Cool Breeze Sailing Charters LLC

We're back on the water and taking bookings, spots are available for Father's Day, 4 of July and Sail250!
Treat dad to a private sail around the Baltimore harbor.
Book online @ www.coolbreezesailingcharters.com!

There's no better way to get to know your boat than doing the hard work and looking over every inch of the boat. Cleaning the hull, sanding and painting the bottom and knowing you've done a good job. Total cost was under $800 and that could have been double if I had the boat yard do it. I was done in 3 full days, no rushing. She looks great! Let's go sailing!

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Working my ass off painting today and trying to get her finished and back in the water tomorrow afternoon.

They are closing the lighthouse store on Boston st in August. Big discounts up to 20% on bottom paint.

West Marine, a national chain of boating supply stores, will close four Maryland locations as part of a nationwide restructuring.

🎥: Josh Davis, The Baltimore Sun

It's getting hot out here so I put the canvas back on and added new 400w speakers in the cockpit area. We are styling now, let's go catch some wind! 😄⛵

WEEKEND ESCAPE: CHESAPEAKE BAY SAILING ADVENTURE

Mayo, MD → St. Michaels → Annapolis aboard a Hunter 34.

Hoist the sails, take the wheel, and chart a course for the perfect weekend on the Chesapeake Bay with Cool Breeze Sailing Charters.

This is not a spectator cruise. This is full-participation sailing — where you're invited to trim the lines, navigate open water, and take the helm of our sleek Hunter 34. Whether you're a seasoned sailor sharpening your skills or a curious first-timer eager to learn, this hands-on adventure is built for you.

YOUR ITINERARY

Saturday Morning — Depart Mayo, MD
We cast off and set a course across the Bay. Feel the breeze fill the sails as you settle into the rhythm of the water. Along the way, our experienced captain provides guidance on sail trim, points of sail, and helmsmanship — or simply offers tips while you soak up the sun on deck.

Saturday Evening — Dockside at the Chesapeake Bay Maritime Museum, St. Michaels
We tie up for the night right in the heart of historic St. Michaels at the renowned Maritime Museum. Step ashore and explore exhibits celebrating Chesapeake boatbuilding, oystering, and bay heritage. Then gather for a relaxed dinner dockside as the sun sets over the harbor. In the morning, wake to coffee and breakfast with waterfront views before the museum opens — a private, peaceful start to your Sunday.

Sunday Morning — Sail to Annapolis
Back underway, we set sail for Maryland's capital. Put your new skills to work or simply relax and enjoy the ride. Dock in downtown Annapolis in time for lunch at one of the city's beloved waterfront spots — the perfect toast to a weekend well spent.

THIS TRIP IS FOR YOU IF YOU WANT TO:

· Steer a 34-foot sailboat under the guidance of a pro
· Build real, practical sailing skills
· Explore St. Michaels from the water
· Enjoy dockside dining and museum access
· Kick back with sun, salt air, and good company

No experience required. Just bring your sense of adventure and a willingness to pitch in. Contact us at 4103369912 or send us an email to [email protected] for more information.