To clarify:

you have a total of five nights?

you want to spend them between Charlottesville AND Annapolis or Chincoteague?

It's not clear to me either but it reads as though the five nights are between DC and Baltimore and then they continue on to Charlottesville, VA from there.

If you're staying between Baltimore/DC you can much more easily visit Annapolis before heading on to Charlottesville.

As for Chincoteague, getting there and back (to an airport) will take time, there's a lot of water to navigate around but if I had the time that's where I would go.

Two completely different places, both on the water.

Annapolis is the state capitol, so it is a bustling yet charming small city. The historic core is great for walking. Chincoteague, as AnnMarie notes, is completely different. More a beach vacation-type feel but with a year-round community. Definitely further from the BWI-DC area, so it does depend on how much time you have. If you are looking for a change of pace from BWI-DC, I would pick Chincoteague, too. But, if you have enough time, you could stop in Annapolis for an hour or two and continue to Chincoteague.

You are going to be doing a LOT of driving. Charlottesville is west of DC--a couple of hours drive one way. Chincoteague is at least 3-3.5 hours drive from DC area, depending upon where you are in the DC/Baltimore area. Annapolis and Chincoteague are light years apart as far as tourist appeal. Annapolis is more yuppie, Chincoteague, while a vacation spot, is much more old Eastern Shore--it is a fishing village. The ponies can be seen at the National Park. Annapolis would be much closer than Chincoteague drive wise. It depends upon what you want to do and see.

Sorry for the confusion. We are spending 3 nights in Baltimore. My father in law is taking part in a program that brings WWII Vets to DC to see the memorial and they are putting everyone up in Baltimore. After he goes home, my husband and I will go to DC for 2 nights on our own. It is then that we wanted to go to Charlottesville, VA for a few nights. It sounds like a lovely area. The next part is where I am confused. It sounds like Chincoteque is just too far. Perhaps we just go to Charlottesville after DC and then drive to Annapolis for a couple of days.

What a wonderful program!

Traffic aside, it's an easy drive from DC to Annapolis. From Annapolis you could take a day trip over to my neck of the woods, the eastern shore. It's an easy, scenic, drive that takes about 45 minutes. Google St. Michael's, Easton, Oxford. Lots to see and do and a lot of great food!

I've been to both, they are both great. Used to go hunting Canada geese on the Eastern Shore and we would stay the first night in Annapolis cause our flight got in late. Lots of good seafood restaurants.

The Eastern Shore is terrific been there a lot of times, too bad oysters will probably not be in season then, but soft shelled crabs will be, that is some mighty fine eating. We spent two days one trip driving the whole of the Eastern Shore and love those towns, we also visited Chincoteague and Assateague (my late husband's cousin lived in Chincoteague), as well as Chestertown, St. Michaels and many other places then drove across the bridge at the south end. Terrific trip.

Thanks so much! As it turns out, we could only book 3 nights in Charlottesville because graduation is the next week end. So, we will go from DC to Charlottesville. After 3 days (Friday), we thought we would head to Annapolis for a couple days. The Eastern Shore sounds wonderful. Maybe just spend a night in Annapolis and 2 on the Eastern Shore? Or does it make more sense to just stop by Annopolis for the day and head right over to the shore. We love the idea of the beach and good seafood.

Its a lot of driving but here's an alternative. From Charlottesville, drive I-64 to the Hampton Roads area where you will turn north onto the Chesapeake Bay Bridge Tunnel which will take you to the Va. Eastern shore. Coming up the Eastern Shore, you'll be able to visit Chincoteague and then Assateague Island (Note - you have to come inland to drive from Chincoteague to Assateague Island.). On your way back to Baltimore/DC, you'll go right thru Annapolis or spend your time on the Eastern Shore in St. Michaels or Easton.

It really depends on what you want to do, read up on what each area has to offer and decide from there.

The 'Eastern Shore' as it's referred to isn't the ocean, it's the Chesapeake Bay and its tributaries. Easton, Oxford and St. Michael's are in close proximity to one another but only Oxford and St. Michael's are surrounded by water. There isn't a beach per se although there is a small beach area in Oxford known as The Strand.

Although mid-May is still early in the season, if you do decide to visit the Eshore, be mindful that traffic coming across the Chesapeake Bay Bridge (east) is heaviest on Friday afternoon and Sunday afternoon, Route 50 west, can be a parking lot.

Hope this helps. I love it over here, there is so much to do, but if you're looking to relax on a beach you will want to go elsewhere.

Here's a link to information for the Eastern Shore,

http://www.easternshorevisitor.com/maryland-eastern-shore.html

Thanks so much for the help. We do not necessarily need to be sitting at a beach. Having water in our view is great. I like the idea of putting Annapolis after the Eastern Shore. Makes sense. Of course, we are heading there on a Friday. Darn. Do you think that is a deal breaker? We don't mind a bit of a drive, but I don't want it ended with sitting for hours in traffic. I will check out the site. Maybe with our timing of going on a Friday and our limited time, we should just skip the shore and spend a couple days in Annapolis and/or maybe Alexandria ???

Like AnnMarie C, I am also an Eastern Shore native, and have spent many day in Annapolis (married a USNA man, got married there). I also went to UVA, so I am familiar with all three places!

Personally, I would not do the drive up to Hampton Rds. Like Rte 50 W on a Sunday, 64E (the road from C'ville to Hampton Rds) can be a parking lot on a Friday, with people going to the beach. The traffic in general around Hampton Roads is a nightmare! Not recommended on a Friday.

What I would recommend is this: leave Charlottesville on Friday; drive to Annapolis (3 hours flat with no traffic - did this many times in college while dating my husband). Spend Friday night in Annapolis to avoid the Bay Bridge/50 E crowd that's driving to Ocean City. Peruse Main Street, tour the Academy, stay at the Marriott or Westin downtown (or once of the many B&Bs).

Leave Saturday morning and head to the Eastern Shore, where you could stay in Chestertown or St. Michael's (Oxford, where my grandparents lived, is a fun ferry ride from St. Michael's and you can walk around the whole town in an hour or so). I recommend the Inn at Perry Cabin in St Michael's and the Brampton Inn or Imperial Hotel in Chestertown.

On Monday morning, head back to BWI (1.5 hrs flat from Chestertown, about the same from St. Michael's).

****An important thing to consider is Commissioning Week in Annapolis, when parents of graduating misdhipment descend upon the city and most hotels are booked. This year it is May 17-24, with the actual commissioning (graduation) on Friday, May 24.*** This may change your schedule slightly.

Let me know if you need any help or have any more questions!

Thanks again! SO much good information. Since we would be going into Annapolis on May 17th, I decided to grab a room asap. We booked 2 nights, and can cancel the one after we get "the next step" figured out. Our flight on Tuesday leaves DC in the late afternoon. We need to turn our car in by 4pm. How long does it take to get from St. Michael area to DC. Perhaps we could jut make that trip on the day we leave if we give ourselves enough time.

No problem! You are smart to book a hotel.

St Michael's to DC is 1 hr, 45 minutes - I'd give yourself 2 and 15 to be safe. But it is DEFINITELY doable to make that trip on the day you leave.

Annapolis really comes alive during Commissioning Week. It will be great! I have tons of recommendations for restaurants there, so let me know if you are interested.

As for St. Michael's, be sure you take the ferry from Bellevue to Oxford (I mentioned that earlier) and eat at Schooners Llanding (not a misspelling - it has two l's!) for lunch, or the Robert Morris (the best crabcake you'll ever have, but doesn't have the waterfront of Schooner's). The Crab Claw in St. Michael's is THE place to pick crabs, and there are tons of little antique shops that are so quaint. The Chesapeake Bay Maritime Museum is a must, too.

Let me know if you have any other questions. If you need more specific info on your trip, feel free to send me an email too - louisagehring@gmail.com.

Again, thank you. We have revised the end of our trip, as everything was booking up and it just seemed to make more sense. We booked 2 nights at The Historic Inns of Annapolis (The Maryland Inn had an available room) and then 2 nights in Old Town Alexandria at The Hilton. Happy to get any restaurant recs. The Maryland Inn had a couple bad reviews so may see what else is around in our price range.

You can't beat the Maryland Inn for location...a lot of the other b&b's/historic inns may already be filled up, but if you're going so you can stay in the right area, this is a good one.

Cantler's (a local crab house) is a must in Annapolis. It's away from downtown, less touristy, and terrific. Grump's is a local favorite for breakfast, if you like big breakfasts (one of those places where servers dress in pj's). Joss is a sushi place on main street that doesn't take reservations, and has one of the highest Zagat ratings - if you like sushi, it's excellent! There are also several restaurants in Eastport (the Chart House, Carrol's Creek, Lewnes' steakhouse) that are excellent, and show you a more toned down side of town. Finally, for an afternoon/early evening drink as the sun is setting, I'd get a spot outside at Pusser's which is right on "Ego Alley" (named for where people with big boats pull up and dock just so their boats can be seen...but it's right in the heart of downtown and great).

Have fun!

Thanks for all of the tips. I will take them with me. After seeing some of the reviews of the Maryland Inn (great location, but this particular part had a lot of complaints about the rooms), I booked a room at the Springhill Suites, Marriott. I still have both reservations, so need to make a choice. Any opinion?

Not a prime location (sort of on a random road near the Mall/other shopping centers), but will give you a standard Springhill Suites experience. Downtown Annapolis doesn't have ton in the way of parking so if I were you I'd try to stay in that area.

Would the Westin Annapolis be out of your price range? I see it's abour $30 more/night (starting at $209) for those dates. It is in a perfect walking location. Other options would be O'Callaghan Hotel (also on the same great street, and I see the rate is $169)or the Loew's (on the same street as Westin and O'Callaghan as well) for $199.

Totally forgot that for a great beer and atmosphere check out the Ram's Head! Often have great live shows as well. Don't miss it (it is within easy walking distance of the three hotels I just mentioned).

Thanks again! After a lot of research on tripadvisor for hotels I booked The O'Callaghan Hotel and cancelled the others. I did not want to be out on a random road. I like a central locatiom. I am set. Sadly, your area will need to wait until another trip.