Call 410-939-2869 to book your daysail!

Please Note: If you have not sailed with BaySail before, you will be required to fill out and return a 

DAY CHARTER APPLICATION form prior to approval of your rental.

We offer a fleet of 22 foot keelboats to practice your skills at the head of the Chesapeake Bay, also new to our fleet is a Hunter 33′.

Contact our office to book your day rental for either half day (9 am – noon or 1 pm – 4 pm) or a full day (9 am – 4 pm).


Rent DaySailers

-> Capri and Cal 22′ – Known for their sweet sailing performance in nearly all conditions, the Capri and Cal 22s have been winning the hearts of sailors for generations! These 22s have a comfortable cockpit and full cabin with seating for five.


-> Hunter 33′

-> Club BaySail -> 40 to 50% discount on our fleet of day sail rental (Capri 22’ and Cal 22’)

  • Bronze package -> 10 – ½ day rental (5 weekdays and 5 weekends) for $1260 (plus MD 11% tax)
  • Silver package -> 16 – ½ day rental (8 weekdays and 8 weekends) for $1680 (plus MD 11% tax)

DaySailer Rates

Capri 22′ and Cal 22′

1/2 Day: $210.00

Full Day: $305.00 plus tax

Hunter 33′

1/2 Day: $325.00

Full Day: $475.00 plus tax

Havre de Grace Sailing

Because of our convenient location just off I-95 in historic Havre de Grace, you will be driving less and sailing sooner if you choose to charter with BaySail. Charter the Chesapeake… and enjoy sailing one of the world’s finest cruising grounds. Whether you are in the mood for a fine dinner at a bustling harbor or a quiet day in a secluded cove, the Chesapeake Bay offers enough attractive and interesting cruising spots to keep most sailors busy for a lifetime. BaySail offers a choice of daysailers and captains for private instruction. A full range of sailing courses is also available, all of which are certified by the American Sailing Association (ASA). ASA certification ensures that our school complies with an established and comprehensive program. Plus, ASA certification is recognized worldwide by sailing professionals and yacht charter companies.