If you want to do St. Michaels area (Oxford, Tilghman Island, Annapolis, Chestertown, etc.) you probably want to start from Sandy Point State Park near the Bay bridge. The advantage is that the price is very reasonable for a nice launch facility and you can park there for up to 14 days for the launch price (the parking limit is not strictly enforced AFAIK). Kent Narrows is also a good starting point, but I don't know about the parking arrangements. I have launched out of Sandy Point for multi-night excursions on the Bay a number of times without any problems.
If you want to anchor out, the Wye Island NMRA is a nice area, but the black flies during the day can be a b**ch in warm weather.
But again, you need to choose whether you want a north bay or mid-bay experience. Allowing only a few days for a gathering pretty much means you should pick one or the other.
If you want to do the north bay, then Havre de Grace is a good place to start. The parking there is the launch fee ($10 two years ago) for a any number of days. There is (was) no published limit how long you can park, you just have to let the dockmaster know when you plan to be back.
Some of the places mentioned have limited moorings available for transients. 5 or 6 boats is probably ok without specific arrangements (especially during the week). If you are talking about 30 boats, better to have this arranged in advance with the destination marinas otherwise the boats are going to be scattered around the available moorings, which will probably be in different marinas.
Also, be prepared for the prices. Some places are pretty inexpensive (e.g Chesapeake City = free (without power), but not a lot of spaces). St. Michaels or Annapolis could be around $100/night for a 22 with power. Depends on what else is happening when the gathering occurs. Got to figure on ~$3/foot LOA when thinking about marinas for short term transients on a weekend. This gives an idea of the rate+power. Some places have 2 night minimums and/or minimum fees. For instance, one marina in St. Michaels had an $80 minimum + $15 power/night in 2021 on weekends. Having a group show up may enable a discount. FWIW, where I live in MI, the transient rate is ~$30/night including power.
If you want to anchor out, the Wye Island NMRA is a nice area, but the black flies during the day can be a b**ch in warm weather.
But again, you need to choose whether you want a north bay or mid-bay experience. Allowing only a few days for a gathering pretty much means you should pick one or the other.
If you want to do the north bay, then Havre de Grace is a good place to start. The parking there is the launch fee ($10 two years ago) for a any number of days. There is (was) no published limit how long you can park, you just have to let the dockmaster know when you plan to be back.
Some of the places mentioned have limited moorings available for transients. 5 or 6 boats is probably ok without specific arrangements (especially during the week). If you are talking about 30 boats, better to have this arranged in advance with the destination marinas otherwise the boats are going to be scattered around the available moorings, which will probably be in different marinas.
Also, be prepared for the prices. Some places are pretty inexpensive (e.g Chesapeake City = free (without power), but not a lot of spaces). St. Michaels or Annapolis could be around $100/night for a 22 with power. Depends on what else is happening when the gathering occurs. Got to figure on ~$3/foot LOA when thinking about marinas for short term transients on a weekend. This gives an idea of the rate+power. Some places have 2 night minimums and/or minimum fees. For instance, one marina in St. Michaels had an $80 minimum + $15 power/night in 2021 on weekends. Having a group show up may enable a discount. FWIW, where I live in MI, the transient rate is ~$30/night including power.