Planning mostly luck
On my trip the weather started out not so good with yes at the Marina very nice but on way to montauk the wind built to about 30 and had to delay one whole day until the wind died down,started out very cool for sure.
You never know what the weather will be from year to year,for the most part things were good most of the trip with one or two sqaulls along the way,from Montauk to below NJ was the worst waves and wind.
Weather will be the deciding factor if going inside or outside,my plan was all offshore until the auto and weather reporting stopped working so we ducked in at Cape hatteress inlet ( very bad inlet )to try repairs but no good no auto or weather radio so out again at Moorehead City( very good) offshore to Ft Pierce.
Yes a lot of planning and spare parts for engine,froozen food and canned and boxed foods,energy bars,fresh fruit, lots of drinking water,35 gal fuel in tank and 30 gal of fuel in jugs,extra fuel filters,offshore life raft,ditch bag,extra flash lights,on and on.
We were 100 miles offshore at times so we were much more prepared for any emergency,first aid kits,sea sick pills,our plan was from NY straight to Bahama's and than to Florida.
I had all the charts cruising books,3 handheld GPS and Raymarine C-80 and radar,had Sirius weather radio stopped working do to bad cable,now working but have not done offshore trips yet.
In Jan I sailed down around Keys and up to Punta Gorda,everything was great and good weather until last 1/2 day,you do want to make sure your boat is good to make along trip with lots of motoring and sailing
Nick