Weekend boat to single/short hand on the Chesapeake

[Medved]

Hi all, I am looking for suggestions on builders and models to use on the Chesapeake bay by myself or with a friend. I am not a very experienced sailor. I used to own a 36’ power boat and recently certified to ASA 104. I am looking to continue building sailing experience. I realize this is a bit broad, but looking to start somewhere. I know one of the questions will be budget, so the best way I can put it is this... I am willing to spend money on a boat that would make sense and at this point would prefer not to use that as a limiting factor, but instead as an input into overall decisions.

[thomm225]

I've been using a Bristol 27 on the Southern Chesapeake Bay and Atlantic Ocean for the last 11 years.

I paid $2,000 for it but decided to fix it up a bit over the years and put maybe another $8,000 in it for a replacement mainsail, dodger, mainsail cover, autopilots, paint, solar, SH GX2200 VHF/GPS/AIS and Raspberry Pi 4 computer for chart plotter w/OpenCPN, replacement engine (outboard 5hp, 4 stroke), outboard brackets, settee cushion, alps sleeping pads, hand helm Suunto compasses, LED Cabin Lamps, shades, etc.

Friends of mine have boats like the Catalina 27 and 30, Westsail 32, Alberg 30, Hunter 35.5, C&C 29 Mk II, etc they use on the bay and ocean here