How To Spend 2 Days in St. Michaels, Maryland

My husband, Max, had a few vacation days to burn so we decided to take a quick trip to St. Michaels Maryland. After visiting Tilghman Island last year and stopping in St. Michaels we were excited to explore the area even more. It’s a quick two hour drive from the D.C. area and feels like you are in a totally different place. We kept saying we felt like we were in a mini Charleston or Cape Cod. Below you’ll find our recommendations for how to spend a couple days in this bayside town.

Where to Stay

I choose The Wildset after seeing this video on youtube! It was in a great location, staff was great, and even the basic king room was spacious and lovely. The interior design was very current and we loved the light breakfast each morning. The lobby even has a great coffee shop if you like iced coffee drinks like me! They also have bike rentals and a fire pit out back with free s’mores for guests. My only small complaint is that they didn’t have a pool and it was really hot the couple days we were there. Thankfully, the AC was blasting in our rooms so we were still very comfortable. Staying here really made the trip!

Where to Eat

Max and I are vacation purests – we pretty much like anywhere with good food and a water view. This trip had lots of both. Our top favorites were Foxy’s and Harrison’s Harbor Lights. Both are right on the water so you can eat and drink with views of the water and all of the gorgeous sailboats. We ordered lots of seafood and enjoyed everything. We also enjoyed Corah’s Corner – their smoked fish dip was amazing. We also ate at Awful Arthurs and while it wasn’t bad at all, the food was our least favorite. All in all, we didn’t have a bad meal the whole time so I count that as a win.

What to Do

I’m definitely the kind of person that likes to do things on vacation so between all the lovely restarants we did explore a bit. The first day we arrived we spent a couple hours walking around the Chesapeake Maritime Museum. It didn’t sound like it would be that much fun but I actually really enjoyed it. You can climb to the top of a little lighthouse and there are tons of exhibits on all kinds of topics. The views are also really great so its worth going just to walk around and sit and enjoy the views. Tickets are $16 for adults but well worth it.

The real highlight of the trip was our Sailboat trip. We booked through Sail Selina II and did the sunset champagne tour. It was SO much fun and so peaceful out on the water. The crew was really fun and we met a lovely family from Pennsylvania. It included drinks (champagne, beer, wine, sodas) and light snacks so it was the perfect thing to do before dinner. The tour wasn’t cheap (I believe tickets were $95) but definitely something I would pay to do again.

Otherwise, we took a long bike ride with bikes from The Wildset and enjoyed the paved bike trail (ask the front desk where to go to get on it!) We also walked around a shopped a bit – I really liked the Chesapeake Trading Co Store. I had planned to do a bit more exploring of antique stores but the afternoons were quite hot so we ended up taking a bit of time to nap each afternoon.

Final Thoughts

This trip really reminded me that its not always about going to far places, sometimes its just about exploring somewhere new. It was so nice to just hop in the car and arrive two hours later! We are already talking about going back and exploring some more, maybe in the Spring or Fall this time. It’s the perfect place for a little getaway and would be perfect to celebrate an anniversary, or even as a girls weekend!