Annapolis is widely regarded as the sailing capital of the US and should feature prominently on any sailing enthusiasts list of day trips. Getting there from Richmond will require a two and a half hour drive across the border into Maryland, where you can anticipate hours of fun and entertainment both on and off the water. Experience Annapolis from a scenic Annapolis Harbor Cruise, experiment with yachting on the Schooner Windward or let the kids have fun on a Pirate Adventures excursion. Canoeing, paddle boarding and kayaking are other fun Chesapeake Bay adventures. Off the water you can enjoy the galleries located in the vibrant Annapolis Art District, go shopping on Maryland Avenue or feast on fresh Maryland Blue Crab and Rockfish.

Weekend itinerary if you decide to stay longer:

Stay:

The Annapolis Inn, Gibson’s Inn, The Reynolds Tavern

Where to Eat:

Chick & Ruth's Delly, Chart House Prime, Bean Rush Café

What's Nearby:

U.S. Naval Academy, St. John’s College

Ready to go?
Step 1: Visit the website and book directly and/or call ahead to confirm their hours.
Step 2: If you are spending the night, search for Hotel Deals nearby. Read the reviews, then call the hotel directly to book and ask for a romantic, kid-friendly or pet-friendly amenity if you need it.
Step 3: If you are flying, compare Flights. Book directly with the airline, add your frequent flier number and reserve your seat.
Step 4: Estimate your driving time using Google Maps (click the blue 'Directions' arrow in the search box).

Need some more help?
Read our Reservations & Travel Planning Tips guide.