Thanks for all the good pre-trip planning info! Here's what we found for our first time sailing the Keys for 5 days (1/2 day to start, 3 full days then 1/2 day to finish).
Chartered Blue Moon, a Hunter 41 (5' draft) with
Florida Yacht Charters : Bareboat Charters : Bahamas Sailing Vacations : Sailboat Charters : Flotilla Sailing : 360Yachting.com out of Key Largo (basically a good company).
Slept aboard night before start which gives more time to review boat systems plus always cool to be at a marina vs a hotel.
Forecast was for light and variable, partly sunny, highs to 73 - that changed to overcast, light rain and northerly winds steady 22 to 25 with gusts to 28 - but I'm gettin' ahead of myself.
Plan was to sail Bahia Honda then with a southerly wind, ride the stream 60 miles back to Largo on the last full day.....best laid plans....mice and men...??
Planning concerns were primarily 1) availablilty of anchorage options and 2) quality of holding for overnight anchoring
Here's what I found...
The Keys offer great sailing closer to home than say BVI or Bahamas ( each has pros and cons). In the Keys you get a chance to deal with shallow water ops, dodging countless lobster trap buoys, and beautiful water.
Anchorages are no problem, if the wind is right and you can find a "wave shadow" to avoid a rolly overnight - we had a smooth anchorages every night because of the northerly wind - if it had been easterly we'd have had to duck over to the NW side and been much more constrained.
The holding was great! Two anchors out every night in 7' to 9' of water, backed down at 1500 rpm and it held greatin the steady 20 - 25 kt blow.
Anchored Rodriquez, Long, Indian and back to Rodriquez Key for overnights.
Didn't continue to Marathon because it would have been a bash on the return to Largo.
Overall great trip with half canvas, 4' - 6' seas in Hawk Channel, good food, good rum and great crew (Cindy).
We didn't get to sail the plan but we had a blast. Will do it again sometime.
Cheers!