Annapolis Travel Guide From A Local!



I get asked a lot about ideas for what to do in Annapolis and had so much fun recently showing off the city to a group of bloggers with Visit Annapolis! Today I’m going to do a little recap of our trip – and also share my top 10 things to do if you’re visiting Annapolis from out of town, or just a local who wants to get better acquainted with this beautiful spot! You can also see my Kid Friendly City Guide to Annapolis right this way.

Picture of Lacey & I above (wearing Draper James from Rent The Runway)

Where To Stay

Hilton Garden Inn Downtown: Brand new with nautical inspired decor, this hotel is located on upper West Street which is home to several great bars and restaurants and a nice spot to call home base. All of our out of town bloggers stayed here and had a wonderful experience!

Historic Inns of Annapolis: For a more historic approach to your visit try one of the inns downtown – they are beautiful and offer a unique way to experiences your visit!


Annapolis has several really great places to eat – and here are my favorites to suggest to people visiting!

Iron Rooster: Iron Rooster has since expanded to several locations but started here in Annapolis, they serve breakfast all day and you’ll likely be greeted with a wait since it’s such a popular spot. I have to say, it’s worth it! Put your name on the list and then take a walk around Ego Alley. Be sure to order a pop tart for the table to share! It’s also kid-friendly if you have patient kiddos who can wait!

Vin 909: Hands down, my favorite restaurant in town! Another one that unfortunately doesn’t take reservations and if you don’t arrive when they open you can expect to wait at least an hour. But  – that’s ok when you can drink a glass (or bottle) of wine out in their beautiful yard. Pizzas, small plates and the best pulled mozzarella plus a really great affordable wine list!

Boatyard Bar & Grill: I always tell people to venture over to the “Maritime Republic of Eastport” away from the touristy part of downtown. It’s a working boat community with the most adorable houses, a great dive bar and this fun local restaurant that has really good seafood and cocktails. Oh – and the crab dip is a must order!

Level + Metropolitan: I group these together because they are similar but two entirely different establishments. Both offer great craft cocktails and a bar scene later in the evening but also boast delicious food menus – the small plates at Level are my favorite for groups!

Annapolis Ice Cream: There are a lot of ice cream spots in Downtown Annapolis but the very best is Annapolis Ice Cream. It’s made fresh and boasts an amazing assortment of flavors that change daily!

The Red Bean: Has great coffee drinks and afternoon affogato (my favorite)!

What To Do:

Naval Academy: You can’t visit Annapolis without taking a visit to the Naval Academy! Explore on your own or take a walking tour!

Banneker-Douglas Museum: Visit the state of Maryland’s official museum of African American heritage.
William Paca House & Gardens were built in the 1760s and are full of history! If you’re up for walking try one of the Colonial Walking Tours!
The Maritime Museum  is a great place for kids and adults to learn about the ecology of the Chesapeake Bay and Annapolis’ maritime history. They also host weddings and events – and it’s such a beautiful waterfront spot for a visit.
Schooner Woodwind: Experience Annapolis like the locals, by boat with a sunset cruise on this beautiful sailboat!
Maryland State House: Step inside the historic Maryland State House where the Maryland General Assembly
In Eastport wearing this Rebecca Taylor top from Rent The Runway, Abercrombie jeans & espadrilles 
Now here’s how we packed a ton into a 2 day media tour for our bloggers!
Breakfast at Iron Rooster followed by a walking tour of the Naval Academy. We unfortunately had a rainy, stormy few days but a few bloggers ventured out on the Schooner Woodwind for a cruise before exploring town on their own and meeting back up for dinner at Carpaccio.
Started off with breakfast at Miss Shirley’s Cafe and then a walking tour of Annapolis and tour of the state house with Watermark Tours . Then we met at Lightbox Studios (a great place for photoshoots and events!) and a painting lesson with local artist, Kim Hovell and a really good lunch catered by Main & Market. Local business, Maine Cottage set up an adorable and colorful lounge! Everyone took a rest before meeting at The Maritime Museum for oysters, bubbly and a fun educational session. We ended the evening in Eastport at Boatyard Bar and Grill.




Annapolis Travel Guide From A Local!



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