It’s time to make Mom feel extra, extra special this year and there are so many ways to achieve that on your next trip to Annapolis, MD. A waterfront retreat like this one offers unlimited activities and scenic views for you and your mother to enjoy. Annapolis has everything to do from visiting historic sites to wine tasting to sailing the Chesapeake Bay…and a lot in between, too. How else can you show thanks to the woman who gave your life? Celebrate Motherhood extravagantly this year, and let us share our ideas on how you can give your mom the best Maryland experience

Go for a stroll at City Dock

The City Dock is a fun place for people-watching on a nice afternoon in Annapolis. Known as Ego Alley, it’s the spot for captains to show off their boats and their boating skills as they navigate the narrow area. It’s a great place to take your mom out on a relaxing evening walk and just chat. Crowds tend to gather by the water to watch the boats come in and dream about buying their own one day. Take in the sunshine while sitting outside at one of several dining establishments that allow you watch the boats cruise in and out of Ego Alley.

Take her on a cruise

If you’re strolling by the dock, take Mother’s Day a step forward and delight your mother with a scenic cruise. Take in everything that this marine paradise offers and sail across the bay on this blissful Sunday. Two of the most popular ways to get out on the water are on the Harbor Queen or the Schooner Woodwind. One of the most attractive features in the city is the Annapolis waterfront. And there’s no better way to appreciate the beautiful Severn River and Chesapeake Bay than to go for a cruise.

Hop on a trolley tour

Other than marine entertainment, strolling down Main Street Is bound to give you a great taste of Annapolis. Together with your mom, gain a greater appreciation for all this cute place has to offer & hop on an Annapolis trolley tour. In just an hour, the guide will give you a quick walk through 350 years of history while driving by some of the prettiest buildings around. You’ll see lots of top Annapolis attractions, including Victorian houses, colonial mansions, views of the Severn River, and, of course, the Naval Academy. A trolley tour is one of the best things to do in Annapolis because you see a lot quickly, and it’s easy on your feet, which is a valuable experience to have with your family.

Book a tasting at Great Frogs Winery

Treat your mom to a little wine and book a tasting at a winery, not too far off from downtown Annapolis at Great Frogs Winery. Established in 1999 on an old tobacco farm, Great Frogs Winery takes advantage of Annapolis’ naturally sandy soil to grow French Bordeaux varietals. The grapes are expertly crafted into more than a dozen wines showcasing white, rose, and red varietals and blends. Book a weekend tasting of their wines or a full wine, cheese, and charcuterie sampling experience to see the best of what Great Frogs Winery has to offer.

Mother’s Day Brunch

What better way to celebrate Mother’s Day in Annapolis than enjoying a hearty brunch by the bay. This waterfront city is home to many restaurants that serve mouth-watering dishes that are bound to make your mom filled with joy. Enjoy a brunch at O’Learys Seafood!  The food is delicious, and O’Leary’s will be the easiest way to get mom a Mimosa before or after your stroll through the city. At Chart House Restaurant, the view can’t be beaten. Other places to try are also Boatyard Bar and Grill & Severn Inn

After a day of wandering through the city, you and your mom can unwind on a weekend “stay”-cation and spend the rest of the holiday being pampered at our seaside resort, Annapolis Waterfront Hotel. Mixing the vibrancy of this maritime city with a legacy of sophisticated hospitality, choose from  our spacious & bright guestrooms, completed with luxurious amenities and decorated with a palette inspired by the sea. Treat your mother with the serenity of harbor views or an overlook on downtown Annapolis, with its pretty, polished cityscape!