Chesapeake sailing--western or eastern shore? - SailNet Community
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post #1 of 14 Old 07-11-2013 Thread Starter
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Chesapeake sailing--western or eastern shore?

We are seriously considering retiring to either the Annapolis and points south area (western shore) or the Easton area (eastern shore). We've done a lot of fresh water sailing but not salt water. What are the pro's and con's of being based and sailing in each area? THanks!
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post #2 of 14 Old 07-12-2013
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Re: Chesapeake sailing--western or eastern shore?

So many issues:

1. Maryland vs. Virginia;
2. Northern/Middle Bay vs. Southern Bay;
3. Urban/suburban vs. rural;
4. Northern vs. Southern; and,
5. Bay vs. Ocean.

Annapolis is one of the premier sailing locations on the East Coast, with an active racing calendar and plethora of sailing related enterprises. If you are interested in racing and are willing to live in Maryland, the Annapolis environs is probably your best bet. There are also many nice cruising spots within a day sail of Annapolis. Baltimore is a decent size city with a major league football team, baseball team, historic downtown and sprawling suburbs.

The western shore of the Bay from Annapolis all the way to Solomon's Island is fairly well-developed and covered by subdivisions. South of Solomon's is less populated and more rural. Outside of Flag Harbour, there are few places to keep a boat south of Herring Bay and north of Solomon's directly on the western shore, although there are many beautiful waterfront communities.

Solomon's Island is a great, small harbour and sailing town with a number of marine businesses. South of Solomon's Island is predominantly rural until you reach the Tidewater area of Yorktown, Hampton Roads, Norfolk and Virginia Beach.

It is not unusual sailing south of Solomon's to see few if any other sailboats on the water on a given day, particularly on a weekday.

Virginia and Maryland are quite different states, culturally, religiously, economically, politically, and socially. It is no coincidence that the Mason-Dixon line delineates the North from the South, although Northern Virginia is quite similar to the Maryland suburbs of D.C.

The northern Bay on the Western shore is rather hilly and becomes flatter and flatter as you go south toward Tidewater. The Bay opens up and becomes saltier as you head south, with the widest portions just south of the Potomac River. If you desire to sail in the Atlantic Ocean, the southern Bay offers easier, quicker access than points north of the Potomac River. Somewhere north of Solomon's, it is almost always faster to travel north to the Chesapeake & Delaware canal and down the Delaware Bay to sail in the Atlantic.

The Eastern shore is predominantly rural, with agriculture, particularly chicken farming, as it primary business and some light industry. There are a few historic tourist towns like Chesapeake City, Chestertown, St. Michaels, Oxford and Cambridge, scattered in the northern stretches of the Eastern shore. The Eastern shore of the Bay south of the Choptank River becomes more shallow and marshy and sparsley populated, outside of a few towns like Crisfield and Cape Charles. Much of the fishing industry on the Eastern shore has been decimated by the poor health of the Bay. The Eastern shore offers easy driving access to the beaches of the Atlantic, including Bethany, Rehobeth, Ocean City, and Chincoteague.

If you want to retire in a college town, there are a few to consider in the Bay area, including Baltimore, Chestertown (Washington College), Annapolis (Naval Academy and St. Johns), St. Mary's City, or Williamsburg (William & Mary).

There are so many great books to read about the Chesapeake Bay area and sailing. Some of my diverse favorites for understanding the region are "Beautiful Swimmers" by William Warner, "The Floating Opera" by John Barth (fictional slice of life in Cambridge, Md. in the '50s) [or even Barth's "The Sot Weed Factor" for a satirical historical view], and "Cruising the Chesapeake" by William Shellenberger. One day I will probably get around to reading Michener's book, although I have so far been intimidated by its hefty size.

You could very easily spend several months, or several years, enjoyably exploring your options for relocation by cruising the Bay aboard a sailboat. There are only a few months in the Winter when it is too cold for comfortable sailing.

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post #3 of 14 Old 07-12-2013
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Re: Chesapeake sailing--western or eastern shore?

There is a huge economic difference between the eastern and western shores of the bay as well, living on the eastern side is lot less expensive.
I grew up in Cambridge Maryland and now reside outside Annapolis. I can tell you both sides are good and James covered it well.

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post #4 of 14 Old 07-12-2013
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Re: Chesapeake sailing--western or eastern shore?

Virginia consistently ranks in the top 10 best states for retiree's while Maryland rates near the bottom. You are going to have to make a decision on whether your desire to live in a neat town with nearby urban areas by the water trumps other considerations. I love many areas in Maryland both on the Bay and in Western Maryland, however I would never live in the state.

In Virginia it seems most of the areas with access to the bay are fairly to extremely rural. Small western shore towns to consider in VA would be around Reedville (can be stinky from the Menhaden rendering plant), Kilmarnock, Irvington, Urbanna, and Yorktown/Gloucester Point. Kilmarnock, Irvington and Urbanna are neat little towns but the emphasis is on little. Its quite a distance to an urban center from any of them.

The most rural areas would be around the Yecomico and Coan Rivers, Deltaville, Gwynns Island and around Mobjack Bay. Deltaville is arguably the nexus of sailing in Virginia with many good marina's and boat yards. Having sailed from Deltaville for several years I can attest that the services available there are as good or better than those in the Annapolis area and are generally about 15-20% less for the same service. Slips in nice marina's may be 50%-75% less than the Annapolis area. The vast majority of boaters you'll meet in Deltaville live in Richmond or points more distant.

More urban areas would be around Hampton and Norfolk but I am not super familiar with these areas.

On the eastern shore your options would be Onancock (a long motor to the bay) or Cape Charles.

Good Luck.
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post #5 of 14 Old 07-12-2013
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Re: Chesapeake sailing--western or eastern shore?

I grew up sailing around Annapolis (there is a photo of me ice skating in Spa Creek Marina as a teenager when it froze one winter and one of me sailing as a teen with my Dad, recently posted on my Facebook page), kept a boat on the Rhode River in Mayo, MD, and most recently kept my boat on the Coan River on the Potomac, and now Urbanna on the Rappahannock River.

It is still somewhat startling to notice how many more boats are out on the Bay between Deale and Baltimore. In contrast, the lower Bay south of Solomon's is deserted and huge. The lower Potomac is about as wide as the Bay is near the route 50 Bay Bridge. It is not unusual to sail for a day and see only 2 or 3 other boats. As the Bay south of Tangier Island is nearly 20 miles wide at its widest, you can sail on a diagonal for half the daylight hours before approaching the opposite shoreline. I like the rural character of the Virginia Bay area. It is beautiful to drive along rolling farmland outside of Richmond to the Bay, punctuated by a few small towns here and there, such a contrast to the wall-to-wall suburbs and hustle and bustle of the D.C. area.
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Re: Chesapeake sailing--western or eastern shore?

Jameswilson, hit on one of the things I most miss about Deltaville. I bought my first boat in Deltaville and my first 5 years of sailing experience were in that area. While sailing down there my idea of a crowded anchorage was if I could see 2 or more other boats. Crossing to the eastern shore you were out of sight of land for an hour or more so you got the "big blue marble" experience even through you were in well protected waters.

Sailing from the Herring Bay area south of Annapolis, I can see the eastern shore and even if I couldn't the steady stream of large powerboats headed up Eastern Bay would point the way. There is no such thing as having an anchorage to yourself up here and more often than not boats are anchored so close that dragging down or having someone else drag down on you are constant concerns.

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post #7 of 14 Old 07-12-2013
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Re: Chesapeake sailing--western or eastern shore?

Easton, MD on the Eastern shore, might be an option. It was voted 8th best small town in America. It is close to St. Michaels, Annapolis, a good hospital, shopping restaurants and golf courses.

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Re: Chesapeake sailing--western or eastern shore?

Moving a boat into Va waters means a personnal property tax assessed by what ever county the boat is in on Jan 1st. I have a 25 years old boat and there is a wide range of values that could be assigned. Does anyone here have experience dealing with this matter? The boat will be located in Deltaville.
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Re: Chesapeake sailing--western or eastern shore?

I grew up in The Peoples Republic of MD, (away from the water unfortunately) and have lived in VA for the past 23 years. Maryland has some of the most ridiculous laws and procedures in addition to taxing the hell out of you. I doubt I will ever move back.
BUT, the sailing and racing community is huge. Admiral and I have been discussing this very issue for some time.
I probably will just stay in VA and move closer to the water as well as spend my time sailing the lower Bay esp. since it seems to have better and more consistent wind. To say nothing of the lower density of other boaters as has been mentioned above!

Western shore is more expensive than Eastern shore in both states but I think the Western shore has more to offer as far as what a retired couple would be seeking. Quick access to GREAT, not good, but GREAT medical care, culture, multiple airports (I live outside DC and between BWI, DCA and IAD I can be almost anywhere in the US in 2 flights), better scenery as well as easy to go to the hills if you are so inclined.

Oh, and definitely go sailing on Mobjack Bay. I used to work down there 30 years ago and while it's a bit more inhabited, it's still pretty quiet.
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Re: Chesapeake sailing--western or eastern shore?

Lower Bay, western shore seems most practical in almost every category. But if you like solitude then eastern shore rules.

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