Crising to the Islands Mon
First of all, you don't have to go all the way to Key West (unless you want to) to get around to the Atlantic side for a gulf stream crossing. You can run down to Marathon Key where there is a 65' bridge at the Moser Channel. Then you can run up the Hawk Channel to Key Largo (anchor at Rodriguez Key or get a slip at the Bahia Mar Marina) and then head out through the reef there and go to the Bahamas. But, if you want to do Key West for some hanging out, that is fine too.
Actually there is another bridge further north of Marathon, but the waters of Florida Bay are very shallow and while you can make it with your 5'5" draft, you might have problems. At Moser, you won't.
The biggest thing is to watch for a weather window. In January there will be a lot of unsettled cold fronts and you want to have a nice crossing over the gulf stream. Whatever the wind and sea conditions are in Florida, figure it will be 6 times worse in the middle of the gulf stream. So, pick your weather or you will have one very uncomfortable ride.
Not sure where you want to go or how much time you have, but most go to Bimini or Cat Cay and some go to West End. Depends on whether you only have a few weeks, or a few months. If you only have a few weeks (after you get to the east coast of Florida), then Bimini is about all you can do figuring you might have to wait for a gulf stream crossing weather window. Assuming you have a bunch of time, if you want to go to the Abacos, then sail to West End, stay and clear at the Bahama Bay Marina (very nice) and then work your way around the north end of the Grand BAhama Island to the Abacos.
If you are going to go to the Exumas or Nassau, then go to Bimini, clear in Alice Town and then head around north rock across the banks past Mackie Shoals to NW Providence Channel light and then head toward Nassau. Or, you can clear south of Bimini. Keep south of the Gun Cay light and motor around to Cat Cay and clear there. Then head across the banks past the Russell Beacon to the NW Providence Channel light and then to Nassau.
If you want to hit the Berry Cays on the Way to Nassau, you can go into Chub Cay or anchor around Whale Cay, but unless you want to mess around the Berries, might as well go to Nassau if that is ultimately where you are headed (or to the Exumas).
You should bring your passport. Upon clearing you will have to get a cruising permit and pay $150 (boats up to 35'). Have them write in that a Hawaiian sling is permited (otherwise they have said you cannot use them) so that you can use one for spearing fish and lobster. Provision as you would for any long cruise (another topic).
If you go to Nassau and want to find a slip, then I suggest the Nassau Harbour Club. It is east of the two bridges between New Providence and Pardise Islands. Peter is the Harbour master there. It once was a hotel and had a restaurant, but it is now a staging area for the building of nearby Rose Island where (bummer) modernization is being introduced. But, the marina is open for transient boats. The real nice thing is across the street from there is a shopping center with a great grocery store, liquor store, hardward store, Internet connection, clothing store, etc., which is much nicer to shop in instead of the maniacal shopping in downtown Nassau.
From Nassau you head out the east channel past Porgee Rocks to Hybourne Cay and then down the Exuma chain.
For charts, I would get the Explorer Chart books. They are fantastic and very informative.
If I knew where you were going, I could give you more places to anchor.
If you are going across the banks, then you can anchor anywhere. It is shallow there. Just have an anchor light burning.
You can anchor behind Gun Cay or rent a slip for the night at Cat Cay. You can anchor in the Alice Town/Bimini Harbor, or rent a slip. You only want to anchor along the outside of Bimini or anywhere along that area during the day. There can be some good swells in there at night and the holding is not good. Honeymoon Harbor, south of Bimini and north of Gun Cay is a good anchorage, however, if you need someplace to duck into in the middle of the night and then you can clear in either of the two places when they open up.
Hope this helps. Let me know more of your plans and I probably can be of more help.
I'm preparing for a cruise for the first time from Clearwater to Key West and maybe to the Bahamas in January 2009 in my 30' sloop with 5'5" keel. Any suggestions for anchorages, equipment to bring, cautions? I have a Garmin 440s and Scitex sounder for backup. Any special prep for leaving US to go to Bahamas? If I love cruising where should I go after the Bahamas?
thanks in advance,
Dan