Continuing to Cruise the Lower Chesapeake Bay – Wineries, Friends, Weather Windows and Crossing to the Eastern Shore

When last we left you, we had just left the Rappahannock River and made a last minute decision to anchor in Little Bay – instead of making a longer cruising day towards Reedville.

This proved to be quite serendipitous, and lined up some stops we wouldn’t have considered otherwise.

Our Slooper pace allows us to embrace that when we feel so called.

I had originally intended this post to catch us closer to real time, but we’ve just been up to so much that we’re splitting this into multiple posts.

This one will capture our adventures of finishing up the western portion of the lower Chesapeake and then crossing over to the Eastern Shore – and covers May 14-19.

As always, pick your poison – video or written, or embrace the power of ‘and’ and do both;

Stop 1: Dividing Creek Anchorage – Kilmarnock, VA

We visit amazing places. No doubt. But it’s the people that keep us inspired to continue our nomadic life.

Our fortuitous stop at Antipoison Creek, instead of heading straight to Reedville – gave serendipity a chance to catch up with us. For a message arrived from long time follower Beth moments after we set the anchor.

When we say long time follower.. she’s been following since the beginning. Back in the T@b days when we first met and hit the road together.

Turns out Beth and her husband live just a couple creeks up the Northern Neck. With an anchorage nearby that we could get ashore.

So that’s where we headed.

We spend a lovely day getting to know each other, and learning their story of embracing their sailing dreams.

We hiked Hughlet Point Nature Preserve, explored the quaint town of Kilmarnock, an afternoon tasting wine at Good Luck Cellars and a tasty Thai/Sushi dinner out. We even borrowed their truck to do a provisioning run.

Meeting people who have been following along is the most magical part of our journey. The opportunity to see how others are pursuing their dreams, and seeing our sharing reflected back.

So please.. if you see us coming near you, don’t hesitate to reach out! We’d love to meet up!

Stop 2: Mill Creek Anchorage – Wicomico Church, VA

In our RVing season, we absolutely love staying overnight at wineries as part of our Harvest Hosts membership (affiliate link saves you 20%).

And we always used to joke:

‘Unfortunately, there aren’t too many wineries with docks we can get to’.

So when we saw that Jacey Vineyards along the Northern Neck of VA (part of the Chesapeake Bay Wine Trail) welcomes boaters to their dock – we knew we had to go!

We ducked into Mill Creek Anchorage off Ingram Inlet for the night, got the drone up to confirm the location, called to confirm instructions and took the dinghy over.

This time of year, they’re only open Friday evenings (with live music) and Saturday afternoons. So timing is essential. Had we not stopped to visit Dividing Creek, this would not have lined up for us.

We were too late to get a reservation indoors for dinner – but we had a lovely patio table. The entire staff was super friendly and welcoming, including meeting the winemaker himself.

We enjoyed dinner with a bottle of their excellent Cab. And brought home two bottles of their outstanding Malbec to enjoy later.

Wineries with docks.. it’s a thing!

(There was also a cidery on the wine trail accessible by water on Dividing Creek. But timing & weather to get to both with their limited hours just didn’t work out.)

Stop 3: Backcreek Anchorage – Reedville, VA

Some weather systems would be moving through, so we decided to cross Ingram Bay to Reedville – a common stop for those transiting the Chesapeake Bay.

Nicely protected with options for anchoring and free overnight dockage in town.

We opted for anchoring, and found a spot with not too many crab pots around where we could set the anchor in already building winds.

Reedville, once sporting the highest per capita of millionaires in the USA during their fishing boom, is now .. well.. doesn’t have much.

There’s a maritime museum (every town around here seems to have one – we have learned more about the fishing and crabbing industry than we thought possible), an ice cream parlor and two restaurants actually open.

And by ‘open’ we mean if you happen to align with their limited hours (seems to be a theme!).

Which all and all, is fine for an overnight. But the weather kept us pinned down for three.

Every time the winds would take a break for a bit and we thought we might duck out and give the bay a try – an experienced frazzled cruiser would set anchor near us ducking in with daunting tales of bashing waves.

So we made the best of it… after all, we have no schedule to keep.

And our next intended adventure was crossing to the Eastern Shore… we wanted pleasant conditions.

(Non) Stop 4: Crossing the Bay, Routing Through Tangier Island

After waiting out some very windy conditions in Reedville for several days, a potential weather window we had been keeping an eye on opened up a couple hours earlier than expected.

This would be our first crossing of the Chesapeake Bay to the Eastern Shore, and we wanted it to be as tame as feasible.

Forecasts were showing 1-2 foot waves, and we know to expect potential for 2-3 footers as the reality.

So we weighed anchor and set out, crossing a conga line of returning fishing vessels.

As we left Ingram Bay, the swells from the north were gentle and we were able to align them to take them on the quarter – a pretty comfortable, but swelly, ride.

By the center of the bay, we encountered some 2 footers, maybe an occasional 2.5 – 3′ – but the ride remained bouncy but comfortable.

We tried not to gloat, but it’s always worth a hoot to celebrate overcoming new challenges and not being eaten by Krakens or Lava Monsters. Or being caught in one of the numerous crab pot buoys scattered about (even in 80′ of water!).

We routed through Tangier’s Island – an isolated fishing village that is a step back in time. We’ve heard it’s an interesting stop, but our weather window was short before we’d be pinned down again.

But it was fun to pass through, and hear the unique Colonial era dialect still spoken here. And, we could always come back via ferry.

As we exited into Pocomoke and Tangier Sounds, conditions were much more calm, and we made it to our planned weeklong destination of Crisfield to hunker down for some predicted windy conditions and the holiday weekend ahead.

Real Time Update

We spent a few weeks poking around the Eastern Shore, which we’ll catch you up on next post. We found another weather window to cross back over and enter the Potomac River.

We’re slowly making our way up river, checking out more small towns as we go.

We’ll arrive to Washington, DC by the end of the week, where we have an extended stay planned. We’re very much looking forward to some big city life – museums (not about crabbing!), eclectic dining, biking, theater, history and more!