Finding Grand Cayman Events is easy with this up-to-date calendar.

When you venture out to any part of the island, you’ll find plenty of exciting events and things to do in George Town, Grand Cayman, Seven Mile Beach, and beyond.

Head to a beach BBQ, a music festival, or a fishing tournament – and so much more – your next epic day is ready and waiting in Grand Cayman.

Check back often for updates to the calendar and even more ideas for how to enjoy Grand Cayman all year long.

Cayman Natural Hair Show

Harquail Theatre, FJ Harquail Cultural Centre , Cayman Islands

Celebrate the culture of beautiful natural hair with Cayman’s 3rd Annual Natural hair show! This grand display of crowns for all occasions will bring together naturalists from all hair types, across the island and the world for an evening of unforgettable hair art display. Enjoy showcase of Natural Hairstyles from salons all over the island, […]

Saturday Session at Kaibo

Kaibo Beach

Nothing lifts the spirit like good music. Head out to the Saturday Sessions at Kaibo Beach to enjoy chill out tracks play on the decks, and live musician Denys Carbo playing saxophone to lunchtime diners. It's the soundtrack to your awesome weekend!

Dinner Jazz, Union Grill & Bar

The Cresent, Camana Bay , Cayman Islands

Thursday night is Jazz Night at Union. Listen to the polished sounds of local legend Devon Edie on sax. Thirsty Thursdays just got a whole lot better! Dine at a table or the bar.

Corona Sunset Session at Macabuca

857 North West Point Road, West Bay, Grand Cayman 857 North West Point, West Bay, Cayman Islands

Enjoy Corona sunset sessions at Macabuca. There'll be Corona specials from sunset to late night. Live dj, BBQ (5pm-10pm) and Happy Hour until 10pm!

Open Canvas at Karoo Grand Cayman

Karoo Camana Bay, Grand Cayman

Every Wednesday, Open Canvas provides a public venue for local artists to display their talents and work on their latest creations. Art enthusiasts can join the gathering and watch paintings come to life one brushstroke at a time. Bring your own art supplies! Additional Information Please bring your own art supplies.

Live Band Thursday at the Hive

Canal Point Drive, off West Bay Road, Seven Mile Beach, Grand Cayman

Sing and dance along as live local musicians take to the stage at The Hive every week! Enjoy happy hour from 4pm-7pm, followed by a delicious plate of BBQ and finish with a live show by one of Cayman's local bands.

Jam Night Mondays, GT Post

The Outpost at Rackams, George Town Waterfront

Join The Outpost at Rackams for Jam Nights! Join other musicians and enjoy creating/listening to live music. Drink specials and the largest variety of imported craft beers exclusive to this location. Let's Jam, Cayman!

Stingray Award 2025

Grand Cayman Marriott Beach Resort , Cayman Islands

The Stingray Tourism Award is an annual event hosted by the Cayman Islands Tourism Association (CITA), celebrating excellence within the tourism and hospitality industry of the Cayman Islands. The event honors individuals, organizations, and businesses that have significantly contributed to enhancing the island's tourism sector, whether through exceptional service, innovation, or commitment to sustainable tourism practices. Held […]

International Scuba Diving Hall of Fame

Hotel Indigo Cayman Islands , Cayman Islands

Join us for an unforgettable evening as we honour the first-ever all-women cohort inducted into the International Scuba Diving Hall of Fame. Set against the stunning backdrop of the Hotel Indigo, this inspiring celebration will spotlight the courage, brilliance, and legacy of women who have made waves in the world of diving. From captivating stories […]

Wine & Cheese Tasting

Le Petit Bar

Le Petit Bar Tasting Series 2025–2026 From September 30 to May 28, LPB transforms into a world of unforgettable wine & spirits adventures — from rare Bordeaux verticals and Escape-the-Cellar puzzle nights to indulgent pairings of cheese, charcuterie & chocolate. Why pick just one tasting… when you can have them ALL? Season Passes Now Available   Grand Cru Pass ($1,350) – […]

Pilates for Pink 2025

Camana Bay ARC Centre, Cayman International School

Pilates for Pink 2025 – Heart + Core Date: Saturday, October 4, 2025 Location: ARC, Cayman International School Time: 9:00 AM – 10:00am – Pre Pink Party, 10:00am – 11:00am Pilates for Pink Power Workout Join us for Cayman’s 19th annual Pilates for Pink — a high-energy, all-levels Pilates mat workout that moves your body […]

Miss Global International 2025

Hotel Indigo Cayman Islands , Cayman Islands

The Annual Miss Global International Pageant Returns to Cayman! This October, the Cayman Islands proudly hosts the empowering and highly-anticipated Miss Global International Pageant for its 21st edition, a beacon of transformation and inspiration. Women from every corner of the world will unite, competing for the esteemed title of Miss Global International 2025. Prepare for […]

Our Favorite Things To Do

From the renowned Stingray City to a trip to a turtle Centre to cultural activities at the Mission House, explore Cayman Visitor and find the Grand Cayman places and activities – on and off the beaten path.

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