Travel Guide: A Coastal Getaway To Annapolis, Maryland

One of my favorite quick jaunts from DC is Annapolis, Maryland. A charming, historic town on the water, that also happens to be the capital of Maryland (no, it’s not Baltimore), it’s just under an hour from DC but feels a world away.

Despite how many times I’ve been to Annapolis for crabs, shopping, sailing, strolling the storied streets, I had never actually stayed there overnight, so I was delighted to stay with Annapolis Waterfront Hotel, which is the only hotel in the area that’s on the water. The Friday before the Fourth of July seemed like the perfect time to make a trip up there and, despite the heat, it was a lovely nautical getaway.


You know first on my agenda for any trip is, “Where and what am I going to eat?” As soon as Adam and I had dropped off our bags, we walked downtown to Harry Browne’s, right by the Maryland State Capitol. The restaurant has a super old school, Art Deco era vibe and gorgeous views of the Capitol and the surrounding homes. When the waiter told us that glasses of wine were $5 at lunch, I became one of those ladies that drinks white wine at 1 p.m. on a weekday. Our meal was the standard Annapolis fare that you will find at most every restaurant in the area — crabcakes, crab everything. But, it was delicious, and the ambiance made the meal.

For dinner, I did want to shake it up a bit and look beyond crabcakes, even if that is what Maryland does. We walked up to Vin 909 in Eastport, which was a charming restaurant in an old house that had a bit of an artsy, homey vibe. It seemed filled with locals from the neighborhood on a Friday evening and the back patio is laid back and perfect for enjoying a leisurely weekend supper. We split a salad and pizza while drinking craft beer and it was exactly the kind of relaxing meal that you want when traveling.

A quick and yummy breakfast of croissants, coffee, and bagel sandwiches the next morning at Bean Rush Cafe was the ideal way to close out the weekend, though I wished we’d discovered its neighborhood of West Annapolis with more time to explore. Just another reason to go back!


I’ve been to Annapolis for everything from crab picking to touring the Naval Academy to shopping, but on this particular trip we took an afternoon sail on the Schooner Woodwind. On a gorgeous 74 foot sailboat, the crew takes out two hour tours around the Annapolis area. There’s beer, wine, and more aboard the boat, and even on a hot day like we had, it’s a refreshing way to spend an afternoon. The crew couldn’t be friendlier and will give you all the intel on spots to check out around the city.

Pro tip: if you have a card for a VIP beverage, make sure you get the koozie at the ticket counter before you get on the boat. They will not honor it if you don’t already have the VIP koozie!


We stayed at the Annapolis Waterfront Hotel, which is located right on the water in downtown Annapolis and a quick walk across a bridge to the darling town of Eastport. You won’t find a more convenient spot for exploring all of Annapolis. Whether you’re looking to shop, eat, get out on the water, or enjoy the historic sites, you’ll never be more than a 10-15 minute stroll.

Plus, you can’t beat the nautical touches throughout the hotel from the vintage Naval Academy photographs to the anchor motifs to the navy and white color theme. The C.O. Bigelow bath products are also a wonderful touch.

If you’re planning a trip to Annapolis, let me know and I can give you even more recommendations! On the flip side, if you have any amazing restaurants or fun experiences in Annapolis that I must try on my next trip, be sure to let me know.

Thank you to Annapolis Waterfront Hotel and the Schooner Woodwind for hosting me during my stay in Annapolis. All opinions and images are my own and you can bet I’ll be back soon!


1 Comment

  1. Monica {Cake and Lilies}
    July 18, 2017 / 12:17 pm

    Love AWH so much!! Annapolis is da besttt. Love your photos, too!

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