MARYLAND STATE - Here’s a top-day trip itinerary for Annapolis, Maryland, designed to give you a mix of history, culture, waterfront charm, and delicious food—all tailored for a memorable day out. Annapolis is compact and walkable, so this itinerary focuses on the downtown area, with options to adjust based on your interests.
Morning: History and Exploration
8:30 AM - Breakfast at Chick & Ruth’s Delly
- Location: 165 Main St, Annapolis, MD 21401
- Start your day at this iconic Annapolis spot, which has been open since 1965. It's a local institution known for its massive crab cakes and hearty breakfasts. If you’re there at 8:30 AM, join the daily Pledge of Allegiance—a quirky tradition. Try the “Colossal Crab Cake” or a classic like eggs with homemade toast. Expect to spend about $10-15 per person.
- Time: 45 minutes to 1 hour.
9:30 AM - Maryland State House
- Location: 100 State Cir, Annapolis, MD 21401
- Walk 5 minutes up Main Street to this historic gem, the oldest state capitol in continuous legislative use (since 1772). It’s free to enter for a self-guided tour, open from 8:30 AM to 5:00 PM. See the Old Senate Chamber, where George Washington resigned his commission in 1783, and enjoy the rotunda’s architecture. Bring your ID for security. In February, it’s a cozy indoor start.
- Time: 1 hour.
10:45 AM - Stroll to William Paca House & Garden
- Location: 186 Prince George St, Annapolis, MD 21401
- A 10-minute walk from the State House, this 18th-century mansion belonged to the Declaration of Independence signer. Tours ($12/adult) run hourly, with the next one likely at 11:00 AM. The house offers a peek into colonial life, and while the gardens may be dormant in February, they’re still scenic. If you prefer to skip the tour, enjoy the exterior and move on.
- Time: 1 hour (tour) or 15 minutes (exterior).
Midday: Waterfront and Lunch
Noon - City Dock & Ego Alley
- Location: Dock St, Annapolis, MD 21401
- Wander 5-10 minutes downhill to the waterfront. Known as “America’s Sailing Capital,” Annapolis shines here. Stroll along Ego Alley, a narrow channel where yachts parade (fewer in winter, but still picturesque). Bundle up—it’ll be chilly by the water—and soak in the Chesapeake Bay vibe. Pop into Susan Campbell Park for a quick view, or grab a coffee from a nearby vendor if you need to warm up.
- Time: 30-45 minutes.
12:45 PM - Lunch at Boatyard Bar & Grill
- Location: 400 Fourth St, Annapolis, MD 21403
- A 10-minute walk (or quick drive) across Spa Creek to Eastport, this spot is famous for its award-winning crab cakes—voted best in Annapolis for over 20 years. Go for the crab cake platter ($30ish) or a lighter crab soup. It’s cozy indoors with a nautical vibe, perfect for February. Reservations are bright but not required midweek.
- Time: 1 to 1.5 hours.
Afternoon: Culture and Shopping
2:15 PM - U.S. Naval Academy (Visitor Center & Museum)
- Location: 52 King George St, Annapolis, MD 21402
- Walk 15 minutes back toward downtown and enter via Gate 1 (bring ID for security). The Visitor Center is free and open from 9:00 AM to 5:00 PM, with a film and exhibits on Academy life. The Naval Academy Museum in Preble Hall (also free) has two floors of naval history—think ship models and John Paul Jones’ crypt. Guided tours ($12/adult) are available but take 90 minutes; skip if short on Time.
- Time: 1 to 1.5 hours.
3:45 PM - Main Street Shopping
- Location: Main St, Annapolis, MD 21401
- Exit the Academy and head 5 minutes to Main Street. Browse boutiques like preppy sailing gear shops or quirky stores like Back Creek Books (rare nautical finds). It’s a charming, historic strip—perfect for souvenirs or just window shopping. Indoor warmth keeps it comfy in February.
- Time: 45 minutes to 1 hour.
Late Afternoon: Wrap-Up
4:45 PM - Coffee or Snack at Annapolis Ice Cream Company
- Location: 196 Main St, Annapolis, MD 21401
- Cap your day with a treat from this local fave. Open until 6:00 PM, they churn fresh ice cream daily—think Peanut Butter Oreo or Chocolate Brownie Batter ($4-6). Grab a scoop or a hot drink to warm up before heading out.
- Time: 30 minutes.
5:15 PM - Departure or Sunset Stroll
- If you’re driving back (e.g., 45 minutes to D.C., 30 to Baltimore), head out now. Sunset’s around 5:45 PM, so if you linger, catch it by City Dock for a final waterfront moment—dress warmly!
Total Time: ~9 Hours
- Distance Covered: About 2-3 miles walking, all manageable in downtown Annapolis.
- Cost Estimate: $50-75/person (food, tour, extras).
- Tips: Wear layers and comfy shoes. Parking is easiest at the Hillman Garage (150 Gorman St), which costs $2 2/hour. If history is not your thing, swap a site for a boat tour (e.g., Watermark Cruises, if running) or more shopping.
This itinerary balances Annapolis’ highlights—history, seafood, and maritime charm—while keeping you cozy in February. Enjoy your day trip!
