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We Made the Bay by May


For Loopers, (those doing the Great Loop), one general goal is to be in the Chesapeake Bay by May, to keep on pace with hitting good weather throughout the loop. So we hustled a bit up the east coast to make it here in time (and have some flexibility to explore the area). We both have spent time in and around the bay--whether out on a friend’s boat in Annapolis, eating crabs across the bridge at Harris’, spending time with family in Neavitt, MD, or grabbing happy hour at the Wharf on the Potomac. But we were still amazed at the variety of this area--truly no two spots are the same, yet each has something unique to experience. We only scratched the surface of what to see and explore but here were some of our most memorable spots.


Stingrays in Deltaville, VA


This small town north of Norfolk near the mouth of the bay had some of the clearest bay water we’ve seen--and full of stingrays. After docking, we took our dinghy to a small sandbar off the marina for a quick swim and watched where we stepped (well Tim did...I didn't get off the boat).


Deltaville Marina

Google Maps / Active Captain


Smith Island Cake and Crabs on Chesapeake’s Islands


Went through Tangier and stayed the night at Smith Island. The islands’ residents (about 1,000 combined) have their own dialect and many of their families date back to the 1600s. We had some of the best seafood--crabcakes, softshells, and rockfish, cake, and a beautiful sunset from the beach a short dinghy ride away from where we docked.


Smith Island Bakery Google Maps / Active Captain

Swan Island Beach

Google Maps

Tylerton Town Dock, (great to dinghy to)

Google Maps / Active Captain

Drum Point Market on Tylerton (a MUST see) Google Maps


Military Presence on the Potomac

After cruising through countless backyards lining the ICW waterways in the south, the Potomac seemed surprisingly undeveloped--not a lot of houses and instead, military bases that lined the coast. As we were heading towards the 301 bridge, we were hailed by a ranger boat who gave us a specific route to ensure we were out of firing range from nearby military activity. It was a nice change of pace though not getting waked by passing boats.


No Traffic in DC

Docked at Mt. Vernon and walked the grounds (very cool since we have been listening to George Washington’s biography), pulled up to Olde Towne for lunch, anchored in Georgetown, and spent a few days at the Wharf. While we lived in DC for a few years, seeing these sites from the water (and traveling without any traffic) beats waiting for the Metro underground any day.


3 Sister's Anchorage

Google Maps / Active Captain

Market Docks at The Wharf Marina Google Maps / Active Captain


Tiki Bar in Solomons Island

With Mom on board, we spent the night at Solomons Island, a small island full of marinas, restaurants, and an infamous tiki bar, off the Chesapeake Bay. After being greeted by members of the Solomons Yacht Club, aiming to be the “friendliest club on the bay,” which is hard to beat when they greet you with free drinks in their bar, we walked around the town, grabbed famous Mai Tais at the Tiki Bar, and dinner. Fun spot and only 1.5 hours drive from DC.


Solomons Yacht Club

Google Maps / Active Captain


Nooks and Crannies of Maryland

We’re finding one of our favorite things to do is a stop over for a meal or walk around a town. So after anchoring near St. Mary’s, we stopped for breakfast at Courtney’s, a restaurant that’s been around for over 40 years near the very tip of Southern Maryland. Having grown up in Maryland, navigating the bay shows there is still so much more to the state to explore and see.


Price Cove Anchorage

Google Maps / Active Captain

Courtney’s, a restaurant

Google Maps / Active Captain


Big Waves in the Bay

Some days the bay was smooth as glass and others we had lifejackets on inside trying to get through 4 foot choppy waves. It got so choppy water was flooding our dinghy (we forgot to take the drain plug out) and then once we did drain the dinghy, the waves flipped the dinghy over. Luckily we got it under control, and then we took a nap while Tim took us to calm waters in Annapolis. They say the boat can handle more than the captain and every day we’re testing those limits for both Sweet Day and ourselves.



Great People All Around

One of the best parts about this chapter in our journey is all the friends and family we were able to see. If you were one of the ones we were fortunate to see these last two weeks (the pictures below don't even capture everyone we saw) thank you for letting us share a small part of our life on Sweet Day--we were honored to have you aboard!