Annapolis/ St. Michael's Maryland

We are going to Annapolis (staying in Annapolis) and St. Michael's (day trip) for a few days (midweek) in mid September. Are there any not to miss sights (besides Naval Academy) or places to dine? Brewpubs, crab houses, etc are great, it does not have to be jacket and tie.

DIS people have always made the best suggestions in the past and we have found many undiscovered places in our travels based on their tips. I always try to do the same for others as well!

Thanks so much to everyone!!

This post made me so happy!! We moved down to FL about a year ago from PA and a bunch of my in-laws live in Maryland - right on Kent Island!! We use to visit them all the time and that is one thing I miss a lot!! One trip we even drove to St. Michael's!! This post brought up all those good memories!!

The Hilton Garden Inn is a nice hotel. When my husband's cousin got married at the Kent Island Yacht Club right there, the HGI was the hotel they picked for their guests. It's right near the Jetty though, which is their night club with music and sometimes live bands. We went there after their wedding and it was a lot of fun but the noise might carry to the hotel. We ate at probably every restaurant that's near there, too.. but really that's all there is to do. My favorite thing to do (and the first thing I always did when we arrived) was to go to the Crab Deck for an orange crush!! They are delicious and it was my favorite spot to get one! I'm not a seafood person so I would always get the turkey club but everything we ate there was good and we loved eating on the water, however, they are a lot of tour buses that stop there so take that into account. Our cousin's rehearsal dinner was at Bridges which was also good. My husband's aunt and uncle's favorite spot to get a drink and hang out at night is the Big Owl Tiki Bar.

My favorite place for dinner is probably Annie's which is on the other side of 50. That is more upscale but still island casual. They also have good orange crushes :) Our other cousin works at Red Eye's Dock Bar next to Annie's and they say it's a good time. I was only there once for a short time and all I remember was how cold is was. We must have gone in either March or November lol. We always seem to eat breakfast at Ram's Head Shore House because 1) it was either there or Cracker Barrel and I don't like eating at chains when I travel and 2) the owner was actually BFF's with my father in law. He has his own brewery called Fordham Brewing Company. There's a few around - I think in Annapolis and I remember eating at one in Baltimore Harbor.

We just walked around St. Michael's because it's so cute with different shops and eateries. I can't remember for the life of me where we ate at. I think it might have been some hotel? Same goes for Annapolis - I just remember walking around and seeing all the boats that were docked. Our other cousin leaves in Annapolis and we met up with them for dinner at Rustico Italian Restaurant. I wish we got to see the Naval Academy and stuff. We'll just have to plan another trip :)

I hope you have a great time though!! We loved visiting there and I hope you do too :)

ETA: My brother in law loves Adam's Ribs so he makes us eat there all the time. It's very good if you're looking for a BBQ place!
 
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SMorgan711 - Thank you so much for the great tips! I am even more excited to go. The places you suggested sound terrific!! I plan to Google them over the weekend and add them to our list.

I really appreciate the time you took (and others who responded) to put this together for us. I follow DIS Boards quite a bit and respond whenever I can. The people are very nice and helpful.

Once again, Thank You So Much!!
 
SMorgan711 - Thank you so much for the great tips! I am even more excited to go. The places you suggested sound terrific!! I plan to Google them over the weekend and add them to our list.

I really appreciate the time you took (and others who responded) to put this together for us. I follow DIS Boards quite a bit and respond whenever I can. The people are very nice and helpful.

Once again, Thank You So Much!!

You are so welcome!! I actually don't post a lot but I had to reply! It was such a coincidence that it was Kent Island, Annapolis and St. Michael's because those are all places that I had visited and that I have family connections to! It was truly my pleasure because it was nice reminiscing about our family memories :) Plus I love to travel but I'm not really into touristy things and I've always found that the best places are ones off the beaten path that only the locals know about. Another tip I found handy is asking someone working at the front desk of the hotel places that they recommend. We love traveling to the Finger Lakes and found the best breakfast spot that way!

BTW in case you didn't get the hint from my first post - have an orange crush at least once during your trip!!!! :)
 
I recently moved from Kent Island, we lived there for 12 years. the area is ver pretty, you should have a great trip!

Our favorite place to eat on Kent Island is Adams Ribs. They have an excellent selection of microbrews, and great food (not just bbq). Our favorite dining place overall in the Annapolis area is Lures in Crownsville.
 
SMorgan711 - Thank you so much for the great tips! I am even more excited to go. The places you suggested sound terrific!! I plan to Google them over the weekend and add them to our list.

I really appreciate the time you took (and others who responded) to put this together for us. I follow DIS Boards quite a bit and respond whenever I can. The people are very nice and helpful.

Once again, Thank You So Much!!

Muddy Rivers (not sure how to tag you) but I just talked to some of my in laws and they recommend the key lime crush at the Big Owl Tiki Bar. Apparently it's a new drink there and it's delicious! I'd love to hear of your travels when you get back!!
 












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