Annapolis, Baltimore and More – Wrapping Up our 2025 Chesapeake Bay Cruising Adventures!

After Labor Day weekend was over (affectionally also known as ‘Nomad Liberation Day’) – we left the Chester River, re-entering the Chesapeake Bay.

After a few weeks of poking around quaint small towns on the Eastern Shore of the upper bay, we decided we were ready for some bigger city life. And we had two big cities ahead of us – Annapolis and Baltimore!

We knew each would be longer stays, and we had just about two months left remaining in the cruising season before we’d need to store Y-Not for the winter.

These final tales are a wrap of our 2025 cruising season, and take us from September 2 to October 24, 2025.

As always, here’s our video version if you prefer to follow along that way:

Stop 1: Spa Creek Mooring – Annapolis, MD

We back-tracked a bit to Annapolis in some comfortable if not choppy conditions. We crossed under the Bay Bridge, and entered the Severn River to the city run mooring field on Spa Creek.

We took a first come first serve ball in the ‘Front Forty’ right off the Naval Academy and downtown. At $35/night, they’re a bargain for the location – and even better with their weekly rate which gives one night free.

We enjoyed easy access to Annapolis and Eastport to explore around.

We had US Naval Academy right off our bow, waking up every morning to Reveille. The campus is open during daylight hours to the public (with a security check), which was marvelous for runs and strolls. We took a tour of the chapel and building with a docent, and spent an afternoon at the museum. It was fascinating, particularly the ship model collection on the second floor – these intricate scale models of actual warships built from the 1650s to 1840s.

A Navy game was scheduled while we were in town, so got some last minutes tickets.

We also toured the state house and local museum, took in an Oscar Wilde play at the Colonial Players theater, indulged in a lot of dining out – favorites included Joss Sushi, Potato Valley, Vida Taco Bar, Boatyard Grille and Forward Brewery. And there are multiple locally made ice cream shops – more than we could get to! But we enjoyed them all, with Annapolis Ice Cream earning its top nationwide rating.

We also hit the B&A rail trail for a long run.

We also had the pleasure of meeting up with AGLCA Harbor Hosts Amy & Scott over sushi and lingering conversations!

With some high winds abound from the south, we ended up staying a total of 9-nights on a mooring ball in Annapolis.

It got a bit rolly at time as swells came in off the bay, but it was mostly tolerable.

We managed to only need to run the generator a total of 6.5 hours (and that was mostly to allow the ice maker to catch up, and run a load of laundry). And ended up hauling in about 70-80 gallons of fresh water by watertainers, and utilized the pump out boat before leaving for just $5.

A very pleasant and enjoyable stay. Thanks Annapolis for providing such an affordable & convenient option to stay right downtown!

Stop 2: Dobbins Island Anchorage – Gibson Island, MD

After a stop in Annapolis, we spotted a few opportunities to anchor out in various rivers & creeks before heading to our next extended stop in Baltimore.

First up, turning up Magothy River – where we spent two evenings anchored off of Dobbins Island.

The island itself is privately owned, with a newly built home on it. And it’s for sale, apparently.

This is quite the destination for beaching boats upon for time on a sandy beach and sometimes sandbar the emerges – both of which have been deemed public access.

Our first night was tranquil and shared with just one other boat. We enjoyed a lovely sunset!

The next, it had a bit more activity – but nothing too disruptive at all. But can see why the private island is not so private feeling. I think we’ll skip making an offer on it

Stop 3: Horse Farm Anchorage – Gibson Island, MD

On a whim after two nights behind Dobbins Island along Magothy River, we decided to check out an anchorage referred to as ‘Horse Farm’ just under a mile away.

We were looking forward to a day watching horses on the shore.

When we arrived, we noticed what looked like a race starting corral on the shore. A quick search revealed that in the morning this little cove would be the location of the ‘Swim Across America’ charity swim with over 400 swimmers covering a distance of 1 or 3 miles.

We intuited that provided we were allowed to stay, this would mean there would be no leaving the anchorage until it was done.

And sure enough, moments later a kind Maryland Marine Police officer puttered over to let us know if we stayed, we couldn’t leave until after noon. But we were welcome to stay and cheer them on! Heck YES – we’re in!

We got up early, and watched all morning long. It was fascinating to watch these endurance athletes lap us. In jelly fish, no less (we ourselves had gotten stung just the day before on our own swim – just a slight tickle).

Exhilarating to the end. 1 and 3 miles is no joke.

And we cheered watching the last of the bunch come ashore. Being lapped by 400 swimmers!! WOW!

It was inspirational, especially considering we’ve been toying with the idea of building up to our own first triathlon experience by adding in swimming to our repertoire of long distance cycling and running.

Stop 4: Rock Creek Anchorage – Riviera Beach, MD

After 3 lovely days at anchor along Magothy River with no shore access – it was Sunday. Which is run day.

And for that, we need land.

We do keep active with paddle boarding, swimming, yoga, weights and our onboard stationary bike. We manage to continue to close all our Apple Fitness rings every single day (over 1600 days in a row now!).

But we need to walk and run too! We need land to explore upon. One reason open water world expedition cruising has no appeal for us (except perhaps on a large cruise ship).

Chris spotted Fort Smallwood park off of Rock Creek where we could anchor and get ashore to a 1.5 mile paved trail. So we anchored at the mouth of the creek off of the Patapsco River and got a couple laps in.

We then moved a little further in for greater protection and heard live big band music coming from Mike’s Crabshack. Having cooked onboard for as long, we decided it was time to eat ashore too.

We enjoyed a lovely rockfish meal (we’ve become quite the fans of rockfish – sorry, not into the crabs) and music before a stunning sunset!

Stop 5: Henderson’s Wharf Marina – Baltimore, MD

And now, our next extended stay. We transited up the Pataspo River, through the remains of the Frances Scott Key Bridge and past Fort McHenry – and arrived to our 5-week reservation at Henderson’s Wharf Marina in historic Fells Point.

We selected this location after several recommendations, and liked their upfront simple and flexible pricing ($10/ft for the first week, then just $5/ft for each additional week). Electricity, taxes and parking included. In slip pump out was contracted with Harbor Pumpout, who were simply fabulous!

The free parking and close proximity to an Amtrak Station meant we took a day to head back to Norfolk, and drove our van Blooper up from where we had stored her at Atlantic Yacht Basin for the summer. Giving us local transportation and ability to get her caught up on routine maintenance for the van season ahead.

And since we were considering storing in water here for winter, the marina offered an easy switch to seasonal pricing if that’s what we decided.

The marina itself is self-described as minimal. Which is just our style. Well maintained floating docks with super wide slips was just perfect for our stay. They do have bath & laundry facilities, and are quite accommodating to the daily flood of packages.

But it’s all about the location – right smack dab at the point of Fells Point. Easy access to ample dining, bars and live music (not that we very often partake). And right along the Inner Harbor Promenade, which gave us great running access.

We found ourselves leaving the Fell’s Point area quite often to explore further afield – so perhaps a different location more inner harbor might have been better for us – but certainly more expensive and less flexible (no parking). And heck, we need walking points.

It was a jam packed 5-weeks.

• We caught several shows: Ziggy Marley & Cake at Pier 6, Water for Elephants at the Hippodrome, Baltimore Symphony (accompanying a showing of Jurassic Park) and Hair at Vagabond Players.
• We did several museum tours: Museum of Industry, Public Works, Fort McHenry, Historic Ships of Baltimore and Walters Art Museum, Baltimore Zoo and the National Aquarium.
• We were in town for Trawler Fest, Fells Point Fun Fest (a weekend of vendors and live music right off our dock), the Baltimore Runfest (Chris ran another marathon – I just did a half around the inner harbor) and The Great Chesapeake Bay Schooner Race.

We left with our hearts full of memories and adventures. Baltimore took some time to get our groove on with, it’s a bit gritty in places. And wasn’t always our vibe. But we found it, and once we did – we loved it.

We ultimately decided we’d be more comfortable having Y-Not hauled out for winter storage, instead of in water storage at a marina. So we made arrangements in the Upper Chesapeake and headed out for some last adventures of the season.

Stop 6: Turner Creek Entrance Anchorage – Glencoe, MD

After our extended stay in Baltimore, we had a few days to play around with before we needed to start winter storage preps.

So we set the navigation software to the Sassafras River, moving on up to the upper Upper Chesapeake, and anchored nearby the nature preserve.

The fall colors are starting to illuminate our views, and it’s was a lovely way to decompress after some city life.

Aside from getting ashore for a chilly hike, we stayed aboard and enjoyed being dive bombed by bald eagles.

Stop 7: Havre de Grace Anchorage – Havre de Grace, MD

One last stop of the cruising season before we store for winter – and of course we chose Havre de Grace, MD.

We had countless recommendations for this cute little town, and they are quite deserved.

While it’s rather chilly, we opted to anchor just offshore on the river. The conditions were otherwise perfect and we only needed to run the generator a couple hours a day to keep up with running the heat pumps.

We got to climb the lighthouse, tour the lightkeeper house, tour the Lock House, the mural park and hike/run the lovely trail that leads from there. There’s of course other museums, but we’re kinda museumed out.

There were also not one, but two, small festivals going on with vendors in town we checked out. We visited a brewery, ice cream and found GF Italian food at La Cucina.

All and all.. a fabulous way to cap off a wonderful season of cruising the Chesapeake Bay!

Real Time Update

After a busy week shuffling things from Y-Not to Blooper and getting everything ready for winter storage – Y-Not is hauled out and winterized (and soon to be wrapped too).

And we’re back to van life!

We’re already in Florida and will soon be catching up with friends & family for the month ahead, and then we intend to head west to Arizona to spend some time with Zephyr at our lot in Benson, AZ.

We’ll have one final post wrapping up our Chesapeake Bay Cruising season – and then it’ll be van posts for the months ahead!