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Best Day Trips From Harbor East Marina

Updated: Sep 15, 2023


Baltimore is a beautiful and historic city that’s definitely worth seeing to the fullest, but for boaters who’ve seen all the sights and long for new ones, there are plenty of fun day trips you can take from Baltimore.


Harbor East Marina is just a couple of hours away from some fantastic destinations that are definitely worth adding to your itinerary. Check out our top recommendations for the best day trips from Baltimore!



Best Day Trips from Harbor East Marina

Annapolis, MD

Less than an hour away from Baltimore, Annapolis is the state capital of Maryland and a historic city located right on the shores of the Chesapeake Bay. This beautiful city is full of picturesque historic buildings, waterfront dining and activities, and a laidback atmosphere that’ll make you never want to leave.


Annapolis is best known for its waterfront and historic district. Thanks to its prime location on the Chesapeake Bay, boaters love visiting Annapolis to explore its waters, whether through kayaking or your own private vessel. Annapolis has a rich maritime history best exemplified by its Maritime Museum and its extensive Historic District and docks.

Hungry for a bite to eat? No worries! Annapolis has some excellent dockside restaurants that offer not just good food, but beautiful views of the waterfront, such as Carrol’s Creek Cafe, Chart House Prime, and Latitude 30°. When you have the opportunity, a day trip to Annapolis is a no-brainer!


St. Michaels, MD

St. Michaels is a charming little coastal town about an hour or so away from Baltimore. Its beautiful harbor makes it a popular destination for boaters and sailing enthusiasts and is an excellent place for outdoor activities. In fact, it was voted one of USA Today’s Top 10 Best Small Coastal Towns! And it’s no wonder — St. Michaels is home to many a scenic view, historic homes and places that each have a story to tell, and homey restaurants and inns that you’ll never want to leave.


Take a cruise down the Miles River and see historic riverside estates, stroll along the streets and the stunning waterfront, have a shopping spree and enjoy the small-town vibes at Talbot Street with its many fancy boutiques and vintage antique shops, learn more about the town’s history at the Chesapeake Bay Maritime Museum and the Classic Motor Museum, and have your fill of oysters, wine, and more at one of the town’s many annual festivals, such as OysterFest and WineFest.


And be sure to get a taste of some delicious Maryland crab and other fare at one of the many upscale restaurants in town, such as Bistro St. Michaels, Limoncello, and Talbot 208. Or, for a more unique experience, have brunch at T at the General Store, housed in an old renovated general store building that still keeps its classic facade. And that’s not to mention the many craft breweries and wineries that litter this town, like Lyons Distilling Co., St. Michaels Winery, and Gray Wolf Craft Distilling.


St. Michaels is the perfect place to kick back, relax, and feel right at home — it could very well be your new home away from home!


Havre de Grace, MD

Less than an hour away from Baltimore, Havre de Grace is a beautiful city in Maryland that makes for a wonderful day trip. It is named after the port city of Le Havre in France, which was originally called Le Havre de Grace, or “Harbor of Grace”, and it definitely earns that name!


This historic city is located right at the head of the Chesapeake Bay, making it a premier spot for boaters and anyone looking to have some watersports fun. Havre de Grace is a picturesque and gorgeous town to explore with plenty of historical attractions, romantic sights, and mouth-watering tastes and smells.


Enjoy a serene stroll along the Havre de Grace promenade by the Susquehanna River, tour the Concord Point Lighthouse which is a popular landmark of Havre de Grace, step into history in the town’s five-mile historic district and the Havre de Grace Maritime Museum, spend a day on the greens at the Bulle Rock Golf Club, or go shopping for unique antiques and souvenirs at one of the many antique shops in Havre de Grace’s historic district.


And if you get hungry, no one does seafood like Havre de Grace. MacGregor’s Restaurant, The Promenade Grille, and Backfin Blues Creole De Graw bring you amazing views and even more fantastic food, from steamed crabs to classic American fare.


Cambridge, MD

About 2 hours away from Baltimore and 30 minutes from St. Michaels, Cambridge is a gorgeous city renowned for being a city of the arts and universities. Not to be confused with the city of the same name in the UK, Cambridge is one of the oldest colonial cities in the country and is absolutely steeped in history.


You can start off your day in Cambridge by exploring downtown Cambridge, filled with historical buildings such as the Christ Episcopal Church, retrace the steps of Harriet Tubman from her official birthplace to the Harriet Tubman Underground Railroad Scenic Byway, take pictures at the Choptank River Lighthouse and Long Wharf Park, have a glimpse into the city’s rich history at the Visitor Center at Sailwinds Park and the Richardson Maritime Museum, immerse yourself in the arts and culture of the Eastern Shore at the Dorchester Center for the Arts, and take a scenic detour to Blackwater National Wildlife Refuge. Then, have a meal at one of many local favorites, such as Black Water Bakery, Cindy’s Kitchen, and Porter Soul Food.


Be sure to pay this lovely little town a visit when you’re in the area and they’ll make it well worth your while!


Chesapeake Beach, MD

Chesapeake Beach is Maryland’s very own premier beach destination. Just an hour away from Baltimore, Chesapeake Beach is the perfect place to catch some water and sun — if you can’t fit Ocean City into your itinerary, that is. Nevertheless, this cozy little beach town promises to be a wonderful, relaxing getaway, especially for boaters.


It’s a popular destination for sailors and marine enthusiasts who adore it for its calm, pristine waters and scenic beaches. It’s also a great place to go fishing, surfing, and swimming, especially at its resident water park. If you want to get to know the town and its history a little bit more, there’s the Chesapeake Beach Railway Museum and the Surf Art Gallery & Museum, or if you prefer to take your time and just enjoy the town’s laidback vibes, you can walk along the Chesapeake Beach Railway Trail or watch the sunset from its golden sandy beaches.


Hungry for a bite to eat? Chesapeake Beach has some excellent dining options with lots of seafood and classic American fare, such as the 1936 Bar & Grill, Boardwalk Cafe, and Baia Coastal Italian Kitchen & Wine Bar.


Kent Narrows

The Kent Narrows, also known as the Kent Island Narrows and simply the Narrows, is a waterway in between Kent Island and the Delmarva Peninsula. It connects the Chester River in Maryland to the Eastern Bay and runs through the community of the same name in Queen Anne’s County, Maryland.


The Narrows are a fantastic destination for boaters. The waterway is an outstanding place for many watersports and water activities, such as boating and especially fishing. If you just want to get out on your boat and feel that sea breeze on your face, Kent Narrows is a hidden gem of the Eastern Shore that you’ll simply love.


The Kent Narrows waterfront also features prime dockside dining and a veritable feast of famous Maryland crabs and seafood. You can find the best seafood in Harris Crab House, The Jetty, or The Narrows Restaurant.


Hart-Miller Island

Hart-Miller Island was once two separate islands, the Hart and Miller Islands, before they were combined into one. Now, Hart-Miller Island continues to operate as a Hart-Miller Island State Park, which is only accessible by boat.


Located east of Baltimore near the mouth of the Middle River, Hart-Miller Island has up to 1,100 acres worth of land and is brimming with fun, outdoor activities, such as hiking, camping, bird watching, and picnicking, and also features a 3,000-foot sandy beach. The island is a hidden haven for boaters and nature lovers and thanks to its close proximity to Baltimore, it makes for a quick but exciting new way to spend a day outside of Baltimore.


When you book a slip with us at Harbor East Marina, you don’t just get access to all of Baltimore, but you get close to some of these amazing places just a couple hours away from Baltimore as well. Whether you’re going by boat or road, these day trips from Harbor East Marina are sure to be well worth a visit.


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