places to visit near DC: Annapolis Maryland

8 Great Things to Do in Annapolis

8 great things to do in Annapolis is my curated list of fun activities, historic destinations, and tasty dining and drink based on many visits to Maryland’s capital city.

My wife and I were fortunate to be included in the #DCTravelBlogger group hosted by the Annapolis Visitor Bureau. Our 24 hour visit included a stay at the luxurious Loews Annapolis, which featured this amazing stained glass window in our 5th floor lobby.

things to do in Annapolis: Loews Annapolis stained glass by Charles McCool for McCool Travel

places to see in Annapolis: Loews Annapolis stained glass

This list of 8 great things to do in Annapolis is my curated list as a result of several visits.

8 Great Things to Do in Annapolis

Annapolis: On the Water

Heck yeah, I can create a separate post of 8 Great Things to Do in Annapolis just on the water. Rent a kayak or SUP. Go fishing or crabbing. Take a boat tour on Harbor Queen. Ride on a classic schooner. Walk the plank and shoot water cannons from a pirate ship. Learn to sail at a sailing school. Ride the water taxi (only $3 across to Eastport, $8 maximum). Sail on a private sailboat (OK, you have to know someone). Swim. Water ski. Windsurf or kite surf. Eat, drink, sun bathe. Hmmm, maybe enough for two 8 great things to do in Annapolis on the water posts.

Sailing on Chesapeake Bay from Annapolis

where to go in Annapolis: Sailing on Chesapeake Bay

Harbor Queen Annapolis

things to do in Annapolis: Harbor Queen

Naval Academy

Speaking of water, there is also no denying that Annapolis is a Navy town. While the US Naval Academy is guarded, there are some public entrances and attractions. The easiest and most popular is probably the John Barry gate along Prince George Street near the City Dock area. Commodore Barry was the founder of the US Navy and there is a memorial to him just inside the gate.

US Naval Academy, photo by

US Naval Academy, photo by

The nearby visitor center has a short film on the history of the US Navy and Naval Academy, poignant displays, and a gift shop. The Admissions Office is on the second deck (upstairs level) if you want to scare—I mean encourage—your children. Worship services and three dining options and are available to visitors. Public tours cost $10.50 per adult.

Sailing Hall of Fame

It certainly makes sense that America’s Sailing Capital hosts the National Sailing Hall of Fame. Personally, I like to visit Halls of Fame to be inspired by persons who excel at their passion.

Ice Cream

The only time I did not see at least several dozen people in line at the Annapolis Ice Cream Company was Sunday morning—before it opened. Walking around, I spotted several other ice cream shops. Did I try any? NO! Obviously I must return to Annapolis.

things to do in Annapolis: Annapolis Ice Cream Company by Charles McCool for McCool Travel

where to eat in Annapolis: Annapolis Ice Cream Company

Annapolis Ice Cream Factory line

popular Annapolis Ice Cream Company (with the lurking Maryland State House)

Kilwins Ice Cream Annapolis

Annapolis casual eats: Kilwins Ice Cream

Irish Pubs in Annapolis

Our #DCTravelBlogger group was treated to lunch at Galway Bay Irish Pub and sampled their Irish egg nog—try it around the year end holidays! Walking around town that afternoon and evening, I said, “there’s another Irish pub” more than I expected. I did not count but, while researching, found four other Irish pubs (and other non-Irish pubs) and one Irish store. Annapolis also hosts an Irish Festival in July.

Galway Bay Irish Pub, Annapolis

Galway Bay Irish Pub, Annapolis

Galway Bay Annapolis egg nog

Annapolis restaurant: Irish egg nog at Galway Bay

Galway Bay Irish egg nog Annapolis

things to do in Annapolis: Galway Bay Irish egg nog Annapolis – Sláinte

Annapolis History

OK, did you know that Annapolis served as the first Capital of the United States of America? For 9 months at the end of the American Revolution, Congress met at the Maryland State House and Annapolis is considered the first peacetime capital of the new nation. History oozes from every brick. Visit historic St. Anne’s Church—whose congregation included two Declaration of Independence signers and Francis Scott Key (he wrote the Star Spangled Banner), the cozy alleys, pre-Revolution taverns, and historic homes.

1747 Pub Annapolis

things to do in Annapolis MD: 1747 Pub

Cabbage Alley Annapolis

Cabbage Alley, Annapolis

Annapolis historic district marker

things to do in Annapolis MD: Annapolis historic district marker

St. Anne's church Annapolis

where to visit in Annapolis MD: St. Anne’s Church


Visiting a winery in Annapolis was a pleasant surprise. Our wine flight tasting at Great Frogs was accompanied by local artisanal cheeses, fruit, and marcona almonds. The port wine was my favorite and is sold in cool one quart maple syrup glass containers. I cringed at the $50 bottle price but, you know what, I should have bought one. When I return for my ice cream adventure, I intend to buy a bottle.

Great Frogs wine tasting Annapolis

things to do in Annapolis: wine tasting at Great Frogs

Great Frogs wine bottles Annapolis

where to drink in Annapolis: Great Frogs wine bottles

People Watching in Annapolis

Ego Alley, a narrow stretch of water off Spa Creek near the Annapolis City Dock, is among the places to see and be seen. In case it is not obvious, boaters and yacht owners show off their craft along ego alley, especially on brilliant weekend days. Pusser’s Caribbean Grille is a remarkable location (along Ego Alley) for a meal, snack, or drink.

Walking around town, mainly along Main Street, on Saturday night and Sunday morning, we saw countless youngsters dressed in their finest white Naval uniforms. Almost all had “Class of 2019” on their name tags, indicating that they are incoming freshmen. Good luck to the new midshipmen! Look for action near the Alex Haley and Kunte Kinte memorial at City Dock. When the crowd is heavy, at least two men are making balloon animals for kiddies of all ages. Buskers (street performers) further congest the already crowded area.

What are your suggestions for things to do in Annapolis?

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8 Great Things To Do in Annapolis published on 25 August 2015.


8 great things to do in Annapolis is my curated list of fun activities, historic destinations, and tasty dining and drink in Maryland's capital city.

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42 Responses to “8 Great Things to Do in Annapolis”

  1. hotmamatravel July 3, 2018 at 8:53 pm #

    We love Annapolis when we visited. We did the Harbor Queen tour and enjoyed live music at Galway Bay Pub. Actually there were many places that had live music and the best part was that we could bring the kids along to enjoy the music too.

  2. Christina thomas April 13, 2016 at 12:13 am #

    I need to go for the ice cream! Oh and the wine! Cheers to a fun trip!

    • McCool Travel April 18, 2016 at 7:55 am #

      Annapolis is a nice foodie (and wine) town with a big sailing problem. 😀

  3. mariamichelle117 April 12, 2016 at 7:14 pm #

    I still have many states to visit and Maryland is one of them. I had no idea there was so much to do there. I think I would like the sailing museum and I know I’d love the ice cream!

  4. Jaillan Yehia April 12, 2016 at 6:31 pm #

    You had me at Irish Pubs to be honest 🙂

  5. Sanket D. April 12, 2016 at 12:26 pm #

    Haha! There’s a Galway Bay in Australia? That’s pretty interesting. Galway’s one of my favorite places in the world. Loved reading about your sailing experience too. Definitely on my to-do list that one!

    • McCool Travel April 18, 2016 at 7:58 am #

      Thank you, Sanket. Wow, I might have to visit the Australia Galway and compare to Ireland.

  6. Irene S. Levine April 11, 2016 at 8:11 pm #

    When we lived in DC, we kept a sailboat in Annapolis. Love the place!

  7. travelwithmarilyn April 11, 2016 at 6:11 pm #

    I always enjoy idea articles…well done!!

  8. Jan April 11, 2016 at 12:51 pm #

    I’m sure, like many others, I only knew about Annapolis as a Navy town. Loved the idea of the Great Frogs wine and cheese tasting. I agree with you about visiting a Hall of Fame. Wimbledon was so impressive and the Sailing Hall Of Fame would be interesting too.

    • McCool Travel April 11, 2016 at 2:15 pm #

      Wineries are popping up all over the midAtlantic and US East coast, so I should not have been surprised. But I was.

  9. Jack Moscrop April 11, 2016 at 8:07 am #

    Wow, it’s hard to know where I would start with such a fab list of things to do!

  10. Grey World Nomads April 11, 2016 at 6:37 am #

    First I thought by your pictures Annapolis is in Greece. Guess I must work on my geographic skills 😉 #anapolis #greece #maryland

    • McCool Travel April 11, 2016 at 2:11 pm #

      Love it. Maybe there is an Annapolis building, at least, in Greece.

  11. Suzanne Fluhr April 11, 2016 at 12:38 am #

    Hmm. Some people seem to think Philadelphia was the first capital of the US. I’m sure there’s all sorts of subtlety and nuances involved in why each city makes this claim. (To perhaps state the obvious, I’m from Philly.) One of my college friends was employed by Maryland’s scenic river program. She got to keep the/an official state canoe in her garage.

    • McCool Travel April 11, 2016 at 2:16 pm #

      Philadelphia sure has a lot of history and quaintness. Great town, I mean city.

  12. Lauren W. September 22, 2015 at 12:29 pm #

    You forgot “Arts”! For a smaller city, Annapolis boasts a huge number of performing arts organizations, art galleries, and music venues. My favorite is the Annapolis Summer Garden Theatre, an outdoor community theatre that presents musicals outdoors in the summertime at their historic venue at City Dock. So much fun!

    • McCool Travel September 22, 2015 at 5:54 pm #

      Just ran out of room! Annapolis is very arts-y. Thank you, Lauren.

  13. suereddel August 29, 2015 at 7:36 pm #

    Great timing on your post! We have friends who just moved to Annapolis and we can’t wait to visit them. We’ll definitely share your finds with them and try them out ourselves when we visit.

  14. Cathy Sweeney August 29, 2015 at 1:48 pm #

    Well, I’m a little ashamed that I didn’t know that Annapolis was the first US capital m– or maybe I just forgot. I’ve never been to Annapolis and it looks like I’ve been missing out on some great experiences. Would definitely like to try the port. If you’re regretting that you didn’t buy the $50 bottle, it must have been very, very good.

    • McCool Travel August 30, 2015 at 9:08 am #

      well, if you do visit, let me know. Just an you from me so I can play tour guide, and go buy that port!

  15. santafetraveler August 28, 2015 at 4:39 pm #

    We loved Annapolis- such a historic city. We have the Chesapeake with us every day- we have posters of two of Marion Warren’s famous Chesapeake photos (the Thomas Light, and skipjacks) hanging on our walls, a souvenir from a long ago DelMarVa vacation.

    • McCool Travel August 28, 2015 at 9:46 pm #

      Nice gifts. Fun to collect things for our trips. I bought chili covers for Christmas lights in your fair town and break them out every December.

  16. Kay Dougherty August 28, 2015 at 10:17 am #

    I lived in the D.C. area and then Baltimore for a total of about 15 years and always loved to visit Annapolis. It looks as if it’s added a lot of businesses since then. I got a smile out of the reference to “ego alley” because I’d forgotten about it.

  17. Carole Terwilliger Meyers August 27, 2015 at 7:40 pm #

    I did not know that Annapolis was the first Capital of the United States of America. But now I do! I’d also love to tour the Naval Academy. Sound like a getaway-worthy city.

    • McCool Travel August 28, 2015 at 9:48 pm #

      It is a great destination. Close to DC and Baltimore.

  18. Jessica August 26, 2015 at 6:17 pm #

    Thanks for joining us. We also had the perfect weather Saturday!

  19. Paula McInerney August 26, 2015 at 4:14 am #

    I have to admit that I had not heard of Annapolis in Maryland. Like Australia, America is such a large place. I had to google where it was. It does appear that it has a lot going for it, with a water location and rich history

    • McCool Travel August 27, 2015 at 6:42 am #

      I hear ya. I know a handful of major cities in Australia but you (and others) write about such cool places I have never heard of. That’s a great thing.

  20. Elaine J. Masters August 25, 2015 at 3:43 pm #

    I love the combination of history and new uses. Looks like you had a perfectly delicious day.


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