wine list is one of the most extensive on the island, but the waterfront terrace is the star attraction. Be sure to get there in time for sunset.

7. Of everything one could do on a first visit, what’s the one most memorable thing to do?

Organizing a private charter to Stingray City is a bucket list activity not to be missed. There are lots of good operators available, but I’d recommend Captain Adam of Cayman Luxury Charters for the high quality of both the boats and the crew. If you aren’t going to make the drive to the north side of the island, you can also include a visit to at Starfish Point and Kaibo on your cruise.

8. What would you advise first-timers to take a pass on? Said another way, what’s popular but a bit over-hyped?

Visiting the West Bay and Barker’s National Park shows you a more rural and traditional side of life on Grand Cayman, but wouldn’t make my itinerary again, especially for a shorter trip.

9. What’s a good stop for return visitors, who have already done all the “first timer” recommendations?

I’m looking forward to the 2025 opening of the Mandarin Oriental Grand Cayman. The ~100 room hotel at St. James Point in Bodden town promises multiple pools, beach, a luxury spa and two restaurants.

10. Is this a good vacation for families with kids? Teenagers? Romantic partner? Solo traveler? Any or all of the above?

Solo travelers might find Cayman’s limited nightlife a little lonely, but otherwise Grand Cayman is a welcoming destination for all types of travelers. It’s especially appealing for couples seeking an easy getaway to place where nothing (from getting there, to deciding where to stay, to finding a great meal) is stressful or difficult.

Describe the Cayman Islands in three words.

Easy, comfortable, flat!

tips on having the best first luxury vacation trip to the Cayman Islands

Those are the tips our expert insider has to share regarding how to have the best first luxury vacation trip to the Cayman Islands, including when to go, where to stay, top restaurants and activities. Personally, we’ve visited twice, and we’re keen to make another trip soon.