Where to go for winter sailing? Florida or California? - SailNet Community
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post #1 of 44 Old 07-19-2018 Thread Starter
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Where to go for winter sailing? Florida or California?

I work remotely for a software company and am planning to relocate south for the winter so I can keep sailing. This is my second summer of sailing my Pearson 28 on Lake Michigan, so this winter the plan is to purchase a boat close the the area I want to spend winter in, live on it, sail as much as possible, and then either (a) keep the boat and stay there, or (b) put it on the hard and come back to Lake Michigan next spring.

I will be keeping my apartment here in Wisconsin while I'm gone, in case I decide living aboard sucks and want to bail on this experiment.

Originally the plan was cruise around the florida coast, but now I'm considering SoCal as well.

So anyways, I'm looking for 3 main criteria:

1) Warm weather obviously

2) Cool places to weekend sail to, or places where I can cruise to and still work during the day with access to internet and electricity

3) Fun area surrounding the home base marina/mooring/whatever

I'm 31, single, and would be nice to be in an area where there will be people around my age, women in their late 20s etc.

The ideal fantasy liveaboard marina would be near a beach, have a path along the water that people use to jog/walk/bike on, and have lots of restaurants, bars, and coffee shops all in a central location nearby. With lots of spots that regulars congregate at.

I don't expect to find the perfect place, but I'm open to all suggestions.

St Pete, FL area. St Pete has a year long waiting list, but there's a marina called Regatta Point nearby. Although not sure if it'll be all retirees with nothing to do around the area.

Florida Keys. There's a cheap mooring field in Marathon.

Long beach area? Not sure if there's a giant waiting list.
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post #2 of 44 Old 07-19-2018
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Re: Where to go for winter sailing? Florida or California?

California is nice for day sailing but not so much in the winter. Typically not a lot of wind in the winter, relatively cold out on the water during this time of year, and last but not least...it's costly compared to most other places.

The nicer areas have waiting lists but if you look around you can probably find a more affordable location all depending on your budget and how close you want to be to the breakwater.

Liveaboards are a minimum 30' (if you do it by the book) and cost a significant increase in slip fee. Mooring is an option and can save cost at the expensive of convenience if willing to make the trade.

Plenty of women in your age group around but if you want to find them closeby its best to look at the surrounding area to see the local demographics as they vary from older salty dog marinas to yuppie yachties type marinas and everything inbetween. But hotspots for partying abound if you are willing to drive a little no matter what marina you ultimately decide on.

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Re: Where to go for winter sailing? Florida or California?

Winter is prime sailing season here on the Gulf Coast. This past season from January through the end of May we had most every day ranked as very good to excellent for sailing with prevailing winds comfortably over 10 mph. If you looking for Prime Sailing Season then Winter on the Gulf Coast of Florida is an excellent choice.
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Re: Where to go for winter sailing? Florida or California?

You could do a LOT worse than Saint Pete / Tampa area.

There is a reason for the wait lists and folks hang on to them. You might post an "in search of" add on Craigslist to see what pops up. Maybe someone would sub their slip to you for a few months. Maybe give St Pete Municipal marina a call and see what's for sale that might not be advertised. Boats I've seen selling there usually include an option to retain the slip.
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Re: Where to go for winter sailing? Florida or California?

Eastern med.
Antigua.
Balerics.
Azores.
Thailand.
So many choices if your willing to be an expat for part of the year.
If you’re going to be in one cruising ground to can have full internet security and telecommute using local services. You may need to get a certificate of compendency and set up a service for mail/sorting out financial transactions. But not hard to do.
Personally know many people doing this. We (and many) snow bird to eastern Caribbean from New England. First year it’s weird to be the foreigner but that quickly passes.

s/v Hippocampus
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Re: Where to go for winter sailing? Florida or California?

Basically, you have just described Ala Wai Marina in Waikiki, Hawaii to a T. Of course, when I was there the internet wasn't even a gleam in Al Gore's eye, but I imagine there is excellent internet there today.

"Any idiot can make a boat go; it takes a sailor to stop one." Spike Africa aboard the schooner Wanderer in Sausalito, Ca. 1964.
“Believe me, my young friend, there is nothing - absolutely nothing - half so much worth doing as simply messing about in boats.” ― Kenneth Grahame, The Wind in the Willows

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Re: Where to go for winter sailing? Florida or California?

There are plenty of decent boats with slips in local marinas for sale in the Tampa Bay area and at reasonable cost at least for the boats, there are plenty of young folks in the area and numerous places for jogging, bicycling and entertainment aside from sailing. This area is also known as one of the best places in the country to start up a restaurant so plenty of food, drink, etc establishments just about everywhere.

The Pinellas Trail (Fred Marquis Pinellas Trail) is one of the bicycling/walking/jogging/skating parks and goes from St. Petersburg to Tarpon Springs:
Pinellas County, Florida - Park & Conservation Resources - Pinellas County Trail Guide

Plenty of County Parks too for outdoor activities with shelters, boating, tennis, etc:
Pinellas County Florida - Parks & Preserves
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Re: Where to go for winter sailing? Florida or California?

Quote:
Originally Posted by lschmidt25 View Post
Long beach area? Not sure if there's a giant waiting list.

I am not sure the waiting list for Long Beach but they had 30 foot slips available last I checked bigger might have a waiting list. The weather in winter there is not nearly as nice as summer but not bad compared to Wisconsin's winters. Most nights in the 40s with occasional cold snaps in the 30s but usually in the 60s during the day. The winter weather there is like summer weather in Wyoming where i now live. I have considered a boat in Long Beach for a winter home.

The cruising out of Socal is mostly to other Socal marinas or to Catalina. I have only been to Catalina in late October but loved it, two harbors is nearly deserted, which is more my pace. There are also the Northern Channel Islands which have no facilities but provide some great cruising, just not sure I would want to be there in a winter storm, which are few and far between, but serious when they hit.

I would consider Long Beach for winter only if you are looking for a year around place to live and sail. Florida might be a better winter sailing ground. I would not want to deal with the heat, humidity of hurricanes of summer.

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Re: Where to go for winter sailing? Florida or California?

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Originally Posted by SeaStar58 View Post
Winter is prime sailing season here on the Gulf Coast. This past season from January through the end of May we had most every day ranked as very good to excellent for sailing with prevailing winds comfortably over 10 mph. If you looking for Prime Sailing Season then Winter on the Gulf Coast of Florida is an excellent choice.
Not a single afternoon thunderstorm? Amazing!

"Any idiot can make a boat go; it takes a sailor to stop one." Spike Africa aboard the schooner Wanderer in Sausalito, Ca. 1964.
“Believe me, my young friend, there is nothing - absolutely nothing - half so much worth doing as simply messing about in boats.” ― Kenneth Grahame, The Wind in the Willows

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Re: Where to go for winter sailing? Florida or California?

Think to yourself

DO I WANT TO BE IN FLORIDA IN SUMMER ?

Then relocate to the Eastern Caribbean.
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