Travel Love…Annapolis, Maryland

Until this past weekend, I had never been to Annapolis.

Sad, really.  I had no idea what I was missing.  But now, I know.  And return I shall.

So how did I end up in this charming waterfront town, 5 hours from home?


guide to annapolis

We had some great friends recently move to Baltimore, and finally, we were able to take a nice weekend and make the drive north to Charm City for an overdue visit.  I’m going to tell you all about the sights and sounds of Baltimore soon – worry not – but this post is about Annapolis.   I did LOVE Baltimore.  So much, in fact, I’d consider renting a place there just to be able to visit and stay as often as I wanted.  Which would be a lot. 

But let’s talk a bit about Annapolis.


On Saturday, we boarded our friends gorgeous new boat (Thanks, Captain!) and made our way out of the Inner Harbor of Baltimore.  We headed south through the bay, stopping to get gas at the most charming dock (aren’t those chairs adorable?) where there was a fun restaurant/bar a few steps away.  That will be a fun place to head back to someday!


After about an hour in AMAZING weather on the boat, we pulled into the harbor at Annapolis and docked, then made our way up into town.  O’Brien’s is where we ended up settling in for lunch.

IMG_6581I’ll be 100% honest here…I am not a huge bar food lover.  I’d rather eat at a restaurant that has a bar versus a bar that merely serves food. 

O’Brien’s has changed my attitude about that.

The prices were very, very reasonable (pork belly sliders and fries or scallop sliders for under $8)…but even better than the prices?  The choices.  The specials of the day were the pork belly sliders I mentioned, as well as a Double Decker Surf & Turf Burger.

I had to have it.  Well, I had to have them both…so I made Jon order the sliders and I took the burger.

I’m nice that way.

So first, I tasted the pork belly slider.  Topped with a little spicy coleslaw, the belly was incredibly tender, not tough, and downright succulent.  I was kind of afraid to even try the Surf & Turf for fear it wouldn’t live up to those sliders.


How silly of me.

First off, the name of Burger is a little misleading, as there was no burger on this sandwich at all.  It was three layers of bun, sandwiching seared scallops and the same pork belly from the sliders.  Crispy onion straws and more slaw rounded out this inspired dish..and I have to say y’all – this may very well be the best thing I have ever eaten.

It’s at least the very best sandwich I’ve ever had.  And that’s saying a lot, as I love sandwiches and have had my share of excellent ones.  It’s just at this point in time, I can’t remember a single one of them, because all I can think of is the sandwich from O’Brien’s.

Yeah…it was that good.  So, if you are ever in Annapolis – give it a go.  You won’t be sorry.


We continued up the bustling charming streets after lunch, ducking into quaint clothing and jewelry shops, touristy haunts, and of course, cupcake shops.  But the place that won me over was the Seasons Olive Oil and Vinegar Taproom.

Oh sweet Lord, you guys.

Every flavor of vinegar and olive oil you can imagine – and you get to taste all of them before you buy.  I wish I could have afforded one of all of them, but I settled for 4.  A Tangerine Olive Oil, a Blackberry Ginger Vinegar, a Coconut Vinegar, and Peach Vinegar.


I kid you not, I could drink the Peach Vinegar.  I can’t wait to get home and make a salad worthy of that stuff.  In-credible.  Really.  Summer cooking is going to be way too much fun with these things in my cooking arsenal.  When I go back, the Red Apple Vinegar and the Black Cherry Vinegar will be mine.  Yes, they will.

Hopefully we will make it back to our sweet friends place later this summer (why must I have to travel so often for work?  I need some free weekends and have but 2 until July!)  so that we can make the trip down to Annapolis again for some more sightseeing.


IMG_6657And boating.  I think I could get used to that lifestyle.

Who couldn’t?  Especially with great friends who have such a love for life and for each other?  So much fun.  We are so, so lucky.

Thanks Jeff & Ann for the wonderful (truly, best weekend I’ve had in AGES) weekend.  We miss you both already!

So…who here has been to Annapolis?  Where did I miss?  Where do we need to go next?  And, if you’ve ever been boating up and down the Chesapeake Bay area, please – let us know your favorite spots to cruise into.  Little dives, big towns – you name it.  Our friends are brand new to boating, and looking for great places to visit.  Help us out, will you?

Have a great week everyone!

Spread the love