Where to retire and sail

Mar 1, 2016
262
Oday 28 Tracy's Landing
i just retired and need a place to live where I can sail and cruise in my 28 foot O’day. I live near wash DC. I sail in the Chesapeake now and had eyed Mobile Bay, or Clearwater and thinking maybe New Bern NC. I want warm climates and expansive sailing space but not the ocean. Is the NC ICW too limited in protected but wide sailing as I suspect?
 
Oct 30, 2017
183
Catalina c 27 Lake Pueblo
Is it safe to assume you are looking for day sails and maybe some weekend cruises?

It would help to know the type of sailing you are looking to do?
 
Jun 8, 2004
10,024
-na -NA Anywhere USA
Be glad to talk with you about the Pamlico and albermarle sounds from the standpoint is a retired Catalina and Hunter dealer for North Carolina now retired. Even sailed the Potomac and Chesapeake bay. Send a private messag
Crazy Dave Condon
 
Mar 1, 2016
262
Oday 28 Tracy's Landing
Thanks
Is that better than New Bern? I sailed
The Potomac near DC and had to tack every 20 minutes. Too much
 
May 12, 2004
1,502
Hunter Cherubini 30 New Port Richey
Can't go wrong anywhere on the west coast of Fl. from Tarpon Springs south. You have a choice of the ICW or out in the gulf. Good gunkholing just about everywhere. Lots of passes in and out although some can be tricky. From Tarpon, a 24 hour sail to Charlotte Harbor then another 24 hour sail to the Keys. Or just a series of day sails. With your draft, (I'm thinking 4 feet or less), you will have very few restrictions on where you can go.
 

jviss

.
Feb 5, 2004
6,745
Tartan 3800 20 Westport, MA
In my fantasies, I would spend the summer where my boat is now, on the South Coast of Massachusetts, cruising Buzzards Bay, Nantucket, Martha's Vineyard, Newport, Block Island, and the LI Sound; and in the winter - I don't know, maybe the Bahamas?
 

Johnb

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Jan 22, 2008
1,420
Hunter 37-cutter Richmond CA
In my fantasies, I would spend the summer where my boat is now, on the South Coast of Massachusetts, cruising Buzzards Bay, Nantucket, Martha's Vineyard, Newport, Block Island, and the LI Sound; and in the winter - I don't know, maybe the Bahamas?
And with excursions to the Hudson and Erie canal, finger lakes, Canada, and great lakes. Wonderful scenery, friendly people and great historical interest.
 
May 4, 2005
4,062
Macgregor 26d Ft Lauderdale, Fl
Charlotte Harbor. good water depth for day sailing. affordable housing.

but go north to the chesapeake in the summer, or RI. its muggy and buggy in the summer.
 
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Oct 10, 2011
619
Tartan 34C Toms River, New Jersey
If it was my choice:

Winter in the FL Keys, and Summer in Chesapeake bay or Long Island sound.
I totally agree with you except for the Long Island sound. The Chesapeake is a far better summertime and early fall sailing area. Just my opinion.
 
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Jan 1, 2006
7,040
Slickcraft 26 Sailfish
Let's go back to NC. Albemarle Sound is plenty big enough for your adventures and so is Pamlico. They can get snotty and have a reputation for that. Coastal NC is not so easy to access. You have to consider that. As for the West coast of FL. you need to be careful that you're not in an area where it's a long trip to where you can put the sails up. For instance, when we stayed on Siesta Key we rented a power boat. It was a long ride out to where you could speed up in a power boat and would be long trip in a sailboat. Naples was worse.
 
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Likes: Will Gilmore
May 24, 2004
7,129
CC 30 South Florida
It is definitely limited when compared to the Chesapeake Bay but it has a fair sailing area for day sailing and overnight trips. We sailed the area for around 7 days a few years back and set out from Washington, NC down the Pamlico river to Bath and across the Sound to Okracoke. Neat little Island. Went up the Neuse river into New Bern and on the way back entered the Punjo river into Belhaven. Stayed at hotel and even though they were full they opened up a pool side storage cabin for us. We needed some supplies and asked how to get into town and they gave us the keys to an old Chevy and pointed us in the right direction. We had some of the best Mexican food as the area is permeated with Mexican Restaurants. We never did go up to the Albemarle Sound but I was familiar with Kitty Hawk and Elizabeth, NC. The USCG has a huge air base facility there. The sounds are shallow but being from Florida and used to sailing in thin water it was nothing. The thing is that when the wind kicks up them Sounds can get pretty nasty. I always say that your sailing area is just as big as the amount of free time you have to sail. For a retired person that likes to sail the area could quickly become rather small. Florida has become rather expensive but has a lot to offer in terms of sailing. Rather than Clearwater I would second the suggestion of looking into Punta Gorda. Ft . Myers might also be a better option. As far as Mobile in the upper Gulf of Mexico I cannot comment as I have sailed no farther than Pensacola.
 
Jun 8, 2004
10,024
-na -NA Anywhere USA
Spoke with Randall last night suggesting to look between Washington, NC and New Bern, N C giving a lot of advice as I was the Catalina and Hunter in the area until retirement.
 
Mar 24, 2013
59
Hunter 1990 Hunter 30 Kentucky Lake
I have to recommend Kentucky Lake with Kentucky Dam Village Marina and especially Lighthouse Landing Marina. The lake itself is very good size with a nice sailing scene. Plus there’s a canal that connects to Lake Barkley and the wonderful Green Turtle Bay Marina. If you want a major excursion you can take the Tombigbee all the way down to Mobile Bay and the Gulf. Not to mention it’s part of the Great Loop. Kentucky itself isn’t to bad with taxes either. Grand Rivers Kentucky is a quaint little town between the lake and Paducah only 20 minutes away if you desire a more metropolis style living. Good healthcare with Lourdes and Baptist Hospital.
 
Jan 1, 2006
7,040
Slickcraft 26 Sailfish
Kentucky Lakes and Tennessee Lakes are an interesting entry. A relative of mine is retired in Tennessee and fishes a number of lakes sometimes professionally. He's loving life. Cost of living is very reasonable - so far. I'd like to hear about the suitability for sailing in some of these places.