So, if you've ever spent a weekend wandering around the brick sidewalks of St. Michaels, Maryland, you know the vibe. It’s all about the blue crabs, the maritime museum, and that specific smell of brackish water and old cedar. But for the last quarter-century, there’s been one very specific silhouette on the Miles River that basically defined the harbor: the Sail Selina II.
She isn't just another boat. Honestly, calling her a "boat" feels a bit like calling a vintage Porsche a "car." She is a 1926 Crosby Catboat, a 41-foot masterpiece of mahogany and brass that somehow survived a century without losing her soul. But here is the thing that’s been hitting the local grapevine lately: after 25 years of dominating the boutique charter scene in St. Michaels, Captain Iris Robertson is officially retiring.
It’s a huge deal. For many, Sail Selina II St Michaels MD was the only way to see the bay without 50 other tourists screaming in your ear.
What Made the Selina II Experience Different?
Most people who visit the Eastern Shore end up on big "head boats" or tourist ferries. They’re fine, but they’re loud. The Selina II was the opposite. Captain Iris, who is actually the granddaughter of the original owner, ran things with a "six-guest maximum" rule.
That wasn't just some marketing gimmick. It was about stability and silence. Because the boat has a massive 16-foot beam (that's the width, for the landlubbers), she doesn't tip or "heel" over like those racing sloops you see in Annapolis. You could literally sit in a plush captain’s chair with a glass of champagne and not worry about your drink sliding into the bilge.
The cruises usually broke down like this:
- The Champagne Sunset Sail: This was the heavy hitter. Two hours of watching the sky turn neon orange while the crew served up hors d'oeuvres and an open bar.
- Wine Tasting Cruises: They’d bring out three whites and three reds, usually local or boutique picks, and you’d sip your way past the lighthouse while Captain Iris told stories about her grandfather, Samuel Hird.
- Beer Tasting Sails: Basically a floating craft brewery tour featuring Maryland microbrews.
- Private Elopements: Captain Iris is actually ordained. She’s married dozens of couples right there on the deck, often with just the two of them and the wind.
The 1926 Tech (That Surprisingly Still Works)
It’s kinda wild when you look at the specs. We’re talking about 1,000 square feet of sail on a 48-foot mast. When that gaff-rigged sail catches the wind, the engine goes off, and the only thing you hear is the water lapping against the wood. It’s hauntingly quiet.
The engine itself is a piece of history—a 68hp Westerbeke. Fun fact: it’s the same type of engine they used to use in those iconic double-decker London buses. It only pushes her to about 7.5 knots, but speed was never the point. You don't get on a 1926 catboat because you’re in a rush.
The details are what get you. The polished bronze. The original wainscoting in the cabin. There’s even a ship’s bell with a rope tied by a master knotsman, containing a hidden piece of paper with a Psalm written on it for luck. Most people never notice that. They’re too busy looking at the bald eagles or the occasional porpoise that wanders into the river.
The End of an Era in St. Michaels
Captain Iris announced that 2025 was her final season. It’s bittersweet. The boat is actually staying in the family—it’s headed up to New York to be cared for by her niece—but the "Selina II" era at the Harbour Inn & Marina dock is wrapping up.
If you're worried about what happens to the dock space, don't be. The Bells, who run St. Michaels Sailing Charters, are stepping in for the 2026 season. They’ve got the Lady Patty, a 1935 ketch, and Epiphany, a modern 44-foot catamaran. They’re great boats—bigger, can hold up to 13 people—but they aren't the Selina.
There’s a specific kind of magic in a boat that was built as a "knock-off" of a Crosby Catboat because the owner wanted something "like a Crosby, but bigger." That’s the Selina II’s origin story. Samuel Hird wanted a boat that could handle the rough waters of New York’s Shelter Island but still look elegant enough for a Sunday social.
Why People Keep Coming Back
Honestly, it was the storytelling. Most captains just point at the lighthouse and tell you when it was built. Iris would tell you about the 60 hours a week she spent varnishing the mahogany or the mystery of the antique gauges on the dash that look like they came out of a Model T Ford.
It felt less like a tour and more like you were a guest on someone’s private family yacht. Which, technically, you were.
Actionable Advice for Your Next Visit
If you missed the chance to sail on the Selina II before her departure, you can still capture that same "small-town harbor" magic in St. Michaels, but you have to change your strategy.
- Book the Lady Patty for History: Since the Selina II is moving on, the Lady Patty (built in 1935) is now your go-to for that vintage wooden boat feel. She’s a ketch, meaning she has two masts, and she’s got some serious racing history behind her.
- Go Mid-Week: St. Michaels gets absolutely swamped on Saturdays. If you want that "mellow" feeling the Selina was famous for, book a Tuesday or Wednesday sail. The river is emptier, and the service is always more relaxed.
- Check the "Wind and Paddle" Packages: A lot of people don't realize you can bundle your sail with a kayak or paddleboard rental from Shore Pedal & Paddle. It’s usually a 10% discount and gives you the "full" water experience.
- Stay Waterfront: If you're coming for a romantic milestone, stay at the Wades Point Inn or the Harbour Inn. Being able to walk from your room directly to the dock is the whole point of a St. Michaels getaway.
The departure of the Selina II marks a shift in the local maritime landscape. While the harbor will still be full of white sails and expensive fiberglass, that 1926 wooden catboat was a living link to a different century.
Next Steps for Your Trip
- Check the official St. Michaels Sailing Charters website to see the 2026 schedule for the Lady Patty and Epiphany.
- Visit the Chesapeake Bay Maritime Museum while you're in town; they have a permanent exhibit on the history of catboats and the local skipjacks that defined the region.
- If you're looking for a private charter, always call ahead—the six-to-thirteen passenger boats fill up months in advance for holiday weekends like the 4th of July.