Cruising Division – Adventure, Friendship & Sailing Fun!

 

If you love the idea of casting off the lines, exploring new harbors, and sharing unforgettable moments with a lively group of fellow sailors, the Cruising Division is for you! We organize a variety of social activities and sailing adventures designed for those who enjoy the journey as much as the destination. Whether you’re a seasoned cruiser or just beginning to explore the world beyond your home slip, you’ll find a warm and welcoming community here.

Each year, our cruising calendar is filled with exciting getaways, from relaxed two- or three-day weekend trips to more ambitious voyages around the Chesapeake Bay—and occasionally even to distant destinations like New England or North Carolina. We choose scenic anchorages, quaint ports, and fun stops where our group can raft up, share docktails, enjoy potluck dinners, and swap sea stories under the stars.

Cruises are open to boats of all lengths and crew compositions—from couples and solo sailors to families with children or grandchildren. No prior cruising experience? No problem! These outings are a perfect way to build skills, gain confidence, and cruise in good company. Our friendly fleet of cruisers loves helping newcomers learn the ropes.

Above all, the Cruising Division is about enjoying life on the water, forming lasting friendships, and creating memories that will last a lifetime. Whether you join us for one cruise or make it to them all, we promise you’ll come back with stories, smiles, and a renewed love for the cruising lifestyle.

Let’s go places together—register for a cruise and join the adventure!