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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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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.

Sent from my LG-H918 using Tapatalk
 

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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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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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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.
 

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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.
 

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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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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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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!
 

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Think to yourself

DO I WANT TO BE IN FLORIDA IN SUMMER ?

Then relocate to the Eastern Caribbean.
 

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Not a single afternoon thunderstorm? Amazing!
A few but no lava flows or Tsunamis/tidal waves plus a lower cost of living. You can drive your own car here too if you wish while some of the other places are going to cost a lot more to get to and back from.

Summer here on the Pinellas County Peninsula is easier to deal with than summer in New England such as North Eastern Massachusetts (I lived there for over 30 years and know about this first hand) where it gets about 10 degrees hotter in the Summer and over 100 degrees colder in the Winter however the original poster was asking about buying a boat locally and staying for the just the Winter. Its not until mid July that you really get into the full swing of the summer weather pattern and the more frequent afternoon thunder storms.
 

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For me, Marathon gets the nod. Having been there several times, I know most of the better haunts, the crowd was a bit older, but not as rowdy as those in Key West, and the prices are definitely lower than Key West. When I performed as a musical entertainer in Marathon, I had a fair number of young ladies in the audiences, but most were in their 30s - not 20s. The exception was when I played during spring break -then the girls were much younger, taller and built like Barbie Dolls. That only lasted a couple weeks though.

The sailing opportunities were nearly endless, with some great options. Some days I sailed the ocean side, across Hawk Channel to Sombrero Light, and snorkled in 30 to 50 foot visibility over the reef, which was just 12 feet beneath the surface. Other days, when it was too rough on the ocean, I would opt to sail the gulf side, often dropping the hook near a coral head and catching supper in the form of a bunch of Mangrove Snapper, an occasional grouper and cobia.

Best of luck on wherever you decide to go,

Gary :cool:
 

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What's not to like about Florida in the summer!? The oppressive heat and humidity keeps the snowbirds away!
That's why I didn't buy a home in Tampa. I worked in Tampa for 17 years and it was so refreshing to hit the cool wave of air of the Pinellas County Peninsula when riding my motorcycle home in the Summer. Tampa Electric rates were much higher too when I moved here so it was an easy decision to choose cooler summers, lower utility bills and lower property taxes.

Then it still gets a tad cooler when you hit the inter-coastal area's of Clearwater/St Pete.

You have to choose wisely.

The SnowBirds while irritating at times do help lower my property taxes so I can live with them. If we could just teach them how to use and drive through a rotary.
 

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I think the OP was looking for a place to liveaboard where he can go sailing in winter, while being near a city with women around his age. He is not looking to retire to Thailand or the Med.
 

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I was enthralled with Fisherman's Wharf Marina near Fort Myers, FL, which caters to live aboards, easy access to some great sailing and fishing in the nearly Gulf and some nice restaurants and nite clubs within walking distance.

All the best,

Gary :cool:
 

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Think to yourself

DO I WANT TO BE IN FLORIDA IN SUMMER ? SNIP!

.
Hell NO! You sweat your head off the moment you step outside and worry about hurricanes full time.

We get the hell out of FL from July to September. Favourite places are Newport Beach, CA, Marina Del Rey, Ca and San Fco Bay. SAn Francisco is great a huge sailing area in protected waters, Temp in low to hight 60's year around and lots of party places new. You can actually go up the rives quite far to new areas.

Caribbean is great from February to end o May.

:2 boat:
 

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Hell NO! You sweat your head off the moment you step outside and worry about hurricanes full time.

We get the hell out of FL from July to September. Favourite places are Newport Beach, CA, Marina Del Rey, Ca and San Fco Bay. SAn Francisco is great a huge sailing area in protected waters, Temp in low to hight 60's year around and lots of party places new. You can actually go up the rives quite far to new areas.

Caribbean is great from February to end o May.

:2 boat:
Hurricane season is mid June to mid November and typically we have much fewer of them then the Eastern Pacific Basin so its not really true that you have to worry about hurricanes full time. We are talking about Cooler Coastal Living on the Gulf of Mexico in the St Pete area and not the Central Everglades so few are really sweating their heads off unless they are dressed highly inappropriately for the climate. Some days at high noon it may get a bit intense for vigorous physical activity however that's not a really big deal since its time to kick back in the shade for a refreshing lunch anyways. My relatives in California do have to worry full time about mud slides, out or control forest fires and earthquakes along with the chances of Pacific Tidal Surges and Part Time about Seasonal Eastern Pacific Basin Hurricanes. Both are big States and along with their pluses have their problem areas this is true.

Note that the original poster was asking about winters in Florida around the St Pete coastal area while your saying no to that because of July, August and September weather.

To date in the Atlantic Basin there have been 3 named storms with only 1 having the potential to put Florida at risk while the Eastern Pacific Basin has had 7 with more than one having a chance of turning and hitting parts of California or causing rough seas. Today there is currently no concern in the Atlantic Basin due to a Saharan Plume along with a Westerly Sheer while in the Eastern Pacific Basin there are currently several areas of concern being tracked where hurricanes could develop.

Today was a great day on the water on the Inter-coastal and out on the Gulf of Mexico. We had about 50 boats out today despite the spotty scattered showers that popped up every now and then. Clearwater Beach and Sand Key were bustling with skate boards, joggers, picnickers, beach goers, swimmers, wind surfers, kayaks, Hobie's/Beach Cats, Opti's, 420's, SunFish, Sports Fishermen and the Sailing Centers were really hopping with families enjoying Summer Vacation together.
 
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