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Chesapeake Marina/Location Recommendations - fall/winter/spring


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We has an idea to bring our boat down from NY to the Chesapeake this fall to keep it in a marina for the fall and spring shoulder seasons. We figure warmer waters means we can get a little more sailing in the shoulder seasons, but more importantly we can use it as a floating condo to get out of the city for weekends.

Needs:

  • Slip in a marina
  • Bathroom and shower facilities on site
  • Can handle draft (5'8")

Would be nice:

  • Close to a small town worth exploring
  • Not super expensive
  • closer to New York the better for driving purposes

Anyone have any recommendations we could look into?

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You have some decisions to make. This is a good idea in general with some warnings:

1. *Sometimes* we sail 12 months a year. I have been sailing on Christmas in a short-sleeved shirt a few times. Every now and then we get the winter from hell. It is pretty rare now, but not impossible.

2. The ideal place for you would be Annapolis, but that really kills the "not expensive" part of the operation, depending on what "not expensive" looks like to you. Maybe by NY standards it isn't bad.

3. Havre de Grace would be the easiest drive and also has Amtrak. It is also at the cold end of the Bay and has fresh water, so it might freeze before anyplace else.

4. Branching off I-95 to Delmarva gives you Georgetown, Rock Hall, Chestertown, Saint Michael's, and Oxford. All of them are small towns, or REALLY small in the case of Georgetown, and all have marinas. They might be a lot smaller and quieter in winter than you might be expecting. Saint Michael's is the most active place in winter. Chestertown has a college, so it doesn't go dormant in the winter, but you are 5+ hours up a river. It is a LONG way to get out of the Chester and go someplace else.

5. Baltimore has a lot going on and the rates are not bad. I stay away from there, it certainly is not a "small town" vibe. Some of the "lots going on" isn't necessarily good.

6. Here on Kent Island rates are good at marinas, but it isn't exactly a town the way some places are.

7. If you forgo the short drive part, you could go down to Onancock, Cape Charles, or someplace over by Norfolk. It is a longer drive but frequently warmer down there.

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Kent hit the nail on the head, and I would second all he has said.  No traffic (ok, no such thing really) means Annapolis to Long Island a 4.5-5 hour drive, and Norfolk an 8 hour drive. Staying on the Eastern Shore allows you to go farther south and eliminate some of the traffic hassles.  Western Shore has more towns that with life over the winter.  Annapolis, Solomons Island, Fishing Bay, Hampton, Norfolk on the Western Side.  Norfolk can be considered Eastern or Western, as you can go straight up the Eastern Shore to NYC area.  Having lived in Annapolis, Solomons, and Norfolk, it is certainly warmer (5 maybe 10 degrees) on the Southern End of the Bay then the Northern end.  But the occasional Winter from hell or 2 feet of snow from a Nor'easter still can happen in Norfolk as well.  Annapolis is more dollars than Norfolk as well.  Prices generally go down as you go down the bay.  Generally.  Norfolk holds a PHRF race first weekend of Dec, as well as Jan 1st, and starts spring races in late Mar/early April.  Both of those can vary from sunny and in the 70s to cold and snowy...Late April to end of May/early June, and late Sept into early Nov are really, generally very nice times to be sailing...

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Haven Harbor at Rock Hall is my favorite marina on the bay. You could start there and follow the color change of the leaves south. 

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12 minutes ago, Mizzmo said:

Haven Harbor at Rock Hall is my favorite marina on the bay. You could start there and follow the color change of the leaves south. 

We too love Haven Harbor. We have done cruises to Rock Hall in November and late February. In November the waitress at Durdings was lonely and kept giving us free pie. It is a nice place with friendly people but fairly dormant in winter. I think we got a free slip in February for braving the ice to get there. Yeah, back in the day there was ice, not so common now.

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I kept our boat in Hampton for 15 years prior to moving north to Mystic.  I still have a small townhouse in Williamsburg VA to allow my wife & I to see family and friends.  We remain members of Hampton YC after being here in Mystic for the last 6 years- it's a great place with great sailors and a nice town.

Delivering the boat from NY to the Chesapeake is quicker and easier if you stay outside- don't force yourself to go around Cape May, up the Delaware, through the C&D to A-town.  That will easily add a day, possibly 2,  to your travel.  

Commuting back/forth can be done via train, which is my preferred mode of travel going back and forth.  With 2 weeks advance tickets, it's only $45.00 each way.  Cheaper than gas to drive.

My recommendation is Hampton or Norfolk, or Little Creek, with several marinas in the area.  Also consider Cape Charles, although the train will not get you there.

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1 hour ago, Peenstone said:

Delivering the boat from NY to the Chesapeake is quicker and easier if you stay outside- don't force yourself to go around Cape May, up the Delaware, through the C&D to A-town.  That will easily add a day, possibly 2,  to your travel.  

 

If you are trying to get to Norfolk as fast as possible, that is true. If you want to see things, there is LOT to see between Cape May and Norfolk going via the C&D if you want to make a cruise out of it.

 

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Thanks for all the good suggestions. Looks like I have some research to do, but this is a great start. I think in the end, ease of access from NYC will win out. Hampton and Norfolk are just a long way to travel for even a long weekend. So staying in the northern Chesapeake probably means using it more, even if we have to haul for the coldest months. 

I am going to look at St Michaels, Havre de Grace and Rock Hall as a start. I am not sure we can pull it off this year, but we would love to make a new routine with this.

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19 hours ago, freewheelin said:

Thanks for all the good suggestions. Looks like I have some research to do, but this is a great start. I think in the end, ease of access from NYC will win out. Hampton and Norfolk are just a long way to travel for even a long weekend. So staying in the northern Chesapeake probably means using it more, even if we have to haul for the coldest months. 

I am going to look at St Michaels, Havre de Grace and Rock Hall as a start. I am not sure we can pull it off this year, but we would love to make a new routine with this.

We don't haul out in the winter, we have an ice-eater in case of freezes. Havre de Grace is the best access, but it is a ways up a narrow channel to get anyplace else, so Rock Hall and Saint Michael's are better bets for easy cruising. You can make a fun trip by starting at HdG, driving to Rock Hall, and then Saint Mikes. You can stop by Easton and Oxford too to get a feel for the area.

If you want a side trip of a few miles, check out Kent Island - Castle Harbor on the north side and the several marinas on Kent Narrows. The Island probably has the best marina rates, but you will have to see about the town aspect of it. If you want to win bonus points with your wife, end the trip at a B&B in Saint Michaels ;)

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On 9/8/2021 at 11:34 AM, Peenstone said:

I kept our boat in Hampton for 15 years prior to moving north to Mystic.  I still have a small townhouse in Williamsburg VA to allow my wife & I to see family and friends.  We remain members of Hampton YC after being here in Mystic for the last 6 years- it's a great place with great sailors and a nice town.

Delivering the boat from NY to the Chesapeake is quicker and easier if you stay outside- don't force yourself to go around Cape May, up the Delaware, through the C&D to A-town.  That will easily add a day, possibly 2,  to your travel.  

Commuting back/forth can be done via train, which is my preferred mode of travel going back and forth.  With 2 weeks advance tickets, it's only $45.00 each way.  Cheaper than gas to drive.

My recommendation is Hampton or Norfolk, or Little Creek, with several marinas in the area.  Also consider Cape Charles, although the train will not get you there.

And you now also have Breeze Air from Norfolk to Providence (or Bradley) for about $40-50 each way, and only an hour in the air.
 

I have been flying Breeze this summer a bunch between Charleston and Providence, and I can firmly recommend it.  (Also the flight has great timing: leave CHS at 5pm, land PVD 7pm, turn around and back in Charleston by 9:45).

 

It’s no frills, but it’s founded by the same guy who created JetBlue, and so far it has been similar.

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On 9/11/2021 at 8:37 AM, kent_island_sailor said:

We don't haul out in the winter, we have an ice-eater in case of freezes.

Ok, time for a super dumb question from a cold water sailor. If you don't haul out, when do you work on the bottom paint/fairing, seacocks, etc?

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37 minutes ago, freewheelin said:

Ok, time for a super dumb question from a cold water sailor. If you don't haul out, when do you work on the bottom paint/fairing, seacocks, etc?

When I need to paint the bottom I haul out for a few days, usually in August. We do still have travel lifts and so on ;)

My last seacock replacement I did in the slip. I used one of my pine plugs to avoid getting sprayed.

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Most yards have "relatively" less dry storage space down on the bay (and points farther south) and dry storage costs are often higher then slip fees.  So most of the time, you'd haul for a couple days to a week or two depending on the work list, every couple 2-3 years around the time you need new bottom paint.

There are yards that have larger dry storage, where you can pull out for a season if the list to be accomplished is "long and distinguished"

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14 hours ago, Crash said:

There are yards that have larger dry storage, where you can pull out for a season if the list to be accomplished is "long and distinguished"

I love the concept of a "distinguished" cleanup list.  One that has a full professorship in some ancient university.

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Winter haul is a pain for bottom paint. Most people don't haul out until after it is too cold to paint. Then in the spring you get endless chilly rainy days that aren't good for painting. Then we have "instant summer" where you go to bed and it is 45 degrees pissing down rain and wake up to 85 degrees. Then everyone wants their boat painted on the same day!

In August business on the hard is slow, you can haul and launch when you want to, and you aren't blocked in by 5 other boats that are not ready to go. Plus when you get a nice day for sailing in January or February you can go out. The last few years we have actually had more nice days in January and February than March and April!

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I wouldn't consider Havre De Grace.  It is a long way to get out to useable water because of the shallows up there.  There are quite a lot of marinas in the Middle river area if you wanna stay north of the Bay Bridge, a couple have been recently revamped.  There are some nice spots in the northern Bay on the eastern shore, but the trade off is being further from many services.

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I've been watching this thread with interest. We've done this and highly recommend it. We are NYC-ish based and have had our boats everywhere from Charleston to Maine. There are many great suggestions here, but the ones that aren't Annapolis are suboptimal, in my opinion, and there is more to consider.

First, the weather isn't that much better for Sept/Oct. We've done fall a couple times and the time we wintered over, we didn't get to enjoy spring because of COVID. But, anchoring in Manhasset Bay is as nice as most of the Bay spots. Then, if you're looking to return to NYC on the early end, April into May is a hard ride up the NJ coast in the cold.

Next, a lot of the towns that should be awesome, close down late September at the latest. While the Bay should have an amazing shoulder season, everyone has to return to kids sports, watching football and not sailing. So, the out of the way places relying on tourist dollars are basically closed. Great for quiet anchorages, but you can do the same in Greenwich Cove or the Sandhole.

Lastly, f the Delaware. Just F it. It's a hate mission every time. Worst sea state I've ever seen, and I spent my first 25 years on the great lakes, the home of the cold, miserable hate mission. 

So, why do I still recommend it?

  • New cruising grounds are always fun. Even if everything is closed and the pissy rain is getting both you and the dog soaked, it's just somewhere new to have a look.
  • Cheap winter storage. Less than half the price of NYC-ish if you shop around a little. But don't leave it late or you'll get f'd. Also, the cheapest places are cheap for reasons. I can share more over PM, but we had a rough experience at a beautiful facility owned by complete assholes.
  • Winter projects are much more civilized. Polishing and waxing for 3 days between christmas and new year cost me in AirBNB, but I was wearing a tshirt and the spring wax took no time at all.

My recommendation is to look at Back Creek in Annapolis and specifically, the apartment complexes. There is no traffic! None! It's not like Newport where you have to eat 95 bullshit no matter the season, weather, time of day or being smart and taking the Hutch. You get hammer down in NJ, lock the cruise at 85 and the next thing you know you're over the bridge.

Work the apartment complexes for your slip. They operate marinas as amenities, not businesses. For you, this could mean a 45' slip with 12' of draft, power and water for less money than your monthly bar bill. Seriously. You can walk to the Boatyard**, downtown and all the places that matter when you don't feel like anchoring in St Michaels because everything is closed.

**When Jesus came to Newport and declared the food at Cooke House overpriced but directionally tasty and the drinks at IYAC the way he intended, he blessed Annapolis with the Boatyard. Then he burned down all the local YCs, rebuilding them better so you have other really nice places to drink, while preserving Davis' Pub as everyone's dinghy-reachable safe haven. Amen.

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On 9/16/2021 at 12:10 AM, penumbra said:

I've been watching this thread with interest. We've done this and highly recommend it. We are NYC-ish based and have had our boats everywhere from Charleston to Maine. There are many great suggestions here, but the ones that aren't Annapolis are suboptimal, in my opinion, and there is more to consider.

First, the weather isn't that much better for Sept/Oct. We've done fall a couple times and the time we wintered over, we didn't get to enjoy spring because of COVID. But, anchoring in Manhasset Bay is as nice as most of the Bay spots. Then, if you're looking to return to NYC on the early end, April into May is a hard ride up the NJ coast in the cold.

Next, a lot of the towns that should be awesome, close down late September at the latest. While the Bay should have an amazing shoulder season, everyone has to return to kids sports, watching football and not sailing. So, the out of the way places relying on tourist dollars are basically closed. Great for quiet anchorages, but you can do the same in Greenwich Cove or the Sandhole.

Lastly, f the Delaware. Just F it. It's a hate mission every time. Worst sea state I've ever seen, and I spent my first 25 years on the great lakes, the home of the cold, miserable hate mission. 

So, why do I still recommend it?

  • New cruising grounds are always fun. Even if everything is closed and the pissy rain is getting both you and the dog soaked, it's just somewhere new to have a look.
  • Cheap winter storage. Less than half the price of NYC-ish if you shop around a little. But don't leave it late or you'll get f'd. Also, the cheapest places are cheap for reasons. I can share more over PM, but we had a rough experience at a beautiful facility owned by complete assholes.
  • Winter projects are much more civilized. Polishing and waxing for 3 days between christmas and new year cost me in AirBNB, but I was wearing a tshirt and the spring wax took no time at all.

My recommendation is to look at Back Creek in Annapolis and specifically, the apartment complexes. There is no traffic! None! It's not like Newport where you have to eat 95 bullshit no matter the season, weather, time of day or being smart and taking the Hutch. You get hammer down in NJ, lock the cruise at 85 and the next thing you know you're over the bridge.

Work the apartment complexes for your slip. They operate marinas as amenities, not businesses. For you, this could mean a 45' slip with 12' of draft, power and water for less money than your monthly bar bill. Seriously. You can walk to the Boatyard**, downtown and all the places that matter when you don't feel like anchoring in St Michaels because everything is closed.

**When Jesus came to Newport and declared the food at Cooke House overpriced but directionally tasty and the drinks at IYAC the way he intended, he blessed Annapolis with the Boatyard. Then he burned down all the local YCs, rebuilding them better so you have other really nice places to drink, while preserving Davis' Pub as everyone's dinghy-reachable safe haven. Amen.

If you are used to New York City levels of activity, Annapolis is probably the only viable choice for lots of stuff going on. Saint Mike's is pretty active through Christmas and we usually do a December cruise there, but I can't say I have been there very often in January through March. Bonus points of Annapolis is a year-round live-aboard community.

https://www.annapolis.gov/169/Docking-and-Mooring

The harbormaster allows live-aboard winter docking. We used to have a mooring and did this two years in a row. It was really fun to have a "home" in downtown Annapolis especially on New Year's eve and rate was not bad. You'll have to ask if you can sail, some years they want the boats to stay put. Get a slip, not a bulkhead spot, or you may have to move for the night for the Parade of Lights in December.

warning: Not all the apartment/condo slips allow living aboard. I am not sure if you would count being weekend visitors, but I did know of one condo-commando that delighted in getting boats kicked out if he found people staying on them. Ask about that.

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