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Book Now & Secure Your Spot
We have new offers posting all the time. We reserve our group space well in advance to provide you with the best price possible and give you the flexibility to pay over time. Which trip will we see you on?
HiBEARnation 2025
Our Annual Fall Cruise to the Caribbean offers a last chance at sun and fun on the beach before the chill of winter sets in!
Bigger Cruise 2026
Our bi-annual cruise partnership sets sail for Alaska in 2026. CruisingBears.com joins forces with BiggerCity (the social/dating app) to create BiggerCruise.
Our European adventure sets sail in Switzerland and ends in Amsterdam just before the World Pride Canal Parade!
World Pride River Cruise 2026
Set Sail into Adventure!
Come join us on the high seas for a trip filled with laughter, love, and celebration...where you belong, and where the adventure of a lifetime awaits!
Future Trip Ideas...
