05/31/2026
Im baffled 🤔
I started this business out of my love for adventure and being near or on the water. Let's sail!
05/31/2026
Im baffled 🤔
05/30/2026
We had a great day on the water with new guests. Good sun and good wind makes for a good time!
05/29/2026
It's a beautiful night to spend on the water.
05/27/2026
Cool Breeze Sailing Charters LLC offers day and evening private Charters in the Baltimore area and in the Annapolis area. Would you like to book a special event with friends at a concert at Pier 6? We gotcha! Would you like a weekend sail to historic St Michaels? We gotcha? We can handle 2-6 passengers for special occasions like birthdays, family outings and girls/guys night out! Food and drink are welcome!
05/24/2026
It's cold and wet but still a good day to be sailing!
05/18/2026
I appreciate each and every opportunity I get meeting new people who employ me to be on the water. It's a blessing that I don't take lightly. I had horse breeders onboard today and their horse won at Laurel while he was on the boat with friends! That is so cool! If you enjoy sailing or being on the water, book a sail! We offer 90 minutes to all day charters. The couple I posted were celebrating their first year anniversary from Virginia. Book online www.coolbreezesailingcharters.com. Come for a sunset set sail or cruise around the Baltimore harbor.
05/11/2026
Monday morning at rest after 2 days sailing the Chesapeake Bay. We dropped lines in Mayo MD and sailed across the Chesapeake Bay to St Michaels for the night leaving Sunday morning for Annapolis MD. The City dock area in Annapolis was very crowded with boats and nowhere to dock so we motored through "Ego Alley" and then on back to the home port in Mayo. No issues and a good time had by all. Thank you Lori, Duane, Sam and Candi for a wonderful weekend! Who's got next? Are you looking for some weekend adventure with friends on the water? Check us out at www.coolbreezesailingcharters.com
Sailing across the Chesapeake Bay !
| Monday | 10am - 7:30pm |
| Tuesday | 10am - 7:30pm |
| Wednesday | 10am - 7:30pm |
| Thursday | 10am - 7:30pm |
| Friday | 10am - 7:30pm |
| Saturday | 10am - 7:30pm |
| Sunday | 10am - 7:30pm |