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Skipjack Rebecca T. Ruark

4.7 (3 reviews)
Closed 11:00 am - 1:00 pm, 6:00 PM - 8:00 PM

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St. Michaels Sailing Charters - Our guide

St. Michaels Sailing Charters

4.9(125 reviews)
8.2 mi

We first sailed with Captain Iris 10 years ago with our children. This year we chose to return for…read morea Monday night for a moonlight cruise. Captain Matt and first mate Mike were top notch. Informative and attentive. Weather was perfect in our eyes, clear with almost full moon. Wasn't much wind, but the Salina II sailed beautifully. Plenty of beverages, great history of a beautiful vessel, and a photograph worthy sunset. Thank you so much for a wonderful night!

I needed to get away, and saw this excursion via Eric Oranges' wine happenings. Wine tasting and…read moresailing! Right up my alley. I booked and made reservation at Harbour Inn- I love that I stayed at before. Approached by a spry lady, I was asked my name - she turned out to be the granddaughter of this 1926 New England Charter, Capt Iris. Very personable and knowledgable as she pointed out things along St Michaels banks e.g., The Perry Inn and the focal point filming of The wedding crashers. The name Selina, itself had family virtue and significance-pronounced different ways, the one I remember is as in Selena Gomez. We were also quizzed on how many tons the vessel weighed. My guess way low-16 tons!!. We marveled at the woodwork and upkeep of the ship and hours to maintain- not to mention gas cost. We were offered our choice of beverage- I had a tasty Chardonnay, although I'm not sure the brand. The first mate. Was agile at that point coasting in a nice spot to put up the sail, beautiful as the sky was starting to cast its evening glow with the sunset. It was truly relaxing as we made small talk about catfish and enjoyed the ambiance. I then had a second Pinot Noir however the water being a little choppy declined a third- we were Rockin ! a little with wind picking up. It was a very enjoyable outing and I would do it again in a heartbeat! Next time I want to be at the helm lol, if only for a photo shot. Speaking of photos...a picture paints a thousand words...btw the name means 'moonlight'

Photos
St. Michaels Sailing Charters - Tour the St. Michaels waterfront and harbor in the Selina II, a classical and beautiful sailboat

Tour the St. Michaels waterfront and harbor in the Selina II, a classical and beautiful sailboat

St. Michaels Sailing Charters - The group on board

The group on board

St. Michaels Sailing Charters - So beautiful

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So beautiful

Tilghman Island - Work boat racing ...Tilghman on Chesapeake Yacht Club

Tilghman Island

3.5(2 reviews)
0.6 mi

Once a year its "Tilghmans Island Day" at the firehouse and Kronsberg Park with oysters, crabs, and…read moreshrimp benefitting the Tilghmans volunteer fire department. If you truly love seafood this is the festival for you. This is the day of celebrating the Chesapeake Bay waterman and seafood with work boat racing, anchor throwing, crab eating contests, oyster shucking, and boat docking. Tilghman's island is only 3 miles long and is located about 11 miles from St. Michaels, and is an old fishing village. If you have never been to Tilghmans Island its cool to see the "W" houses which is a unique architectural style to the island. The Knapp's Narrows drawbridge is the busiest drawbridge in the nation and averages over 10 k openings per year. If you have never seen a skipjack Tilghman Island has the oldest working skipjack on the Chesapeake Bay built in 1886 over at Dogwood Harbor. The music was great this year with Birddog and the Road Kings in the park and picking/eating crabs. The Tilghman on the Chesapeake Yacht club was a beautiful place to watch the work boat racing and most breathtaking view of the Choptank River and Harris Creek. FYI 1 dozen crabs were $35.00,

one of the many small islands that sits at the edge of chesapeake bay. we came to watch the sunset…read moreand that we saw, as well as many old school farm houses, farm animals, and even an old school gas station. i think the gas station was the highlight of my short trip here since i'd never seen an old school gas station. there were one or two restaurants here, but they appeared pretty quiet, even for a sunday evening. generally speaking, pretty barren, at least in the wintertime. will have to try coming back in the summertime to see if things liven up here.

Photos
Tilghman Island - Oysters with horseradish and crackers ...the normal accompaniments.

Oysters with horseradish and crackers ...the normal accompaniments.

Tilghman Island
Tilghman Island - A small fishing village unless you come for Tilghman Island Day

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A small fishing village unless you come for Tilghman Island Day

Skipjack Rebecca T. Ruark - boating - Updated May 2026

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