Two years ago I brought my Morgan 323 down to Ft Myers Fl via the ICW and outside. It was a great trip. We did not spend any time fooling around and the tripo took from 6/21 to 7/29. We came through the Great Dismal Swamp, something I would recommend.
Draft is something to be considered. My boat draws 4 feet and I bottomed a couple of time and got stuck, not to hard once. If you take the Dismal Swamp route be careful, I found my underwater tree.
Anchorages are many and picturesqe. Boat yards are abundant. But it is a long trip, from RI to North Ft Myers is 1658 miles.
The weather is to be watched, but in my estimation is not a cause to not go. If a big storm is coming you have lots of warning and can adjust accoringly. I am assuming you are not planning on goiung "outside" with your inexperience.
I would buy a neat litle book on the ICW, it gives drawing of channel intersections etc. I cannot remember the name but it is available in Marine Book stores and is well worth the $20.00 Also the cruising guide is an essential thing to have.
If you plan to stop in Atlantic City DONOT stay in the NJ State Marinia. It is operated by Trump, I paid $125 for a night. If you plan on Manasquam be careful of the tide, they are fierce.
The C&D Canal is a pirce of cake, the Md side (west) has a great place to drop anchor
(Cheasapeak City.) Annapolis is great, expensive but neat. Norfolk is a busy place, if you intend to take the Dismal Swamp route when you get to Mile Marker 1, turn right.
Charlestown, Savannagh, Jacksonville Beach are all ok, over-rated in my estimation. St Augistine is great. The Indian River, Canaveral, Melbourne etc are great and boater friendly.
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Elizabeth City NC is great, free slips to transients. The C&D