The Inn at Perry Cabin and the Return of the Fleet

I wanted to share with you the beautiful Inn at Perry Cabin today. Located in St. Michaels, Maryland right on the waters of the Chesapeake Bay it is Americana at its finest. It’s a short flight from New England and only a 4-hour drive from Fairfield County, Connecticut.

The Inn at Perry Cabin was built by Samuel Hambleton in the early 1800s. Hambleton called his home “Perry Cabin Farm” when he retired to St. Michaels in 1816, and designed the north wing of the manor house to resemble Commodore Perry’s cabin on his flagship, the USS Niagara. Today, the Inn at Perry Cabin is a boutique 78-room resort, combining historical architectural features with classic American design and a celebrated nautical identity.

The inn was once owned by Laura Ashley and scenes from the movie Wedding Crashers were filmed on the property. Those are fun facts that add to the allure, but truly, the inn is luxury at its finest and should be on your radar. This 5-star historic inn is everything you’d want in a vacation and it’s simply a beautiful place to explore. From the cuisine to the recreation, it will be a place you want to visit again and again. It’s definitely on my radar now for a family vacation. Also, they offer pet-friendly accommodations, so we could bring Zoey, which is a bonus! She would love it just as much as our boys!

The inn has a spa, an amazing on site restaurant, a tavern, tennis courts, a swimming pool, a phenomenal links golf course, croquet court, lawn games, bicycles to take into town, beautiful water views, and last but not least—an amazing fleet of motor and sailing yachts. The surrounding area is so fun to explore too, but you really could just stay at the resort and feel like you are miles away at this timeless paradise.

This trip, I visited in April for the Return of the Fleet. Each year, the inn has a kick off celebration and blesses the fleet for the upcoming season. I enjoyed a day of boating and sailing that ended with a Veuve Clicquot champagne celebration on the lawn when we arrived with the fleet and docked at the inn.

I’ll share details about this inn, my accommodations, the Return of the Fleet experience and some great day trip ideas that are 20-minutes or less from the inn.

The Grounds

The grounds at the inn are meticulously cared for and lovely to stroll. You are greeted by a long paver path upon entry and it’s lined with boxwoods and flowers. A valet greets you upon arrival and will bring in your luggage for you.

Outside the inn is the grand patio and some spectacular water views. The green lawn is lush and has Adirondack chairs perfect for reading a book, enjoying a drink, and watching the boats sail by. The patios at the inn have fire pits and conversation areas fit for evening gatherings and drinks. We enjoyed it with our group the first night we arrived and it was lovely with the glow of the moonlit water in the background.

So many things are in bloom and come summer the hydrangea bushes will put on a show. This spring visit, we were greeted with lots of daffodils and tulips all around the inn. There are gardens and courtyards a plenty and so many gorgeous blooms to spy. Come the summer months, the hydrangeas all around the inn will be in bloom and I imagine that is quite something to behold.

Here are some photos of the grounds at Perry Cabin…

Inside the Inn

The interiors are quite exquisite at the inn. There are plenty of nooks to sit and enjoy. I love the mix of traditional furnishings, nautical antiques and accents, and collectibles. Upon entering, there is a lovely staircase and parlor. We spent an evening in there with a night cap. Next to the parlor is the Main Lobby where you check in. Their on-site restaurant named STARS and the Purser’s Pub Tavern are all located in the main inn and have walk-outs to the great lawn and a courtyard.

Here are some shots of the interiors for you…

My Accommodations & the Restaurant

I had a Water View Suite which was just lovely. A living room with a fireplace, a separate large bedroom with pocket doors, and a huge master bathroom complete with double sinks, a soaking tub, and walk-in shower. My living room walked out onto a deck with a table and chairs and I just loved starting my mornings off there with a coffee in hand watching the sunrise.

Plenty of amenities are provided including:

  • robes & slippers

  • bath and body products

  • Nespresso maker & coffee, mini fridge

  • 2 flat screen TVS with cable and streaming

  • a writing desk and WiFi access

  • plush luxury bedding and towels

Breakfast at the inn is delightful and a great way to start your day. The restaurant offers a hearty menu with small plate options in their sunny STARS dining room. Everything I had here was delicious and presented beautifully. All the produce, meat, and seafood are sourced locally and used fresh in season. Executive Chef Gregory James has taken great care in creating an ever-changing menu that will arouse your tastebuds.

Also, we had an intimate private dinner the first night of our stay. Dinner here is quite special at STARS. Walking down to our private dining room, the lobby and restaurant became transformed with dim lighting and candles flickering atop a grand piano and every table.. It was quite a lovely ambience that added to the dining experience. When in Maryland you have to try the crab and now I am ruined for getting crab cakes anywhere else! I will have dreams about those crab cakes! Also, the inn offers outdoor seating on their patio and for a more intimate and private dining experience you can book one of their greenhouses on the water.

The Return of the Fleet

I was so thrilled to be here for the Return of the Fleet! As you may have caught on by now, I love being on the water— be it sailing or boating. I was thrilled to have an entire day aboard a few of the vessels in their fleet. We were blessed with such great weather that day! It was in the 70’s and sunny most of the day.

Our party motored out to Annapolis in the inn’s Hinckley motor yacht, Five Star. We joined the Captains ready to bring the fleet back to the inn for season. Five Star is a beautiful yacht and you can book it for a private charter. Also, the inn offers a butler service and will pick you up in Annapolis and you can arrive to Perry Cabin already checked in and in style. Drinks and charcuterie can be arranged for your time aboard the yacht.

Once we arrived to Annapolis, we docked and enjoyed a packed lunch aboard Five Star. The inn can provide this service for you when you book a day aboard one of their boats. Since this was a celebration, we popped some champagne to enjoy for the 4-hour sail back to the inn.

Our party divided into smaller groups and we each boarded different sailboats. I joined my party aboard Stargazer and we all set sail out of Annapolis. Sailing the Chesapeake Bay is a wonderful experience. There are lighthouses to see along the way and plenty of picturesque water views to behold. It was so relaxing aboard Stargazer and Captain Scott even let us take turns steering the boat for awhile to get a feel for it. There was nothing better than feeling the breeze and warm sun with such great company! I love to sit out on the front of the boat and it made me dream of summer! It’s fast approaching!

Once we arrived close to the inn after our day on the water, we could hear bag pipes as we prepared to dock our boats. The lawn was adorned with Veuve Clicquot umbrellas and guests cheered us on was we arrived. It was quite the sight to see! The fleet had arrived and once everyone was on the lawn a priest offered a blessing of the fleet. The “Don’t Give Up the Ship” flag was raised for the season and we all honored our brave military men and women, our first responders, and teachers. We all toasted to the season and the celebration began. Once the ceremony was over we all mingled and enjoyed champagne and hor d’oeuvres. Lawn games were set up for guests to enjoy and we had a lovely time.

It was such a great way to kick off the season! I’d love to come back with the family. The boys would love sailing the bay. It’s one of those historic and timeless places you’ll want to revisit year after year.

The Inn at Perry Cabin hosts several weddings and receptions throughout the year and would make the perfect location for your special day. They have weddings right on the water and have outdoor grounds and gardens complete with lights and a large pavered patio perfect for your reception.

Perfect Day Trips from the Inn

There is plenty to see and do outside the inn too. Here are some ideas that are close to the inn for a little day adventuring…

Bike or walk into town and explore St. Michaels— The inn is right next to the downtown and it is full of quaint shops, cafes, and restaurants. We enjoyed shopping there on our last day of our stay. There are museums to enjoy too. It is a lovely town and you can grab a meal where the locals go if you want to mix it up one night.

Embark on a 20-minute Scenic Drive of Waterman Territory— Tilghman Island is a three-mile long island with shopping, fresh seafood, and striking natural beauty. Visit the Phillips Wharf Environmental Center and the Tilghman Waterman’s Museum.

Visit Easton— Easton is just a short 20-minute drive from the inn. The historic Town Center is lovely and there are plenty of Colonial and Victorian buildings and homes to admire. It offers lots of boutiques, art galleries, and antique shops. Spend a morning or afternoon at Pickering Creek, a 400-acre Audubon Center and wildlife sanctuary.

To make a reservation and plan your Inn at Perry Cabin experience visit:



I’d like to thank the Inn at Perry Cabin for an amazing stay and experience. I only share places that get my stamp of approval. All thoughts and opinions are my own.

Until next time,


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