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Trip Report - 3 week circular tour around Chesapeake Bay

Bristol, England
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772 posts
691 reviews
Trip Report - 3 week circular tour around Chesapeake Bay

Chesapeake Road Tour - Trip Report

We have recently returned home to the UK after completing a road trip round much of Chesapeake Bay and ending in Shenandoah National Park.

As this trip included time in Maryland and Virginia, I am posting this report on both forums.

I have posted reviews of virtually all the restaurants where we ate and places of interest that we visited. Hotels and apartments were either booked direct, or through AirB&B or (for one apartment) through TA.

Day 1 - We started in mid September in Washington DC where we collected a rental car at the airport and drove to Annapolis where we stayed for 2 nights at Gibsons Lodgings right in the heart of the city and within walking distance of shops and restaurants. We ate one night at the Dock Street Bar and Grill and the other night at the Federal House Bar and Grill. We also sampled a crepe from Sophie's just round the corner.

Day 2 - During the one day we had, we took a trolley ride round the historic center, explored local shops, drove down to Edgewater to visit London Towne and made a trip down the western shore of the Bay as far as Chesapeake Beach.

Day 3 - we crossed the bridge and cut off at Kent island, to explore both sides of the I-50 highway, ending up having lunch at a delightful bar / restaurant Big Bats cafe in Stevensville. Then on to Cambridge for 2 nights where we stayed at the Comfort Inn & Suites and had dinner that evening at Carmela's Cucina in town.

Day 4 - we used the Oxford - Bellevue ferry to Tilghman Island and drove right down to the end of the island, stopping for a drink at Characters Bridge restaurant and going back up to the top to explore St Michaels before returning back to the "mainland" to call in to Easton and find the Third Haven Friends Meeting House (one of the oldest places of worship in the USA which has been in continuous use since it was built - 1684).

Day 5 - we drove across to the Atlantic shore at Rehoboth Beach, via route 392 in order to try to explore some of the locations described in the book "Chesapeake" by James A Michener (who inspired this road trip). Then down the coast to stay one night at Ocean City (Econolodge Seafront). This was not our normal choice of location, but we quite enjoyed the boardwalk experience and dinner at Shennanigan's .

Day 6 - drove back across to the east shore of the Bay to Crisfield, where we took the pre-booked 12.30 cruise to Smith Island. We were unable to explore much of the island because of high water levels, but what we saw was interesting. We had a takeaway snack lunch from the restaurant by the dock and explored what there was to see. Not a lot. Having subsequently visit Tangier Island (from the other shore) we would recommend that as an option for seeing island life in Chesapeake Bay, rather than Smith Island, which doesn't make much effort to welcome tourists.

When we returned to Crisfield, we drove across to Chincoteague Island (on the Atlantic coast again) where we stayed 2 nights at the Comfort Inn & Suites - probably the best hotel accommodation of the entire trip.

Day 7 - we explored Chincoteague and went out to the wildlife reserve and went on a previously booked trip with Captain Spider, who gave us a wonderful 2 hours out on the bay at sunset. Dinner that night at Don's Seafood restaurant.

Day 8 - drive to Norfolk VA via the Bay Bridge - an interesting experience. Stayed 3 nights in a house rented through TA. An amazing house and an amazing experience. Bubba's Crab House for dinner that night.

Day 9 - we explored around Norfolk, visited the Botanical Gardens (probably amongst the best we have seen in any city anywhere in the world), did some shopping (we had to occasionally) and enjoyed the extraordinary house designed after the style of Frank Lloyd Wright on a grand scale.

Day 10 - drove out to Virginia Beach, stayed there for a few hours, lunch at Jumpin Shrimp restaurant, then a long inland tour back to our house, just to see some of the countryside.

Day 11 - we drove to Reedville (on the west side of the Bay) via the lovely Colonial Parkway - Yorktown, Williamsburg and Jamestowne. That was a full day and we needed more time to do justice to each of the places.

We stayed for 3 nights at the Bay Motel - basic but excellent and good value.

Dinner on two nights at Tommy's restaurant.

Day 12 - explored the area locally and had a picnic under the shaded area by the motel with friends who joined us.

Day 13 - Trip to Tangier Island - a better experience than Smith Island - excellent lunch at Hilda Crockets restaurant.

Day 14 - Drove to Richmond VA. Stayed in a delightful house for 2 nights rented through AirB&B.

Day 15 - The visitor centre advised a tour of the State Capitol - excellent advice - terrific guide. Then visited St Paul's Church and went to the observation deck on City Hall.

Day 16 - On way out of Richmond, we visited the Lewis Ginter Botannical Gardens - very good kid-friendly gardens with excellent cafe for lunch. Drove to Charlottesville and stayed at another house rented through AirB&B for 2 nights. We visited the downtown visitor centre and planned the next day activity before having a Happy Hour drink at the Red Pump Kitchen in the lovely downtown pedestrianised mall..

Day 17 - Breakfast at Timberlake Drug Store and Soda Fountain, before catching the free trolley out to the UVA campus. There we visited the recently re-opened Rotunda and wandered around the original campus area (designed and built by Thomas Jefferson). Dinner at Petit Pois restaurant downtown.

Day 18 - early start for a pre-booked tour of Montecello - a fascinating experience and we easily spent 5 hours there and did all the available tours. Late lunch at nearby Michie Tavern (interesting and enjoyable experience) before having a sunset drink at the Blenheim Winery. Dinner on the deck behind our house.

Day 19 - The plan was to drive along Skyline Drive through Shenandoah NP on our way to Luray for our final 2 nights. The weather was rain and cloud with little chance of views from the top, so we drove part way up the valley before taking a chance and cutting up to the top where we hoped to have lunch at the recommended Big meadow Lodge. Too late for lunch at 2pm so we were directed to the nearby Wayside Inn. A disaster. Not much in the way of views either. Then on to Luray to check in to the Hillside Motel for 2 nights and dinner with live music at Mimslyn Inn.

Day 20 - our final day before flying back to the UK, so mostly spent re-packing cases for the flight and a little exploring in Luray - a delightful town. Dinner downtown.

Day 21- Drove to IAD Washington via a fun lunch experience at the Ap[ple House restaurant at Lindon VA. Evening flight departure.

A great and memorable trip.

Bank Street Books
Gift & Speciality Shops
The Market Collective
Gift & Speciality Shops
Primitive Corner
Gift & Speciality Shops
Level Contributor
1,198 posts
1. Re: Trip Report - 3 week circular tour around Chesapeake Bay

Thanks for the report. I've lived here all my life and have never done some of the things you did

Western Ireland...
Destination Expert
for Sligo, Charlottesville, Virginia, County Donegal, Western Ireland
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21,831 posts
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2. Re: Trip Report - 3 week circular tour around Chesapeake Bay

Chris H,

Thank you for sharing your visit to Virginia with us on the Forum, great info for those planning a future trip to Virginia.


Memphis, Tennessee
Level Contributor
2,923 posts
910 reviews
3. Re: Trip Report - 3 week circular tour around Chesapeake Bay

Thank You for sharing your excellent itinerary & experience.

VA just moved way up on my Bucket List!

Annapolis, Maryland
Level Contributor
1,106 posts
6 reviews
4. Re: Trip Report - 3 week circular tour around Chesapeake Bay

My in laws used to have a house in London VA. Our kids loved The Apple house and the warm donuts.

We live in Kent Island........awesome to see you came over here. We love it here.

You had a great trip!!


Richmond VA USA
Destination Expert
for Richmond
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1,313 posts
5. Re: Trip Report - 3 week circular tour around Chesapeake Bay

You found some great places. I'm so glad to hear that your trip went so well and that you found so much to enjoy.

Charlotte, NC
Level Contributor
134 posts
55 reviews
6. Re: Trip Report - 3 week circular tour around Chesapeake Bay

I'm originally from Maryland. You make me want to go back and do that trip! What a lovely report and an unusual itinerary. Fantastic. I do love Monticello. I could spend hours there. Thanks for posting!

Any Beach
Destination Expert
for Myrtle Beach, North Myrtle Beach, West Virginia
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11,545 posts
153 reviews
7. Re: Trip Report - 3 week circular tour around Chesapeake Bay

What a great report! Thanks for sharing!

Level Contributor
444 posts
282 reviews
8. Re: Trip Report - 3 week circular tour around Chesapeake Bay

Very Nice!

9. Re: Trip Report - 3 week circular tour around Chesapeake Bay

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