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Old 11-01-2021, 08:16   #16
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Re: Chesapeake bay cruising advice

Lists given could last a lifetime. Your boy is a little young but I would strongly recommend Potomac to Washington and any of the Smithsonians.
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Old 11-01-2021, 08:18   #17
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Re: Chesapeake bay cruising advice

I lived there for six years (Annapolis). It's pretty easy cruising (at least when it's warm!). Lots of cool little towns. Running aground is rarely a big thing as most of the bottom seems to be soft mud. You do have a lot of large commercial traffic, even late at night, but they are pretty easy to avoid.

If your deal is: day cruise, tie up, find a cool restaurant, and sight see, you can't do any better. The lists in the posts above about covers them all.

If it wasn't for the winters and taxes, we would have never left.
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Old 11-01-2021, 08:19   #18
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Re: Chesapeake bay cruising advice

If you want to go for towns, the obvious ones have been mentioned but one in particular may be the only one left with a grocery store within walking distance from the dinghy dock and that is the small historic town of Urbanna, on the Rappahannock. Also on the Rappahannock is the Corrotoman River, which can handle deep draft sailboats and has lots of gunk holes. And Carter's Creek which has some really nice homes to marvel at as well as the Tides Inn for a nice dinner. A short walk will take you into Irvington which has a nice farmers market the first Saturday of the month, May through October I think.
The lower Potomac River has too many anchorages to mention, but the St. Mary's river is worth exploring and up to Horseshoe bend at St. Mary's College, nice grounds to walk around.
I'll second Onancock Virginia, small, quaint and some nice restaurants, art galleries and historic homes and gardens.
Cape Charles is worth a visit but you need to plan on a marina there as there is no anchorages.
In settled weather, Kiptopeke State Park has a nice beach, good fishing and plenty of hiking trails
Rock Hall, St. Michael's, Annapolis are musts. Baltimore is a big city and can be iffy at night but probably safe during the day. Fell's Point area has been revitalized, so that's a good bet.

The Chesapeake can take a lifetime to explore, something like 11,000 + miles of shoreline to explore!
July and August are usually hot and sticky, lighter winds and thunderstorms. May, June, September, October are beautiful and sublime
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Old 11-01-2021, 10:13   #19
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Re: Chesapeake bay cruising advice

seven weeks? start at bottom and see it all.
august and four year old? find swimming pools and bug spray. No wind and hot
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Old 11-01-2021, 11:53   #20
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Re: Chesapeake bay cruising advice

The Maryland Cruising Guide is your best source...Annapolis is a must---I am a lifelong resident of Maryland

https://www.amazon.com/Maryland-Crui.../dp/0999403206
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Old 11-01-2021, 13:43   #21
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Re: Chesapeake bay cruising advice

We spent July-October this year in the Chesapeake. Documented our visits and travels daily on our Facebook page. Feel free to check it out at BreatheSailDive.

http://www.Facebook.com/breathesaildive
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Old 11-01-2021, 14:04   #22
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Re: Chesapeake bay cruising advice

I see Onancock mentioned several times above. It is one of our favorite cruising destinations. It is also the home town of Virginia's Governor Northam. A couple of years ago, my wife and I went there and I asked the dock master if he knew the governor. He said Onancock is a small town and everyone knows everyone else. He then smiled and said "in fact, I took his sister to the prom!"
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Old 11-01-2021, 14:21   #23
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Re: Chesapeake bay cruising advice

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Originally Posted by sasirles View Post
I see Onancock mentioned several times above. It is one of our favorite cruising destinations. It is also the home town of Virginia's Governor Northam. A couple of years ago, my wife and I went there and I asked the dock master if he knew the governor. He said Onancock is a small town and everyone knows everyone else. He then smiled and said "in fact, I took his sister to the prom!"
I remember Ralph from Little League. He was starting when it was my last year. (different teams)

I did have a picture of him at Onancock HS but can't find it right now.

We all (in Virginia) went to either Cape Charles, Central, Onancock, Parksley, Atlantic, or Chincoteague High School. That from the bridge all the way to Chincoteague.

They are all closed now and Onancock is nothing like it used to be which was a really busy place back in the day, but it's nice to visit now but the stores for groceries are now out near the main highway a few miles away

This just after desegregation and Ralph could have gone to the all white private school at Broadwater as his dad I believe was a judge and could afford it, but he chose to go to Onancock Public School.
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Old 11-01-2021, 14:22   #24
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Re: Chesapeake bay cruising advice



I really recommend this guidebook. We have spent part of the past 4 summers on the Chesapeake and this is our go-to guide.
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Old 11-01-2021, 15:43   #25
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Re: Chesapeake bay cruising advice

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Originally Posted by wizoc View Post
Lists given could last a lifetime. Your boy is a little young but I would strongly recommend Potomac to Washington and any of the Smithsonians.
If you don't want to transit the Potomac you could catch a train from Hampton or probably also Baltimore to D.C. Covid willing the museums/mass transit will be available. I'd think the entire family would enjoy the national aquarium in Baltimore.
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Old 11-01-2021, 17:04   #26
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Re: Chesapeake bay cruising advice

I would heartily endorse my hometown of Cambridge on the Choptank River. It's got history, great restaurants, and a deep-water port, all walkable from the municipal marina or Cambridge Yacht Club.
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Old 12-01-2021, 04:34   #27
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Re: Chesapeake bay cruising advice

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I would heartily endorse my hometown of Cambridge on the Choptank River. It's got history, great restaurants, and a deep-water port, all walkable from the municipal marina or Cambridge Yacht Club.
Plus James Michener wrote a great historical fiction novel about that area called Chesapeake and the sailors that came from there.

https://thefederalist.com/2018/08/24...ames-michener/
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Old 12-01-2021, 05:31   #28
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Re: Chesapeake bay cruising advice

Smith and Tangier Islands
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Old 12-01-2021, 06:03   #29
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Re: Chesapeake bay cruising advice

This is a pretty good video of Tangier Island.

We used to see them a lot more often on the mainland when crabbing was still big in the 1970's

They still have their old Elizabethan accent ......

We used to fish on the wrecks near Tangier on our small 14' power boats. Its 12 miles out from the mainland

It took me a long time to stop with the backward talk after I left the area. We did the same on the mainland nearby as those on Tangier.

https://www.pri.org/stories/2014-07-...-piece-history

BBC - Travel - The tiny US island with a British accent

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Old 13-01-2021, 04:49   #30
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Re: Chesapeake bay cruising advice

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Go to Tangier Island and dock at Mr Parks, he's been there since I was a kid. Get a golf cart and grab crab cake from Lorraine's. It is an easy walk, the cart is just cool way to get around on the Island.
Tangiers Island is one of the last places on the Chesapeake that is a traditional fishing village where the islanders still survive by working the Chesapeake (fishing, crabbing).

Go to the in-water Martime Museum there and see all the classic boats - also you and your little guy/gal can be a "Apprentice Boatwright for a Day" where the Head Boatwright will let you (and teach you how to) actually work on some of their wooden boat projects.

They also used to have a deal that if you join the Museum, you can tie up your boat at their docks. Don't know if they still have it.
Fair winds!
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