What's the purpose of your trip? How long do you want to stay? What area do you want to stay in the most? Where are you coming from?
Maryland is broken into the eastern shore and the western shore which is separated by the Chesapeake Bay. The Chesapeake Bay links both shores by a 4 mile bridge that has two different spans the east and west bound sides. The East bound side costs $4 per car every time you go over it.
Kent Island and St Michaels are both on the eastern shore while Annapolis is on the western side.
Kent island boasts some nice restaurants and that's about it for tourists. Seriously, there is nothing else but some grocery stores (Dh works at the best one!
), other stores and houses. Nothing touristy to do or see besides some boats at the drawbridge docking area. Kent Island is a strip on US route 50 that has a bunch of chain restaurants and stores if you go off the main highway it's only because you are local and know where you are going which has to be to someone's house.
St. Michael's is a small tourist destination town about 35ish minutes from Kent island. This town is much less commercialized. It's a place most people take a day trip to and just walk or bicycle around town all day. They have small boutique shops, bed and breakfasts, an inn, mom and pop shops, etc. There's a small ferry that you can take by car or foot a few miles down the road called Oxford Bellevue Ferry that you can take over to the next town, Oxford that is also a lovely small town like St. Michael's. Both are lovely day trip places.
Annapolis is going to be a whole other story. It is a small city. Movies, naval academy, mall, every chain restaurant, target, strip malls, night activities, people out all the time, public transportation, everything, everywhere. St Michaels will shut down by 8pm maybe 9. With nothing to do afterwards. Kent island while they have one 24 hour grocery store everything else will shut down by 9ish.
I haven't stay at Hilton Garden but they do do donate to our school fundraiser every year. They are a clean nice hotel but they are connected parking lot to parking lot to the two local bars that stay open late. I haven't stayed there so I don't know if this would impact the sounds or sleep there, etc. While it's not quite as high scale if you wanted to avoid that issue and stay in that same area I'd try Holiday Inn Express it's also on the water but across on the other side of Rt 50. I'd avoid the third hotel in that area Best Western.
All that being said depending on your intentions I would skip staying on this side of the bay/ bridge and probably stay on in Annapolis instead. They have alot more to do. You are going to be getting up and probably traveling to Anapolis everyday and while it's only 8ish miles away that 4 mile bridge is a pita. I'd look into the day trip cruises that take you from Annapolis to St Michaels for the day and tour the area that way.
Sorry for being so long winded. Hope that helped.
Thank you to everyone for all of the wonderful tips. Looking forward to a great time!
