Lighthouses, Shipwrecks, and the Charming Sea Port of St. Michaels, MD

After a quick overnight stop in Kilmarnock, VA, we continued on northward in the Chesapeake Bay. We had a nice leisurely cruise that Easter Sunday and made a point to zigzag a little in order to get up close to some of the gorgeous lighthouses dotted throughout the bay. The Chesapeake has many offshore, standalone lighthouses marking shoals and there is something about them that is just hauntingly beautiful.

Many of them are abandoned, but some, such as the Thomas Point Shoal Lighthouse near Annapolis, still function in all their glory! This is probably my favorite lighthouse in all the Chesapeake, and is the last of its kind still standing.

Many of the screw pile cottage-style lighthouses like this one have since been moved to museums on land, such as the ones in Solomons, MD and St. Michaels, MD. The Thomas Point Shoal Lighthouse was built in 1875 and they even offer boat trips out to tour the building!

There’s also another notable point of interest when cruising the Chesapeake. Just off the coast of Smith Island is the shipwreck of the American Mariner, that the Navy still uses as an active live fire target ship! It is still referred to as Hannibal, which is what the original target ship was called. It always makes for such cool photos in the middle of the bay and is a site to see for sure!

American Mariner or "Hannibal" as it is still called after the first target ship

We had originally planned on going to Annapolis that night, but midway through our day, we decided to shift course and cross the bay to instead visit St. Michaels, MD. We had always heard that this was a very charming little town, but had not managed to stop there yet, so we decided that this was finally the day we would! We arrived just before sunset, got anchored and settled in for the night. We could tell the town was charming, even from first glance!

The next day after work, we dinghied up to the town and found a free dinghy dock near the museum next to the Crab Claw restaurant.

We were in dire need of groceries at this point, so we decided to take a quick walk into town and see what we could find nearby for provisions. There's a cute little footbridge that we had to walk over to get into town. It was kind of like something you'd see on Fear Factor walking over it because there were dozens of huge carpenter bees swarming all around it as if to be guarding entry and if we wanted to get groceries, we had to walk across it! Halfway across, a duck had made a nest in one of the flower boxes and someone was so kind as to build a wire encasement to help protect her and her babies from predators. How cute!

The downtown area is very quaint and reminded us of a mix between Mystic, CT with its seaport museum and red roofs, and Martha’s Vineyard. There were cobblestone sidewalks, adorable colonial houses with a dollhouse vibe similar to Oak Bluffs in Martha’s Vineyard, although a bit dialed down from that.

There were cute little eclectic shops and eateries housed in old homes rather than traditional storefronts, and it just exuded charm.

We found a cute little shop called Gourmet By The Bay that was much closer to the boat than the actual grocery store in town, so we decided that we’d just get enough for a couple of days and call it good. At first glance, this shop doesn't look like much and inside looks to be just wine and snacks, but if you venture a little further inside, there is a full meat case in the back stocked with fresh cuts of steak, ground beef, bacon, chicken, etc. They also have coolers with fresh fruits and veggies and prepared gourmet meals to go. We were thrilled to leave with eggs, oat milk, fruits, veggies, flank steak, bacon, apples, oranges, asparagus, romaine lettuce, artisan bread and crackers, and I bought a beautiful salad that was full of color along with a homemade blueberry vinaigrette that was absolutely delicious! Sometimes, it is the small things that make us excited in this lifestyle!

The next day after work, we took Bella back to shore with us and went for a nice long walk around town, sightseeing and stretching our legs for a bit!

There’s a Christmas shop in town and we collect Christmas ornaments from each new place we visit, so we made sure to pop in a grab an addition to our collection! They have an entire room dedicated to nautical Christmas décor in this shop, so we easily found one that aptly represented the town of St. Michaels, depicting the lighthouse from the museum that is a prominent feature on the shoreline of this port.

We’ve been trying to save money lately, so we didn’t indulge in any of the restaurants in town, but there are lots of great options and Foxy’s Marina Grill and Bar looks like it is a ton of fun in the summer months. We found that we are visiting this area a bit ahead of schedule for the season, and a lot of stuff is either just opening or not quite open yet. It was nice to experience the town in spring all to ourselves though!

The maritime museum in town looked very neat and you can even go inside the lighthouse there that used to be out in the Chesapeake. The entrance to the museum is an old drawbridge that makes for quite a unique gate to the property!

Overall, we’d highly recommend a stop to this quaint little town on the Delmarva Peninsula and we will definitely be back!