I just don't understand all the Key West Bashing.... Any anchorage other than some lonely bight only big enough for one boat, will at times be rough. You want calm all the time? Get a slip!
To the OP: Throughout the Keys there are many beautiful places to
anchor. The suitability of each to YOUR needs is the determining factor in which one is for you. If you need
employment, your best bet is KW, followed by Marathon, then Largo, then Islamorada. If you are interested in provisions/repairs, again KW is 1st. Similarly if you enjoy spending time ashore; there is much more to do "in" KW than the other Keys.
KW has two City-owned
Dinghy docks; one at Key West Bight, one at Garrison Bight. The later being solely for the use of the City-owned
Mooring field. The one in KW Bight is open to transients for a fee (I think $80/month last I checked). There used to be a nice grocery store there at the
dock, but alas has closed.
If you are planning a long stay and want a real secure
mooring, there are literally TONS of old ship chain, shrimp boat anchors, and such scattered about. Many find it advantageous to shackle to such. Otherwise typically a
CQR or Bruce type anchor holds best around KW, but I've sat on Danforth styles in some pretty good blows there.
The City-owned mooring field is another option, but gets pricey at (about) $250/month which includes shore side showers/toilets, Pump-out, and an exclusive
dinghy dock with
security fence.
In
another thread on the same topic, I posted some pix locating all of the above.