Best of the Chesapeake: Wrap Up of our 2025 Cruising Season – Favorite Stops & Statistics

Our 2025 cruising season was dedicated to just the Chesapeake Bay.

We departed Chesapeake, VA on the southern end on April 25, 2025 and had our final stop in the northern end in Havre de Grace, MD six months later.

Great Loopers following a more traditional 1 year journey might only have time to spend a couple weeks on the Chesapeake Bay.

But we had heard from enough that it’s an area they wished they spent more time. Since we’re Sloopers, we decided to take that advice and devote some time to poke into nooks and crannies.

Here’s our video recap with the highlights, cruising statistics & costs as well as our attempt at picking our Top 10 favorite stops:

From our notes in recording this video, here’s a text recap as well:

Cruising Stats

• 50 Unique Stops (most Loopers might make 3-6 stops?)
• 962.5 nm (if we had taken a direct route from Chesapeake, VA to Havre de Grace, it would have been 185 nm)
• 155 Engine Hours
• 77 Generator Hours
• 456G Fuel – $1,637
  • Averages: $8.11/daily / $243/Mo
  • 3.5GpH / 1.8 MPG
• 137 Marina Nights – $9,351
  • 40 nights in DC (and more than 1/2 of our marina costs)
  • 39 nights in Baltimore
  • 65 Anchored
  • 12 Mooring – $281
  • Averages: $45/daily / $1350/monthly
• 51 Bridges (24 of these were from our many sea trials at Atlantic Yacht Basin)
• 1 Lock

Boat Up Wineries

One of the many surprises of the season was that we found 3 wineries that we could access from close by anchorages that offered dingy docks:

• Mill Creek – Jacey Vineyards
• Wicomoco Creek – Bordeleau Winery
• Kent Island – Cascia Winery

There were others too, but their opening hours didn’t align with our timing.

Local Ice Cream Stops 

The Chesapeake Bay seems to have an abundance of locally made ice cream, and we did our best to sample as many as we could.

Here are towns where you can find locally made delights:

• Urbanna
• Pokomoke City
• Reedville (brought in from Richmond)
• Salisbury
• Leonardtown
• DC (x3?)
• Occoquan
• St Michaels (x2)
• Oxford (The Best!!!)
• Chestertown
• Annapolis (x3)
• Baltimore
• Havre de Grace

Maritime Museums

Almost every town we stopped in had a maritime museum – from the life cycles of crabs and oysters, to wooden boat building. Oh – and duck decoys.

Here are towns where we toured museums:

• Irving – Steamboats
• Reedville
• Deltaville 
• Crisfield
• Solomons Island
• St. Michaels (the largest?)
• Havre de Grace

Favorite Stops

We hate picking favorites, but we also wanted to give you some guidance on towns go focus on if you have a more limited block of time. So here’s our best stab at picking our top ten favorite stops of the season.

Top 10:

• Urbanna
• Colonial Beach
• Washington, DC (our favorite!)
• St. Michaels
• Oxford
• Wye Island
• Kent Island
• Annapolis
• Baltimore
• Havre de Grace

Ok, we can’t do.. here’s five more.

Runner Ups:

• Yorktown
• Mill Creek – Beautiful, and wine.
• Solomons
• Salisbury
• Mt. Vernon

Want to poke deeper into any of our segments? Here’s links to our blog posts:

• Free from the Boatyard – and Back to Cruising! Our 2025 Intentions Ahead
• Lower Chesapeake Bay River Cruising – The York and Rappahannock: Great Loop Cruising
• Continuing to Cruise the Lower Chesapeake Bay – Wineries, Friends, Weather Windows and Crossing to the Eastern Shore
• Cruising the Lower Eastern Shore of the Chesapeake Bay – Crisfield, Pocomoke City, Onancock & Salisbury
• Potomac River Cruising Adventures to Washington, DC – Great Loop Side Trip
• 40 Days Docked in Downtown Washington, DC – Museums & Monuments Galore!
• Returning Down the Potomac River and Back to the Chesapeake Bay – Great Loop Side Trip
• Choptank River Adventures – Upper Eastern Chesapeake Bay: Great Loop Cruising
• Eastern Bay & Chester River – Upper Chesapeake Bay Great Loop Cruising
• Annapolis, Baltimore and More – Wrapping Up our 2025 Chesapeake Bay Cruising Adventures!

Final Thoughts

At the end of the season, we asked ourselves if 6 months was too much?

And we both agree, if we had it to do over again we’d likely compress it down to 3-4 months, but still enjoy extended stops in DC and Baltimore.

After all, there’s only so many maritime museums one can visit.

And that’s a wrap of our 2025 cruising season! Y-Not is now safely blocked on land, wrapped and winterized – and we’re back to van life for a few months.