Hello, my husband and I want to stay on the Eastern Shore the end of September. (We're coming from Germany and staying in the DC area and thought it would be a nice break).

Since we'll be there mid-week it looks like we can get some discounts. We're willing to pay up to $150/nt and we want a place on the water. We have narrowed it down to these places. Any comments/suggestions would be helpful. Choices are: The Oaks, Wades Point Inn, Great Oak Manor, George Brooks House (I know this last is not on the water, but it looks very nice).

Also, any suggestions on who to pick for a 2-hour skipjack sail?
Thanks!

For dining, I would suggest the Robert Morris Inn in Oxford. Best crab cakes in the world, even James Michener agrees. The Robert Morris also rents rooms if you are interested.

Hi

Chestertown is a lovely area as is Oxford Md. As we've gone sailing many times from Annapolis up through eastern bay to the back door of st Michaels, we have always come around Black walnut Point at the tip of Tilghman Island. It is one of the prettiest retreats I have ever seen. The inn is also convenient to St Michael's, Oxford, and the quaint little restaurants in each and on Tilghman Island itself.

It has its own website and honestly, I have no connection to it.

Tilghman Island is much more like a real Eastern shore waterman's town with scores of working watermen. Harrison's Chesapeake House is world-famous for its crab cakes and country family style eating.

Hi Steve & LN,
thank you for your replies. I found the website for Black Walnut Point and it sure does have a good location!

I'd like to take a sail on the Bay. Do you know who I should pick?

We stayed in Chestertown altho not on the water.(The Imperial Hotel-which I would recommend in a heartbeat if you can get a room off the porch in front) I'd recommend Waterman's in Rock Hall for great crabs and beer as well as The Blue Heron in Chestertown for a nice meal. The crab cakes are great here..we went back twice for the same!

I'll check out some places in Annapolis for you. Also when you decide where you'll be staying, give another post and I'll (or someone here) will try to get back with some recommendations.

Right up the road from Black walnut Point is the actual little town of Tilghman Island and Buddy Harrison has a restaurant, crabbing business, little hotel, gift shop, and I'm wondering if he doesn't have something like a that available. I'll check around.

Hi again:

In St Michaels Md - delightful little town where the townspeople fooled the British from shelling their town in the war of 1812 by placing all their lanterns on the 2nd stories - there's a charter company that does day sails and you can see the site and the information at http://www.Oystercatcher.com

If you are interested in spending a longer time period on the charter let us know.

"If you are interested in spending a longer time period on the charter let US know."

LN, are you advertising your own charter company?

No - no - I'm sorry you misunderstood and took it that way. I have no companies or businesses that have any connection to this or what I write on this site. We often go around the Chesapeake Bay by boat. I have always or we have always loved the Black Walnut Point site - as far as a charter goes this was one that I saw on google.com. Anyone can find similar sites on any search engine.

Please do your own checking and I'll not point out any sites that I've seen.

My favorite hotel on the eastern shore is the Hyatt resort in Cambridge. Gorgeous new hotel right on the water. The concierge should be able to assist you with whatever arrangements you need, including sailing. It is also pretty close to Oxford, a charming small waterfront town that warrants a walk-through. Chestertown is quite a distance away, although doable as a day trip.

LN, no need to withdraw your input - it's obvious you have some experience in the area and I'll bet your suggestions are great ones.

It was just the way you typed that one sentence.