Curator’s statement
Grand Cayman is the ultimate weekend getaway—with numerous direct flights from the East Coast, you can leave mid-morning and be relaxing poolside by early afternoon. Where you choose to stay sets the tone for your entire experience, and the island offers a range of options, from boutique charm to high-end luxury accommodations. Spend your days lounging by the crystal-clear turquoise water or dancing with locals at live music nights. No matter where you land, you will be sure to find an abundance of local cuisine along with genuine hospitality that will have you wondering why you hadn’t done this sooner.
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Things to do in Grand Cayman
Caribbean spiny lobster exploring a shipwreck
Bonny Moon Beach Club
This prime waterfront spot offers plenty of chairs in the sun and shade and a popular restaurant serving wood-fired dishes, fresh seafood, and signature cocktails. Pro tip: Rent a daybed and you’ll receive a food and beverage credit—the best way to make the most of your beach day.
Stingray City
As the name suggests, this experience will allow you to get up close and personal with stingrays. Rumor has it kissing a stingray brings seven years of good luck! Most day trips include additional stops for snorkeling at Coral Garden and holding starfish at Starfish Point. Pro tip: For lunch, Rum Point is known for local food, beachfront tables, and stunning views of the waterfront—don’t miss the mudslides!
Kassette
This on-site boutique at Hotel Indigo is a curated collection of local finds that range from chic island outfits to vibrant accessories and charming gifts for all ages. Trust me when I say one visit is not enough. It’s the perfect place to pick up souvenirs for loved ones—and yourself!
Bioluminescent Bay
Embark on an unforgettable evening cruising out to the island’s north shore for a Bio Bay adventure. Pro tip: Plan ahead with a high-energy playlist to enjoy sunset views with a cocktail in hand before swimming in the glowing, starlit waters.
Scuba diving
With more than 200 dive sites surrounding the island, there is truly something for everyone—from deep walls to swim-throughs and vibrant corals. Turtles are abundant, and, if you’re lucky, you might just see an eel making its way through the reef! Pro tip: Pirate Divers is known for their small, personalized dive trips and will arrange pickup and drop-off from the beach right in front of your hotel.
Rent an exotic JetCar
For the thrill-seeker, rent a JetCar, a high-performance sports car retrofitted with a jet-ski engine and propulsion. These specialized vehicles let you skim the ocean at high speeds for an unforgettable, adrenaline-pumping experience.
Places to eat & drink in Grand Cayman
Pepper’s
This is the place to go for the best (and largest portions of) jerk food on the island. Live music on Friday and Saturday nights draws a crowd, and the energy is electric. Pro tip: Even if there’s a wait for an outside table, it’s worth it—grab a drink and enjoy the live band while you wait.
Tillie’s
Located at the Palm Heights hotel, Tillie's offers refined Caribbean cuisine in a lush, tropical setting. Pro tip: Book a table on the beach for lunch or sunset, but opt for the restaurant patio for dinner to enjoy the ambiance once the sun goes down.
Pom Pom
Located at Hotel Indigo, this is the only rooftop bar in Grand Cayman, offering unmatched sunset views, Latin-inspired shareable plates, and exotic cocktails.
The Hive
A vibrant open-air bar full of locals and tourists with affordable drinks and smoked barbecue. Pro tip: Go at 4 p.m. for happy hour specials and barbecue or at 10 p.m. when everyone will be dancing to the local DJ set.
Backroom
This hidden gem is an intimate cocktail lounge embracing ambiance from the Prohibition era, known for its cigar and cocktail pairings but also a great-low key spot to wind down at the end of the night with friends.
Library by the Sea
Located at the Kimpton Seafire, this is a standout cocktail destination that is recognized as one of North America's 50 Best Bars. The menu is divided into chapters by genre (Rare & First Editions, Sci-Fi & Fantasy, Nostalgia) and every drink delivers a unique experience, with waiters sharing the narrative behind the cocktail when it's served.
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Brittany Coyle
Brittany Coyle
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For more inspiration and insider recommendations, visit our Cayman Islands page.