Thrilled sailor, owner of '86 272 O'day

[rc52go]

We've explored the Chesapeake with our little O'Day and fell in love with her. The "we" being my husband and I, our two dogs and two cats. Say hello to cozyness! Other than that we are jammed now, because this is our first time down the intracoastal. Currently debating which coast to sail to the Keys from given our 27' size and limited 10 hp westerbeke original engine. So we are going to need all the help you experienced Florididian sailors can give us.

[smackdaddy]

Hey rc, welcome to SN. You'll love the place.

[CalebD]

There are a bunch of other O'Day owners here so you are in the right place.
Does your O'Day 272 have a winged keel, plain shoal draft or fin keel?
I got a chance to go on a 272 that had a winged keel this past fall and we had a lot of fun. That boat was a bit tender but the owner had it for many years and knew when to reef it. What he did not know is that when we went aground in an ebbing tide in LI Sound that the winged keel would keep the boat upright, even when all the water had gone out. When the water came back in some 5+ hours later (8' tidal range) we motored out of there.
I am no Flordidian but what is nice about either the east or west coast of FL is that there are inside and outside passages almost everywhere. The inside routes can be a little shallow which is why I ask about your keel type.
Welcome to sailnut.

[endoftheroad]

When are you starting your voyage?

If you are leaving this time of the year and doing it from the Chesapeake you will be faced with several periods of high winds.
It's not much concern for motoring as it is being sure your anchor is dug in real good every night.
We did the ditch last winter from North Carolina to Key West and had many blows in mid 30's and even 40's but our ground tackle was alot of chain and some very huge anchors.
In fact we had a fellow poke fun at us at an anchorage one calm night about that big anchor on our boat. Of course that wasn't our only anchor but the one in question would have only been used for a "lunch" or maybe a calm weather anchor on a 40 footer but looked large on that small sailboat's foredeck.

But serioussly, you will be in some wilderness anchorages and be anchoring in many different and unfamiliar grounds.