Using your numbers, doing 1,000 nm in 10 days means you need to make 100 miles per day average. This might mean you have to keep moving in some really unfavorable weather
and leave little time to see the sights. Your route
is doable and could be most enjoyable
If you make 6 kts average (not that easy in a 27'er) you will have to sail and average of 16 2/3 hours per day.
Give yourself more time or lower your expectations on how far your going. Do, however, get on the boat
and go somewhere. You will love it. How about including the Dry Tortugas
, then back to the west side of FL?