Massachusetts to Southeast USA

I'd be down to do this when it's not Hurricane season. I know a lot of people feel comfortable just going around them, but being from the east coast, I feel like that time of year, the weather can change on you real fast and it'd be better to do that trip in the summer I think. I have very little sailing experience at this point, though I have been trying to learn everything I can. I am hoping to be doing this in the next few years too. Saving for a boat has not been going as planned though.

Are you planning on going offshore the whole way or down the ICW? The ICW is a piece of cake and just about anyone with any skill can make it. There are tons of “great loop” guide books that spell out every detail and even every stop if you wanted to follow the pack. I’ve done it 3 times in sailboats from 32ft to 19ft, it’s pretty simple. If you have to stop for 2 weeks every month it’s going to cost a good amount in marina stays and mooring balls unless you really trust your ground tackle but I wouldn’t leave a boat unattended for two weeks at anchor. Mooring balls are the cheaper option but they disappear around the south Chesapeake. From then on it’s just docks but some out the way docks can be relatively affordable. Biggest thing with the ICW when you get south of NC is a Reliable motor because the chnnel gets narrower and the current gets up. Lot of places in the Carolina’s, and Georgia it’s too narrow to sail unless you have perfect beam reach wind which you won’t because the route turns so much. You don’t need a crazy fast or powerful motor just something that won’t breakdown. In the 19ft I could only do 4.5 knots in flat water and had no issues running the channels or the inlets. If doing the ICW the only place you have to go off shore is NJ. Just run Long Island sound to the east river. Hop down the jersey coast, up the Delaware through the canal, down he Chesapeake, I like the the dismal swamp and go that way. Take any route through the NC sounds to moorehead city/beaufort and then there’s just the ICW or off shore the rest of the way south.

Honestly you won’t be sailing much if you do the ICW, LIS, Chesapeake, and NC offer the best options but if you are on a schedule you will be motor sailing even when your sails are up.

I normally tried to be in New York City around mid October so your timing is perfect, the weather is normally comfortable all the way down. And hurricanes have normally stopped or slowed enough you should be fine.

I wouldn’t stay in Charleston unless you have work there. Charleston harbor is terrible to anchor for more than a few days. Big water where the waves can get up, high current, lots of commercial and rec boat traffic that throw huge wakes. People will fly right by you at anchor and a foul bottom that has eaten tons of anchors. Some of the small towns in the Carolina’s offer much better places to hang out long term. NC sounds or Florida offer much better long term options, NC gets colder in winter obviously but Florida is much more crowded and the cops are quicker to harass you if you stay more than a few days at one spot. I find it’s best to find a few good anchorage within a few miles that have shore access and just bounce around every 2-4 days. South Carolina has a few small towns that are nice too and might make decent options for long term stays like Beaufort.

I’d offer the help but just moved to Washington to boat the sound and inside passage.

Running offshore is not bad if you time the weather windows and use the “safer” inlets. That trip could be made in one week or so, depending on weather no where you want to end up.

If you have any other questions, let me know.