Weekend in Annapolis: A Friendly Guide to the Perfect Getaway

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.

🏛️ Day 1: Discover History & Local Culture

Explore the Historic District

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.

⚓ Get on the Water: Sail, Cruise, or Paddle

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!

🎉 Seasonal Events & Local Fun

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)

🧗 Adventure & Outdoor Activities

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.

📸 Don’t Miss: Sunset at City Dock

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.

🛏️ Where to Stay: Hotels & Hostels

After a full day of exploring, you’ll need a cozy place to recharge. Annapolis offers a variety of accommodations:

Top-Rated Hotels

• 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

Budget & Social Stays

• 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.

🍽️ Where to Eat: Best Restaurants in Annapolis

Get ready to eat well! Annapolis has some unforgettable food spots:

Seafood & Local Favorites

• 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

Brunch & Coffee

• 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.

🌟 Final Thoughts

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.