WELCOME Welcome to Chumley’s BearCruises, the original and finest Bear (and Bear-friendly!) group vacations. Created by Mark ‘Chumley’ Singer in 2003, our sailings offer you the opportunity to meet hundreds of amazing, diverse and friendly men from all over the world. Our goal is to search the best possible ships, prices, events and itineraries so that you can make your precious time yours – fill your days and evenings with exciting activities, or lay by the pool and soak in the sun – it’s your time and you work hard all year long for it, and we want you to enjoy every minute of it.

After years of performing and hosting fundraisers in the Philadelphia region, Chumley began hosting small groups on Caribbean sailings at the request of local sponsors of Philly’s popular GayBingo, which Chumley and Carlota [persona of Chumley’s buddy Michael Byrne] created and hosted for many years. Seeing how well the group dynamic worked, Chumley’s furry brain started to ponder the possibility of being surrounded by bears while at sea… Not being the ‘all-gay-all-the-time’ cruise type, Chumley realized that many others in the bear community would prefer to enjoy all that the modern cruise industry offers – state of the art ships and the best cruise lines, the camaraderie and warmth of the bear community, and of course the amazing savings over the outrageous costs of those all-gay sailings. Each year hundreds of men from all over the USA (and many from other countries) convene in our departure city to begin an adventure that is often described as one that is reminiscent of summer camp… you will make friends to last a lifetime. But be warned; Chumley’s BearCruises are extremely addictive – more than 2/3 of our guests return year after year - we invite you to experience our group sailings and find out why.