A Day on the Bay: Tilghman Island, St. Michaels, and Sailing on the Selina II

What started out as a romantic day on the Bay for the hubby and I turned into a day trip for the entire family the following week — that’s because there was plenty to do for just the two of us, and plenty for the boys to enjoy as well.

The plan for the romantic date: Drive to Tilghman Island, MD, look around the island, then find a nice place and have lunch. From there, drive the few miles to St Michael’s, meander around the town a bit and get ice cream cones for dessert, then go sailing on the Selina II with Captain Iris and her first mate, Frank. And that’s pretty much how it went.

Tilghman Island has been an island of many names. According to wikipedia history of the island, the island was known in Maryland’s land records as the Great Choptank Island, but then it took on the names of a succession of its owners. When granted to Seth Foster in 1659, it became known as Foster’s Island. In 1752, it came to the last family to own it, the Tilghman’s. They owned it for more than a century, until the mid-19th century, when James Seth purchased the island and began selling parcels to local farmers and oystermen in the area. Their name stuck.

Boat-building and blacksmithing, as well as fishing, oyster-dredging, and farming were the primary industries of the island, for the next century. Oyster-shucking and canning companies started in the 1890s, and at about the same time, the island’s guest houses began filling with Baltimore families seeking an escape from the city heat. Although the seafood industry is now much diminished and the shucking houses and processing plants are being replaced by upscale waterfront housing, it’s still an interesting place to visit — out at the Bay at the end of a long peninsula.

You can still see the “authentic” Tilghman Island, the island of a working skipjack fleet and of the watermen and their families that inhabited the island. The views are lovely, and it’s worth driving down some of the roads to see the different aspects the island offers. The day we were there, the birds played a joke on us. We spotted a brown, largish bird with a white head — and I was excited! A bald eagle! I took easily a hundred photos of her on her nest, with her three chicks. But no — it was an osprey, and had I known my birds better, I would have recognized the white body and the black mask over its eyes as dead give-aways: these are no bald eagles. Still, ospreys are amazing and gorgeous in their own right!

Tilghman Island is separated from the mainland by Knapps Narrows, but is easily accessed by a drawbridge. In fact, that’s also a pretty nice place to have lunch. There are two restaurants there, and for no particular reason we chose The Bridge Restaurant, which offered a pleasant view of the drawbridge and the boats traveling through the narrows, had a menu that featured both fish and burgers, and was tasty. From our table inside in the air-conditioning, we enjoyed watching the folks on the boats as well as various birds, from standard seagulls to ospreys to my favorite bird of all, the great blue heron.

After lunch we traveled the 22 miles back up Rt 33 to St. Michael’s. St Michael’s history is not dissimilar to Tilghman’s — its main industry was shipbuilding until just after the War of 1812 (which it had a role in), then the seafood industry became predominate, as well as offering hospitality to Baltimore elite seeking shelter from Maryland’s hot and humid summers. In fact, next week (10-11 August) the “town that fooled the British” is celebrating the bicentennial of the Battle of St Michael’s with a town-wide celebration, including a parade, a Navy band brass quintet and other live music, 1812 re-enactors, and more. So how did St. Michaels fool the British? An important shipbuilding site, the town was a logical place for British attack. The town’s residents, forewarned that the Brits were positioned on the waters to attack with cannon fire, hoisted lanterns into the trees above the city. This “blackout” fooled the British into overshooting the town’s houses and shipyards, thus saving the town.

Our plan for St Michaels was simple and relaxed: walk along the main thoroughfare, browse among the various boutiques, and find ice-cream. Had it been a bit cooler, we might have been more ambitious, and rented bicycles or even kayaks (there are several places that rent both — TriCycle & Run and Peddle & Paddle, among others) to explore the harbor with. But the day we chose for our romantic date was a cool 95 very humid degrees, with very little breeze to temper the heat. Walking was about all we wanted to do. We found Justine’s Old-Fashioned Ice Cream Parlor, and it looked both quaint and busy (busy being a good sign). Although we didn’t try anything on the “wall of shakes,” the ice-cream and service were good, and worth stopping by. There’s plenty of shade along the streets to walk in, and when it got too hot, there were a variety of shops, from antiques to art shops to dip into to cool down while browsing. If you get a chance, visit the Chesapeake Bay Maritime Museum, as well, to learn more about the local history and heritage, ecology and culture of the Chesapeake Bay. You can easily spend a few hours at the museum, touring the boatyard and exploring the various exhibits.

Several different bay tours and sailing charters sail out of St Michaels, including a tour of Chesapeake Lighthouses (future blog, I’m thinking), excursions on one of the few remaining skipjacks, and various yacht charters, but one stood out: the Selina II, a 2-hour excursion on an historic 1926 sail boat still sailed by the grand-daughter of its original owners. Not only was the boat gorgeous, but each charter only takes six people, so a more intimate setting and no crowds.

No captain, no matter how awesome, can guarantee wind to sail by, and so it happened that the first time we went on the Selina II, there wasn’t enough wind to merit hoisting the sails. But Captain Iris didn’t let that daunt her nor ruin the afternoon. We motored around the Miles River, touring the coastline and seeing the marvelous estates and enjoying the stories she knows about the families that own them. We enjoyed it so much that we decided this was something worth coming back again for, but this time with the kids. With marvelous weather and a blog in mind, we came back the following week, and this time were lucky. Not only was the day at least 10 degrees cooler, but there were fair winds as well. Captain Iris admitted that no two trips are the same — on sailing days, she goes where the wind takes her, and the conversation goes likewise. Extremely knowledgeable about the Bay and its history and culture, Captain Iris engaged the boys on their level, making the cruise enjoyable for them, and allowing the older one to help raise the sail (there’s probably a technical sailing term for that) and both to steer the boat for great lengths of time. On the way home, both boys requested a return trip next year.

The Selina II also offers sunset cruises, dinner cruises catered by local chefs, and wine-tasting cruises, during which Captain Iris offers samples of her current favorites from Spain, Argentina and Italy. Although not a sommelier, she knows much about wines, probably more than most, and when asked about the wine-tasting cruise, began rattling off far more than this neophyte wine-drinker (see my earlier blog) could hope to understand. (Yes, I do plan on returning for a wine-tasting cruise!)

If you’re not within day trip distance, there’s enough to do to keep busy for two days, and there are several B&Bs in St Michaels, and at least one B&B on Tilghman Island. Did I mention the local winery? (That’ll be the subject of a future blog!)

If you’re going in the summer, plan ahead a little. Bring sunscreen and hats, and wear light-colored clothing, because you’ll be out in the sun quite a bit. If you’re going on a sailboat, wear sensible shoes. If you’re staying overnight and planning on walking and exploring the area at dawn or dusk, bug spray wouldn’t go to waste.

Getting There: I recommend visiting the websites listed below. The St Michaels website offers detailed directions from several points of departure, or you could punch in the address of the Chesapeake Bay Maritime Museum into your GPS: 213 N. Talbot Street, St Michaels, MD 21663. To get to Tilghman Island, just keep going down Rt 33 through St Michaels until you come to the Knapps Narrows Drawbridge. Head over that, and start exploring!

Hours: Depends on what you want to do.

Dogs: If you’re there for a day and not planning on going into the museum or taking a sailboat ride, bring them. Many businesses provided water for dogs, and there were many families walking with their pooches along the streets in St Michaels.

Eats: Restaurants in Tilghman Island and in St Michaels offer a variety of places to eat, that run the gamut from the very nice and dressy and equally pricey to less expensive and more family oriented but no less tasty.

Websites: http://www.tilghmanisland.com/ and http://stmichaelsmd.org/
Selina II Sailboat Charter: http://www.sailselina.com/
Justine’s Ice Cream Parlor: http://justinesicecreamparlor.com/
Chesapeake Bay Maritime Museum: http://www.cbmm.org/

Updated May 2018.

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One Reply to “A Day on the Bay: Tilghman Island, St. Michaels, and Sailing on the Selina II”

  1. Thanks for your post and visit! Dogs are always allowed on the Chesapeake Bay Maritime Museum's campus…18 acres of Miles River waterfront. Our indoor exhibit buildings are excluded (we have twelve exhibit buildings in total). Plenty of water bowls and pick up bags throughout campus. Thanks again

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