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

I've made this trip many times (although not for a number of years), and have never found it to be very difficult. That being said, you'll want to make sure you have all the spare parts you'll need for routine repairs along the way- there aren't always contractors available.
Study the charts, follow the markers, and there are plenty of really nice stops to make. If you're planning to make the whole trip inside, it can be a LONG one because of all the no-wake zones.
A search of this forum should give you all the info you'll need. There have been plenty of discussions over the years. My personal favorites are Annapolis, Charleston, Savannah, and St. Augustine.

Belts, filters, hoses/clamps, raw water impellers, pumps, toilet parts. Tough to say more without knowing the boat. Imagine the things that could really ruin your cruise if they fail, and have spares for those things.

Ken nailed it. I d add Southport and both Beaufort to the list. st Simmons is pretty nice too. Anchoring off Cumberland and dinghy if ashore is worth a day too. Wild horses, ruins etc. cape look out is worth a detour as well

Are there still cruiser guides available and chart books?

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

Yes. For the ditch the best chart book is the ICW chart book by… I think it’s Kettlewell or something like that. The charts are organized to follow the general direction of the ICW. It has margins for notes. A must have if running the ditch

if it is still available .

other must have resources are active Captain although since it was bought by Garmin content has gone done. There is also a guy who posts a lot of ICW shoaling updates on line. Forgot his handle. I haven’t had to run the ditch for 8 or 9 years so I haven’t been keeping track

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.

NJ ICW isn’t usable except by outboard powered boats

If time isn’t a factor I really like the ICW. Yea it s a few more miles but the scenery is worth it.

I enjoyed the South Ga section. Yes there are shallow spots but 7’ of tides it’s easy to time it right. Something very peaceful about the low country and marshes.

i did the round trip 4 years in a row before the boat stayed in FL year round. It was a 70 footer but with a 6 1/4’ draft. Timing the tides was critical

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!

Yep!!

Indeed the NJ run is the worst part of the trip. Just plain boring and ugly

cape may is a nice stop then I always ran upnthe delaware into the canal and down the Cheasie. Beware of the Delaware when wind opposes current. It can be downright vicious

many great places to explore in the Cheasie on the way down to Norfolk

I love the trip and agree with others… NO to NJ. Also, I’ll never do GA segment of ICW again. Mud river was super shallow and stressful but I do like St. Simons

Just time the tide. Start later on the day of high tide is in the after noon. Many options

One trip we had been delayed before leaving and I had a deadline to make CT. I ended up running at night with the high tide to make up time. I remember passing by new river inlet NC, right before the marine camp, which back then was a known problem spot. I had to try 4 times to fine the deep water… backing down when the sounder hit 7’ (6 1/4 draft) and trying 20’ to the left. After 3 tries the track looked like a pitchfork. Wasn’t easy to keep the boat oriented at night .

Have you done some short trips in your area? It's just a series of short day trips. Having the right mindset is critical. There is no race, you can run for a few hours and tie up or drop anchor to enjoy a new spot. Pick your weather and go outside if the weather, available inlets and the distances are favorable. Talk to anyone on the dock each afternoon and find out what they think about the area you're going to run through the next day and write some notes on your charts if there are concerns. Enjoy!

Bob423… that’s the name I was looking for

another misconception about the ditch are the nowake zones. North of Stuart FL there aren’t that many even if you include the few “congested areas” with docks and homes that are not “official” NWZ. Back then I made a list but I can’t find it. It was like a total 0f 50nm out 1400. Even if it has doubled by now it a still just 10 % of the run

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.