Eastern Shore Birthday Trip

The Eastern Shore

Kelsey and I had done all the planning (I’ll do a post on it too, although it hasn’t be tested yet) for a trip to Florida to swim with the manatees. Then a tropical storm came through and I had to change all of our plans 36 hours before time to leave. This was our replacement and it was AMAZING.

We left Sunday morning and drove (and drove and drove and drove) to Cape Charles, VA. We made one stop on the way, a beautiful stop but a challenging one…. we detoured to Covington, VA, with the intention of eating a picnic lunch at the waterfall and then seeing a historic covered bridge. It didn’t work out exactly as planned (no food places, longer drive than expected, a road was out and so detours, GPS didn’t get service, etc, etc), but those two sites were beautiful, especially the covered bridge. Absolutely amazing.

That night, we arrived late in Cape Charles, VA. I had gotten the last room available at Hotel Cape Charles, a boutique hotel that we both fell in LOVE with. This whole area was so darling! We booked a kayak tour. It was a GREAT deal for an awesome excursion. It was probably my favorite part of the trip. After our morning kayaking (started at 8), we went to the public beach in Cape Charles. It was Memorial Day and there were probably 30 people out there other than us. The only downside is that the beach is VERY shallow FOREVER, with no waves. So it might be a little boring to some. After some time there, we headed to our AirBnB in Onancock to check in.

Kayaking together

I cannot say enough about this place. Good grief. It was absolute perfection. We loved every second of our stay at The Apartment at Holly Cove and would also have loved The Studio at Holly Cove, if it had been open. They offered use of their kayaks and paddle boards and the dock and shore areas. It’s just a lovely place and I wish we could go back again SOON.  That first night, after kayaking in the creek, we ate at Mallard’s, a place I think we would have appreciated more had we been seafood eaters. 🙂

The next day, we headed to Chincoteague and Assoteague. It was about a 45 minute drive from Onancock. We arrived in the area by 10 and drove around Assoteague. It did cost $20 to drive over. After making the loop in the car, we got our bikes out and biked several loops. (DO NOT DO THIS WITHOUT BUG SPRAY.) It was fun, but so foggy we didn’t see very many ponies. After our visit to Assoteague by land, we headed back to Chincoteague, picked up lunch from Poseidon’s Pantry and ate a picnic lunch. From there, we headed to the marina to meet for our boat tour of Assoteague. We loved Captain Bill. His boat left a LOT to be desired. And the price seemed a little steep for the conditions of the boat. However, Bill was a nice guy and had a lot of info to give us. After our tour with Bill, we stopped at the MUST STOP place, the Island Creamery. It was EVERYTHING WE HAD HEARD AND MORE. Delicious. After a visit to the park and a little bit of shopping (not much to see), we headed back to Onancock where we ate at the Irish pub (do not recommend).

Sights of the Island


The following morning, we got up early to eat breakfast at Janet’s. What a DARLING place and such great food! Following that, we went a minute or two away to the wharf where we met our ferry to go to Tangier Island. This was such a cool little day…. the ferry ride is about an hour each way and the time at Tangier Island was so pleasant. We walked the main side of the island, then took a golf cart tour. After that, we ate lunch, then rented our own golf cart. We drove around everywhere, then ended up at the beach with NO ONE on it. It was amazing. If we ever go back, I would take beach stuff and we would just spend the day on this beautiful empty beach. The locals said it’s always empty. After our ferry ride back, we packed up, grabbed some dinner, and went to bed.

Then we drove back, leaving there at 6 AM and arriving home at 5:30 PM with about 4 quick stops. It was a long drive to do all at once, but I never listen to myself, so….. 😉

Great trip. Five out of five stars.


Athena Davis loves to make memories with her people in special places. She believes in shared time and experiences over things, and she wants to help you make beautiful memories of your own on this gorgeous planet that God created! She is a mom to five, a wife, a writer and a reader, a high school English teacher, and somehow a homebody who loves to wander. Her personal travel passions are national parks/outdoor travel, mission work, and educational/theme trips such as Holocaust education, literary tours, and historical sites. She would love to help you plan the trip of your dreams or just a quick jaunt to make some memories between the day-to-day of life!  Athena would love to help you plan the trip of your dreams or just a quick jaunt to make some memories between the day-to-day of life! Contact her at athena@tailoredtravel.vacations or call 423-284-3755!