Charming cobblestone streets, a prime location on the Chesapeake Bay and centuries of history make Annapolis a great destination for a relaxing weekend trip. Located less than an hour from Washington DC, Annapolis is popular both with politicos looking to escape the Beltway hustle and with visitors to the U.S.Capital who want to experience the mid-Atlantic beyond the National Mall. While you may know Annapolis as Maryland’s state capital did you know it also briefly the capital of the United States in 1783? That is just one of the secrets I found in this captivating town by the bay.
Stay
The Loews Annapolis is my pick for where to base your Annapolis adventures. This four star luxury hotel is within easy walking distance of Main Street, the United States Naval Academy, and everything else historic downtown Annapolis has to offer. Decorated in a smartly modern nautical theme, the sleek lobby and spacious guest rooms are a welcoming retreat from your day exploring Naptown. Be sure to stop by BAROAK for a taste of moules frites by award winning Chef Teddy Folkman.
Do
History
With over four centuries of history and a rich mid-Atlantic heritage, Annapolis is known as a “Museum Without Walls”. While strolling through the charming brick paved streets of the historic center stop by the historic St. Anne’s Church, visit the homes of one of the three signers of the Declaration of Independence that called Annapolis home or watch history being made in the Maryland State House.
United States Naval Academy
There’s no denying the U.S. Naval Academy is the anchor of downtown Annapolis. Training the leaders of the United States Navy since 1845, the Naval Academy currenty offers 18 different majors and enrolls 4,400 midshipmen. Life for a midshipmen is strictly regimented and you can often spot plebes, or freshmen midshipmen out in town in their crisply pressed uniforms. You don’t have to enlist to pay a visit to the Naval Academy, public guided walking tours are available from the Armel-Leftwich Visitors Center.
Visit a Winery
Wine doesn’t immediately come to mind when thinking of Annapolis but the folks at Great Frogs Winery are looking to change that. This charming winery is located just minutes from downtown Annapolis but feels worlds away. Pay a visit to the rustic farmhouse turned tasting room for a sample of their best vintages. My favorites were the 2013 White Squall, a buttery white blend of Chardonnay, Viognier, Traminette and Marsanne; and the 2013 City Dock, a luscious port-style dessert wine.
Get out on the water
With over 533 miles of shoreline and the Chesapeake Bay as its backyard, there is no better way to experience Annapolis than out on the water. Known as the “Sailing Capital of the US”, a steady parade of sails can be seen throughout the bay while kayakers and paddle boarders prefer to explore the miles of streams and inlets around Annapolis. Got something a little more relaxing in mind? Hop aboard a sightseeing cruise on the Harbor Queen or a sunset cruise on the Schooner Woodwind.
Eat
Seafood
With the abundant waters of the Chesapeake Bay Bay nearby it’s no surprise the seafood reigns supreme on Annapolis’ menus and none more so than Maryland’s famous crab cakes. While who makes the best crab cakes is a hotly contested debate among locals its worth it to sample a variety and come to your own conclusion. Start your crab cake crawl with crab cake topped eggs Benedict at the Boatyard Bar and Grill in the quirky neighborhood of Eastport, Annapolis’s answer to Key West. After a busy morning exploring the city’s historic sites stop by Galway Bay Irish Pub for the combo platter of crab cakes and fried oysters for a true taste of the Chesapeake. Later that evening unwind with a romantic dinner at Carrol’s Creek Cafe, where you can savor their signature crab cakes as you watch the sun set over the harbor.
Ice Cream
Several ice cream shops line brick paved Main Street but only one of them consistently had lines out the door. Annapolis Ice Cream Company has won “Best Ice Cream in Annapolis” for the past 10 years running and makes over 36 flavors of ice cream fresh in store every day. Of course you’ll find classics like chocolate and vanilla but Annapolis Ice Cream Company also shows its creative side with flavors like lemon poppyseed and strawberry nutella.
Rich in history with a vibrant culinary scene and a prime location on the Chesapeake Bay, Annapolis is a great destination for a relaxing weekend trip. Have you visited this charming bayside town?
I was graciously hosted by Visit Annapolis but as always all opinions are my own.
Polly says
I was traumatized at a young age by a cross country training camp at the naval academy, but I think I might be able to return and enjoy it at this point 🙂
Brianna says
At least you wouldn’t have to run this time!
Tess says
Wow! Great photos! I am from Washington DC, not far from here, and I love seeing a local place! Safe travels 🙂
Brianna says
Thanks Tess! DC is a favorite of mine, I go up there pretty often.
Charles McCool says
Ice Cream! I must return to Annapolis simply to visit all of those ice cream shops. Lovely photos.
Brianna says
I am also one would would definitely travel just for ice cream.
Stephen Garone says
Nice tips. Thanks!
Brianna says
Thanks Stephen!
Vicky and Buddy says
I loved this post! Maryland has always been one of my favorite states and I try to visit every few years. I need to spend more time in Annapolis though. Especially to eat more ice cream! 😉
Brianna says
Eating more ice cream is always a good idea.
Beth says
This looks like the best way to spend a weekend…especially this Labor Day weekend! I’d love to spend a day on the water, followed by wine and seafood. Thanks for the list to get started!
Brianna says
Annapolis is the perfect place to do all three!
Valerie says
Wow! I was born in Maryland but haven’t been back since I became a more active traveler; it seems like it has grown into such an interesting destination to visit… and the food looks fantastic (it also helps that now that I’m an adult, I like seafood more 🙂 ).
Great post, and cool to learn that Annapolis likes working with bloggers too!
Brianna says
Annapolis surprised me, it’s such a cool little city.
Katja - globetotting says
Annapolis looks beautiful!! I don’t know this part of the States at all but I’ve heard lots of good things. I had never heard of Annapolis before now though. I’m sold on the water, the wine and the ice cream! 🙂
Brianna says
It would be a great option as a day trip from DC.
Bobbi Gould says
I have never been hear before but the history sounds fascinating! I had no idea there was ever even a capital of the US? They need to teach these things in high school. I would have paid much more attention 😉
Brianna says
Washington DC, the current capital, is just an hour away.
Mallory says
Seafood. History. Waterfront. Wine. Ice Cream. Say no more. You’ve got me hooked! Looks like a glorious place to visit.
Brianna says
What more could you ask for?
anna says
The seafood looks so good! Must be super fresh as well. I have to admit, I got too distracted by the food photos that I couldn’t concentrate on the rest! :p Now, where to find some crab cakes while in Java? x
Brianna says
I’m sure Java has some amazing seafood as well.
Laura says
I’ve visited Anapolis many times while living in DC and I love it. It has a real charm that you can’t find often and it right on the water which is even better. Love it.
Brianna says
You hit the nail on the head, gotta love a place that still retains its charms.
annita says
Food looks great! Worth a trip for the cuisine.
Brianna says
Definitely.
Kimberly Erin @ walkaboot.ca says
I have spent my share of time on the East Side of the USA, but the country is SO BIG I just have so much more to see. Places like this make me want to put on a sun dress, eat ice cream and roam. I will be putting much more time into the states in the future 🙂
Brianna says
The US is so vast and varied, each area has its own unique charms.
Jessica van Dop DeJesus says
Great recap of our #DCTravelBlogger trip to Annapolis! Glad you were able to join us!
Brianna says
Thanks for organizing the trip, it was great to see you as always!
Jessica van Dop DeJesus says
Great recap of our DCTravelBlogger trip to Annapolis! Glad you were able to join us!
Amanda & Brian - Eat_Work_Travel says
Looks like you had a lovely time in Annapolis! Those crab cakes look spectacular. It’s been several years since we’ve been there and being able to experience the history, eat well and even visit a winery is the recipe for the perfect weekend!
Brianna says
History, food and wine; what could be better?
Jolanta | Casual Travelers says
History, wine, seafood, and sailing? Why haven’t we visited Annapolis before?! I’ll have to make sure we stop there next time we’re in the area! Thanks for sharing all the tips on what to do once we’re there.
Brianna says
It’s less than an hour from DC and would make a great day trip the next time you visit the US capital.
travelling chingrita says
I’ve heard wonderful things about cruising Chesapeake Bay’s shoreline and can only imagine how tasty the seafood is. Crab cake benedict for breakfast? #win
Brianna says
#breakfastwin.
Brooke of Passport Couture says
I didn’t know anything about Annapolis, but I can see why it’s a great getaway from the city. I’d be interested in visiting the historic sites for their architecture! Thanks for sharing this unique location.
Brianna says
Annapolis definitely kniws how to do it right.
Jennifer @ Made all the Difference Travel Blog says
I really want to go sailing at Annapolis. The water looks amazing. I wouldn’t mind hanging around the Naval Acadamy and watching the eye candy wander by.
Brianna says
I thought the same thing until I realized I am technically old enough to be their mom lol.
Lindsay Nieminen says
My hubby loves American history ( we are Canadians) and would love to visit the Naval Academy! ( I think he secretly dreamed of joining the navy!) the town looks beautiful and I would love to get out on the water!
Brianna says
Annapolis is a great stop for any history buff but especially someone who is into Naval history.
RobRob@TravelLatte(.net) says
What a cool post – Crab cakes? Ice Cream? Wine? Sold! I’ve never been to Annapolis, but we have been thinking about another trip to the DC area so I’m making notes. No, actually, I’m just bookmarking this post! 🙂 Glad I followed the #WeekendWanderlust linkup!
Brianna says
I’m so glad you found this post helpful, Annapolis is a great little town.
Tamara says
I love Annapolis. Well I’ll admit, I love just about everywhere on the Chesapeake Bay. It has been years since I stayed overnight (the Loews looks great) but I did have dinner at Carrol’s Creek last year when I was passing through.
Brianna says
Carrol’s Creek was amazing, I’m still dreaming about that dinner!
Heather | girlichef says
Crab Cake topped Eggs Benedict!? Annapolis looks like a fun place to spend a few days. I love the thought of a Museum without Walls.
Brianna says
The crab cakes here are reason enough to visit.
Andi says
My parents lived here when they were first married, but I have never been. Looks like a great place for a weekend getaway!
Brianna says
Time to dig up some family history?
Kelly @ TastingPage says
I used to live in Baltimore so Annapolis was always an easy, and fun day trip for us. I wasn’t there when there were wineries though. I have to go back and check them out!
Brianna says
You can never go wrong with a stop to a winery IMO.
Nyssa | The Cultureur says
Annapolis looks lovely — been on my list for some time now!
Brianna says
Annapolis is charming, I absolutely loved it!
Murissa says
Looks like a perfect getaway – ice cream and wine are always a couple key ingredients!
Brianna says
ice cream and wine are great any weekend!
Chanel | Cultural Xplorer says
Annapolis looks like a lovely place to visit. I keep telling myself that I want to explore more of the DMV area in the future 😀
Brianna says
It is a charming area and not that far from NYC!
Jennifer Kaye says
Thanks for the great write up of our town! And you have a wonderful picture of both of our Schooners sailing on the Bay! Thanks for the mention #1, and if you wouldn’t mind sharing your photo… it could also win you a Boat and Breakfast package on our boat for 2016. (A great reason to come back.) We have a photo contest and you can enter the pic of both schooners. http://www.schoonerwoodwind.com/2015-photo-contest/
Thanks so much for the mention and the great blog of our favorite city!
Brianna says
Thanks so much Jennifer! That sounds like a really cool experience, I’ll definitely check it out!
Esther Lee says
this place looks so charming! And I’m a fan of any city / town near a body of water! 🙂
Brianna says
It is a wonderful place for a quick weekend, you and Jacob would love it!
Gloucester toes says
So so amazing
Hugo says
Nice little town to explore. I prefer such places with some history and that look like an open air museum.
Had no idea Annapolis was once the capital of the US. Always learning.
I would definitely try those ice creams!
Brianna says
There was a lot about Annapolis that surprised me but I had a fantastic time there.
Carol Colborn says
We passed through Annapolis in 2010 but failed to see anything but the Naval Academy. Didn’t even get to know it was once the capital of the US.
Brianna says
The Naval Academy is pretty spectacular though isn’t it?
Fiona says
It looks truly stunning. I love the parts of the US with heritage. And of course I love wine! Definitely worth a visit
Brianna says
I too love discovering areas with a long history and who doesn’t love wine?
Chris says
It is so hot outside right not that ice-cream looks delicious!!! My neighbour to the south always surprises me with these picturesque little towns and cities. Very nice place. Great post!!!
Brianna says
That’s the great thing about the US, we have so many different places to explore!
Erica says
Annapolis sounds like a great weekend getaway. I could spend an entire day just exploring its streets and eat my way around!
Brianna says
Heehee, that’s just what I did!
Claire says
Thanks for the tips. Annapolis sounds like a great place to visit. If it’s got a winery and good seafood i’m sure i’ll make my way there one day haha
Brianna says
Seriously, what more do you need?
Christina says
Outside of theme parks, I have not really explored Maryland. Annapolis sounds like it would be a nice weekend getaway. With the kids, the Ice Cream Company will be a must!
Brianna says
The Ice Cream Company is definitely worth the trip!
Vicki Louise says
You had me at visit a winery.. oh and getting out on the water.. and the food. Yup, You have convinced that this would be an awesome destination for a weekend away!