Sailing and Crabs: 24 Hours in Annapolis

As I mentioned on our previous post about our Day at the Bay stay at Loews in Annapolis, we are looking for experiences closer to home. We decided to go on a little weekend escape to Annapolis, a picturesque seaside town on the Chesapeake Bay. Just a 45 minute drive from DC, it's a world away from the Capital with its colonial homes, small town charm, and beautiful boats lining the bay. Although it was such a short drive, we truly felt as if we were on a proper holiday.

The BLT at 49 West

We began our stay with a light lunch at 49 West, a cozy coffeehouse on West St. There, we had a simple yet delicious BLT by the window and engaged in a little people watching. There, we discussed our itinerary for the next day as we listened to the jazz from the masters class practice from the back of the restaurant. We couldn't resist the urge to return the following day for coffee, this time we were entertained with the bossa nova sounds of a local guitarist.

View from the Schooner Woodwind

After our lunch, we had a leisurely walk to the dock, admiring the beautiful colonial homes which line the streets of Annapolis. At the dock, we boarded the Schooner Woodwind, a beautiful 74-foot sailboat which gives a picturesque view of the Chesapeake Bay. Although it was an unseasonably cold and cloudy June day, we truly enjoyed the tour. There, we sipped on wine and craft beers and admired the gorgeous sailboats and daydreamed about how lovely it would be to have my own sailboat. The crew was friendly, sharing their sailing stories from Annapolis and to the Virgin Islands.

The Dutchman Trying His Hand at Sailing

After sailing, we built quite the appetite and decided to have dinner at Cantler's Riverside Inn at the recommendation of the concierge at Loews Annapolis. We wanted a local experience beyond West street. After a few and turns into a residential neighborhood, we found this quaint and lively restaurant by the riverside. It was a Saturday evening, crowded, but the wait is worth it. We indulged in Maryland Crab, seasoned with Old Bay, in true Maryland style, bacon wrapped scallops smothered in tangy BBQ sauce, and a sweet ending of homemade key lime pie. The manager, Bruce gave me a tour of the restaurant where I got to see the crabs from the moment they are picked until they are steamed to perfection and delivered to the table. As we dined there, we decided to make this place a must for our upcoming guests coming from Europe for an authentic Maryland Crab experience.

Freshly Picked Crabs at Cantler's

The following day, we boarded on a Discover Annapolis Tour trolley. I usually have an aversion to big bus tours and this tour was the complete opposite. The trolley is small and intimate and Mark, our tour guide had great anecdotes to share with us as we admired the colonial mansions, the Naval Academy and the docks which line the bay. As the weather warmed up on Sunday, I was grateful we had AC on the trolley. This is a great way to see the city if you schedule your trip during a hot and muggy Maryland day.

On the Trolley

This trip came at the right time as my father is terminally ill and had the opportunity to have this experience before heading home to be with him and my family. It is great to know that only 45 minutes away from DC you can have a relaxing and beautiful experience by the sea.

*A big thanks to the Annapolis Tourism Board and Loews Annapolis Hotel for the travel tips! Curious about the Day at the Bay Package? See my previous blog post about the amazing experience

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Sailing and Crabs: 24 Hours in Annapolis

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