AHOY!

THE TOAST: Join us daily at 5pm to raise a glass in celebration of our nautical heritage. You’ll discover fascinating tidbits about the Inn, learn about our namesake, Commodore Oliver Hazard Perry, and the iconic battle cry “Don’t Give Up the Ship” dating back to the war of 1812.

 DINNER AT STARS OR A CASUAL EVENING AT PUB: Indulge in waterside dining at PURSER’S STARS, where a roaring fire and a glass of cabernet set the tone for an elegant evening. The menu highlights the best of the Eastern Shore, featuring locally sourced ingredients harvested at their peak—like fresh oysters in season that pair nicely with a glass of champagne or a crisp French chardonnay from the thoughtfully curated wine list. 

BREAKFAST AT STARS Wake up to a leisurely breakfast at STARS and energize for the day ahead.

WINTER AFTERNOONS Sip and Paint for a relaxing artistic escape. Gather around one of the many fireside places and challenge friends with a selection of board games or Trivia complemented with light bites and beverages. 

Perfect your swing with a private lesson at Links at Perry Cabin with our PGA Pro. Stay after and practice your new pro tips with unlimited simulator play. 

Explore the charming town of St. Michaels and peruse an array of boutiques offering post-holiday discounts. 

Weather permitting, visit the front desk to grab a cozy IPC blanket and step outside to unwind by the iconic waterfront firepits Relax in the comfort of your room, where the ambiance of your fireplace creates a peaceful retreat. Enjoy a refined bottle of wine and an assortment of culinary selections from the in-room dining menu as you unwind and take a little time to yourself.

BON VOYAGE: Start your day with a leisurely breakfast at STARS or maybe indulge in a rejuvenating morning at the SPA. Guests with a SPA treatment may enjoy a 1 PM check out. Be sure to stop by The SHOP at Inn at Perry Cabin for nautical-inspired gifts and artisanal accents to remember your visit.

 AHOY!

RELAX BY THE MILES RIVER: Settle into an Adirondack chair by the water, soak in the sunshine and live music, and order up fresh local oysters and a refreshing beverage.

DINNER AT STARS OR A CASUAL EVENING AT PUB: Indulge in waterside dining at PURSER’S STARS, where a roaring fire and a glass of cabernet set the tone for an elegant evening. The menu highlights the best of the Eastern Shore, featuring locally sourced ingredients harvested at their peak—like fresh oysters in season that pair nicely with a glass of champagne or a crisp French chardonnay from the thoughtfully curated wine list.

BREAKFAST AT STARS Wake up to a leisurely breakfast at STARS and energize for the day ahead.

 SUMMER AFTERNOONS Make the most of summer afternoons with a mix of relaxation and exploration: Partake in the popular guided walking tour of the Inn and St. Michaels, where you’ll uncover stories of the War of 1812, the town’s rich history, and how the Inn originated and grew into what it is today Lounge by the infinity pool and enjoy the sunshine, frozen beverages, and selection of salads and sandwiches at the High Tide Pool Bar.

Head to Links at Perry Cabin for a challenging round of golf or indulge in the pure bliss of self care at SPA at Perry Cabin. Explore the Chesapeake Bay via private charter and head to Annapolis aboard Five Star, a 55' Hinckley Talaria for lunch and a little shopping. Set sail aboard one of our five sailing vessels for a serene journey on the Miles River and experience the wildlife and beauty of Maryland's Eastern Shore. 

BON VOYAGE: Start your morning gazing at a peaceful sunrise from your balcony or waterside Adorondack chair then make your way to STARS for a hearty breakfast. Don’t forget to visit The SHOP for a special souvenir to remember your stay.

AHOY!

THE TOAST: Join us daily at 5pm to raise a glass in celebration of our nautical heritage. You’ll discover fascinating tidbits about the Inn, learn about our namesake, Commodore Oliver Hazard Perry, and the iconic battle cry “Don’t Give Up the Ship” dating back to the war of 1812.

DINNER AT STARS & NIGHT CAP AT PURSER’S PUB: Experience unforgettable waterside dining at STARS, where a roaring fire, festive décor, and live piano create the ultimate holiday ambiance. Afterward, enjoy a cozy nightcap in Purser’s Pub, where a selection of fine bourbons and whiskeys await.

HOLIDAYS IN ST. MICHAELS Celebrate the season in St. Michaels, where holiday charm and timeless traditions come together in a truly magical way. The festivities begin in November with the Waterfowl Festival (November 14–16), showcasing wildlife, art, and conservation, and the Eastern Shore Sea Glass and Coastal Arts Festival - Holiday Edition (November 22), featuring unique local crafts and coastal-inspired creations.

BON VOYAGE: Start your day with a leisurely breakfast at STARS or maybe indulge in a rejuvenating morning at the SPA treatment may enjoy a 1 PM check out. Before you depart, stop by SPA. Guests with a The SHOP for nautical-inspired gifts, artisanal accents, and the must-have gift for everyone on your list.