Bill, I've done several trips in 26-footers leaving from the Stuart area. For the time frame you have, I recommend the Abacos.
From Stuart, I either take the
ICW or outside down to the Fort Worth Inlet as wind indicates. There is free
anchoring all over with a grocery store, gas station,
marine stores and beach all within an easy walk. (I recommend you do not leave your
dinghy at the park after dark) If the winds are light, I'll leave from Palm Beach and
motor over to West End. If it's a south or west (not common) I'll sail or motorsail. If the winds are strong out of the SE, I'll continue on south to
Fort Lauderdale and leave from there. It's possible to anchor in Lake Boca if you can't make it to
Fort Lauderdale in a day. If I need to wait for weather, I may wait it out at anchor in Palm Beach instead of paying for a marina in Fort Lauderdale. It's fairly easy to get out of the Fort Worth inlet at night if need be. As others have said, wait for weather when crossing the stream. This is a lesson I learned the hard way. Fortunately at the time you are planning, cold fronts and strong north winds should be rare. (If I stay at a marina in Fort Lauderdale, it's been the Las Olas which has a convenience store across the street and is an easy walk to the beach.)
As for guides, I agree Dodge's book is the best. I like Wilson's for the yellow pages that include prices. The explorer chart
books are good for detailed maps.
If you are on a
budget or just don't like
marinas, it's possible to anchor out every night. As I said above it's easy at Palm Beach and I've anchored out many times at West End instead of picking up a slip. From West End, you should be able to make it to Great
Sale, but can stop at Mangrove if you left late, maybe to clear
customs. I've also arrived at Great
Sale at night and anchored along the west side in prevailing SE winds.
Many cruisers head straight to Allan's
Pensacola, and down to Green Turtle from there, but if you like more deserted islands, I highly recommend taking in some of the northern Abacos. Realize, you may not be able to pick up any VHF weather reports in the northern Abacos.
In the Abacos, Marsh Harbour is best for reprovisioning, but you can also pick up supplies at places like: Grand Cays, Green Turtle, Treasure Cay, Man-O-War, and Hope Town. Fresh fruit can be hard to find and many
food items such as bread may only be in stock after the local
ferry arrives. You can anchor in Marsh Harbour and use their town
dinghy dock for
provisioning,
laundry, crew changes, etc.
When returning to the U.S. and Stuart, I've always headed straight back to the St. Lucie Inlet. Including one time under sail with no
engine. The channel changes from time to time, but my experience has been they at good at changing the markers.
I've always launched at Indiantown. Sometimes I've had the marina launch my boat with their travel
lift, but I've also used the town
ramp downstream of the train bridge. I've found this to be an excellent, long
ramp, good for trailers needing a bit of water. I've never seen it crowded. Being above the locks there are no tides or wave action. Docks on both sides of the wide ramp. I've always kept my vehicle and
trailer at the Indiantown Marina, but check out the self
storage place as well. There is a West
Marine and Home Depot easily available in Stuart if you need last minute items. I've also made good use of the auto store and
hardware store in Indiantown. The campground at the St. Lucie Locks is a good, affordable place to stay in the boat for night while it's still on the trailer.
The cheapest way to call home I've found is to buy a pre-paid Batelco
phone card once over there which will
work at most public phones. I was also able to get weather on my
iphone a couple times when out of VHF range. The Abacos, like most of the Bahamas are shallow water. Taking the time to study the tide tables and be comfortable with only a couple feet of water under your
keel at low tide really opens up many wonderful opportunities.