Annapolis, Maryland: A Must-Stop for Snowbirds Headed South

If you’re driving down from Canada to Florida, you’re probably looking for spots worth checking out along the way—without adding too many extra miles. So why not make your pit stop somewhere new and exciting?

Ditch the Washington traffic on I-95 and take Route 301 instead. It’ll lead you right to Annapolis, the capital of Maryland, and trust me, it’s a stop you won’t regret!

Why Stop in Annapolis, Maryland?

The Perfect Pit Stop 

About 9 hours from Montreal or Toronto, Annapolis is the ideal spot to rest up for a night (or two) and recharge for the next leg of your trip.

Seaside Charm 

Set along Chesapeake Bay, Annapolis will charm you with its salty breeze, sailboats, cute historic houses and charming cobblestone streets. 

Everyone visiting that town will enjoy a walk along the City Dock to soak in the salty air, admire the boats and relax in the laid-back atmosphere of this port city.

A City With History

Annapolis is one of the oldest cities in America and was even the U.S. capital for a bit! These days, it’s the capital of Maryland.

The city’s history is on full display, with red-brick buildings that tell tales from centuries past. You’ll definitely want to snap a picture of the Maryland State House—the oldest state capitol still in use in the U.S. It’s an architectural gem.

Quaint Pastel Houses 

One of the highlights of Annapolis: its cute, pastel-coloured wooden houses! You’re guaranteed to fall for Pinkney Street, a charming lane lined with old homes, including a little pink house that’s Insta-worthy from every angle!

No need to worry about cars blocking your shot—it’s a one-way street with no parking. At the end of the street, you’ll find the Shiplap House, one of the oldest buildings in town, complete with a white picket fence.

Explore by Foot 

Annapolis is super walkable, so take your time and wander around on foot. Start on Main Street—where all the action is—and meander through the side streets. There are plenty of scenic spots to discover. Don’t worry about getting lost—the city’s compact enough that you’re never far from a landmark. Clean, safe, and easy to navigate, it’s the perfect place for a leisurely stroll.

The Flavours of Annapolis: Where to Eat and Drink?

For Coffee Lovers 

Start your morning at Brown Mustache Coffee, a local favourite with a cozy, relaxed vibe, a cute decor, and a garden. It’s the perfect place to unwind before hitting the road again.

Alternatively, try Rise Up Annapolis, a popular local chain with several locations around town, including one by the water.

For an Exceptional Meal

If you’re in the mood for a culinary treat, Preserve is THE spot for you! This popular restaurant boasts creative cocktails and a refined, seasonal menu, focusing on local ingredients. Foodies will love it here, especially if they’re on the hunt for a healthy, delicious meal.

For an Indulgence 

Feeling up to a challenge? Head to Chick & Ruth’s Deli, a famous American diner with a colossal 6-pound milkshake on the menu! Yes, you read that right: 6 pounds of pure frozen indulgence. Between the retro vibe and gargantuan portions, this place is a challenge for your appetite and a treat for your taste buds.

For a Historic Tavern Experience

Annapolis is like stepping back in time to when maritime trade was the lifeblood of the East Coast. What better way to immerse yourself in that era than with a visit to a historic tavern?

Middleton Tavern, one of the oldest taverns in the U.S., offers an interesting experience. Or for an even deeper dive into history, check out Reynolds Tavern and 1747 Pub, a true historical landmark where you can enjoy a beer in a period setting.

Annapolis Is Worth the Stop!

With its rich history, coastal charm, and mouthwatering food scene, Annapolis is the ultimate pit stop to break up your drive and avoid D.C. traffic.

Make it a stop on your way south—you’ll leave feeling refreshed, recharged, and ready to hit the road to sunny Florida. And don’t forget to get a quick travel insurance quote from soNomad while planning your winter in the sun.