Home Forums Hunting & Shooting Hunter's Campfire Advice from any sailboat owners

I am a newbie to sailboats. I figure it is alot like learning to fly, seeing the sails are airfoils, so I am comfortable with the aerodynamics. I'm thinking I just need a few hands on lessons from an experienced sailor and I can pick it up. My question is this . . . I am looking to buy a home in Pensacola Fl for retirement in the next two years. I would like to sail as my retirement hobby. Do you sail boat owners recommend I start with an 18-23 footer to learn on, then sell it to buy a larger boat, or go with a 27-32 footer to learn on,? Here are some of the boats I have been considering . . .


18 footers





23 footers



32 footer

Start with a small boat and learn the basics, then keep in mind it's tough to sail a larger boat without knowledgeable help.

Take some ASA courses to get a feel for the 'rules' of sailing. Then join a sailing club and experience as many different boats as possible by crewing for others; this will have the added benefit of learning the tricks from numerous sailors. Make sure you do some offshore time to make sure you're up to it (some folks just can't get out of the bay without getting sick). Once done, charter a boat or two to get a feel for what you like/don't like. Then go shopping for a boat. Smaller boats will teach you a bit quicker than larger boats, but the same principles apply. If you're going to sail the Keys to the Bahamas, be aware of the draft of the boat you choose and leverage the experience of folks who live in that area.

As a counterpoint, some say to just buy a small boat and get out there today. That is what I did after taking the ASA 101.

*I am a lake sailor (past) not an offshore/ocean guy, so much of this advice is what I've seen offered to others in your shoes over the years. I'm far from an expert, but have owned from 12' to 26' sailboats*

Thanks for your all's advice Snyper and Sock.

Moving into your new place in Pensicola is first. When you have time find a sailing club or marina that rents boats there.

Decide if your wife wants to try it and if anyone gets seasick.

While I was a rifleman and hunter I was asked to go 1/2's on a cottage on an island in Long Island Sound that came with a Sunfish sailboat. I was in my late 20's then, lean and active. The Sunfish looked like sissy stuff but it became a challenge to go to windward, navigate and work the tides.

Then cruising on the 25', then 30', then 35' sailboat became a primary activity and my wife took to it as well. Now in senior retirement we have sold the boat and cottage on the water and kept the one in the woods.

We sailed some of the North East coast of New England on vacations and belong to yacht clubs.

Depends upon the boat and how it's rigged. You'll quickly outgrow any size you get so just skip one ass kicking and go midrange 23-27.

I'm sailing a 25 footer up to SE AK next May/June....I wish it was bigger.lol

Richard Bach once wrote that the reason Aviators like airplanes and sailboats is that both free you from the constraints of time. The airplane because it compresses time over large distances and the sailboat because you're simply not going to go very fast and you can't do much about it.

I raced dingy's in college and skippered and raced up to 44' boats in my time including racing J boats in Pensacola. Owned a 24' San Juan with another NFO at Whidbey for 8 years.

For my 2 cents you can learn a lot more about how sailing really works in a smaller boat but unless you're just going to day sail, which I enjoy a lot, or race a planing hull like an International 14 then go with something like a 22-26' boat.

Are you going to sail it alone? Get a roller furling headsail. Get an auto helm. In NPA sailing that single handed would be very easy most of the time. With an auto helm on ours I could even fly the Spinnaker myself in light wind. I also recall racing in the bay where we had to drop anchor to keep from being swept out of the bay there is so little wind. Get ready to motor when you need a Bushwhacker at the Sandshaker

Bigger is in many ways easier but if you're single handing you will need some power winches (or wenches your call!) and frankly as far as there sailing part it's not as much fun unless you're off shore on a good reach as a smaller boat.

Buy used! Tons of good boats out there no one uses anymore.

Something I've always wanted to learn.

I will say that sailboats are some of the most beautiful works of art on the water - if you spend big bucks.

I live on Lake Michigan - lots of sailboats in the 2 marinas here in town but I rarely if ever see them leave their slips.

I too first sailed a Sunfish when I was a flight student in Pensacola. That is what lit the dream of someday owning my own blue water boat to sail the Caribbean.

Saw this house for sale in P'cola. The sailboat parked in the driveway caught my attention.

Kinda hard to say what size you need without you saying what your use will be. Going out on the occasional evening vs. cruising to the Bahamas, big difference.

Ultimately want to sail the Bahamas when I feel I am experienced and safe enough.

Google Earth is new to me for looking at places.

Google Earth

You can learn basics in small craft on your own over time.

Or you can crew with experienced sailors on whatever comes along and learn how to survive the unexpected and excel in seamanship.

My first experience in sailing was a 12 meter crewed by absolute maniacs in a Santa Anna wind 'round the island during a race. Her name was Soliloquy and one of the lads near lost his arm when a halyard slipped.

Sailboats are a joy, and they can kill you quicker than a .45 if you are ignorant, stupid or both. Big fast boats are addicting and without mercy.

Get one large enough to go to sea in and one with a good seagoing design. I spent a couple of years living on a 32 Roberts in the Bahamas 32 years ago. I wish my Wife wanted to give it a try,I'd do it again.

Sailboats usually seem to be a mans follie/enjoyment vehicle. It's best to learn how to sail on a smaller sailboat or dinghy, and cruise on a larger more comfortable boat. It seems that aren't enough creature comforts for women on the long cruises.

Sailboats motion through the water is a lot nicer than power boats too.

Try it and you will like it.

Go hang out at a marina on race nights, yu can walk up and down the dock just saying "crew?" Someone will take you on as movable ballast. Keep your eyes and ears open and you'll learn a lot. I raced everything from lasers to 70 footers on both Chesapeake Bay and the ocean to Bahamas,

Just for your info: The two happiest day's in a sailboat owners life are the day you buy one and the day you sell it.

I have never been on a sailboat but have owned a few power boats. For me anyway, I always wanted something a few feet bigger no matter what I owned. Two-footitis is what it's called.

Boats seem to shrink the minute you splash them off the trailer.

Just sold my last boat and took the cash and picked up another 3rd generation 4-runner.

Best of luck with your upcoming retirement!! How exciting to have a new passion. Best of health and fortune. God bless.

Thanks for the heads up. I am going into this with both eyes open, much with the same safety attitude I had when learning to fly.

100% of my sailboat experience came 40 years ago when I rigged up a sail on a 17' canoe. It was slow and cumbersome but it was still fun. It didn't let you do anything other than sail. You had to stay alert to what it was doing or it could go over. It got kind of boring just tacking back and forth while paying strict attention to the boat.
I'd like to try it again, though, but with a boat made for the job.

Having spent half my working life as a yacht carpenter, and sailing the Chesapeake Bay both racing (a Beneteau 39) and day tripping, I'll second the motion for starting out with a one-man day sailor. Learn the basics, have fun with it, immerse yourself in the "sailing culture" and then decide where to go from there.

Having been on blue water when heavy seas were threatening to kill me, believe me when I tell you that no boat will seem big enough under those circumstances.

I can't resist the old adage: "The two happiest days in a man's life are when he buys his first sail boat and when he sells it!"

Having been on blue water when heavy seas were threatening to kill me, believe me when I tell you that no boat will seem big enough under those circumstances.


I was aboard an aircraft carrier in the pacific ocean during a typhoon. We were just sailing around the edges of it and still taking green water 65' down the deck past the bow. I can attest that the feeling is just the same as being on a 24' sailboat in a squall with 10' waves on Chesapeake Bay.

At 72 I've lived aboard and been a boat builder for over 1/2 my life and have learned a couple things.

The cost of boat ownership grows disproportionately as the size grows. It costs many times more to own and operate a 30' boat than a 20' boat.

Learn to sail before buying a boat you don't know how to sail.

Small boats are the most fun.

I just retired 3 months ago. Now I get to learn to sail as a retirement hobby. Grew up on Lake Ontario so I'm no stranger to big water. Been on water most of my life (and underwater scuba diving) but never got around to sailing until now. All the sailing folks around here told me to take lessons at the local yacht club where they start you out on the small stuff. That's how you learn the basics. Then you can build on that experience. I'm just starting but someday my dream is something in the 23-27' range just for pleasure sailing. It's great to experience sailing, I've been on 'em enough but never really learned how until now. Now that I'm retired I finally got enough time AND money to swing it.

I really appreciate all the feedback. It seems the consensus is start small, learn, the go from there.

"More cruises have been sunk by Women than rocks".