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Paul Annapolis · 09-12-2019, 07:14

I sent you a PM thanks

RickG · 09-12-2019, 07:20

It's hard to beat the sailing in the Chesapeake. We used to keep our boat at Herrington Harbor and could do a beam reach for 26 miles to St. Michaels. We spent a winter in Charleston, then Marathon, and we're in the Virgin Islands this winter. Not much sailing in Charleston and it gets cold and rainy; St. Johns Yacht Harbor is a great marina with good liveaboard community when we were there.

Marathon has a great community and sailing. It has walkable access to groceries, Home Depot, West Marine, etc. There is bus service to the Key West airport and Budget has cheap rental cars at the Marathon airport (no commercial flights). The City Marina mooring field was perfect for us. We made dozens of friends and keep in touch.

We hauled our boat this summer at Puerto del Rey marina in Fajardo, PR. Great marina and people, but the insurance was 4% of hull value. We'll be in Grenada next summer.

If it were me, I would buy the boat and register in Maryland and keep it there in the summer. You can get to Marathon in less than two weeks doing offshore overnight hops from Beaufort, NC. If you don't want to do that, keep the boat in Brunswick, GA and enjoy much lower summer insurance.

The Bahamas are wonderful. We sailed through there on our way to the Virgin Islands via Dominican Republic and Puerto Rico. We will be back to both DR and PR for the smiling people, low prices, and good sailing. The South shore of PR is great.

Don't wait. An inexpensive 35-foot boat will take care of the two of you nicely.

Cheers, RickG

capnorv · 09-12-2019, 08:09

I know this will sound crazy, but I'm going to bring it up anyway. Ever thought of the West Coast cruising grounds between the Salish Sea and SE Alaska? Been puttering around there for twenty years year around, and it probably has all your looking for. Heck, you may just give up your thought of a Colorado Summer home unless it's for grandchildren. Glaciers, Meadows, hiking, lakes, mountains, they're all there in plenty. Along with many all weather anchorages and temporary berthing, if needed.

Michael Pope · 09-12-2019, 08:27

Here here ! I have been sailing the Salish Seas since 47 Thats 19 not 18
and there are still lots of anchorages I have not enjoyed yet. Weather super reliable but no wind only August and September . The rest of the time mixed but always bearable You will never regret it! Michael Pope

capnorv · 09-12-2019, 10:07

Quote:

Originally Posted by Michael Pope

Here here ! I have been sailing the Salish Seas since 47 Thats 19 not 18
and there are still lots of anchorages I have not enjoyed yet. Weather super reliable but no wind only August and September . The rest of the time mixed but always bearable You will never regret it! Michael Pope

Well heck, I was talking recent full time. I was probably conceived there in "55 and have spent at least a month or two there ever since myself. I know my Granddad hung out there in the 20's.

Bentwings · 09-12-2019, 10:14

You will have to decide what your interests will be in retirement and what your age and health conditions are at that point.
Having dealt with totally unexpected healt issues and living aboard I can discuss some things that could take your life. When we are in our prime we think we are bullet proof...that why military wants you when you are young.

I’ve had two strokes, one before I moved to the boat and one after I moved. No stroke is small, they can devastate you very painfully. Both happened with health care pretty close by but could have been much more serious had I not been able to get to medical attention as quickly as I did. So far other than being told to never play sports again some vision issues and I’m a fall risk. Must not fall,ever. I’m ok. Even so I try to have instant phone available, my dog seems to know if I have issues and I do train dogs this is a new event to work out.

With that now on your mind began tracking friends, co workers and others...you are a statistic. You need to be in very good health for your age down her on the waterfront.

I would not venture out on the big seas my self. So I would direct you to inland fresh water living. Since you noted multiple homes I think early on this would be good for the cold weather part. I’m up in Minnesota on the Mississippi River. River cruising is fine for me.
I used to live near Lake of the Ozarks and it a huge lake with hundreds of places to explore and visit. There is about any activity you like available. They have winter boating events that are spectacular. Christmas boat decorations and relates cruise ins.

Lots of boats for sale there. I’d look at 45-50 footer in your position. I have a winter cabin heater of the truck style plus new AC with reverse flow heating these work down to 40 deg water temp. Mine is currently blowing 85 deg heat with the water tem at 34 deg. Fantastic. Our marina shuts the laundry and bath house down for the winter but I make do with daily trips to the “y” for exercise and bath. Then weekly laundromat. The bigger boats have all this on board. We do have city water year around for the liv aboards.

As for the boat you will have ongoing maintenance to deal with. Having someone else do it is very expensive but if you can afford it fine. Then it’s mainly boat operations to deal with.

The biggest thing I’ve found is that dealing with the neighbors is much more fun than anywhere I’ve ever lived at. Everyone just seems so happy and ready to pitch in with dockside chord. Keep your dog on a leash, keep him well mannered keep kids in line and park where you are suppose to and all is fine.

JMHO.

Johnknutson · 09-12-2019, 10:19

Great question. What about Mexico?

merrydolphin · 09-12-2019, 10:40

Of course it is all personal choice. If it were me, I would choose the eastern Caribbean. Keep the boat stored in Trinidad in summer as it never gets hurricanes. And there are many yards to choose from. Once ready to sail in winter, you have the entire Easter Caribbean to explore. This will be exciting cruising with a good variety of cultures, and unlike the Bahamas, much more diverse. There are 2 other problems with the Bahamas, one, the winter weather is not very cruiser friendly. The cold fronts chase you all over the place and there are not many all weather harbors. And yes it can get cold there. They have actually had snow! (But rare). And two: the primary feature of the Bahamas is gone, its beautiful underwater world. The reefs are sadly pretty much gone. The E Caribbean also have this problem somewhat but!! There is so much more there. And the other huge plus for the E Car. Is the SAILING. Some of the best in the world. Consistent trade winds all winter long and alway many anchorages available. In fact, you can pretty much anchor on the west side of anything and be safe as the winds as always from the eastern quadrant with extremely rare exception. And lastly, Thunder storms are very very rare in winter. You will get rain to wash the boat down and fill your tanks, but no lightning!! And it will be many seasons before it gets old. We were there for 8 yrs.

liz.w. · 09-12-2019, 12:21

Hey! I love your dream and that you’re looking so far out into the future, but I do think it’s important to insert into this conversation that everything will be wildly different 12 years from now. Cost and climate in particular. If you’re seriously considering making any investment now it would be a good idea to really take that fact under consideration. Particularly if you’re thinking about the keys (or even other parts of Florida). Things are changing massively and with increasing velocity in coastal areas all over the world, which is absolutely not to say don’t do it (if anything don’t wait!) but just be cautious about getting attached to a plan that may become impossible to execute.

Cadence · 09-12-2019, 13:09

Quote:

Originally Posted by skipmac

Charleston SC was one of my favorite stops on the ICW. Lots of really good restaurants, marinas not outrageously expensive, easy to get around.

But winters it is a bit colder than I would like on a boat.

Charleston seldom goes below freezing. That said, I have recorded 19F one time in years. Lasts about 4AM and may be 70F the next day. It is moderate.
last night was a low of 51. FYI I guess it is what you like. I might look at Beaufort, SC. Georgetown may be better financially?

Johnknutson · 09-12-2019, 13:53

Thank you, Trinidad sounds wonderful. We just bought a boat and are hoping to start cruising within a year or two.

**hpeer** · 09-12-2019, 14:02

Quote:

Originally Posted by DMCantor

We've been doing exactly what you suggest since I retired 10 years ago. We keep our boat in the Caribbean, sailing back and forth to the US is way too much work for us. That means that hurricanes are very much a consideration. We have mostly kept our boat on Grenada for the hurricane season, though we did leave her on Curaçao for a couple of summers.

In the summer we split our time between our home near Annapolis and several weeks in Switzerland. I think Colorado would be an excellent choice, especially if you have some connections there.

I’m curious about Curaçao particularly how you proceeded away from Curaçao. Did you move to the Western Caribbean or make your way back to the Eastern side?

I’m considering staying next season in curaçao vs. Grenada. I’m just wondering if that move commits me completely to doing the Western!Carib the following year?

The Traveler · 11-12-2019, 05:08

Quote:

Originally Posted by RickG

It's hard to beat the sailing in the Chesapeake. We used to keep our boat at Herrington Harbor and could do a beam reach for 26 miles to St. MichaelsG

The Chesapeake is great. I grew up boating on Lake MI (an inland ocean) and have sailed French Polynesia and Bermuda to St. Martin.) I've really come to appreciate the protected sailing conditions we have on the bay.

We also love Annapolis and would have no problem retiring here if we had to. But my wife really misses the mountains and the wonderful low humidity in CO. We also really enjoy climbing and other mountain activities. That's why we're trying to figure out how to have it all! Mountains and no humidity in the summer and sailing in the winter.

You all have given some great suggestions. Assuming the finances are sufficient it seems like there are some great options.