When we arrived we were allowed to check-in early and grabbed lunch at Bay Wolf restaurant before going to the room. Bay Wolf was a great place for lunch, but Harbor Shack was an even better place for dinner! We had dinner and drinks overlooking the water with the locals.
We spent some time sitting by the pool, drove by the beach - which is about the size of our living room - and returned to our room. Our room was called the "Forward" in the Annex building and included a private balcony with the above view of the sun setting over Baltimore in the distance. It was a very nice room with an incredibly soft bed, two large chairs in front of the tv, comfy robes, and it was very clean. The B&B included cookies and coffee in the room, a wonderful breakfast, a nice pool area, and wonderful staff! I would recommend a weekend getaway to Osprey Point Inn! The only thing about the place I wish was different would be that bikes be available for free!
On our way back Sunday afternoon we stopped by Cassinelli Winery. Though most of their 10 wines are dry, they have 2 sweet wines and a dessert chocolate wine which was not a sweet chocolate wine. The tastings are offered Sat-Sun from 12-5 and costs $6. We also walked away with their "Pole Dancer" Sweet Red and two wine glasses (included with the purchase of a bottle), though their other wines were good.
All in all, it was a very nice weekend for two on Maryland's Eastern Shore. =)
