Seeking your help and advice to a newbie....Wanting to buy, and boat in the Keys.

[Suijin]

Others have touched on this but I think the fly in the ointment of this idea is going to be maintenance. A 40' $100k boat is going to be an older boat, and I fear that you'll end up spending much of your precious time when you get to the boat each trip doing maintenance. Cleaning, fixing things that have broken/deteriorated while you were away, and getting the boat ready to head out.

If I were you I would consider going with a smaller boat. A 30-35' boat will be not only less expensive out of the gate, but will cost lest to slip/moor/maintain. You'll get it ready to go each trip faster than a larger boat, within reason, it will be easier to handle, and most can accommodate 4 in relative comfort. You can always move up to a larger boat after you acquire some experience with the boat as well as your routine of travelling to it and getting it ready for a trip if you find that down the road you want to move up in size. You'll also have a much better idea of what you want and need in a larger boat.

[KeepInTune]

KeyTime: Great advice! I really appreciate your similar position and sharing your experience.
BandB: As well, thank you so much.

All: I am convinced that, as it often happens, my initial post was built on romanticism, emotion, and inexperience! I've learned so much just backing away and reading through 1,000 posts and replys on this great and helpful forum.

My plan now: Wait! I'm going to take my time and cruise with a 1-week ASA lesson and get my chops up to speed. As well, if I have a good school and captain, I will gain so much insight and advice. Once complete, I plan on puting my "I'm ready to throw it away.."-funds into chartering a few times around South Florida so that I can get the feel.
Fast forward 1-year: I will be in such a much better place to make informed decisions and have the vision to anticipate many (not all) of the hurdles and challenges with owning, operating, maintaining, and paying for a sailboat and cruising experience.

Thanks to all of you again for your help and guidence. I'll keep you informed with my progress over the next few months and the year. With that will be a few more questions and posts from me, so let me apologize in advance for that (!).
Thanks again!

[gah964]

know a place on stock island 2miles from key west 40ft will cost you 400 a month drydocked.

[sanssouci]

I have a 45 foot sailboat (Dufour) and a private dock on Geiger Key (MM 10). I am looking for a partner.

[Paul Annapolis]

Let's see if we can unpeel this onion...without too many tears....Now this is a great post and thread that makes this forum so...cool. A few thoughts-- when I first read the OP I thought "Oh boy...this is a long and complex set of quetions with many interdependent variables requiring a set of algorithms...." But I digress. I am not a mathematician or physicist but I do have a lot of experience with those types of questions. I am gratified to see so many good answers--with which I agree--and to see the OP evolve as he listens to and considers the replies. The big thing I question is the costs to essentially store a boat and to fly back and forth to use it for a limited time--especially with a new owner unfamiliar with maintenance costs and hassles. Boats that sit slowly die.... So yes, by all means charter--different boats in different places and combine chartering with instruction and you will learn about different boats without a huge financial commitment and sail them in different places AND do it with a friend to split your costs. THEN...consider buying a boat....Yes--and you indicate you will do that on post #17 above...Excellent decision...in my opinion of course--but this is all about opinion but one things stands out--a boat is NOT a good investment. BUT...the one investment you can make is in learning and in proper instruction early on to save you money and the hassle of learning from your own experience. It evens out the sharp learning trajectory. I often return to Thoreau's quote about building castles in the air and then buiding the foundations down to the ground...or maybe building your hull in the air and growing a keel down to the sea surface...uhh okay. Be very careful before you buy a boat--the costs of ownership can be....a: staggering b: humbling c: disastrous d: bank busting e: fill in the blank....Was this helpful?

[westwinds]

I want a boat with 6 foot headroom, blue water, less than or equal to 8' 6" beam, and capable of being towed by a heavy duty pickup. I can then sail on local lakes or the ocean, store it at my house, work on it easily and get to know how to do maintenance. Here is my list of sailboats:

Pearson Triton 28, later have lead ballast
Cape Dory 25D
Bristol Corsair 24 (25) lead ballast, Sailstar a similar boat concrete+iron ballast will have 6" bilge, outboard & inboard
Eastsail 25 cabin block view?
Kaiser 25 high quality
Vancouver 25 (24), hobbyhorse in chop
Cape Dory 26
Voyager 26 MK II, MK I
Westerly Centaur 26, twin keel, designed for North Sea, lots of storage. Less money as looks weird and a little slower sailing.
Cape Dory 27
Cheoy Lee Newell Cadet/Offshore 27
Dockrell 27
Halcyon 27
Nor'sea 27
Rhodes Ranger 29, If Iron then 1900# keel
Taipan 28
Columbia 29 MK I & II best before 1972?
Columbia 29 MK II in 1965 more streamlined

[sanssouci]

Originally Posted by Paul Annapolis

Let's see if we can unpeel this onion...without too many tears....Now this is a great post and thread that makes this forum so...cool. A few thoughts-- when I first read the OP I thought "Oh boy...this is a long and complex set of quetions with many interdependent variables requiring a set of algorithms...." But I digress. I am not a mathematician or physicist but I do have a lot of experience with those types of questions. I am gratified to see so many good answers--with which I agree--and to see the OP evolve as he listens to and considers the replies. The big thing I question is the costs to essentially store a boat and to fly back and forth to use it for a limited time--especially with a new owner unfamiliar with maintenance costs and hassles. Boats that sit slowly die.... So yes, by all means charter--different boats in different places and combine chartering with instruction and you will learn about different boats without a huge financial commitment and sail them in different places AND do it with a friend to split your costs. THEN...consider buying a boat....Yes--and you indicate you will do that on post #17 above...Excellent decision...in my opinion of course--but this is all about opinion but one things stands out--a boat is NOT a good investment. BUT...the one investment you can make is in learning and in proper instruction early on to save you money and the hassle of learning from your own experience. It evens out the sharp learning trajectory. I often return to Thoreau's quote about building castles in the air and then buiding the foundations down to the ground...or maybe building your hull in the air and growing a keel down to the sea surface...uhh okay. Be very careful before you buy a boat--the costs of ownership can be....a: staggering b: humbling c: disastrous d: bank busting e: fill in the blank....Was this helpful?

You will never learn to swim if you don't get in the water.

[KeepInTune]

Paul: extremely helpful. Thank you so very much. I am going to take the ASA course level and then work on charting a few times before I take the plunge. This is been a great resource for me and helpful in shaping a direction that will fit me best

[RKsailsolo]

ASA course to learn 1st. Alternative to 1 is attend sailboat shows. Sailboat shows teach you what you really want while educating you as you go, delivering huge fun in the process. Charter 2nd. Review your plans as you go. Even consider joining a boat club that gives you fractional use.

Cats for $100k will get you dated larger models or very small newer ones. Gemini is about the only one that is reasonable at that price.

Salt water + FL sun + sub tropical seasonal weather changes = major physical challenges to whatever boat you buy. Let these facts of boat ownership in south FL inform your decisions.