Sabatino's is my personal fav. Then, a short 2 block walk down to Vaccaro's for dessert (homemade Gelato and Baltimore's best cannoli's). I would not consider either very "upscale" but to get a real "feel" for Baltimore, these are great.

Power Plant live is a great place for entertainment too. Just about a 5-10 minute walk from Little Italy. Just head back towards the Inner Harbor.

If you like history, Fort McHenry (where Francis Scott Key wrote the Star Spangled Banner after the fort was attacked by the British) is across the harbor. Also, in the harbor is the National Aquarium, a de-commissioned nuclear powered submarine you can walk through and some shopping in the pavillions of the Inner Harbor as well as the mall at the corner of the Renaissance Hotel (a multi-level mall.....I think 4 levels).

Although its been ages for me, for some good nightlife activities, Fells Point is cool (well, it used to be.....not sure about now but maybe someone else whose been there more recently could comment). A short cab ride or you can take the water taxi from the harbor.

Hope that helps a bit.

Sips and Bites, featured in Diners, Drive-ins and Dives, is a not-too-fancy, down-to-earth, diner that serves freshly made foods including a variety of Greek dishes including freshly made crab cakes.

All the suggestions were great!

I went to some museums, went to a bar that had live music. When it poured rain I went into the Historic Ships of Baltimore's Inner Harbor. I had dinner at Standard Grill. It reminds me of our local Hillstone restaurant with the dim setting. The wine selection and food was great! They even catered to my gluten allergy.

Sunday was a beautiful sunny day so I went jogging to sightsee. It was a wonderful weekend!