You know what is better than exploring a new city? Exploring a new city with a bunch of fun friends. I enjoyed the Pocono Mountains trip with the DC Travel Bloggers so much, there was no way I missing a day trip to Annapolis with this bunch. It is hard to believe I have been neglecting this beautiful city for so long. Here are the highlights you shouldn’t miss.

Take a trolley tour.

We arrived at the visitors center after a quick drive from DC. If you drive to Annapolis, there is a parking garage next to the visitors center that is your best bet for parking. Street parking has two hour limits and you can’t keep feeding the meters. So save yourself the trouble and park in the garage. Plus, this puts you at the right place to hop on the trolley tour.

The trolley takes you down back roads, across bridges and just outside of town for an overlooking view, while noting some of the lesser known sites along the way. It’s the perfect way to get acquainted with Annapolis and leaves the main attractions on Main Street for you to explore later.

Grab lunch in town.

After the tour we were good and hungry. The trolley drops off at the visitors center, a short walk from Main Street and an abundance of restaurants. We ate at Galway Bay and enjoyed a taste of their famous egg nog. It’s imported from Ireland and they sell it by the bottle around the holidays. They sell out fast, and to give us a little taste in the summertime the owner had to dig into his own stash. You could also try Reynold’s Tavern on Church Circle, which is rumored to be haunted and serves a high English tea in the afternoon. No matter where you go for lunch, the locals will tell you to order a Maryland crab cake.

Visit a winery for a tasting tour.

A short drive away from town, you will find Great Frogs, a peaceful and sunny winery. We were greeted with overflowing cheese plates and a selection of wines for tasting, two whites and three reds. They sure know what they are doing there! The pairing plates are catered from a shop in town and I was introduced to one of my new favorite cheeses, Humboldt Fog.

Just when we thought it was over, we were brought three dessert wines and a chocolate for pairing with the port. Can you say heaven? Before heading back into town we got a tour of the winery and stopped to try a few cab and syrah grapes from the vine.

Explore Main Street and stop for ice cream.

Back in town, there were only two options. Take a nap or take a walk. Since we wanted to make the most of our day we started walking. Main Street is lined with adorable shops and (most importantly) an adorable ice cream parlor.

The first thing you will notice when you walk into Annapolis Ice Cream Company is all the spoons. It all started one day when an employee couldn’t find any paper so she started doodling on a spoon instead. The managers liked it, tacked it up on the wall and before long each employee started adding their own. Soon customers decided to get in on the fun too. The walls were covered. The fire marshal didn’t like this so they had to take them all down. As a compromise, they were allowed to mount panels on the walls to display the spoons. They apparently have tens of thousands still left to display!

The second thing you’ll notice is the countless flavors on offer. And they’re always changing. I went for salted caramel (I’m a sucker for it) and chocolate chocolate chip. A refreshing treat for a warm, sunny day. I made it half way down the block before I had ice cream dripping down my arm. Some people never grow up.

Enjoy the waterfront.

At the end of Main Street, there are plenty of spots to stop and enjoy the waterfront. In the main square we caught a group performing capoeira to the rhythmic beat of hand drums. All around families and friends were lounging on their docked sailboats.

Take a cruise out of the harbor.

After we had some time to relax, we hopped on board the Harbor Queen for a cruise on the bay. Grab a seat on the top deck for views of Annapolis from the water.

Eat dinner on the water.

For dinner we took a water taxi across the harbor to Carrol’s Creek in Eastport, although it is also a short walk across the Compromise Street bridge. The caprese salad was perfect – loads of mozzarella and the tomatoes were huge. For entrees, they easily accommodated my vegetarian diet with mashed cauliflower and portobello mushroom. And bread pudding seemed to be the biggest hit for dessert, served alongside a mason jar of their sea salt caramel sauce. I also got recs for  Lewnes’ Steak House, Blackwall Hitch, Boatyard Bar and Grill and O’Leary’s in Eastport.

 

Have you ever been to Annapolis? What would you recommend?