The biggest variable is the
weather. Key West is not the best place to find a comfortable anchorage, but there is good
diving close by and lots to do ashore. One of the best
anchorages in the Keys is at Boot Key Harbor about 50 miles, an easy day sail, and plenty to do both
diving and ashore.
Heading West you will hit the
Dry Tortugas after passing several islands and crossing a 40 mile stretch of open ocean. It is possible to make that trip in a week if the
weather allows, but the crossing can be a tall order if the weather is bad.
Before suggesting anything I would need to know what level of seamanship you expect the
skipper and crew to have and just how much shore time is expected. Especially important is what kind of ground tackle and
anchoring experience.