Answer: Visiting Annapolis and hoping to park near the City Dock or Main Street Circle can be a bit challenging, especially on a Friday late morning when the downtown area starts getting busy. However, there are several options for street parking and nearby garages.

Answer: Good question. As of early November 2025, the leaves around Annapolis, MD (and the coastal/central Maryland region) are likely past their peak — many trees have already shed leaves or are showing late-fall colors rather than fresh autumn foliage.

Answer: It sounds like you’ve got a great trip planned! Annapolis and the surrounding area offer some beautiful scenic drives, perfect for exploring while you have access to a car.

Answer: It sounds like you have an exciting trip ahead! The Westin in Annapolis is located in a great area, so let me break down your questions:

Answer: Visiting Annapolis during the holiday season is a festive experience with a variety of events and attractions for families and visitors. Eastport and the downtown waterfront are particularly lively with seasonal activities.

Answer: It sounds like you're going to have a great time in Annapolis! Maryland is famous for its crabs, and you're definitely in the right place to try some delicious crab cakes. Here are a few recommendations for where you can find the best crab cakes, along with some other tasty things to eat while you're in the area.

Answer: It sounds like a wonderful trip! Annapolis is a charming city with a rich history, beautiful waterfront views, and great food. I’ll help address some of your concerns and offer some tips for making your visit as comfortable as possible for you both.

Answer: Annapolis is a charming city with plenty of family-friendly activities that can keep your 6-year-old twins entertained while also letting you enjoy the historic and scenic aspects of the area. The city is walkable, so you can easily combine sightseeing with kid-focused fun.

Answer: The Blue Angels air show in Annapolis is a fantastic event, and there are several great spots to watch the show from. Depending on the specific location of the show and your preferences, here are a few excellent options for viewing the Blue Angels in action:

Answer: If you’re thinking of visiting Annapolis, Maryland this weekend, it’s a good question whether there’s still any storm- or flood-related damage lingering from recent events. Here’s a current assessment, with what we know — and what to check before you go.

Answer: Annapolis is a fantastic spot for seafood lovers, especially if you’re looking for casual, fun dining experiences close to the waterfront. Since you won’t have a car, sticking to restaurants and bars within a short Lyft ride or walking distance from the Westin is ideal.

Answer: It sounds like a fun trip to Annapolis! With limited time for exploring, you can definitely make the most of the time between your arrival and dinner. The Hilton Graduate Hotel is centrally located, so you'll have easy access to several points of interest in Annapolis while walking to McGarvey's.

Answer: If you're looking to play pickleball in Annapolis, you're in luck—there are several great options for both indoor and outdoor play. Whether you’re looking to find a local pickleball group or just want to hit the courts for some fun, there are plenty of places to suit your intermediate level. Here are some of the best spots to check out: