Friday: Check In and Set the Scene

Arrival & Welcome Cocktail at Purser's Pub

Start the weekend strong — and ease into full vacation mode — with a welcome drink at Purser's Pub, the Inn's cozy bar known for its rare whiskeys, bourbons, and top-tier small plates like Maryland Blue Crab Dip and Saint Michaels oysters. Feeling adventurous à la Jeremy? Order the bar's aptly named favorite, "The Wedding Crasher" — a bold mix of butterfly pea flower-infused tequila, St. Germain, and cardamom-black pepper bitters. Time your visit just before dusk to catch golden hour, and if you can, snag a courtyard seat by the fire pit to kick things off in true party-crasher fashion. It's exactly the kind of spot where Jeremy would post up for hours, charming the whole room — until, of course, he made things weird.

Dinner at Stars

Tuck into an elegant meal at Stars, a riverside gem where fresh-caught fish takes center stage and the serene setting feels like your own private oasis. While the entire menu impresses, the standout is the Miles River Crab Cake — served with local spring vegetables, trout roe, and Yukon pommes. And while Sack may have been the antagonist in the 2005 flick, he wasn't wrong about one thing: "Crab cakes and football — that's what Maryland does."

Saturday: Scene-Stealing Adventures by Land and Water

Morning Bike Ride

Channel the energy of that unforgettable Wedding Crashers scene — yes, the one where John and Claire ride bikes and fall (a little) for each other…literally. Borrow one of the resort's cruisers for a breezy morning ride into the charming town of Saint Michaels, where waterfront views and quaint streets set the tone. The only difference? You probably won't wipe out. Stop for coffee at Blue Heron Coffee, a local favorite known for its smooth brews — don't miss the house-made Madagascar vanilla simple syrup — and creative baked treats like Earl Grey tea crème donuts.

Midday Spa Interlude

Post-sailing, unwind with a restorative treatment at the Inn's tranquil spa — the ultimate "reset button" for your rom-com-inspired weekend. The menu features a thoughtful mix of massages, facials, and body therapies, many of which incorporate herbs and botanicals grown on-site or sourced locally. Before or after your service, take full advantage of spa amenities like the steam room or the resort’s infinity swimming pool. After all that activity, a massage is in order — no dramatic fainting required (we're looking at you, Jeremy).

Sailing on the Chesapeake

Take full advantage of the waterfront setting with a private sailing experience or group charter aboard one of the Inn's classic vessels. Cruise the Chesapeake in style on the historic Stanley Norman Skipjack, a traditional oyster dredging boat that offers a uniquely local perspective. Group sails are ideal for a celebratory crew, while private sunset charters bring the romance. Want to take the helm yourself? Sign up for a session at the Inn's sailing academy — so you don't end up like John, totally unprepared when the Secretary of the Treasury (or insert-your-intimidating-authority-figure-here) hands you the wheel.

Lawn Games

If you've still got energy to burn, head outdoors for a friendly game of croquet or bocce — just remember, this isn't tackle football with Sack. No one's here to prove a point.

Saturday Evening: A Toast to the Pointe

Sunset Cocktails and Golden Hour at The Pointe

Assuming there's no wedding underway to crash (see what we did there?), grab a drink and stroll across the sprawling Pointe Lawn — instantly recognizable as the site of the Cleary wedding reception. It's where John and Claire first wandered off from the crowd, trading playful banter and sharing a quiet moment by the water. Recreate the magic of that early spark, then sink into an Adirondack chair and watch the sun set over the river — no awkward family dynamics required.

Private Dinner or Intimate Group Gathering

Indulge in the ultimate Wedding Crashers-worthy finale: a private dinner with your special someone or an intimate gathering with your closest crew. The property features two pristine private waterside dining houses —The Boathouse and The Lighthouse — where guests can enjoy a chef-curated five-course meal paired with exceptional wines, or a few celebratory glasses of Champagne, in true Cleary wedding fashion.

Sunday: Easy Like Sunday Morning

Breakfast at Stars

After a restful night's sleep and a leisurely morning in bed, sit down for a decadent breakfast at Stars. Choose a table inside the light-filled dining room, where windows overlook the peaceful Miles River, or head to the shaded terrace for coffee and tranquil waterfront views. The menu features elevated takes on breakfast favorites — think lemon-blueberry waffles, crab omelets, and smoked salmon sandwiches. And yes, there are muffins — the kind Jeremy could actually enjoy, minus the drama. Wash it all down with a glass of Veuve Clicquot, a mimosa, or a Belvedere Bloody Mary — or keep it simple with a latte or fresh-pressed juice.

Farewell Kayaking

Before heading home, enjoy a serene kayak ride along the clear, calm waters of the Miles River. As you paddle at your own pace, take a few moments to bask in the peaceful surroundings and breathe in the crisp Chesapeake air. Think of it as your Wedding Crashers send-off: no speeding convertible, but just as sweet, especially with your nearest and dearest by your side. It's the perfect mellow goodbye — floating along like the credits are rolling.

The Bottom Line

You don't need a wedding to crash to experience the charm of the Inn at Perry Cabin. Whether planning a romantic retreat or gathering your favorite plus-ones, this is how you do a summer weekend in style. Book now — no RSVP required.