Celebrating a bride-to-be before she ties the knot or gathering the ladies for a much-needed reunion requires somewhere to lay your head after a day of fun. There’s no better place to drop your bags than the Inn at Perry Cabin.

Located in the picturesque town of Saint Michaels, Maryland, our waterfront resort trades crowded nightclubs and exhausting itineraries for relaxed luxury, coastal charm, and good, ole-fashioned bonding. Here at the Inn at Perry Cabin, we have the big three for the best possible girls' getaway: pool, spa, and wine. So from general poolside lounging to an evening of sip-and-paint laughs, our itinerary is designed to help you and your crew unwind, celebrate, and create unforgettable memories on the Chesapeake Bay.

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Friday: Settle In and Sip

Welcome to the Eastern Shore at High Tide Pool Bar

Kick off the weekend with immediate cheers-ing. After checking in, bypass the usual hustle and head straight to the High Tide Pool Bar (open seasonally). Nestled next to our zero-edge pool and framed by lush botanical gardens, featuring Panicle Hydrangeas, Chaste Trees, Canna Lilies, Purple Coneflowers, and Rose Mallow, it’s the ultimate place to shift into vacation mode.

We recommend grabbing a lounge chair or two, grabbing a drink or three, and catching up with your best friends in the afternoon sun. If the weather is cooler, head inside to Purser’s Pub for a roaring fire and sip a flight from our exclusive Rum or Whiskey Tasting experience to warm up the celebrations and your spirits.

An Evening of Art and Wine

For a creative and laid-back evening, sign up for a "Sip & Paint" session. Led by local artist Vickie Fisher, your group can craft their own Eastern Shore masterpieces while enjoying Inn at Perry Cabin's house-selected wines. It’s a wonderful, low-pressure way to bond, laugh at each other’s artistic “interpretations”, and create a personalized souvenir to take home.

Late-Night Bites in Purser's Pub

Keep the evening going with a casual but decadent late dinner at Purser’s Pub. Share plates of Saint Michaels oysters and the legendary Maryland Blue Crab Dip while toasting the guest of honor. The pub opens up to a lively outdoor courtyard featuring fire pits and ample seating, perfect for swapping stories and sharing laughs around the fire late into the evening.

Saturday: Wellness on the Water

Sunrise Yoga & A Walk Through Town

Start your morning feeling centered with a private group Yoga & Meditation session on the riverbank. With mats and towels provided, you can stretch out the travel fatigue (and maybe the poolside High Noons from yesterday) while listening to the gentle sounds of the Miles River. Afterward, take the scenic 10-minute stroll into the heart of Saint Michaels. Spend the late morning browsing the charming boutique shops on Talbot Street and pick up some coastal-chic accessories or gifts for the bridal party.

The Spa at Perry Cabin: A Group Reset

The afternoon is yours to indulge at the Spa at Perry Cabin. Inspired by the natural beauty of the Chesapeake, our spa is a serene haven. Book side-by-side botanical facials or rejuvenating massages. Or if you don’t want to miss a moment with your girls, keep the group together by utilizing the steam room, unwind in plush robes in the relaxation lounge, and let the everyday stress completely dissolve.

Rally on the Har-Tru Courts

If your group prefers a little friendly competition over the spa (or if you want to do both!), book some time on the Har-Tru tennis courts. Whether you drop in for a private clinic with our pro to perfect your swing, or just rally for fun, it’s a high-energy way to work up an appetite for dinner.

Saturday Evening: Coastal Elegance

Sunset Sail on the Water

Cap off your Saturday night with an exclusive sunset sail tailored to your group. Board a private charter to glide across the water as the evening light paints the horizon. Your crew will enjoy a relaxed atmosphere complete with chilled wine, light bites, and unbeatable coastal views. It provides a stunning, intimate backdrop where you can raise a glass, play bachelorette games, and celebrate the bride (or your friendship) with the Miles River stretching out around you.

Sunday: Farewell on the Miles

Brunch at STARS

Sleep in, pack at your leisure, and gather your group in the light-filled dining room at STARS 'cause a decadent Sunday brunch is non-negotiable. Order a round of Belvedere Bloody Marys or mimosas to accompany elevated coastal breakfast favorites like crab omelets or lemon-blueberry waffles. Take your time enjoying the tranquil waterfront views before you have to say your goodbyes.

A Final Paddle

Before you hit the road, grab some kayaks from our fleet for a peaceful paddle along the Miles River. Our "Kayak the Miles" guided (or unguided) tour is a serene way to get out on the water one last time. As you glide past the historic harbor, take a moment to breathe in the crisp Chesapeake air and capture one last group selfie on the water. It’s a refreshing, grounding way to conclude the ultimate girls' getaway.

The Bottom Line

Your girls' trip should feel like a true escape. Whether you are planning a sophisticated bachelorette party or an annual friends' trip, the Inn at Perry Cabin offers the perfect blend of coastal relaxation, refined dining, and tailored activities. Book your stay and let our Guest Services team help you craft an itinerary your friends will be talking about for years.

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