Churchill's Cigars Cayman


Winston Churchill is one of History’s most well-known cigar smokers, and it is said that he discovered the joy of cigars whilst visiting Cuba on a working holiday in 1895. So what better namesake for Grand Cayman’s longest established retailer of Cuban Cigars.


Churchill’s Cigars has the largest selection of genuine Cuban and other internationally renowned cigars on the island from famous brands including Cohiba, Montecristo, Partagas, Romeo y Julieta, H. Upmann, Hoyo de Monterrey, Punch, Rocky Patel and many more.

Making the choice

Whether you are a cigar aficionado or a beginner, our expert team can help with your selection. From the subtle differences between Honduran and Cuban tobacco leaves to how fine cigars should be stored and cared for, they will make sure that you have everything you need to enjoy this experience.

Duty Free

Duty free purchases of cigars are available for cruise ship passengers only at this time. If you are visiting from the USA, this is the first time in 50 years where US citizens have been able to freely take home Cuban cigars. The duty free allowance for the US is up to 100 cigars, so buy a box!


Although Duty Free is only applicable for Cruise Ship passengers at this time, Churchill’s Cigars is known locally to have the lowest prices and best quality and selection on the island.


From essentials to novelties, you will find curious gifts and accessories all year round in Churchill’s Cigars. Authentic Cuban souvenirs, torches, cutters, wooden ashtrays, artwork, humidors and Cuban Coffee to name just a few.

be the first

to know

With the end of the USA’s import restriction, Cuban cigars are in high demand. Be the first to know when we receive a new shipment.

Churchill's Cigars Cayman

The Island Plaza Duty Free Shopping Mall (under Margaritaville)

Churchill's Cigars Cayman

Welcome to Churchill's Cigars Cayman

You must be 18 years of age or older to enter this site.

You must verify that you are 18 years of age or older to enter this site.