Grand Cayman: The Little Black Dress of Beach Vacations

Icon Share

SHARE

Advisor - Kate Van Dell
Curated By

Kate Van Dell

  • Beaches

  • Family Travel

  • Luxury Travel

  • Tropical Vacations

  • Couples Travel

  • Cayman Islands

  • Relaxation

Advisor - Grand Cayman: The Little Black Dress of Beach Vacations
Curator’s statement

This is the little black dress of beach vacations: timeless, flattering, and always a good idea. It works for a long weekend or a full week—easy to slip into, never fussy, and somehow exactly right every time. Grand Cayman is where you go when you want a truly nice vacation but do not have the bandwidth to overthink it. The beaches are pristine, the service is top notch, and the food is consistently good. It is English-speaking, safe, and incredibly easy to get to. You will be on the beach 10 minutes after clearing customs. We loved the Ritz-Carlton Grand Cayman so much that we went back two years in a row, and every single person I have sent here has had a wonderful time. It is one of those rare destinations where everything works. Your kids are happy, you are happy, and the hardest decision you will make all day is whether to order another cappuccino at breakfast.

The Fora Difference

Book with Kate to access exclusive perks and experiences on your trip.

Icon Travel Perks
Killer perks

Free upgrades, spa credits and more—we got you

Icon Recommendations
Personalized recs

Customized travel planning for your style

Icon Inside Knowledge
Insider knowledge

Expert advice from people who’ve actually been there

Where to stay in Grand Cayman

Unlock perks by contacting Kate to book your trip.

Things to do in Grand Cayman

Ambassadors of the Environment at the Ritz

This is not a kids’ club. It is a collection of à la carte activities for kids and families, led by naturalists with PhDs in subjects like sharks, coral reefs, and coastal ecology. They also happen to be some of the kindest people you will meet. Activities include snorkeling expeditions, mangrove kayak tours, iguana encounters, and sand dune ecology walks. Definitely book in advance if you are traveling during peak weeks, as the most popular options fill quickly.

Walk Seven Mile Beach

Wide, soft sand, calm turquoise water, and beach service that always seems to know what you need before you do.

Charter a boat for the day or at sunset

A full day gives you snorkeling, exploring, and time on the water, while a sunset charter is pure Caribbean magic.

Places to eat & drink in Grand Cayman

Taken at Luca

Taikun

Possibly our favorite sushi restaurant outside Japan. The fish is exceptional, the presentation is elegant, and the setting feels celebratory.

Luca

Sleek and modern, with warm service and one of the most beautiful sunset views on Seven Mile Beach. A perfect choice for dinner with friends or a romantic evening.

Andiamo

Canal-side Italian at the Ritz. Open-air, relaxed, and very family-friendly, especially after a long day on the beach. Around 5 pm, the staff feeds the leftover food to the carp at the canal-side dock, which kids love to watch. They are impressively big fish, but do not worry, I have never seen one make it onto the beach.

Tillie’s

At Palm Heights. We always go here, and everything is delicious. It is the kind of place where you can have a long, relaxed meal while your child plays in the sand right next to the table. Chic but unpretentious, it feels like a true vacation moment.

Coccoloba

At Kimpton Seafire. A playful mix of beach bar and taco shack. Order fish tacos and a spicy margarita with your feet in the sand.

Regazzi

For nights when you want to stay in, we have pizza from Regazzi delivered to the room and eat it while watching the sunset over the ocean. It is easy, delicious (tastes like it was delivered from Italy), and makes the balcony feel like the best table in town.

Need to know

You drive on the left, so if that makes you nervous, skip the rental car. The island is easy, safe, and straightforward. Couples only need two swimsuits and a willingness to order another round. Book both your dinners and your Ambassadors of the Environment activities early if you are visiting during peak times.

Advisor - Kate Van Dell

Travel Advisor

Kate Van Dell

Get in touch with Kate

Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can expect a response from Kate within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).

For more inspiration and insider recommendations, visit our Cayman Islands page.