Pulling into the intimate waterfront town of St. Michael’s, Md., is like stepping back in time. A quaint, two-line street dotted with unique boutiques and a sprinkling of restaurants is reminiscent of a luxury Mayberry. Nestled behind the main street are docks upon docks, for this is sailing country, and visitors to the area are here to get on the waterways leading to the Chesapeake Bay, one of the most renowned sailing areas in the U.S.

Turning down the long drive to the Inn at Perry Cabin, it feels as if you’re entering a grand estate. Originally an 1800s home to Purser Samuel Hambleton, aide-de-camp naval Commodore Oliver Hazard Perry, the north wing of the manor house was designed to resemble Perry’s cabin on the flagship “Niagara.” The home was converted into a farm and riding academy in 1952. The Greek Revival-style home was converted into a six-bedroom inn and restaurant in 1980, then expanded in 1989 to 41 rooms and suites. In 2003, it grew once again with the addition of 40 more rooms and suites.

Today, the Inn overlooks the water and a small dock from which to embark on daily sailing lessons and excursions. Adjacent to its expansive green, manicured lawn is a cottage housing the spa, fitness center and infinity pool and pool bar. Sprinkled throughout the back lawn are Adirondack chairs for pulling up a quiet chair and sharing some family time as the sun sets over the Miles River. While this is a relaxed and quiet inn, kids are plentiful — and surprisingly just as relaxed and quiet as the adults. Tranquility is soon to be found at the Inn at Perry Cabin.

The Inn at Perry Cabin feels more like a grand home estate with just 78 guestrooms and suites. Rooms are equipped with flat-screen televisions, free Wi-Fi, a fruit bowl (filled with apples during our stay), and plush robes. Nightly turndown service includes homemade cookies.

Guestrooms
Twelve signature rooms are smaller in size and provide garden views. State rooms are decorated in antiques and Studio Rooms are not recommended for families due to their small size and period furnishings.

Suites
For families, the Master Suite is our favorite choice. The rooms are outfitted with a king-sized bed and oversized couch and chairs in a separated sitting area with working fireplaces, large closest spaces, oversized bathrooms and a mini fridge and counter area for converting into a mini-kitchenette. For the best views, select the Water View Master Suites with French doors opening onto a balcony. Families can select adjoining rooms. While connecting rooms are not available, you'll see children using the balconies as a way to enter their parents' room.

Offshore Sailing School
Whether you've never sailed a day in your life or have some experience working the ropes, the Sailing Academy program is right for families. Two-day Learn to Sail Getaway courses provide a morning classroom session, a four-hour morning sail, a break for lunch, then four-hour afternoon sail aboard a Colgate 26 sailboat. Week-long programs are available, where by the end of a week of sailing, you'll be charting courses and sailing on your own without an instructor! A maximum of three people are allowed per sailboat, and children should be 7 and older and know how to swim. In order for children to sail without parents, they should be at least 12 with some sailing experience. Lessons by the hour are also available, if you're just looking for a taste while on your vacation.

Outdoor Pool
The infinity pool is open 7 a.m. to dusk (10 a.m. on Thursdays) with plenty of water loungers available to idle away an afternoon. The poolside bar, which opens at 11 a.m., serves light lunch fare and beverages. The pool is open Memorial Day weekend through Labor Day weekend.

Complimentary Bicycles
Cruiser-style bicycles (that blend right into the Mayberry-esque fill of the St. Michaels) are provided free to guests. Bike through the heart of St. Michaels or connect to the new paved trail along marshes.

Chesapeake Bay Maritime Museum
Located next door to the Inn at Perry Cabin, the 18-acre complex of restored buildings and new structures filled with Bay artifacts tells the history of the Chesapeake Bay's waters, as well as preserves it heritage. Families will learn about boat building, waterfowl and yachting, and highlights include a 100-year-old "screwpile" lighthouse.

Stars
Serving breakfast, lunch and dinner, Stars overlooks the dock and provides an elegant dining spot, helmed by a seasoned chef. Breakfasts feature the standard favorites, while lunches consist of burgers, sandwiches and seafood. At dinner, seafood, steaks and pasta are plentiful. (Breakfast: 7 to 10 a.m. weekdays, 10:30 weekends; lunch: 12 to 2:30 p.m.; dinner: 6 p.m.)

The Purser's Pub
Light fare and drinks are available in this richly appointed pub, complete with fireplace. The pub opens at 3 p.m. on weekdays and noon on weekends, and children are welcome to join in a game of backgammon on checkers.

High Tide Pool Bar
Open throughout the day with service beginning at 11 a.m., the pool bar serves up light fare and beverages to guests firming planted into the cushioned loungers and tables surrounding the pool. The menu consists of a few salads, pita chips and hummus, grilled cheese sandwiches and fresh fruit. The pool bar is open from May through September, weather permitting.

All about the Extras
Wi-Fi
Complimentary Wi-Fi is available throughout the hotel.

Pet Friendly
Pets are welcome to stay here for a one-time fee.

Fitness Center
A small fitness center is located at the Linden Spa, with treadmills, recumbent bikes, free weights and a universal gym system.

Boat Docking
If you happen to arrive by boat there are no boat docking fees here.

The Art of Smart Timing
St. Michaels is a summer destination on the water, and as such, the best time of year to visit is between Memorial Day Weekend and Labor Day Weekends. However, that's also peak season for the hotel. The town's restaurants and shops remain open during the mild fall months, which lead to an even quieter visit (doesn't seem possible) and lower rates. During the winter months, there really isn't enough to keep the kids entertained and the inn is best suited to couples on romantic getaways.

Getting There
The nearest airports will be Baltimore and Washington, D.C., Ronald Regan International Airport, but you will need to rent a car to get to St. Michaels, which is about 90 minutes by car from Annapolis. Following 301/50, you'll continue on 50 until the town of Easton. From there, you'll follow 33, following signs for St. Michaels, which sits on the Miles River, a tributary to Chesapeake Bay.

Getting Around
Families can bike or walk into town but a vehicle would be needed to venture further away from the hotel.

For Mom and Dad
The Linden Spa
A small day spa is located in a cottage on the property next to the inn's infinity pool. Treatments such as massages, facials, body scrubs, manicures and pedicures are available, as well as yoga classes and a steam room.