. Annapolis welcomes me home : Budget Travel Adventures

Annapolis welcomes me home

Annapolis Maryland capitalWalking through the streets of town, I take a shortcut as I grab a bite to eat for breakfast.  As I walk in the door, I chat for a minute with Chuck before I grab a table.  After a quick bite to eat, I say my goodbyes and make plans to meet up with Chuck later.

A stroll through town takes me by the mom and pop shops I’ve come to love.  On the streets, I pass by strangers who seem more like old friends I’ve just met as we smile and say hello.

I’ve made quite a few friends here.  I stop into a restaurant and talk with the owner.  I grab some ice cream and talk some college football with a couple in the ice cream shop.  For dinner, I enjoy a lovely Italian meal with the owner and his friend.  We spend the next four hours eating and hanging out as he introduces me to some more of his friends.

Walking the streets, I remember all the people that I’ve met and all the places I’ve been.  I walk into shops and restaurants and know people by name.  This is my community, my town, and my people – this place feels like home.

I’ve spent a total of four days here.

Yet traveling to a place like Annapolis, I feel that I am at home in my community with people that I know in a place I have grown to love.  I spent time connecting with the locals here and they already feel like friends.  I came here for the College Football Travel Tour but realized that there is so much more to Annapolis than the home of the United State Naval Academy.

Annapolis – a small town rich in history and food

Main St Annapolis MarylandGeorge Washington and Benjamin Franklin roamed the streets.  This city served as our nation’s capital.  Million dollar yachts pass through the harbor each year.  Signers of the Declaration of Independence called this place home.  Many of the buildings in town date to the 1700s.

This city of about 40,000 people is rich in history, money, and culture.  Yet Annapolis doesn’t flaunt any of it.  To even call this place a city is a bit misleading.  This is a small town – a community of people that is warm, inviting, and hospitable.  Six degrees of separation doesn’t apply here – it’s more like zero or one degree.  Everyone seems to know everybody else.

However, thousands and thousands of visitors pass through Annapolis each year.  With the Naval Academy just a few blocks from all the shops and restaurants, midshipman and parents alike fill the streets during the year while tourists and sailors converge by land and sea during the spring, summer, and fall.

With it’s proximity to Baltimore and Washington, many people make this place a destination to enjoy and learn about the history.  The variety of food and restaurants here make Annapolis one of the main reasons why people visit.  Places like Chick & Ruth’s Delly have been featured on shows like Man vs Food and another restaurant, Galway Bay, will be on an upcoming episode of Diners, Drive-ins, and Dives.

Seafood, Italian, Mediterranean, sushi, Greek, steak, wine, cocktails, ice cream – enjoy all of this and more at world class and award winning restaurants all over Annapolis.  You can even say the “Pledge of Allegiance” each morning before breakfast or drink some rum with sailors.  I admit that I don’t care much about food when I travel (yet I am mindful of cheap easy meals when traveling).  However, Annapolis has changed me a little – I enjoyed some of the best food I’ve ever eaten and tried a number of new dishes that I can’t wait to share with others.

History, food, and boats alone would be enough for people to visit Annapolis.  However, this place is so much more than that.

The other side of Annapolis – a community where everyone knows your name

Chick and Ruth's Delly Annapolis MarylandEven though Annapolis gets a lot of tourists, this place gets nowhere near the attention it deserves.  To be honest, I am conflicted.  This is a fantastic community that has so much to offer in terms of culture, food, history, and people.  On the other hand, being overrun with tourists would ruin its charm.

Many people say that their place is really a place of community and togetherness.  While this may be true in Annapolis, I didn’t have to read this in a magazine or guidebook or hear people brag about what a great place this.  Honestly, I didn’t know much about Annapolis before I got there.  Yet I experienced this community myself as I realized how many of my new friends already knew each other.

Marc Lucas is the owner of Piccola Roma Italian restaurant on Main St.  A couple of doors down, he shares an alley with Walter and Nancy Giera – the owners of the homemade ice cream shop Annapolis Ice Cream Company.  Marc allows Nancy and Walter to use his garbage can in the alley.  In return, they supply him with ice cream for his restaurant.

With a variety of restaurants in town, they all realize how each one is a vital part of this community.  Annapolis isn’t a great place if there is just one outstanding place to eat.  However, all of them succeeding – and helping one another – is what makes the food culture here thrive.

An Italian restaurant and a mom and pop diner which says the pledge of allegiance every morning don’t have much in common.  Yet restaurants here support one another, help each other out, exchange ideas about what works and what doesn’t, and even eat at the other dining establishments in town.  When one restaurant is running low on supplies, another restaurant will lend them what they need.

oysters at the Boatyard Bar and Grill Annapolis MarylandAnd this type of community extends to the very people that live and work here.  In various restaurants, I had conversations with strangers about food, travel, football, and more.  During an evening at dinner, a conversation with the person beside me led to me being invited to join the table and have my dinner paid for by my new friend.

While this is the center of government in Maryland and is located just a few miles from the nation’s capital, this isn’t an area that is too concerned with politics.  Governors eat breakfast at Chick & Ruth’s and celebrate special occasions with everyone else in their favorite restaurants.  Here in Annapolis, they are just one of the regular people enjoying all this city has to offer.

While red tape can make things frustrating at times for home owners and businesses, people aren’t as passionate about politics as one might imagine.  People care about the issues and want problems solved.  Even the legislature here takes a bit of a laid back approach as they only meet for 90 days a year – from January until the beginning of April.

Annapolis isn’t utopia.  Housing here is very expensive and homes are in the millions in many parts of town.  Parking is plentiful but you may have to pay for a spot in a garage or use valet parking in a town where you don’t even need a car.  Hotels in town can be a bit expensive at times, especially during big events at the Naval Academy or when the boat shows are in town.  While the weather can be quite pleasant most of the year, snow and cold can shut things down for a bit during the winter months.

However, Annapolis is a great community.  Add to it the Naval Academy and what it offers to this place and it’s hard to imagine a city that has more to offer than this one.  I can’t speak for education (although the one you get at the Naval Academy is one of the best in the country) or politics but the people make this town (it’s so hard to call it a city) worth visiting.  It’s a small town in a big city that really isn’t a big city.  Whether you like history, food, boats, culture, or politics, this isn’t a bad place to spend a few days.

One thing people may not know about Annapolis is that many people here have money.  Yet no one who visits here would ever know it.  Like the history, culture, people, and food, it isn’t flaunted.

I think about the people I met and the places I visited and those memories bring a smile to my face.  The people I met are some of the best things about travel .  And while travel doesn’t always go as planned, moments like this make travel feel more like home.

Annapolis is understated, underrated, and doesn’t get the attention that it deserves.  After spending a few days here, I realize that’s not a bad thing.

What are some of the most underrated places you have visited?

Stay tuned for more features on Annapolis including the US Naval Academy.  Discover things to do, places to eat, and where to stay when visiting Maryland’s capital. 

A special thanks to the Annapolis and Chesapeake Bay Visitor’s Center and all the people I met in Annapolis for their hospitality and assistance during my time in Annapolis.

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Filed Under: College Football Travel TourDestinationsFeaturedUS Naval AcademyUSA


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  1. Annapolis sounds great — friendly, great food and close to a couple of great cities. Since you asked, I think that Milwaukee is very underrated. Lots going on there — it’s not just beer, brats and baseball (although those are great things). I lived there for a few years and loved it!

    • I thought about Milwaukee this summer. I’ve heard some good things about it and would love to visit. I’ve never been to that part of the US so would be fun to explore. Plus I like beer, brats, and baseball (well not a huge fan of beer) so this sounds like fun.

      I love the community in Annapolis. It was not what I expected when I went there but I will definitely be back.

  2. Great report..I love slices of Americana like this. I’m a fan of Sandusky, Ohio…another place where you quickly learn everyone’s name, especially when you visit lifelong residents like I do…

    • It’s great to visit a place where you have connections there that can give you a different look. Meeting so many people that I did, it allowed me to see a part of Annapolis I could never see on my own. I hope to make it to Ohio next year and maybe I will check out Sandusky when I am there. What things would you recommend to see and do? How close is it to Columbus?

  3. Sounds like a great place. You’ve really done a nice job highlighting not just the things to do and see but what the feel of the town is like.

    • Thanks Stephanie! For me, that is the key. Anyone can write a list of things to see and do. However, the experience, the feel, and the people really say a lot about what it is really like to visit there.

  4. I would have never even considered traveling here for a football game or for anything. It sounds like a charming community and a place I would enjoy.

    • Ted, I thought the same thing. That is the type of thing I am enjoying the most about this College Football Travel Tour – the people. This is a fantastic community and a great place to visit – even in the middle of December!

  5. Amanda says:

    It looks and sounds like a great little town! A place that would be right up my alley, I think. Thanks for sharing it with us!

    As for underrated places I’ve been to… hmm. Definitely the Kapiti Coast in NZ, which people told me would be boring, but which was actually fantastic! I also think Wellington often gets overlooked more than it should. And, here in the U.S., Pittsburgh is an amazing city that people don’t seem to think about much (unless it comes to sports).

    • I really didn’t know much about Annapolis but I really liked the design. It’s a great town and really is a great place to spend a few days. I can only imagine how much nicer it would be during the summer.

      As for New Zealand, I’ve never been there but it sounds wonderful. I know it is one of your favorite places to go. I believe there are a lot of places like this that people know about and that are charming but aren’t well known. I honestly would have never thought of Pittsburgh as a city that would be underrated. I guess it has really cleaned itself up from 30 years ago and the industrial city that it was.

  6. Anna says:

    I have been to the States only once – in NY and for us, the Europeans America is very interesting because it is very different! And Annapolis sounds really attractive for me:)

  7. Ann says:

    Hi Jeremy,
    Awesome article about Annapolis. It is wonderful to have so much detail. Honestly, other than it’s location, it sounds an awful lot like Greenville, SC. It is so wonderful to visit a place for a short time and feel that you know everyone in town. The restaurants sound amazing too.

    • Thanks Ann! I talked to a lot of people in Annapolis and many people told me Annapolis is a lot like Charleston, just smaller. They have the history, homes, on the water, local food. It’s very similar.

      I will do more on the restaurants there in a couple of weeks. I don’t care much for food when I travel but this really opened my eyes to how big food is for people when they travel.

      Not sure if you knew this or not (you may) but I was born and raised in South Carolina!

  8. Laurel says:

    I LOVE Annapolis and lived there for 6 months while working. I agree it is underrated. I think it’s a great place to live or visit.

  9. Jenna says:

    I also loved Annapolis when I spent just a day there with my dad (he was living in VA then). It is beautiful, has great architecture, and has a historic feeling. I’m glad you enjoyed your time there! It made me think about doing an East Coast trip sometime soon.

  10. Yes Annapolis is expensive but fun. Spent a weekend in a sailing school just to do it. I knew someone who was a computer dispatcher when I used to repair computers, so , I stayed with her and her husband. It was a great weekend and beautiful weather.

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