Need suggestions for an appropriate style and size of family boat for this area. We will want to fish, do sunset sails, bar hoping, take friends out, that sort of thing.

I don't know what is appropriate with regards to draft, horsepower, overhead (bridge) clearance, etc. I will have use of a slip that can hold up to a 30' boat but I will also want something I can trailer to the Keys to play with on Bay side as well.

We are not into offshore activities, so we can sacrifice a little endurance for comfort.

Money is ALWAYS an object but I want to buy the right boat, the first time without regretting not getting an "upgrade".

This won't be my first boat (experience of freshwater lakes) but I have never owned a boat for the ICW.

Thanks for any thoughts

Not familiar with the St. Augustine side of things, but I have a 24' deep-V bowrider with a 260HP engine that I use in Tampa Bay. I'd say about 80% of the time it's no issue going through the bay and into the Gulf and I prefer it to the ICW because I don't like having to idle around and deal with other boat traffic. Growing up we had lake boats which would be inadequate out here. You see the castle-hulled rental Hurricanes struggling on all but the smoothest of days. I would buy used as there are deals to be had out there and you should be able to get out the door without a trailer for around $10,000. I thought I'd want to bring my boat to one location or another and your mileage may vary on this once you figure out what's right for you. I kept mine in a high and dry marina for the first year and then moved to a private lift due to the marina fucking up my boat more than once. The cost and effort of trailering and then moving the boat I think would exceed the cost of renting a boat when you're in the Keys.

I've spent way to much time on the Hulltruth looking at boats and reading reviews.  We are on the other coast looking at 22-24 foot boats.  They have a Florida section, and boats for sale section.  It is a really good place to browse pictures, and see what features you like.  Basically it is like this place but with boats.

HullTruth

My neighbor recently took delivery of Sea-Fox 226 Traveler to replace his older 22' SeaPro Bay boat.  It's a beautiful boat and has a lot of features his wife and daughters like such as the mini bathroom on the side console.  With a 250hp 4 stroke outboard it's not a speed demon but it moves pretty good and the draft is shallow enough for most areas except the flats.  It's a dual console with seating on the bow and seats on the stern so it has plenty of sitting space for passengers.  It's not a hardcore fishing boat or ideal ski boat but it does everything pretty well and is an ideal family cruising boat.  He has it on a trailer and tows it all over Florida with his Tahoe.

your going to at least have to decide on a style of boat OP.   No one boat style will do everything great.  It sounds to me like you want a center console bayboat, heavy on seating?

And don't fool yourself, if you do like to fish, you will take it outside the ICW.  That doesn't mean you need a battle wagon, just means you have to pick your days.  Plenty of guys I know take flats boats out of Ponce on flat days and fish the beach. 

30' Concept or Spectre center console twin 200 outboards ( there are tons of these around used)  Make sure you get an ALUMINUM trailer.

I'm on the ICW on the Panhandle.  If you truly never will leave the ICW, I recommend you look in to a modern pontoon boat.  They are comfortable, family friendly and surprisingly fun.  They are not our fathers pontoon boats that took all day to go a mile.

24" seafox. I charter those waters

My wife and I just had this conversation.  She is down in Tampa due to work reasons, probably for a couple years.  While I would prefer just to have a Jeep and a flats boat there, a center console is a lot more forgiving and therefore safer.  It also means having a bigger tow vehicle.  As posted above, you will get tempted to run out, a CC will be safer.  I often did the same thing with my old one on lake Erie or down at Ocracoke island.  I had a few exciting moments, and I was not looking to push my luck either.  They trailer fine if you have enough truck to pull them.

Luckily my wife likes to fish, so a CC with decent rear seating is a good compromise.  She can take friends and family cruising, I can fish.  I suggest you hire a charter with a boat similar to your interests.  That's the best insurance there is for making a good decision.  Guide with local knowledge and you are out in it.

CC are my favorite, but my good fishing buddy has a nice pursuit walk around.  its VERY handy for storing stuff that needs to be dry, little better lay out for non-fishing days (like diving or hitting a spring with the family).  The ladies like it because there is a head (although large CC's have them as well).  Same hull as a CC just a different cap, very very very capable boats. 

Thats why I was suggesting OP point us in the right direction. 

The pontoon boat is not a bad suggestion, or one up it to a deck boat.   I've fished, beached, cruised, toured on a friends one of those, it was just fine.  I personally didn't care for the I/O, but that's preference.  I also wouldn't buy one because it's not my thing, they don't ride to well once you get a good chop on the water.  Would i go offshore atlantic side in one?  ehhh, not more than a few miles from the inlet on a VERY nice day, but gulf side I wouldn't be quite as cautious, maybe run some beaches, but there are lots of places to hide in safety if the weather blows up on the gulf side depending where you are.  (still be very careful)  

I just looked at some Pursuit walk arounds, they do look pretty good.

There is more to a Pursuit than looks. Bronze thru hulls, mil-spec wiring and heavy hand laid construction to name just a few. One of the best boats made, period.

Question for you - I will be living in Flagler Beach (ICW side) Is Fort Matanzas to the North or Ponce Inlet to the South my only access to the open ocean?

Thanks for input

I think that is a little small. I'll need a boat at least..... 3X that size ( sorry, couldn't help myself)

Matanzas is north of Flagler..Ponce to the south. Yes . Those are your only two inlets.

I fish.but moved inland so no more salt fun for me. But used to run the icw from daytona to the lagoon. A shit ton.
If I had to pick one thst would suit my needs ( 2 to 4 anglers aka family).
It would be 18-20ft.
Draft very little aka sub 10 inches.
Center console. 
Big cooler lol .

But. That is honestly not what I'd like to have. Lmao.
I loved the 17tt pathfinder I used to cruise flats with.
But it's not a rough water boat.or one to fit wife..kid..me. dog.

Imho you couldn't go wrong with a decent 18-20 cc or Bay boat.

Hell. A carolina skiff..would do it all on the ICW and not break the bank.

No boat is perfect for everything. I am on the Gulf side, Clearwater-St. Pete area. Lots of ICW here, plus Tampa Bay, and of course, the Gulf on the outside.

90% of my boating consists of me and my wife Island and sand bar hopping or sunset cruising with a couple friends or family. Maybe 10% is serious fishing.

We are perfectly happy most of the time with our 20 foot bowrider with a big cooler, bimini top, and decent stereo. When I'm actually fishing, I always wish I had a center console with a t-top, big live well, and a lot less seats in the way. And then, I wish it was bigger so I could run further out.