Best boat-up bars, beaches, restaurants, and clubs in Naples, FL ?

Pinchers is a great raw bar that you can take a boat to of any height. There is a nice area right inside the inlet that I see people beach boats at on the South side.

Naples doesn't have any real "boat up" bars, space is limited.
The Dock (restaurant) at the Naples City Dock can accommodate you if you call ahead. That restaurant is under new ownership and has a bit of a younger feel. Pinchers and The Riverwalk are further north and in Tin City. Getting space there could be a challenge for lunch. Kelly's across the from Pinchers is good for outdoor eating. But right where both those restaurants is the one LOW bridge.

South on Marco is Snook Inn which is pretty good and if you go into the island Mangos is better, but a slow ride in there. No clearance issues at any of these.

I am guessing that CaptJ is referring to Gordon Pass (Gordon River) for beaching on Keewaydin. The south end of that island, by Marco, is a big sandbar party.

Naples is pretty limited in the pull-up bars for lunch. There are 3 clubs that aren't open to the public in that bay.

Further north ( Ft Myers, Captiva) you will find: Doc Fords, Grandma Dot's (call ahead for a slip), South Seas (resort) and Cabbage Key (where Buffet's song "cheeseburger in paradise" was written about).

None of these will you have to worry about bridge clearance.

Just a different scene than on the east coast.

Hahahaha!

Well it is "fun"...just not nearly as much if you are under 55.

5th Ave has a bit of party scene. But even that really is some retired captains of industry trying to dance and not have a second hip surgery.

Stayed at the Cove Inn a few times in Naples.
Lots of dockage and a couple of bars and restaurants right there.
Good food, good place, will come back.

Limited yes. But I've taken a 90' MY in and out of the inlet and all of the way to the Naples boat club without any issues. Have also taken a 70' SF and others. Just limited that you can't go canal cruising. The 70' SF came out of that ritzy neighborhood North of the inlet.

Someone once told me that Naples is where old people go to visit their grandparents.

If I understand what you consider fun. I would say Haulover in Miami, the shoal off of Nixon’s old house on Key Biscayne???, the shoal off of Islamorada, Key West, Peanut Island near Singer Island. There is boat up bar in Jupiter that is quite the scene. On the west coast Egmont Key in Tampa bay. Haulover you may find too fun. That is best observed from afar for most of us.