Weekend Getaway in St. Michaels, MD

Updated: Nov 7, 2019


We packed up our car and drove to St. Michaels, MD for a weekend getaway full of sailing, bushels of steamed crabs and sunsets over the Chesapeake Bay. St. Michaels, located a little over 3 hours from central New Jersey, is an adorable harbor town with a history of ship building & ties to the revolutionary war. Check out our weekend itinerary below!


Day 1

Morning Coffee

Rise Up is a little coffee shack on the outskirts of town with two-sided drive up windows serving a wide selection of lattes, cappuccinos and frozen coffee. There is usually a line, but it’s well worth the wait! Two Dopes Tip: Bring your coffee back into town and drink it in one of the many beautiful parks or on a waterfront bench.

Sail Boat Cruise

Start your morning off with a sailboat cruise around the Chesapeake. We booked a 2 hour tour on the Sail Selina II, which is a meticulously maintained sail boat that is over 90 years old. As we sipped champagne, our fantastic Captain told us about her sailboat, the surrounding waters and its rich history. 

Feast on Maryland Crabs

There are a few different waterfront restaurants in St. Michaels, but our favorite for crackin’ crabs is easily The Crab Claw.  This large crab shack, in the picture-perfect red shingled building, has large wooden tables overlooking the water and buckets of delicious steamed crabs. We had an incredible two hour lunch devouring crabs and watching boats sail by. We love that they serve the crabs with a variety of sides including melted butter, malt vinegar and old bay. Two Dopes Tip: Add the locals favorite – pickle and cheese plate.

Shopping Downtown

The downtown has a nice variety of shops, so whether you’re looking for a souvenir, one-of-a-kind antique or a new hat, chances are you’ll be able to find it in St Michaels! Olivins, a specialty olive oil, vinegar and chocolate shop, offers gourmet tastings and should not be missed!

Rum Tasting

Lyon Distilling Company makes incredible, hand crafted spirits in small pots with raw ingredients. Many of their rums are inspired by the traditions of the local area and eastern shoreline. We stopped in for a tasting and ended up leaving with a few bottles!


Dinner at Ava’s Wine Bar

You can take the Dopes out of Jersey, but you can't take the Jersey out of the Dopes, so clearly we needed to get a pizza! We stopped by Ava's Wine Bar, which is a Zagat rated pizzeria with an extensive wine list, for dinner! We chose the Chef's favorite pizza, which was topped with prosciutto, olive oil and arugula.

Day 2

Chesapeake Bay Maritime Museum The museum opens at 9:00am from May to October making it a great spot to enjoy early in the day. The lighthouse is truly unique and their Chesapeake Bay watercraft collection is the largest in existence!

Lunch at St Michaels Crab and Steak House

The St. Michaels Crab and Steak House overlooks the water with a great selection of outdoor seating. While we could not resist getting more steamed crabs, we also tried the crab balls, crab mac & cheese and crab dip, all of which were delicious! The bloody marys and pina coladas were also fantastic, especially on a beautiful day!

Brewery Visit

If you cannot find Eastern Shore Brewery in downtown St Michaels, look for the huge, illuminated "BEER" sign. With live music frequently playing, an extensive beer selection and tasty bar snacks, you can easily spend a few hours taking in everything this brewery has to offer!


We All Scream for Ice Cream!

Justine's is the spot for ice cream in St Michaels. The small batch, homemade artisanal ice cream is made with local ingredients and inspired by the seasons.


Where to Stay?

St. Michaels has a variety of adorable Bed and Breakfasts, most of which are located right on the main street in town.  If you’re feeling fancy, The Inn at Perry Cabin is a breathtaking waterfront hotel with expansive amenities and was used as a filming location for The Wedding Crashers. We stayed at the St. Michaels Inn, which is an affordable option that is about a 5 minute drive from downtown.  

The Inn at Perry Cabin


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