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The SK Way

The SK Way

A Classic and Preppy Life & Style Blog by Shannon Kirk

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Annapolis Travel Guide

June 1, 2022 · In: Life, Travel

Happy Wednesday, friends! I am so excited to be back with another blog post! This past weekend, my boyfriend and I met up in Annapolis, Maryland for Memorial Day. We had such a fun time and I was so happy that we were able to make it happen! Long distance isn’t always the easiest, especially in the military, so we try and make the most of our time together when we get it! In this week’s post, I wanted to share a little overview of our trip with my recommendations of what to do, where to eat, and more – I hope you enjoy!

United States Naval Academy Chapel

Where To Stay

One great thing about the Annapolis area is that there is no shortage of places to stay! There are plenty of Marriotts, Hiltons, etc. in and around the downtown area. The hotels were slightly more expensive than usual given it was a holiday weekend, but I don’t think you could go wrong with any of your options. If you’re looking for a more luxurious experience, definitely check out the Annapolis Waterfront Hotel. Although more expensive, It is located right in the heart of the downtown area with very close proximity to the historical district, Naval Academy, and more! If I were traveling here during the “off season” I would definitely check this out!

One of my outfits for dinner – linked on LTK!

What To Do

Located about an hour east of Washington D.C, there are so many fun things to do in Annapolis! If you enjoy history, there are so many fun things to explore here! Some of my favorite stops we made included:

  • Naval Academy
  • Harbor Queen Naval Academy & Chesapeake Bay Ferry Tour
    • tourist-y but a great option if you are unfamiliar with the area
  • Downtown Annapolis
    • Historic Section
    • Shops & Local Boutiques
    • Kilwinds Chocolate
  • Walk around the docks/harbor

We did not get a chance to make it to the Annapolis Maritime Museum, but this is also an option along with Kayak & Paddle Board rentals!

dinner at Latitude 38

Where To Eat

We ate at so many amazing restaurants here! I would love to go back and order everything on the menu, haha! If you ever find yourself in Annapolis, definitely check out these spots:

  • Chart House
    • a more formal dinner option with delicious fresh seafood – multiple locations across the U.S
  • Brown Mustache Coffee
    • the cutest independent coffee shop located inside of a small bookstore – order the caramel latte! I promise you will not be disappointed!
  • Naval Bagels
    • local bagel shop with great breakfast sandwiches! The perfect complement to your morning coffee before exploring the Naval Academy and downtown Annapolis
  • Latitude 38
    • a more casual dining experience with typical American food as well as seafood options. I highly recommend the blackened chicken Alfredo!
  • Storm Bros Ice Cream Factory
    • after a long day of walking, stop by storm bros for some ice cream! I had the caramel cookies & cream and it was to die for!

Thank you so much for reading! If you ever travel to Annapolis and end up trying any of these recommendations please let me know! I know you’ll have just as much fun as we did!

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By: Shannon · In: Life, Travel · Tagged: annapolis, classic style, coastal grandmother, coastal living, maryland, mdw, memorial day, preppy style, travel, travel blog, weekend recap, weekend travel

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