Do you have to have a "marina" to stop for the night? 4' 6" draft? sailing day time only? sail down biscayn bay to Angel fish
creek...top of key largo. you can anchor by Bamboo key there on the bay side or anchor inside the creek near the ocean side. go out side to hawks channel...you can sail to rodreques key or if making good time to channel 5 by long key. It's a short sail to Marathon from there if you like or go on down to Bahia honda
...which isn't all that good holding with strong tidal current
...better a little further in thhe mouth of New found harbor. from there at 5 knot
average it's about ten hours to KW bight. Sailing day time only at 5 knots it's a minimum of three days. you can figure the distance as the crow flies or even as some do the mile markers on the ICW
. but for instance, according to the mile markers it's 50 miles from Marathon to Key west. in actual travel it's 58 to 60. At 5 knots there is one to two hours of travel difference. If you only want to sail in daylight I would give myself 4 days. the actual miles traveled from say dinner key to key west anchoring
daily is about 180 miles. 180 miles/ 5 knots/ 8 hrs/daysailing = 4.5 days that is cutting 2 to 3 hrs of daylight anchoring
and weighing anchor, in real time.
If dealing with markers and patch reefs
is the cause of daytime sailing then going outside the reef say off the top of Islamorada and staying in 100 to 200 foot of water
would not only give you unobstructed sailing it would also give you the counter current
from the Gulf stream
, giving you an other 1/2 to 1 knot
in the right direction and cutting your passage
down to two and a half to three days, anchoring at mid evening for a good 8 to 12 hrs rest. the gulf stream
is to close in to go outside further east than Islamorada, the seas could get a little rough on an east wind.
i get a kick out of people saying "oh it's only 92 miles to Ft myers Beach from marathon. I can do 6.5 knots ...only 14 to 15 hrs." but then there is the distance and time getting in and out of the harbors and at 12 hrs they are only off little shark river heading over to anchor in 2 more hrs. It's close to 18 hrs at 6.5 knots cause in actually it's 120+ miles from harbor to harbor.
Good luck and give yourself plenty of time You'll enjoy the trip and probably make better time than you think. 37 footer should make 5.5 to 6 knots on 15 knot winds out of the eastish, comfortably, on that route
. in 15 knot east winds I do 8 to 10 hrs from Boot key harbor to christmas
tree of KW bight, comfortably outside the reef in 100 to 200 foot of water
. Set the sails
and enjoy the ride and company.