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October is here, and there’s plenty happening across the Cayman Islands. From a full month of dining specials and live piano performances to cocktail celebrations and the beginning of Pirates Week, there are lots of reasons to get out and enjoy Cayman this month.
Whether you’re planning your next dinner out, looking for something different to do, or ready for one of Cayman’s biggest cultural celebrations, here are a few October highlights to add to your calendar.
October 1–31
October is the perfect excuse to try somewhere new. Cayman Restaurant Month brings together participating restaurants across the islands with special menus and dining experiences available throughout the month.
It’s a great opportunity to revisit a favourite, discover a restaurant you’ve been meaning to try, or simply make a few more dinner plans this October.
See Cayman Restaurant Month events & details →
October 1, 3, 8 & 10
Add a little live music to your October plans with the Cayman Piano Festival. Across four evenings at the George Town Public Library, audiences can enjoy a programme of piano performances in a more intimate cultural setting.
With concerts spread throughout the first part of the month, it’s an easy way to add something a little different to your October calendar.
See Cayman Piano Festival details →
October 22–29
Later in the month, Cayman Cocktail Week puts the spotlight on the islands’ cocktail scene, with participating bars and restaurants joining the celebration.
Whether you’re heading out with friends, discovering a new spot or seeing what your favourite bar has created for the occasion, it’s one to keep on the radar for the end of October.
Explore Cayman Cocktail Week →
Celebrations begin in Cayman Brac - October 30–31, 2026
Pirates Week is back! The celebrations kick off in Cayman Brac at the end of October before continuing across Grand Cayman and Little Cayman in November.
From pirate landings and colourful parades to heritage celebrations, Caymanian food, live music, family fun and island traditions, you don’t want to miss one of Cayman’s biggest cultural celebrations.
Stay tuned to our Pirates Week events category for confirmed events, dates and details →