Middle Chesapeake Sailing: Annapolis to Solomon’s


Last Updated on November 29, 2021 by Amy

We cruised the southern Chesapeake and then the upper Chesapeake, until finally, we made it to the middle! Despite our circuitous route, we explored more of this region than any other and had a blast doing it. It feels like this part of the Chesapeake is more concentrated. The eastern shore isn’t so far away from the western shore, like it is down south, and it is full of nooks and crannies to drop the hook.

The middle Chesapeake region, at least our definition of it, is from the Potomac River to the Chesapeake Bay Bridge.


We left Rock Hall on September 4th and sailed south. Since the bay gets a lot of southern winds, we thought we’d take the opportunity of dead air to get south in two hops and then work our way back up.

Our first hop south brought us to the West River in Maryland and a tiny town called Galesville. We anchored out in the fork of the river and met some new friends, Tim and family, at Pirate’s Cove Restaurant.

Beyond that, there’s not much to do except paddle around or go for a walk. Thankfully there was a lovely town dock we could use to access shore and a small convenience store to buy basics.

Sunset in West River.

Solomon’s Island

We departed Galesville on the 10th for the second leg to Solomon’s Island. When we passed through on our way up the bay, we dropped the hook in Mill Creek away from the crowds (and on the weekend, Solomon’s Island is very crowded). This time, we picked up a mooring ball with Safe Harbor Zahnisers in order to use their facilities.

Solomon’s Island is a lovely neighborhood and a cute town. We walked often along the boardwalk and around the neighborhood.

Friends told us that the museum here was the best one on the Chesapeake and it was pretty dang good!

Starry Horizons from the Calvert Museum Lighthouse
A sailboat in the Calvert Maritime Museum
Sunset from the boardwalk.

Little Choptank

On the 14th we left the big city (ha!) and moved to somewhere more remote: Little Choptank River. We anchored off Casson Point, where we were all by ourselves. The houses here are older and widely spaced, a much more rural area.

We had a particularly windy day so we flew our kite for the first time! When the wind died, we paddleboarded past the farms and houses. One evening I paddled around Casson Point to join a few local boaters watching the sun set over the mainland.

And everyday we had a bald eagle sitting in a dead tree right off our bow, chatting away.

Sunset in Little Choptank River.
Sunset from the paddleboard.


On the 20th we left for Oxford. This town was recommended by my uncle, who’d left his boat there for the winter years ago. We were expecting some nasty weather, so we made a reservation at the Safe Harbor Oxford. We were so glad we did! We had a very rainy and windy day.

But when the weather cleared up, we went for walks around the town and had a very nice dinner out at the Robert Morris Inn. We also got an ice cream treat at Scottish Highland Creamery.

Wind and waves bring high water in Oxford.
David at the Robert Morris Inn
Pork chop and brussels sprouts at Robert Morris Inn

Dun Cove

We stayed one night in Dun Cove, just north east of Tilghman’s Island to break up the distance over two days…and also to get us out of the marina and quit spending money!


We departed Oxford on Friday the 24th and it was time to get down to business. We moved over to Annapolis, where we dropped anchor for one night out in the main bay. It was extremely rolly, since the weekend was starting and boat traffic in Annapolis is a force to be reckoned with.

After one night we crossed our fingers that a mooring ball would be available in the First Forty, and sure enough one opened up!

We got a lot done in Annapolis – a big grocery run, a trip up to New York City for a family event, caught up with old and new friends and did some shopping.

Seeing the dinner cruise ships coming and going was a blast from the past! Some of them looked so much like my old boats I did double takes.

The mooring field was still very rolly, especially on the weekends. In retrospect, I would go back further into Spa Creek or Back Creek and pick up a mooring ball there. But Annapolis has dinghy docks aplenty and a water taxi to get you further.

Sunset in Annapolis at the First Forty.
Moored off the Naval Academy
Dinner cruise ship in Annapolis.

St Michael’s – Back Door

After ten nights in Annapolis we had a party to attend, so we hightailed it down and around to San Domingo Creek, the back door to St Michaels. This was my choice, and friends were meeting us there so I crossed my fingers that I’d made the right call picking San Domingo Creek sight unseen. Thankfully it worked out perfectly!

We had a pre-boat show Helia get together. There were six of us total, five in the back creek and one in the front. The back creek was amazing; very protected and calm. Almost no boat traffic and a short trip to the dinghy dock made access to town easy. And the holding was good as we got all the boats lined up.

There’s a 1.5-mile walking trail in St Michaels that passes right by the back door dinghy dock. Saturday, during the season, is a farmer’s market in downtown St Michael’s. There are tons of cute little stores, including a few gourmet grocery stores.

With our friends we celebrated my birthday, paddleboarded, swapped boat tours, and had a potluck!

Five Helias lined up!
Birthday paddleboard!

Annapolis, Part II

After a week in the back door, we had to get a move on – back to Annapolis! It was time for the Annapolis Boat Show and we were participating in the YouTube creators booth. More about that later. We had a super-secret anchorage that was just perfect – protected and quiet, even though it was a Uber drive away from the show.

Showing off my new Women Who Sail tee shirt.
At the YouTube Creator booth.
With Frank and Mary Grace at the HH booth.

St Michaels – The Front

On October 20th, after a week of boat show madness, we moved back across the bay, but this time went to the front side of St Michaels. We anchored just outside the entrance on the north side. St Michael’s is quite different in the front. There was WAY more boat traffic coming and going from St Michael’s here.

We were here to meet my mom and uncle Phil. They’re no stranger to visiting Starry Horizons, and they me us in St Michaels (Uncle Phil drove from Plattsburgh). We had a great time checking out our favorite places.

Happy hour drinks on the lounge deck!

Leed’s Creek

Poor weather was coming and we wanted to be some place a little quieter, so we hopped across to Leed’s Creek. The entrance was shallow, but we anchored as far in as we could and were very well protected. There is a dinghy dock at the Tunis Mills Road Bridge, so we were able to walk the neighborhood.

Bird watching in the creek.
Starry Horizons facing the entrance of the creek.

St Michael’s – The Front Part II

We went back to St Michael’s for one night. Weather was rolling in and the harbor was SO empty compared to a few days before. Since there was room, we snuck into the harbor and anchored in the tiny south creek inside the harbor. Despite the cold and windy weather, we explored the Chesapeake Bay Museum and had a final dinner out with Mom and Uncle Phil!

Tucked away in St Michael’s.
Classic power boat at the Chesapeake Maritime Museum.
Big boots to fill at the Chesapeake Maritime Muesum.
The nature trail in St Michaels.

Back South

After dropping my mom and uncle off for their trips home, we immediately got underway for a one-night sail back south to Mobjack Bay in the Southern Chesapeake.

We had a great time here in the Middle Chesapeake. Annapolis and St Michael’s were big hits, and there are plenty of unique places to visit!


  1. It’s great to see you two exploring our “Watery Planet”! You both look great. I try to keep up with your adventures, although, I do not always send comments. In Arizona, we can only dream of a vast ‘sea’ let alone water. If you are both ever in our neck of the woods, give me a call. We have a spare bedroom. I still remember working for your Dad and Mom on the dinner yacht with Cheryl Linville. Good to see a picture of your Mom, Lisa. Haven’t hooked up with her in several years.
    Sandy and Jerry in Sun City AZ

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.