Looking for a charming East Coast weekend escape that blends history, water views, and unforgettable local flavor? Welcome to Annapolis, Maryland — a small city with big character. From colonial streets and scenic sailing adventures to vibrant festivals and mouthwatering crab feasts, here’s your guide to spending the perfect weekend in Annapolis.
Start your morning in Historic Downtown Annapolis, where colonial architecture and cobblestone streets take you back in time. Be sure to visit:
Maryland State House – The oldest U.S. state capitol still in legislative use (visitmaryland.org)
William Paca House & Garden – A beautifully preserved Georgian mansion with lush gardens.
💡 Friendly Tip: Join a guided walking tour with Watermark Tours to dive deeper into Annapolis’s rich Revolutionary history.
Annapolis is known as the Sailing Capital of the U.S. Whether you’re a pro or just want to relax on the water, there’s an option for everyone:
Schooner Woodwind Cruises – Set sail on a classic schooner for scenic views of the Chesapeake Bay (schoonerwoodwind.com)
Capital SUP – Rent paddleboards and kayaks and explore Spa Creek at your own pace (capitalsup.com)
🧭 Pro Tip: Sunset cruises are especially magical—book ahead on weekends!
Annapolis is full of energy year-round. If your weekend lines up with one of these events, don’t miss it:
First Sunday Arts Festival (May–November) – Outdoor street festival with local art, crafts, and live music (firstsundayarts.com)
Annapolis Boat Shows (April & October) – Internationally famous for all things boating (annapolisboatshows.com)
United States Naval Academy Events – Catch a parade, concert, or sporting event at this prestigious campus (usna.edu)
Looking for a bit more action? Annapolis offers some great outdoor and adventure options:
Quiet Waters Park – Miles of trails, art exhibits, and peaceful kayak launches (aacounty.org)
Sandy Point State Park – A beach day on the Chesapeake Bay, just 15 minutes from downtown
Bike the B&A Trail – Rent a bike and ride through 13 miles of scenic Maryland countryside.
🚴 Insider Tip: Pack a picnic and stop along the trail for a relaxing lunch break.
As your day winds down, head to City Dock to watch the boats drift by and the sky light up with color. Grab a bench, an ice cream cone, and soak in the classic coastal atmosphere.
📷 Photo Op: It’s one of the most Instagrammable spots in Annapolis — especially during golden hour.
After a full day of exploring, you’ll need a cozy place to recharge. Annapolis offers a variety of accommodations:
Historic Inns of Annapolis – A blend of old-world charm and modern comfort (historicinnsofannapolis.com)
Graduate Annapolis – Stylish, fun, and centrally located, ideal for weekend travelers (graduatehotels.com/annapolis)
The Westin Annapolis – Upscale amenities with a spa and easy access to downtown
Gideon’s Keep Hostel – A cozy, affordable option for solo travelers and backpackers (check Hostelworld for availability)
Airbnb Options – Plenty of charming lofts and waterfront cottages
🛎️ Tip: Book early for weekends, especially during summer and major events.
Get ready to eat well! Annapolis has some unforgettable food spots:
Cantler’s Riverside Inn – A true Maryland crab house experience (cantlers.com)
Osteria 177 – Elegant Italian cuisine with a local twist (osteria177.com)
Dock Street Bar & Grill – Casual, lively, and great for people-watching
Iron Rooster – Famous for their all-day breakfast and “roosTarts” (ironroosterallday.com)
Curate Annapolis – An artsy café offering great coffee and gourmet bites
🦀 Foodie Tip: Try the crab dip — you’ll thank me later.
Annapolis offers the perfect blend of history, waterfront charm, food, and fun, all within a walkable city that’s easy to explore in a weekend. Whether you’re relaxing on a sailboat, eating your weight in crab, or diving into American history, you’ll leave with a full heart (and probably a full stomach).
For more travel ideas, check out the official Visit Annapolis website — it’s a goldmine of local tips and event calendars.
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