New to this all

Retiring at an early age... my experience is that we never retire (especially if involved with boats ), but that said... Congratulations!

The opportunity to make a complete fool of oneself by not easing into things is significant. I'd suggest getting a 35-45 foot boat, you'll learn a huge amount in keeping things running and operating just in local waters. If you have the $$ to seriously pursue a 60-80' yacht, this will be an inexpensive crash course in what's involved, and an eye opener for operating by yourself. You'd probably still do well to have a manager or day captain.

To find out what kind of boat you like, you have to live on one underway, so charter is the best approach. Bareboat when you've got enough experience... just don't end up like this guy... http://www.yachtforums.com/forums/y...-video-bvi-sailboat-playing-bumper-boats.html

All this said, I know a fellow who was a danger to all in a 15' speedboat 20 years ago, he and his wife made a bundle and retired, and he's now is in the middle of a circumnavigation on a Nordhaven (after first doing a transatlantic with a captain), has his 100T Masters, and is a hell of a self-sufficient skipper. More important, he and his wife are having a BLAST, and are living proof it can be done.

So I say go for it! But tackle it as a really great adventure that requires a lot of learning, and will keep you from ever truly being "retired"!

You are on the right track. I'd say number 4 is a must. And you might want to start with a smaller boat at first. 60 - 80 is a bit big right out of the box for someone who has never done this before.

I've not chartered from these folks but have heard good things... http://www.swfyachts.com/. They do bareboat charters (self captained) and would not charter to a newbie...but I bet if you contact them they'd have some recommendations on skippers they've worked with. The trawlers they charter are a great starting place, most are more traditional and great platforms for learning about vessel operations. More importantly, I bet others here have better suggestions!

Google Jung Charters in Sarasota FL.

You're going to want to figure out how you are going to use the boat. For example, how many days at a time are you going to spend aboard? How far will you travel in a day, in total on your trip, and to what area's. Will you be cooking on board, fishing, diving, eating off the boat, how fast do you want to get there, is fuel efficiency a consideration, is range a consideration. For example a lot of yachts that travel fast Say 25+ knots can only go 250nm without refueling, unless you get into a sportfish. Do you need a large galley, a lot of freezer space, etc etc....... You should have a full time Captain and then will learn from your Captain. Maintaining and keeping a 60' yacht is almost a full time job for 1 person, on a large 80' MY it can be a full time job for two people when you mix in a good amount of usage with that. Charter different styles would probably be your best bet to get an idea.....and not a barebones charter.......I would charter for a week at a time various styles including a motoryacht and a sportfish.....

I'm at this over 50 years recreationally and 23 years professionally. I learn something new every day out there, and faced my own mortality more times than I could ever count. There's just no shortcut to getting experience. If you think of anything over about 46' you'll be required by your insurance company, and glad about it, to use a captain for a specified period of time. Not sure of the insurance company number, but, if you go over 50', figure you'll use a captain for at least 1 1/2 years or one day wish you had. I spent 4 hours cruising with a new boater on a little 18 footer yesterday, and his head was spinning with what we covered. This was after a Basic Boating course and 4 months of reading everything he could get his hands on about boating.

Not sure if you're an aviation buff, but if one were looking to get into a personal jet, it would make sense (indeed there's no other option) to start small and work your way up through the ratings. Call me old school... but there are lessons that need to be learned that are much better (and cheaper / safer) learned in the smaller & simpler craft.

An older well maintained craft can be bought for <10% of what your final purchase will be, or for that matter the cost of a few weeks charter in the larger craft. Even if you take a 100% loss on it, I believe it would pay off in the long run. Frankly, I think the learning part is one of the most rewarding aspects you'll experience, and jumping into the deep end of the pool right off is shortchanging yourself on lots of fun opportunities and memories.

For captains, references from others are most important, and a "test period"of a month or two with the option for either party to back out before a 12 month commitment would be my suggestion.

I have far less experience than most of these folks and was in your position just a handful of years ago.

I bought a smaller version of what I thought I wanted. That happened to be a Bertram 28. I love that boat and continue to use and maintain it as an excellent little reliable runabout perfectly suitable for an overnight or two, fishing, tubing etc.

By owning the boat, you get to learn what it takes to keep all the systems reliable year after year. For me, this has resulted in a spreadsheet detailing all maintenance items, shop names and a running total. Similar to airplanes, the big rehab projects (engine work,paint job, interior, electronics, big electrical or plumbing jobs) are the budget killer. Beyond that, things can settle into a relatively affordable routine.

I'm just not sure how much of that you would learn from chartering a boat ... which is why I never did.

A couple of seasons after I bought the Bertram 28, I went and bought a significantly bigger version. The Bertram 54.

No doubt I have learned lots. My biggest struggle has been with a couple of unscrupulous contractors who each failed in their efforts to rebuild the port side engine on my boat. So the boat sits and contractor #3 has the option to become a hero.

I would recommend a smaller version of what you think you want. If you are worried about wasting money, you might have just failed the first test

I look at it a bit different. I would say get the biggest boat you can afford and leave room in the budget to compensate for your inexperience. You will obviously need to hire a captain to teach you to drive, mechanics to help you with even the smallest problems etc etc. but at least you will have the boat you want. I also think we are in such a economic slump that great deals can be had on larger boats. In a few years these deals might not be here.

My buddy got into boating a year ago and bought a 40 footer as his first boat to help him "learn the ropes." Within 6 months he was proficient enough to operate the next size up and was very disappointed in his decision to start smaller.

Chartering will help you figure out what type of usage you like doing and what type of yacht as well as what you want in a yacht. It will also help with the limitations each design has.

I wouldn't lock yourself in with a Captain for 18 months. On a yacht you're in close quarters with a Captain for many days at a time and a really good mesh of personalities is a MUST. Stress the fact that you want to learn how to maintain the yacht and run the yacht from the Captain that you are hiring. State your intentions as clearly as possible. Some Captains are willing and good at teaching, while others don't have the patience for it or see it as a nuissence. I moved from the US to Belize to take a full time Captains job once, on a verbal agreement and handshake. It worked out fine.

I would go straight to the 60-80' yacht that meets your needs and considering you'll have a captain to teach you both how to maintain it and how to run it. There's no need to go a smaller and to a yacht the does not meet your needs to "learn" if you have a professional standing by your side 24/7 to teach you maintanence and running the yacht. You can also get a great yacht that is not "brand new" and save a lot of depreciation along the way and have the same experiences, just make sure it was well maintained.

I have an owner I work for, he has/had a 30' boat he ran himself and a partnership in a 100'. He bought a 55' express less than a year ago (when he ideally wanted a 70-75' FBMY), with the intentions of learning how to run the express (from me) and then doing trips and captaining the yacht with just him and his wife (keeping me to maintain it) and possibly the kids and guests. After the first trip they found it to be too small to meet their needs mostly in interior volume, the wife has NO interest in getting the lines while docking or anything to that effect, he enjoys Captaining the boat but doesn't want to be stuck at the helm the entire day (so he still brings me along on trips), and nobody is happy and the boat is on the market for sale less than 6 months later. Now he's using this one and we do a 150+ NM trip every 6-8 weeks, but he's really making-do and waiting for this one to sell, to get a larger one that would make everyone happy. Moral of the story, get what meets your needs to begin with.

we are new to this fun boating world too- if i knew what i know now ( whopping 4 months into it ) I would say go look at several boats and invision yourself using it from a space perspective - go for the size you think will accomodate you / family / friends and what you want to do with the boat-

we got a 38 ft 1998 sea ray in june- plenty of room for hubby and i and actually another couple- we went with this boat for size and economy since we didnt know how well we would like this whole spending weekends on the boat idea- played it safe so we wouldnt get hurt selling if we found it wasnt for us- we are already planning to get a bigger boat....lol knowing what we know now , we would have gone bigger

you can learn how to drive and take care of the boat with the captain (s) you hire - the ones we used were great! we had a few day trips with a few different ones as each offers different teaching styles and info -

good luck and happy boating!!!

Basically when hiring a captain for what you want to do you not only want to make sure he/she has the proper paper and back ground qualifications but that they fully understand that you want them to teach you what they know and are skilled at doing so. As others have mentioned you don't want to lock yourself into any one until you have spent a fair amount of time with them and gotten a good feel for if the two of you mesh personally and professionally. And that your family and friends enjoy being around them.
You could start this process with a 30-90 day trail period between the two of you. And then if you mesh build and then taper off from there.

Based on the 18 month with an extension deal, I would suggest you save your money and stop talking to your lawyer about this.

If you are going to charter then buy a boat and hire a captain, yes I would start with the size boat you want to end up with. And if that is an 70 - 80+ footer, then in the end you might find you'll end up hiring a full time mate that can help out with the grunt work and run the boat if need be when your away.