Two weekends ago, myself, Katie, and one of my good friends from college (they first met at my Super Bowl party last year and have really hit it off!) got together for a short weekend trip to Annapolis and St Michaels MD. We spent the night at K’s parent’s house in Annapolis on Friday night–and had dinner at Vin909, which I highly recommend–before grabbing breakfast and getting on the road to St. Michaels, which is about an hour away. It’s an easy ~2 hour drive from DC and is a popular destination for folks living in the DMV! Somehow none of us had ever made the trip, so we chose it for our little weekend jaunt.
The goal was to keep the whole thing budget-friendly, and I think we definitely did that. We didn’t stay in St. Michaels proper (more on that in a minute), only got a hotel for one night (you could easily drive in early Saturday morning!), and were back home by early afternoon on Sunday well in time for grocery shopping + dinner. All three of us agreed that it’s a place we’ll both be visiting again soon and recommending to friends in the area. I tried to stay off my phone and camera as much as possible so these are mostly iPhone snaps…I also didn’t shoot much in the way of the town of St. Michaels, but trust me when I say it has a cute little downtown strip filled with boutiques, restaurants, and bars. If dining al fresco is your thing, you’ll be in heaven!
Where we stayed in St Michaels MD
As I mentioned, we opted to stay a little bit outside St. Michaels and booked a room at the Wylder Hotel on Tilghman Island. While I typically only book direct, we ended up using Expedia due to their generous cancellation policy that the hotel didn’t appear to have (we were planning pretty far in advance so having the option to cancel in a pinch was nice!). This ended up causing a bit of a billing snafu at checkout, so just a heads up to be prepared for a conversation and check your bill if you don’t book direct.
Anyway, billing aside, we had a nice stay…the hotel is really cute but is pretty barebones. I would probably describe it as an upscale, nautical summer camp. It worked well for a night and our favorite parts were probably the waterfront views, s’mores kits (you do have to pay $10 for not many ingredients, so I’d try to BYO if you can swing it) with fire pits, and the complimentary bikes to get around the island. The property was recently completely redone and reopened in April, and our sailboat captain on Saturday evening (more below) mentioned that the owner of the hotel would probably tell you they feel “75% there” in terms of where the property’s at. I’d say this was pretty accurate…there are definitely some kinks to work out and it felt a little pricey for what it was, but it’s evident they’re working on some of the details that’ll give it the luxury feel they’re aiming to achieve.
I’d say the biggest downside of staying here was the distance to St. Michaels…it’s about a 20 minute drive, and there are no taxis or Ubers readily available so you’d have to drive yourself back. We wanted to enjoy a couple of drinks with dinner so ended up eating at one of the hotel’s two restaurants, Tickler’s Crab Shack. The burgers were good but a little pricey. Ending the night with s’mores and chatting with other guests definitely made the night!
What we did in St Michaels MD
We mainly walked around downtown and prioritized popping in and out of stores and paying a visit to the Inn at Perry Cabin (where Wedding Crashers was actually filmed!). It’s a luxurious property with insane waterfront views and all three of us want to return for an overnight stay. We spent a couple hours in their Adirondack chairs and got a tour of their luxury boat–it’s part of an overnight package where they pick you up in Annapolis and bring you back to the property–and people watched with our cocktails.
The highlight of our weekend was our sailboat ride with Lady Patty Charters! We opted for the sunset cruise for $54, which came with champagne. They didn’t open the champagne till halfway through the ~2ish (slightly longer) hour trip, but were making cocktails to order. Katie got the margarita and it was actually delicious! It’s a family recipe and was completely made from scratch. There were only 11 of us on the boat and we were able to walk around and chat with the Captain and fellow passengers…it was really fun and I’d definitely do it again. There are also daytime cruises that are more family-friendly, if that’s what you’re looking for.
One thing to note about the boat–it picks up on the main marina on Tilghman Island, but that’s about .7 miles from the hotel. There aren’t any sidewalks so you could walk and share the narrow road with cars, but we drove…I just took it easy on the champs and drove us back! Something to keep in mind if you’re doing the evening sail and getting done after dark. If you are staying at the Wylder, they do a sail with Lady Patty that picks up at the hotel marina. It’s only offered on Friday night but we’d have done that if it was an option for Saturday!
Where we ate in St Michaels MD
The original plan was to get lunch in St Michaels MD, but we ate huge breakfasts at the Iron Rooster before leaving Annapolis and didn’t need more food until mid-afternoon. We decided to head back into town after our drink at the Inn and ended up at Awful Arthur’s for some seafood. I’d recommend snagging a table outside if you can, but we were hungry and they were busy so we sat inside! The crab dip was our favorite.
As I mentioned, we had dinner at the hotel on Saturday night and after snagging a couple things from their simple continental breakfast on Sunday, opted for a more hearty meal at Two If By Sea before hitting the road on Sunday. It’s a cute little diner literally across the Wylder and I’m glad we opted to stop there!
That’s a recap of our quick trip to St Michaels MD – leave a comment or drop me a line at firstname.lastname@example.org if you have any questions about our visit!