Contemplating making the switch to sail...

Caboteur · Aug 6, 2016

Hi,
All you have in your post is very general & dreamy. Narrow it down... do you want to do this sailing thing full time or partial? Do you want to sell home & disappear in the blue yonder forever? Are you parents or much worse grand-parents? All of this impacts on the planning.
If it's relatively short terms and want to see & live in many areas, you would probably be better off to rent in different areas and not do the long sail between these places. Specially true if you want to do the South-Pacific, southern North-Atlantic, Atlantic europe & the Med. You can even do surf & turf... rent a boat for a few weeks and a land base in same area for a few more.
Your budget for purchase alone is definitely OK. For purchase & outfit for ocean-crossing is tighter. It takes a lot of preparation and forethought to prepare a boat for extensive passages and the boat tends to autodestruct within a short enough period.
Therefore as in most situations you must identify your needs, desires and means very carefully before doing anything rash. In the meantime you can rent the size boat you could afford to buy for a week or two in one of your areas of predilection and see if the dream is a real one or not.
Been there... loved it. Now in & out of cruising, enjoy family & home, cruising to the Bahamas this fall & winter.
Pierre

shemandr · Aug 6, 2016

The amount of $100,000 isn't laughable. Others have done this on far less. But for comfort and safety you will probably spend that number or close to it. If you want to go bluewater cruising a Valient 40, or similar boat, is a good platform. There are many choices but I would look in the 35 to 40 foot area, a sea kindly hull with a good design pedigree. Remember if it's you and the missus you are going to need a boat optimized for a couple to handle. That makes a big difference.
If the blue water sailing is something you might do in the future, buy something good for the keys area now, and sell it when you want to go cruising and buy a boat for cruising then. I would think a catamaran would be excellent for the keys. Gemini or something like that.

jssailem · Aug 6, 2016

Tom. Leaving the dark side is a transition. The cruise becomes the journey not the destination.
Here is a link that might help in boat ideas. Gives a fair review of boats and their abilities for cruising in blue water.
http://bluewaterboats.org/
As Pierre suggests buying a boat right off may be a financial loosing project without clear goals. I bought a project boat for 14K. I've already invested that much in restoring the primary infrastructure "mast and rigging". I'm still not finished. And if I was to offer it up for sale I doubt that I could recoup all of the funds, not counting the time (but for me the time is part of the fun).
So a plan with clear expectations seems like a prudent step. With your boating experience and some sailing understanding you should be able to rent/lease a boat in the Caribbean to see if you like the journey experience.
I welcome you to the idea that you "go where the wind takes you" side of cruising.

rgranger · Aug 6, 2016

The american sailing association (ASA)offers many different classes

Calif. Ted · Aug 6, 2016

I think you just need to find out now if you like to sail and what you like to sail. When I was thinking of going over to the darkside I took a powerboat class thru a club/school, only took one day to decide I hated the ride.
Offshore sailing school is well regarded and near you, they have a six hour class I think that will show you the basics and if you both love it or hate it. Then you got to decide what you like to sail, best way to do that is sail as many boats as possible, I like newer fin keel boats but that's usually a minority opinion on the internet.

Roland5048 · Aug 6, 2016

Right up the coast from you in Lauderdale is Blue Water Sailing. It's an ASA affiliate. They will take you from beginner thru offshore passage making. Flying to a destination and chartering makes sense, both from a practical and financial aspect. You get the experience of foreign ports and the experience of sailing different boats. That should help in defining exactly what you would want out of cruising, or even if you like it, without the hassle of ownership. Remember, cruising is just the opportunity to repair your boat in exotic locations. Good luck.

isaksp00 · Aug 6, 2016

Take one of those classes as suggested, such as an ASA class in coastal cruising, then once "certified" do some chartering (many companies in your general area, such as Moorings, SunSail) and try it out. I would guess none of them would charter to you without a cert from a sailing school, though maybe they would because you have a captains license. Ask them.

JohnVTX · Aug 6, 2016

Take me with you....

Roland5048 · Aug 6, 2016

Don't necessarily need a cert to bareboat. A resume, ( you can put down what you want), the captains license might help and a credit card is really all you need. That last item is the scary part. Do take lessons, though.

Roland5048 · Aug 6, 2016

Prices are all over the board. First tier companies like Moorings and Sunsail have boats less then five years old and are the most expensive. Tier two companies like Footloose, run by Moorings have older boats and are less expensive. Third tier companies like Conch Charters, in the BVI, are even less expensive. Time of year is also a factor. Check the ads in any sailing mag for more info. There is an ASA school in Key Largo. Good luck.
(305) 587-3205 americansailingacademy.com

jssailem · Aug 6, 2016

Another Idea is to get a day sail boat and gain the knowledge of sailing a boat while having a bit of fun.
I looked at the boat rental, and while I think it is a great way to go in your description (lot of boat for rental price - no self maintenance) you still are at the quality of the service company. I think it is a little like renting an airplane. I found an operator that I liked the way they did business, then I got to know the mechanics. They shared the behind the scenes conditions of the various planes in their fleet. That way I stayed in the air when I was supposed to be in the air.
Big companies will be a common standard and will have relatively new fleets trading out or selling share to owners for new boats. The Private business may be good or bad based on the operators. Likely older boats (not always) and may be less expensive. It will take some looking. You should be able to apply the experience you learned in the Power boats to evaluating the basic elements of the rental boats. Things work, electrical power, no damage.
Then there is the Captain Ron theory - "Kick the tires and light the fires. If it's going to happen, Kitty It's going to happen out there. Like I used to say when I was on the Saratoga..."

Anonymous 121765 · Aug 6, 2016

Home's,

Given your sea knowledge, think of it as going from an auto transmission to a stick shift.
It's only another way of propelling you thru the water.

Sailing, is much more physical than operating a powerboat. Make sure you want to take on this challenge.

If wanting to try sailing, I would first start out small & take sailing lessons or, my favorite choice would be to sign on as crew in sailing clubs, where you can learn the ropes & the in-&-outs of sailing first. Then decide if this is the right fit for you. Remember knowledge makes for the correct choices.

Alot of sailors I know got to an age where sailing became too much of a chore physically & then graduated to a trawler. And I got to say that, I love going out with my trawler-sailor buddies, to me they feel like sailboats but with a motor hum.

I myself am a sailor & enjoy flying sideways but, it's a question of different strokes for different folks. I know, I know..........it's all about decisions, decisions.

Just something to think about pal......

CR

Benny17441 · Aug 6, 2016

I recognize that taking courses can cut time on the learning curve and that chartering boats may be a way of limiting losses in case you decide the activity is not for you but by the time you go through this exercise you may have spent $5,000. I'm going to suggest an option with perhaps a slower learning curve but with much more practice time in the water. You can easily find an purchase a 22' sailboat in good condition with an outboard for around $2,000. There are a lot of funky marinas in the Keys where docking fees for a 22' boat are reasonable. Find a sailor in that marina that for a couple of hundred bucks will go out with you 2 or 3 times to show you the ropes and get you started. After that go out by yourself and start practicing. Start on good weather days for a couple of hours and work up gradually to heavier weather conditions and longer outings. In the evenings scour the internet on articles about sailing and sailboats. Digest and practice what you read. With your navigation skill and knowledge of the area you should be taking overnight and distance trips in no time. Believe me when I say that you will learn better boat handling skills in a 22' boat than in a larger one and that when you get ready to transition it will practically be seamless. Once you know what to do nothing happens fast in a sailboat irrespective of its size. If after a year or two you decide it is not what you want then find someone to give you a quick $1,000 for the boat and you are out or if you are ready to upgrade take the $1,000 and use it towards the purchase price of that dream boat you have had time to appraise with some knowledgeable experience behind you. Either way your cost for learning lessons might be only about $1,000. Chuck the slip fees to good times and perhaps new friends.

heritage · Aug 6, 2016

I was about your age when my wife and I bought an older sailboat and took off for a 6 month test cruise of the Bahamas. 6 years later and many islands and countries later, we made it back to Florida. That first year out we slowly developed an appetite for seeing what that next island had in store for us. About half of our friends that we met along the way in the Bahamas got to Georgetown and stayed a few months and returned to the States. Many had planned to cruise on to the eastern caribbean, but for many good reasons, their sense of adventure wasn't strong enough to get them to the next island. I guess my advice to you is to start out in a modest boat that is comfortable and seaworthy. Not a round-the-world boat that you have sunk a lot of money into and would feel obligated to continue cruising past the point of it being fun.

Most of the knowledge needed to operate a cruising sailboat you already have: operating and maintaining the mechanical and electrical systems. Not much different from a motor yacht. We never had trouble with the sailing end of it and didn't find it physically demanding.

Benny17441 · Aug 6, 2016

HO glad to be of help. We have a high affinity for small cruisers especially those that can be trailered to distant sailing venues in a few hours. We keep a 22' Starwind on a trailer just to take trips to different places. We were at a marina in Mystic, Connecticut and someone asked if we had sailed there from Florida to which I responded " yes, all the way up I-95". We have watched the 4th of July fireworks in Washigton, DC from its deck on the Potomac River and been pinned down by weather in Ocracoke in the Outer Banks of North Carolina as well as the Island of Tangier in the lower Cheasapeake Bay. We say the large boat a 32' goes to the Bahamas but the small boat goes everywhere else. Love the way the little boat sails and its simplicity.

rgranger · Aug 7, 2016

I agree with what benny said about smaller boats. They are more responsive so you can really feel exactly how your actions affect the boat. I learned in a 14' dinghy. Larger boats respond more slowly to subtle changes in trim etc

Contemplating making the switch to sail...

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SBO Weather and Forecasting Forum Jim & John

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SBO Weather and Forecasting Forum Jim & John

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