NY to Florida Keys. How difficult will this trip be?

some of the posts we've done over the years......Cape May NJ, Annapolis MD , Tidewater area Norfolk VA- Coinjock (cheapest fuel), Beaufort NC, Charleston SC, Savannah GA, and in Florida, Stuart area, Ft Lauderdale, Miami, Islamorada and finally Key West...happy cruising

Waterway Guide and Cruisers Net also have information. Active Captain still very useful. Then other resources to look at what is on land.

However, the "how difficult" question throws me. Why would it be difficult? Only one reason, Captain. It all boils down to you, your skills, your experience. That is what determines the difficulty.

While I greatly prefer running outside, there are a couple of areas I definitely wouldn't run inside. NJ and south Georgia.

Given your post and comments, your only off shore run is all of New Jersey.
Given good weather, it’s not bad .
Bad weather and it’s hell.
Let the weather be your guide.
From Cape May, I would run inside down Delaware Bay to the Chesapeake all the way to Florida till I got the Fernandina and then consider running outside.
Sounds like you have time in your side .
Forget about going out and around Cape Hatteras etc.
Plenty of anchorages and marinas on your way down to stop at along with help and repairs if needed. And generally much calmer waters.

It’s not a race!

I made the run from Ft. Pierce to Southport late last month. 37' Luhrs drafting about 3 feet. The inside run from Ft. Pierce to St. Augustine was fine, except for a couple of long NWZ for manatees. After you make the crossover at Haulover Canal (heading north), there is a LONG NWZ for manatees near Edgewater, FL. Also bridge timing can be important. My outriggers are 31.5 feet, so we had to open a few bridges and wait for a few others to open on schedule. We ran outside from St. Augustine to Charleston and back inside from Charleston to Southport. Again, there are a few bridges on the inside run.

Bob's Tracks (bob423) are invaluable when running inside. He's a sailboater with a deep draft, so tracks are more important. There are a few spots in SC, Georgia and Florida (particularly between Jacksonville and Fernandina Beach) that I would have been more concerned about without updated tracks. My transducer was working intermittently (and always failing in skinny waters), so I relied on the tracks at times. I used them with Aqua Maps on the iPad and iPhone. The app is free and Bob's Tracks are free. There is a small charge if you want to update the Aqua Maps zones you are traveling through (I think it was $2.99). For what it's worth, our Raymarine MFDs with updated Navionics charts also provided similar track information.

As for stops, we enjoyed Charleston, St. Simons and Fernandina Beach on the way down and St. Augustine on the way home.