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Welcome to Chumley's BearCruises, the original and finest
group sailings for the Bear (and the Bear-friendly!) community.

Created by Mark ‘Chumley’ Singer in 2002, our sailings offer you the opportunity to meet hundreds of amazing, diverse and friendly men from all over the world, and the time to make true friendships that will last for years to come!

We search the best possible ships, prices, excursions and itineraries so that you can enjoy yourself – whether that means keeping busy with activities and socializing, or simply hanging by the pool soaking in the sun – it’s your vacation and you can be as active (or not) as you wish. 


We sail as a large open group aboard regularly scheduled cruises, avoiding the ‘all-gay-all-the-time’ atmosphere of some group charters, and are able to offer amazing savings over those expensive charters as well.


While our annual Fall cruise tends to draw a large group, our Spring sailings are limited and offer a much more intimate trip and the chance to get to know all of your fellow passengers.


Each year hundreds of men from all over the world convene in our departure city to begin an adventure together in an atmosphere that is designed to be warm and welcoming. We invite you to explore the world of Chumley’s BearCruises – ask any of our past guests and find out why so many return with us year after year.

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Our Partners

We thank our partners in the Bear community.

Joining us this soon?  Remember to add your profile to the Events page of your favorite group!

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