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Old 27-05-2024, 11:22   #1
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Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

I read Get Real, Get Gone by Rick Page and he says, “buy a boat somewhere nice, where it is cheap to live, that has lots of easy sailing and move aboard.” But where in the U.S. is best to start such an adventure?

My husband and I decided we’re going to start sooner rather than later — we’re picking a coast and moving in August 2024. And when I say “start,” I mean we’re going to move near water and learn everything about sailing for 6 months to 1 year — including what it takes to be sustainable from a cost perspective (e.g. spending the least amount of time in marinas as possible). Then — assuming we’re still as stoked about it — we’ll plan to sail away “forever.” Our biggest questions though are around WHERE in the U.S. is best to start for niceness, cheapness, and ease. We’re extremely partial to Florida because of the sunshine & warmth, relative affordability, and ability to sail in the winter. Plus, the Caribbean is calling our names! But these are the big questions in our minds right now:
  1. Is Florida — potentially the Gulf Coast areas of St. Pete or Fort Myers — a good place to start learning sailing, anchoring, and potentially living aboard? How’s the sailing community? How’s the niceness, cheapness, and ease of sailing?
  2. If we chose Florida, should we maybe find a way to learn all about sailing August-December — such as volunteering as crew, etc. — and wait to buy a boat until after hurricane season? If so, what are the best ways to learn in the meantime?
  3. Is it really a bad idea to buy a boat in Florida before hurricane season, assuming we’ll be able to “ride it out” unscathed, or is that way too risky? (Note: we're likely going to have only liability insurance because... well, we need to limit costs!)

A little more about us:
We always imagined the liveaboard life was somewhere in our future, but we recently realized NOW is the best time since we currently have the freedom, health, and sense of adventure. We have experience on really small sailboats and one of us is a mechanical engineer. We’re good at learning stuff, super handy, active, and resilient. We’re committed to the U.S. until at least spring/summer 2025 because of our ability to work remotely, keep gaining skills, and continue saving some money for the adventure.

Thanks for any advice and support!
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Old 27-05-2024, 12:32   #2
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

My two cents is always to buy a smallish sailboat cheap and begin learning the ropes. In your case, maybe find a lower 30-foot boat and just start living and sailing her. A lot of people do what you want to do in Florida, but the main problem there is the sailing is lousy except for maybe the Keys. I've spent a lot of time around St. Pete to Ft. Myers, and it is much better than say most of the east coast of Florida, but most of your time will be spent motoring in the ICW or going offshore to nowhere. OTOH, southern New England or the Chesapeake are loaded with interesting destinations, all less than a one-day sail away. Then when the weather gets colder you work your way south to Florida and the Bahamas and back. Do that a couple of times and you will be ready for moving up to a bigger boat knowing a lot more about what it is like and what you want in a boat. Hurricane season in Florida is no joke, and will severely limit when and where you can go. Plus, it is hot, humid, and miserable weather. Even if you end up based in Florida, sail north for much better cruising from May through October. Here's another thread I started on the best place to cruise on the East Coast. https://www.cruisersforum.com/forums...ca-285395.html
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Old 27-05-2024, 13:05   #3
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

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OTOH, southern New England or the Chesapeake are loaded with interesting destinations, all less than a one-day sail away. Then when the weather gets colder you work your way south to Florida and the Bahamas and back. Do that a couple of times and you will be ready for moving up to a bigger boat knowing a lot more about what it is like and what you want in a boat. https://www.cruisersforum.com/forums...ca-285395.html
Wow thanks, for this feedback! Honestly, southern New England and Chesapeake weren't even on our radar (we were debating Florida or maybe the PNW). But your reasoning -- and the additional thread you posted -- make an amazing case! Do you recommend any cool cities in that region as a potential, short-lived, relatively-affordable homebase (e.g. while we're getting started)? Also, we're so tempted to buy our "forever boat" from the start, because we're concerned about navigating the resale, but it sounds like you would advise not to worry about that too much?
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Old 27-05-2024, 13:27   #4
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

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Do you recommend any cool cities in that region as a potential, short-lived, relatively-affordable homebase (e.g. while we're getting started)? Also, we're so tempted to buy our "forever boat" from the start, because we're concerned about navigating the resale, but it sounds like you would advise not to worry about that too much?
It really depends on what you are looking for in a place to live. Big city, small town, rural, right on the coast, inland a bit, ? Affordable housing is not what New England is known for, but there are places with lower costs that aren't the big names. For example, along the southern coast of New England you have bigger cities like Providence in RI that also have more affordable neighborhoods. Income taxes tend to be high in New England, but maybe that doesn't matter to you. Rhode Island has no sales tax on boats or boat services, so there are a million boatyards and marinas with boats for sale. I personally like some of the smaller towns around Narragansett Bay like Tiverton or Bristol, or up the Taunton River like Somerset, or along the south coast of Massachusetts like Westport or Mattapoisett. Cape Cod starts to get pricier and the harbors tend to be shallow. Normally, I say don't get the big boat for your first one since you probably don't know what you really want. Resale doesn't really matter too much if you buy a $10-$20K older small cruising sailboat. With bigger boats I think you are currently buying at the peak of the market, and prices are likely to decline as all of us aging baby boomers age out of boating and die off. OTOH, if you really know what you want, buy it and live on the boat and skip all the cost and hassle of finding a land home. Just be prepared to head south for the winter.
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Old 27-05-2024, 15:35   #5
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

New Bern NC comes up a lot for decent boating and inexpensive living (not sure about the sailing scene). More moderate weather than Chesapeake and still a cool place to live. I live in St Pete FL and it's a great town. Not sure it's cheap though. For sailing, PNW is NOT the place to be. San Diego is probably the premier sailing area in the US though not cheap. SF Bay has a solid sailing scene too (checkout Latitude 38 magazine - free PDF at www.Latitude38.com).

As always, finding a liveaboard slip is near impossible.

Good luck - definitely worth the effort. Cool that it's the female half of the equation reaching out.
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Old 27-05-2024, 16:50   #6
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

Sailboats and Florida are two words that never go with cheap.


Tampa Bay is probably the best place in Florida to learn to sail. It's big, the chop is usually small and the navigation is tricky enough with the shallow water that you are forced to learn what you're doing.


However, about 23 million people ahead of you figured out that Florida is a nice place to live. About a million of them have boats registered with the state.


This means that if you are living aboard, you will pay a minimum of $800 and probably more like $1,000 or more a month for a liveaboard slip for a 35-foot boat, if you can find one.


A good approach is to describe yourself as a cruiser who is staying for a while. That gets you a slip in many cases.



Please don't stay long term in a "free anchorage," where you will end up pumping sewage into our delicate bays and aggravating the locals by dumping garbage where it doesn't belong, docking dinghies on private property, blocking channels, etc.


The state is slowly moving toward restricting anchorages because this is seen as a major problem. It's not a good idea to worsen the situation and possibly help provoke more restrictive rules.


From Tampa Bay, as you figure out what you're doing, there are plenty of short-term anchorages within a day or so that make for fun trips.


Hurricanes, tropical storms and the just-as-rough winter storms are also big reasons to get yourself into a decent marina. Every time one of them passes through, a boat or two in every free anchorage sinks or ends up on the beach. Often, we locals are stuck with the bill.


Lastly, understand that sailing in Florida and many other places is not just 10-knot, 2-foot-seas trips. You'll see some 35-knot winds here and in the Caribbean, along with 8- to 10-foot seas at times.



Marinas and anchorages are filled with boats belonging to people who didn't understand this. Their boats end up as substandard housing for them, not vessels of adventure.


Good luck with your plans.
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Old 27-05-2024, 16:54   #7
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

If you do chose Florida, I'd recommend the east coast over the west coast for a number of reasons.
You shouldn't have a problem finding a slip north of Cape Canaveral.

While the issue of "liveaboard" is a touchy subject, many marina's will accommodate this desire if approached appropriately.
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Old 28-05-2024, 04:27   #8
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

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Originally Posted by Eyeswideorange View Post
I read Get Real, Get Gone by Rick Page and he says, “buy a boat somewhere nice, where it is cheap to live, that has lots of easy sailing and move aboard.” But where in the U.S. is best to start such an adventure?

Our biggest questions though are around WHERE in the U.S. is best to start for niceness, cheapness, and ease. We’re extremely partial to Florida because of the sunshine & warmth, relative affordability, and ability to sail in the winter. Plus, the Caribbean is calling our names! But these are the big questions in our minds right now:
You might consider the Chesapeake Bay. Maybe even Read Michener's book while you think about it.

Home base could be waterfront cities and larger towns (Norfolk-Portsmouth, Hampton, Annapolis, Baltimore), or smaller towns (like Deltaville, Urbanna, Kilmarnock, Solomons, Chesapeake City, Deale, Cambridge), or relatively tiny villages (Galeseville, Rock Hall, Oxford -- that last being where Michener bunked as he was writing).

Florida can be nice, and we enjoyed it when we lived there. (For that matter, Parker was nice when we lived there, too -- but sure enough, not much wide open boating there near you.)

In any case, we find all the anchorable nooks and crannies -- and all the small ports -- around the Chesapeake and associated rivers much more interesting. We've been boating around here for ~35 years or so and there are boatloads of places we have yet to visit. And then there's that pesky hurricane season that insurance companies charge Florida boats big $$$$$ for... if you can get a policy at all.

Given that you'd be on a boat, and interested in being both self-sufficient and mobile, you could also home base somewhere (Chesapeake?) and then go south (Florida? Caribbean?) for the winter. Not an uncommon approach, out here on the east coast.

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Old 28-05-2024, 05:32   #9
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

I learned to sail and lived in NE and sailed out of Salem MA. After being up/down the east coast, to Bahamas, and the Gulf I would say that NE was the best for sailing.

But for learning to sail the location doesn't matter. All that matter is to go sailing. But for getting cruising I feel learning to sail is the easy part, sailing is pretty easy really, learning the other parts of cruising take more time.

BTW I disagree with wasting time and money of a small boat that isn't in line with your end goal. If you want t be a cruisier, learn to sail on a cruiser. If you are going to want a 40' boat don't waste time ona 30'. All you will learn is you want a bigger boat.
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Old 28-05-2024, 05:43   #10
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

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BTW I disagree with wasting time and money of a small boat that isn't in line with your end goal. If you want t be a cruisier, learn to sail on a cruiser. If you are going to want a 40' boat don't waste time ona 30'. All you will learn is you want a bigger boat.
The problem is even if you want a 40' boat you don't really know what to look for in a cruiser without having the experience on a smaller boat. You see it all the time on this forum. Endless threads by people planning on purchasing a big cat or some other huge cruising sailboat and not having any idea what makes a good one, a bad one, or what to look for in a million other details. I am reminded of an older couple we met who lusted after and purchased a big old wooden schooner that would have been a handful for any two 20-year-olds to sail. It was just about the most inappropriate boat for a retired couple with limited physical skills, leading to one disaster after another. They were lucky to survive that purchase. That is an extreme example, and sure if you purchase a mainstream production boat of almost any type it will probably work out, but it is a huge investment in time and money to get wrong because of lack of knowledge. Plus, ultimately, your lives are at stake.
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Old 28-05-2024, 06:05   #11
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

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The problem is even if you want a 40' boat you don't really know what to look for in a cruiser without having the experience on a smaller boat. You see it all the time on this forum. Endless threads by people planning on purchasing a big cat or some other huge cruising sailboat and not having any idea what makes a good one, a bad one, or what to look for in a million other details. I am reminded of an older couple we met who lusted after and purchased a big old wooden schooner that would have been a handful for any two 20-year-olds to sail. It was just about the most inappropriate boat for a retired couple with limited physical skills, leading to one disaster after another. They were lucky to survive that purchase. That is an extreme example, and sure if you purchase a mainstream production boat of almost any type it will probably work out, but it is a huge investment in time and money to get wrong because of lack of knowledge. Plus, ultimately, your lives are at stake.
^^THIS^^
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Old 28-05-2024, 06:14   #12
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

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The problem is even if you want a 40' boat you don't really know what to look for in a cruiser without having the experience on a smaller boat. .
buying a smaller boat sure wouldn't help you learn what you want!

I started with a 39' boat all I learned was that it was too small
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Old 28-05-2024, 06:26   #13
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

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buying a smaller boat sure wouldn't help you learn what you want!
Here's one example I noticed the other day. A guy next to me in the boatyard had just purchased a huge power cat that had the tiniest, wimpiest anchor setup possible. It sported a way-too-small Delta type anchor, and it looked to me like it wouldn't be easy to fit an appropriately sized modern anchor like a Mantus or an Excel, if the windlass could handle it. OK, maybe he won't anchor out much, but if he were going cruising he would need to eventually. Someone who had cruised on a smaller boat would instantly recognize the inadequacy of that anchoring gear.
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Old 28-05-2024, 07:41   #14
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

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Here's one example I noticed the other day. A guy next to me in the boatyard had just purchased a huge power cat that had the tiniest, wimpiest anchor setup possible. It sported a way-too-small Delta type anchor, and it looked to me like it wouldn't be easy to fit an appropriately sized modern anchor like a Mantus or an Excel, if the windlass could handle it. OK, maybe he won't anchor out much, but if he were going cruising he would need to eventually. Someone who had cruised on a smaller boat would instantly recognize the inadequacy of that anchoring gear.
you can apply that thought to 90% of boats you see
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Old 28-05-2024, 08:23   #15
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Re: Best place in U.S. to learn sailing/sailboats for ~1 year before sailing away?

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you can apply that thought to 90% of boats you see
Exactly, but it is much better to know from experience before you get to some island in the Bahamas and you realize your anchor setup isn't working, and your electrical setup isn't working, and your water setup isn't working, and your sail handling gear isn't working, and your navigation setup is no good, and your communications gear is no good, etc. Plus, it is easier to learn about anchoring, sail handling, maneuvers of all sorts, on a smaller, easier to handle boat. Observe many charterboat skippers on their first really big boat trips!
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