I've made the trip several times in different boats from a 32 foot Tahiti ketch
to Island Packet
380 and 40. We usually anchor at Cabbage Key, leave there around 7 AM go out Boca Grand Pass and arrive at the NW channel next morning around dawn. It's about a 24 hour sail/motor sail. Burnt Store would add an hour or two to our typical trip.
If you want to do a two day trip you could go into Indian Key and anchor in Russell Bay for the night. It's a long day sail to Key West from Indian Key, but with summer hours you can make it if you motor
sail. I haven't done it in summer, but have been to Indian Key in November and January with no bugs. If you go to Indian Key, just make sure you stay south of the Romano shoals before heading into the pass. There is a buoy south of Romano shoals that will take you a little farther south than necessary for a 5 foot draft
, but is the safe way in. North of that buoy, you will see some 9 to 10 feet water
, so if that makes you nervous, just take the safe route
. From Indian Key to Key West NW Channel entrance is about 70 NM.