After battling six hours of traffic on I-95 from New York City, our first stop was Annapolis, MD, where we had made a reservation at Annapolis Westin, a newer hotel located outside the center of town. Since we had missed lunch, we immediately headed to the historic center in search of some snacks and libations.
Our first stop was Middleton's Tavern, where we had some drinks and sampled the local crab dip. We then walked down to O'Learys, and had an amazing dinner, including what I would call the simple best crab cake I 
have ever had. Leaving dinner, we walked past the harbor and made our way back to the The Westin, we we enjoyed a night cap in the bar before turning in for the night.
have ever had. Leaving dinner, we walked past the harbor and made our way back to the The Westin, we we enjoyed a night cap in the bar before turning in for the night.In the morning, we crossed over the Bay Bridge on our way to St. Michaels, MD, where we had a reservation at the Inn at Perry Cabin. The Inn at Perry Cabin had been featured a few years earlier in the movie Wedding Crashers, and we were curious to see what it was like in real life.
Our room featured a balcony with a view of the river and the garden below. After checking in, we headed down the street for lunch at the Cra
b Claw Restaurant, a causal spot situated right on the water. While we were there, several boats pulled up and docked adjacent to the restaurant for lunch. Following lunch, we walked around the quaint town of St. Michael's, checked out the local shops, and sampled some ice cream at Justine's Ice Cream Parlour. We ended the day with dinner at Sherwood's Landing, the main dining room at the hotel. Again, we enjoyed some great local seafood, including soft shell crab. The following day, we woke up early for breakfast, and I enjoyed a massage at the Linden Spa, located on the hotel property, which was the perfect end to a long weekend.
Address Book
Middleton’s Tavern
2 Market Space
Annapolis, MD 21403
(410) 263-3323
2 Market Space
Annapolis, MD 21403
(410) 263-3323
310 Third Street
Annapolis, MD 21403
(410) 263-0884
Annapolis Westin
100 Westgate Circle
Annapolis, MD 21401
(410) 972-4300
100 Westgate Circle
Annapolis, MD 21401
(410) 972-4300
Crab Claw Restaurant
304 Mill Street
St Michaels, MD 21663
(410) 745-2900
304 Mill Street
St Michaels, MD 21663
(410) 745-2900
Justine's Ice Cream Parlour
106 N. Talbot Street
106 N. Talbot Street
St. Michaels, MD 21663
(410) 745-5416
(410) 745-5416
