East coast adventure

It s hard to give you an intelligent answer without knowing what kind of boat we re talking about.... 30 footer or 100??

That said, usually April is as early as you want to head north from FL as there is really no point getting to England before may or even June.. in the fall, most boats start south in October. It depends where you re going but most mooring field and marinas go into hynernation by October

Best Months (particularly if you are used to a cooler climate in the PNW):
Carolinas-Chesapeake: April/May, October
Southern New England: June, September
Northern New England: July, August

We are a PNW boat, and are currently cruising the East Coast (although I've done this coast dozens of seasons)

You could easily haul the boat and store it inside during the winter months. Or you can keep it in the Chesapeake or Carolinas during the winter.

Where are you actually going to be living?

With owner and crew based out of San Diego CA we did three years of cruising the Bahamas and the east coast Key West to Boston on an 85' motor yacht from a home port of West Palm Beach, FL.

With owners aboard, a typical trip north would be Palm Beach to Port Canaveral to St. Augustine to Savannah GA to Charleston SC. Then leave the boat for two or three weeks. Come back and head from Charleston to Southport NC to Beaufort to Coinjock to Portsmouth/Norfolk VA where we would leave the boat again for a couple of weeks or more. Then to the Chesapeake and leave the boat in DC, and so on. Combined running inside and outside and taking whatever time the owners wished as we stopped along the way.

We all flew home to CA between trips.

Getting back down south typically in late September was just point A to point B straight shot type deal without guest.

I haven't wintered there, but I've heard you can even enjoy boating in the winter.

http://mvdirona.com/2017/01/winter-cruising-in-chesapeake-bay/

Leaving a boat unattended and unwatched is not a good winter idea in the Chesapeake or many other places. However, a boat properly set up for the cold weather and managed well can be most enjoyable. We boated on the lake in NC over the winter in a runabout, not on 20 degree days but many warmer days over winter. If you're on the boat and have good heat, then the outside temperature isn't going to matter as much, just must take safety precautions. There are areas of the Chesapeake that freeze, shallow areas, but the majority does not.

It really depends on how much use and how well watched the boat is when not used. Is it kept warm, everything protected? Is it monitored to protect against power outages and generator used if any do happen? If I lived in the area of the Chesapeake and had a boat there, I'd use it year round. However, if I was commuting from a distance, then I'd move the boat further south. Several degrees change with every couple of hundred miles.

Kept my boat in the Chesapeake last winter in Baltimore, in the water. Did winterize her mid December and re-commissioned her very early April. Many boats kept in the water and are used year round. Found the that some marina's will check your boat daily or weekly if you are away.
You can get some ice build up at times but none last year. Some marina's have bubblers on hand if needed and some owners have them under boats. Again, no ice last year but some years in Baltimore you can get ice for a week or two.
Had one snow fall of about 4" end of March. Gone in a day. Some years you can get a storm or two of several inches.
There are a few marina's that have covered wells which is a great option. Also, some marina's have very well protected areas to winter in that will allow for year round use.
Knew a couple of boaters that ran down to Atlantic Yacht Basin in Norfolk area. They did not winterize. Cruising is limited out of there.
Just need to find a marina with onsite owners or staff that can monitor your boat. Then you can cruise on good days and not worry about boat when you are away.

It depends. We're 10 minutes from the boat, so I can check whenever I want, and when our marina freezes in I can easily come down and turn on the deicer, etc. We winterize engines and water systems, though, and we have no easy onsite winter water or pump-out... so "visiting" is a dry affair, when sunlight is enough to warm the bridge and/or cabin.

OTOH, there are some marinas, mostly in Baltimore to my knowledge, that cater to winter-time residents. Bubblers in place, in-slip pump-outs, in-slip water, etc. Something like that could work. I suspect that many who take advantage of that don't actually go anywhere in winter, they just enjoy time on the boat in the slip... in downtown Baltimore, which has some attractions. Probably similar in a couple places here near downtown (or close enough) Annapolis, since I'm aware of some liveaboards in this area and they have in-slip water and pump-outs...

Exceptions, of course, but I suspect most of the winter on-water traffic around here is about sailboat racing.

-Chris

If you have no east coast land base, commuting from the west coast, then I'd keep the boat during winter as far south as feasible and not on the Chesapeake Bay. If I lived in Maryland, then I'd keep it on the Chesapeake.

The furthest north we ever kept the boat in winter was Thunderbolt GA. If you are going to button it up between trips and maybe just have a local keep an eye on it, I highly recommend floating docks. Not always possible depending on where you are leaving the boat, but always preferable.