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Old 02-10-2024, 08:56 PM   #1
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Chesapeake Bay members heading south late season

Any members stay on the Bay late into the season before heading south? Even as late as November?

We now live in Colorado and hope to base a boat on the east coast in retirement for travels south in the winter (Keys, Bahamas, etc.) I'm wondering how late is too late to start heading south. For background, we spent a few years living on the Bay near Annapolis and loved boating in the fall. We finally acquired our dream boat, a Camano 31, and brought her down from New York in October. We had the most amazing fall and winter on that boat. Christmas docked in Annapolis, and even spending a snowy week in our marina were really great times. Work relocated me back to CO in April, so we sold the boat and moved back out here.

Our dream is to spend winters aboard a trawler. I'm thinking about keeping it back in the Annapolis area but I'm not sure we should be this far north.

Here's the factors I'm considering:

We love Colorado and don't want to leave too early in the season. We certainly want to enjoy the fall out here so moving onto the boat in November might be good timing. If we do move out earlier, we get to enjoy fall boating on the Bay if she's based there.

We loved cruising around the Annapolis area. Keeping our boat based there offers options for some nice summer trips as well if we miss the water too much.

As amazing as the Bahamas probably are, I think some of the highlights for us will be visiting the towns on the way down. Keeping the boat in FL gets us to the Bahamas too soon and I'm not sure how long we'll actually want to stay there.

But as great as cruising around the Annapolis area was in the Fall and around Christmas, I think the rest of the ICW and the trip down the coast might really suck in December and January. We'd likely need to either leave much earlier, or locate the boat further south. I know it's pretty cold even as far south as Jacksonville in the winter.

Curious if anyone else is in a similar situation and how you handle it?
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Old 02-10-2024, 11:55 PM   #2
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I left on 01/28/16 from Crisfield, MD after a near 2 year refit. There is a noticeable difference once you get to Virginia Beach. If you plan to overnight in marinas with reverse cycle heat, from Virginia Beach south is pretty reasonable. Obviously this depends a great deal on how cold a winter it is. Ice was forming in the brackish water (below 32 degrees) on the morning I left.

Here is the thread:

https://www.trawlerforum.com/forums/...uth-24408.html

Ted
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Old 02-11-2024, 06:45 AM   #3
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We keep our boat on the mid/lower part of the bay on the Northern Neck. I've made the majority of of my trips South in early November but the last few years, due to my wifes work schedule, we have been leaving in late November. The plus side of earlier is that the days are longer & we get to spend more running/anchored time in the outdoors on the bridge and don't have to stay cooped up in the cabin all day. The pluses of leaving later is ,as a rule, the wind patterns generally shift to a more northerly direction ,many times with a westerly component to them , which makes for a more comfortable trip down the Bay. Plus, later in the year, the pesky little flying insects are pretty much non-existent.
Ice is more of a concern in the brackish waters of the ICW south of Great Bridge but it's not something thats encountered often. You just have to pay attention to the weather and plan accordingly. Wind is the biggest thing that we need to watch for the trip South: the Chesapeake, across the Albemarle and the final hurtle , the Neuse.
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Old 02-11-2024, 07:43 AM   #4
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Any members stay on the Bay late into the season before heading south? Even as late as November?

But as great as cruising around the Annapolis area was in the Fall and around Christmas, I think the rest of the ICW and the trip down the coast might really suck in December and January. We'd likely need to either leave much earlier, or locate the boat further south. I know it's pretty cold even as far south as Jacksonville in the winter.

We left Annapolis this year on 1 Dec, did the Chesapeake to Hampton in one day, took a leisurely 15 days for the whole trip to Charleston... and we're here 'til end of March. No issues with cold and ICW marina hopping... although we did have a significant fog event while underway on Currituck Sound. This is our second time here; Charleston is warmer (and warmer ENOUGH, for us) than a winter on the Chesapeake.

And there are boats passing through here on a daily basis, some staying a while, some moving on... mostly moving further south.

We spent one year in Jacksonville, warmer still, still not as warm as West Palm, FLL, Ft. Pierce, etc... but warmer enough.

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Old 02-11-2024, 08:18 AM   #5
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Have left from Deltaville to go to Hilton head late October. Much less traffic and more open anchorages. Much fewer PWCs, small fishing skiffs, paddle boarders and such. Never needed to wait for space in a lock. Have both reverse AC and hydronic heat so other than less time up on the flybridge temperature not a concern. In fact think late October or early November is the best time to travel the ICW. Close friend did it late November early December. Said too cold and had several days of needing to chip ice first thing in the AM. Said it wasn’t snow but slush and freezing rain that had frozen over night. We have 1200nm range at displacement speed so fueling up wasn’t an issue. He has less and did need to search for an open fuel dock at times. That one month of delay seems to make a big difference in what’s open and the weather.

BTW Hilton Head /charleston is far enough south you don’t need to winterize. Might be cold for a day or three but the water temperature remains ok. Lovely weather for a bike ride or walk or even a round of golf except on a few days. Our New England winter clothes stayed in the locker. A light puffy or fleece or windbreaker was sufficient. Fishing remained more than adequate.
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Old 02-11-2024, 11:31 AM   #6
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Ranger58sb,

How was Jacksonville for living aboard? My office is located in Jacksonville so I travel there quite a bit but only have time to see the office downtown. I thought it may be a decent option for basing the boat as well. I think it's protected enough from hurricanes and maybe far enough north for insurance requirements. But, as I said earlier, I think we'd miss all the cruising locations north of there that we'd visit if heading down from the Chesapeake.
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Old 02-11-2024, 11:47 AM   #7
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Thanks for all of your replies. Sounds like I may not be too crazy but shooting for early November is better than later.

For those of you that make this trip later in the season, is it by choice? Or is it just what your schedule allows? If you had the option would you leave earlier? Like I said, we loved our one season of boating on the bay in the winter. The Camano has a nice lower station and the few times we woke up to snow was kind of magical. Nothing much cozier than enjoying coffee in a warm trawler cabin. But there's also negatives to this, condensation, possible damage from ice, etc. And I can see how this could get old if we're actually trying to make it somewhere versus just hanging out. But once we make it south a ways I imagine this isn't very likely.

Everything hinges on finances in retirement but my goal is to find a boat with a nice pilothouse for colder weather cruising (Helmsman 38 is my dream boat) and to be able to afford slips when we feel like it.

We've never been to the Bahamas. We've sailed Bora Bora and from Bermuda to St. Martin. These locations are beautiful but I'm not sure for how long we'd actually enjoy the islands. What is your destination for the winter? Bahamas? Keys? I keep hearing about how tough it's becoming for cruising FL but I think it could be fun cruising south FL, hitting the keys and working up the west side a bit.

Thanks for all the info.

A couple of pics of Christmas in Annapolis on the Camano.



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Old 02-11-2024, 12:42 PM   #8
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For those of you that make this trip later in the season, is it by choice? Or is it just what your schedule allows? If you had the option would you leave earlier?
I left this year in the beginning of November and tracked conditions on the Bay into December. While it's going to vary some on how hard a winter it is, I wouldn't have an issue leaving around New Years. A lot will depend on how your boat is setup with regard to heating. The Bay can cool quickly November / December, but you're at little risk of the water being in the 30s before January. Be flexible. If it's abnormally cold, 2 days gets you to Norfolk and maybe a 10 degree water temperature difference.

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Old 02-11-2024, 02:42 PM   #9
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I kept sailboats for years on the Rappahanock/Northern Neck before going over to power. There was a lot of sailing in November; less so afterwards but some boating for sure in that area all year. I usually left my boats in the water, but I always winterized them as I did not use them in the winter months and the insurance was cheaper with a layover period. I taught at a college so I used the Thanksgving break for winterizing. The HVAC heat pumps would keep the boat warm enough. I was ice-bound once in Deltaville in a cold snap, but the ice was not more than 1/4" and did not last long. That general area is very quiet in the winter months. Not much going on.

A lot of people are now wintering over in Charleston (where I live). There are a couple of places, but none are inexpensive. The Megadock is on the west side of the Peninsula, and is the wrong side for walkers. The marinas over at Patriots Point in Mt. Pleasant by the Yorktown are better. While not on the penisula, there is a many times daily water taxi (15 minutes) to the peninsula and from that (the east) side you can walk pretty much everywhere. A mile radius from the ferry just about covers all.
I repeat my cavet about not being inexpensive, but on the plus side Charleston offers much for the winter over. Good medical care, shopping, excellent symphony, theater, colleges with lecture series and fine arts departments, art galleries, etc. Good air connections for those needing to get back to the home. A lot going on.

IF you base your boat outside of Florida, insurers generally do not like to see customers crossing into FL until 1 December, and they want you out of there NLT 1 June. Hurricane season runs 1 June-30 November.
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Old 02-12-2024, 08:48 AM   #10
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Ranger58sb,

How was Jacksonville for living aboard? My office is located in Jacksonville so I travel there quite a bit but only have time to see the office downtown. I thought it may be a decent option for basing the boat as well. I think it's protected enough from hurricanes and maybe far enough north for insurance requirements. But, as I said earlier, I think we'd miss all the cruising locations north of there that we'd visit if heading down from the Chesapeake.
Great marina, temps OK (and they had a heated pool), groceries practically next door, the nearby town area (Avondale? or some such) was nice and OK for bicycle access, free bus transport for senior throughout the area... but we didn't find downtown being all that special. Not much in the way of waterfront activities.

We did at one time, a couple decades ago, entertain the notion of moving to Jacksonville... but life moved on and we never pulled the trigger on that.

For our Jacksonville trip, winter of 2019-2020, our then insurance required us to be out of FL during the hurricane season. Since then we've changed providers; the current policy doesn't care whether we're in FL or not... and costs more. Lots depends.


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For those of you that make this trip later in the season, is it by choice? Or is it just what your schedule allows? If you had the option would you leave earlier?
Our delay was about being home with family for Thanksgiving. It wouldn't have been impossible to leave earlier, fly home for Turkey day, return to the boat afterwards... but that was more complicated, especially because we travel with a boat cat on board.


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A lot of people are now wintering over in Charleston (where I live). There are a couple of places, but none are inexpensive. The Megadock is on the west side of the Peninsula, and is the wrong side for walkers. The marinas over at Patriots Point in Mt. Pleasant by the Yorktown are better. While not on the penisula, there is a many times daily water taxi (15 minutes) to the peninsula and from that (the east) side you can walk pretty much everywhere. A mile radius from the ferry just about covers all.
I repeat my cavet about not being inexpensive, but on the plus side Charleston offers much for the winter over. Good medical care, shopping, excellent symphony, theater, colleges with lecture series and fine arts departments, art galleries, etc. Good air connections for those needing to get back to the home. A lot going on.

IF you base your boat outside of Florida, insurers generally do not like to see customers crossing into FL until 1 December, and they want you out of there NLT 1 June. Hurricane season runs 1 June-30 November.
That said, the Charleston Harbor Marina folks over on the Cooper River never answered our calls, emails, texts... so we never found out whether staying there might have been an option. We ended up on the Megadock, and FWIW it seems to be well run, they're expanding, and they do shuttles to/from downtown and groceries and so forth. And if you have a car here, all that transport stuff goes away. The January storm was a big deal, though, with winds from the southwest, several boats were damaged...

We stayed over at Ashley one year, winter of 2017-2018, nice enough, shuttle service, etc... .and that time, we didn't bring car down. Not as elaborate at the City Marina, but nice enough. We chose Safe Harbor CCM this time partly to just try something different and partly because of some cost incentives.

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Old 02-13-2024, 12:38 AM   #11
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I agree about Jacksonville's downtown. Not much going on other than some hotels and office buildings. Its too bad there aren't more boating focuses amenities along the waterfront.

I checked out a marina in Avondale the last time I was in town - Port 32 maybe? Seemed pretty nice and the little shopping area nearby had some nice, walkable, amenities.
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Old 02-13-2024, 07:32 AM   #12
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I agree about Jacksonville's downtown. Not much going on other than some hotels and office buildings. Its too bad there aren't more boating focuses amenities along the waterfront.

I checked out a marina in Avondale the last time I was in town - Port 32 maybe? Seemed pretty nice and the little shopping area nearby had some nice, walkable, amenities.
Yep, Port 32 was previously named Ortega Landing, and that's where we stayed. Great place.

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