DAY 1: MONDAY, OCTOBER 27
11:00 AM - 1:30 PM | Guest Arrivals & Welcome Reception | The Cove
Grab a drink from the specialty Crush Bar and enjoy a bite from our food stations. Mingle and relax before we set sail aboard the Catherine Marie for an unforgettable afternoon on the water.
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2:00 PM - 4:00 PM | Private Boat Cruise | Catherine Marie
Set sail from the Chesapeake Bay Maritime Museum for a relaxing afternoon on the water. Enjoy an open bar and a curated cheese & charcuterie spread as you take in the scenic views of Maryland’s Eastern Shore from the deck of The Catherine Marie.
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4:00 PM | Hotel Check-in
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4:15 - 6:00 PM | Relax and Refresh
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6:00 PM - 7:00 PM | Cocktail Reception | The Pointe
Enjoy the golden hour by the water with handcrafted cocktails, passed hors d'oeuvres, elegant food displays, and an open bar. For a truly unique touch, indulge in freshly shucked oysters from the floating oyster station aboard the historic Skipjack Stanley Norman.
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7:00 PM - 9:00 PM | Dinner | The Linden Lawn
Join us for an elegant evening of dinner and drinks served on The Linden Lawn.
Dress Code: Resort chic; jackets required for men. Dinner will be held in a climate-controlled tent; however, please dress appropriately for the weather, as the cocktail reception will take place outdoors. Also, the cocktail reception and dinner are set on grass, we recommend choosing footwear accordingly.
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9:00 PM - 11:00 PM | Late Night Social | Purser's Pub + STARS Terrace & Fire Pits
Wind down the evening with drinks around the fire pits. Football fans, you’re in luck—Monday Night Football featuring the Commanders vs. Seahawks will be playing, and we’ll be serving up some late-night bites to keep you fueled through the fourth quarter.
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DAY 2: TUESDAY, OCTOBER 28
7:30 AM - 10:30 AM | Breakfast | STARS
Start your day off right with breakfast and an in-house barista station. Feeling energized? Head down to The Pointe and warm up your swing with a few golf shots toward the floating target on the river. Don’t worry—our eco-friendly golf balls are designed to dissolve into fish-friendly nutrients, making your morning activity a win for you and the environment.
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8:00 AM - 1:00 PM | Activities & Lunch
Activity Option 1 | Golf: Nestled along the scenic Eastern Shore of Maryland, The Links at Perry Cabin offers a world-class golf experience on a championship course designed by legendary architect Pete Dye. Begin your day with a warm-up session on one of eight state-of-the-art HD golf simulators, then take to the course for a spirited four-person scramble tournament with a shotgun start.​
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Activity Option 2 | Spa: Immerse yourself in a unique spa experience that combines therapeutic bodywork with plant-based treatments made from herbs and aromatics locally grown and harvested on the Eastern Shore. Choose between a 45-minute massage or facial, each designed to rejuvenate the body and spirit. Arrive early to relax in the steam room and begin your journey of total relaxation in style.​
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Activity Option 3 | Sailing Lessons: Set sail on an unforgettable adventure where you and your crew can learn the basics of sailing in a private, hands-on setting. Whether you're a novice or just looking to sharpen your skills, this personalized experience offers the perfect blend of education and excitement on the Miles River.​
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Activity Option 4 | Relax or Explore: Nestled on 26 acres of lush gardens, orchards, and lawns, the Inn invites you to unwind or adventure at your own pace. Play a friendly game of croquet or bocce on the lawn, or up the energy with a match of tennis or pickleball. Prefer a workout? Head to the gym, complete with Peloton bikes. For a change of scenery, take the shuttle or bike into the heart of historic St. Michaels to stroll charming streets lined with boutiques, art galleries, and local treasures.​
11:00 AM | Hotel Check-out