Sweeping harbor views, brick streets, charming locals and scrumptious food - not the kind of expressions I expected to share about my recent visit to Annapolis.

A short one hour flight from Toronto Pearson to BWI Airport was ideal for our weekend jaunt to the city. After a long day of work and travel, we spent our first night in the BWI Region. With a huge outlet mall at Arundel Mills, restaurants, and other amenities nearby, it’s the perfect spot to get settled. The Hotel Arundel at Preserve featured oversized suites, a surplus of amenities, and felt anything but an airport hotel.

On Saturday morning, a short Uber ride landed us in the heart of Annapolis. Our remaining stay was at the Westin Annapolis - a property we loved. Centrally located, it boasted features like an in-house coffee shop, Workout Your Way (have fitness gear delivered to your room), 24-hour heated pool and cruiser bikes for exploring the town.

Hungry for breakfast, we strolled into Downtown Annapolis on a mission. As you begin to approach Main Street, you can’t help but notice Maryland State House - it makes for quite the picturesque scene along with the brick-lined streets and architecture.

Preserve on Main Street was first on our list for brunch. A local spot priding themselves on sustainable products, we feasted on Bloody Mary’s, Potato and Onion Frittata, and Banh Mi. The best side dish at this restaurant? The locals one table over who were eager to assist in our must-do list.

We continued south on Main Street towards the water visiting local boutiques. Favorites that caught my eye were Lilac Bijoux, The Pink Crab, and Brightside Boutique. Zachary’s Jewelers by the water is the perfect spot to pick out a keepsake from your travels.

If there’s one set of plans you make in Annapolis during your stay - it must be a sailing excursion with Schooner Woodwind Sailing. There’s nothing like seeing this city from the harbor. Be sure to try the Seas by the Bay IPA on board - it’s one of two venues that serve it.

As per the locals, happy hour at Sailor Oyster Bar was a non-negotiable. Operating with just a blow torch for meal prep, we were intrigued. Oysters are a no brainer but the Maryland Crab Toast and Potato Salad were equally scrumptious. We then moseyed on over to Vin 909 Winecafé for a casual dinner. The recommendations didn’t disappoint - pizza offerings, wine list, and dessert options were impressive and well worth the wait.

Brunch at the Iron Rooster on Sunday was an event we penciled in early on. Considering locals were willing to lineup outside, in the pouring rain for a meal here - we knew we were in for a treat.

The Bloody Mary was perfection and don’t get me started on their freshly baked pop tart. You can’t come here and order one, or two for the table. The chicken and waffles and crab hash bowl practically had us licking the plates clean.

We walked off our breakfast roaming up and down side streets admiring charming houses and buildings dating back to the 1800s and earlier. Our weekend getaway was coming to a close so we headed back to the Westin Annapolis for a quick coffee top up before finding ourselves at BWI Airport.

You don’t even have to ask if I’d be interested in going back to this charming city. With a half tackled to-do list and a craving for some Maryland Crab, we’re already plotting another weekend getaway before the end of the year!

This blog was written by Krystin Lee of Suburban Faux-Pas Images courtesy of the author.