When looking for a quick getaway with friends, I frequently head to St. Michael’s. I’ve gone by boat a few times, but have hopped in the car and crossed the Bay Bridge the last few visits.
If traveling by boat, we stay onboard; anchored not far from the Inn at Perry Cabin. We take the dinghy to the dinghy dock near the Crab Claw to explore the town and meet up with friends who have also sailed over from Herrington Harbour South in North Beach, Maryland.
By car, I enjoyed where I first picked to stay so much that I’ve booked a room there each subsequent visit.
I stay at the Old Brick Inn, located right on what I would describe as the main thoroughfare through town, Talbot Street. I appreciate the onsite parking, the old-world feel of the rooms and most especially, the free breakfast served in their quaint, cafe-style breakfast room each morning. Not a fan of buffets, I like that we get a private table and have a server who asks how I like my eggs cooked.

The town is walkable, and the boutique hotel is located pretty much right in the center of town. I like to head over early enough in the day to get a late lunch at either Ava’s Pizzeria & Wine Bar or Limoncello. At Ava’s, I prefer the enclosed outdoor seating area with a unique fountain along the back wall. My go-to order at Ava’s is the Ma’s meatball appetizer (we usually end up ordering more than one once we start digging into it) and one of their neo-neopolitan style pizzas (my favorites are the onion tart and the mushroom tart), along with a glass of wine.
If we find ourselves at Limoncello, I order a few appetizers to split, such as the Gamberi Gondola (shrimp, scampi sauce and grilled Italian bread) and the Polenta Con Funghi Misti (polenta, mushrooms, gorgonzola cream and truffle oil). I cannot pass up polenta any time I spot it on a menu. They have a good wine selection and offer 1/2 price bottles on Mondays and Tuesdays (note….that excludes Super Tuscans…).
After lunch, I walk around town and visit shops. I always make sure to stop into Come by Chance to look at the coastal home decor; J McLaughlin for clothes and The Christmas Shop (open seasonally).

A visit to the Chesapeake Bay Maritime Museum to check out any new exhibits and a walk along the waterfront are always enjoyable. If I’m traveling with someone who has never been to the area, we head over to the Inn at Perry Cabin and have a snack at Purser’s Pub so I can show them a few spots where the movie Wedding Crashers was filmed.
For years, I’d seen the sign on the dock for the sightseeing cruise, but had never gone onboard. During a recent visit, I decided to buy a ticket. I’m glad I did and now recommend it to anyone heading to the area. The cruise onboard The Patriot is a 70-minute narrated historical tour along the Miles River. The best deal is to buy a combo ticket for general admission to the Chesapeake Bay Maritime Museum and a cruise. The ship has a full snack bar selling alcoholic and non-alcoholic beverages, snacks and hot dogs. We grabbed a cocktail and headed to the upper deck to be in the breeze. The upper deck has more than 80 seats and the air-conditioned main salon on the lower deck has more than 50 seats. Cruises operate April – November.
Plenty of spots in town offer happy hour and many host live music during evenings. Before I go, I check the calendar at https://www.stmichaelsmd.com/see-do/ for happenings such as festivals and trivia in addition to happy hour and live music.
For dinner, I usually head to Limoncellos if I didn’t go for lunch or to Foxy’s for a burger (they’ll cook them how you like, which is always appreciated). Foxy’s is also a great spot to grab a drink and sit out on the deck and frequently has live music.
My favorite towns to visit are ones that are walkable, and St. Michael’s is perfect for that. During my last visit, I turned off Talbot and headed down a street I hadn’t been down before and discovered Simpatico, a shop offering Italian wines, foods, cheese, olive oils, ceramics, kitchen linens and more, all from Italy. I wonder what I’ll discover on my next trip!
Photo 1: The breakfast room at the Old Brick Inn. Photo courtesy of the Old Brick Inn.
