There’s no denying that life in Downtown Annapolis is something special. With its charming cobblestone streets, stunning harbor views, and vibrant restaurant scene, the city has an irresistible blend of history and coastal energy.
But one of the best parts about living in or visiting Annapolis is how ideally situated it is for weekend adventures. Whether you’re craving a quiet escape to nature, a romantic vineyard retreat, or an urban exploration in a nearby city, there’s no shortage of options just a short drive away.
If you’re considering making Annapolis your home—or simply want to explore more of what the region offers—The Tower Team (thetowerteam.com) can guide you to the perfect neighborhood base for all your weekend getaways.
1. Eastern Shore Escapes
Just across the Bay Bridge, Maryland’s Eastern Shore feels worlds away from city life. With charming small towns, waterfront dining, and tranquil scenery, it’s a top choice for a relaxing retreat.
St. Michaels is perhaps the crown jewel. Known for its maritime history, this quaint town offers boutique inns, fresh seafood, and leisurely strolls along the waterfront. Don’t miss a visit to the Chesapeake Bay Maritime Museum, or a sunset sail on the Miles River. For a true luxury experience, the Inn at Perry Cabin is a beloved spot for spa treatments and fine dining.
Oxford, one of Maryland’s oldest towns, is another hidden gem. Its quiet charm, scenic ferry rides, and cozy B&Bs make it perfect for a peaceful weekend away. You can also rent bikes and explore the flat, scenic trails connecting the waterfront villages.
For a more laid-back day trip, Tilghman Island offers a taste of authentic Chesapeake culture. Enjoy crab shacks, fishing charters, and sunsets that paint the horizon in gold.
St. Michaels is perhaps the crown jewel. Known for its maritime history, this quaint town offers boutique inns, fresh seafood, and leisurely strolls along the waterfront. Don’t miss a visit to the Chesapeake Bay Maritime Museum, or a sunset sail on the Miles River. For a true luxury experience, the Inn at Perry Cabin is a beloved spot for spa treatments and fine dining.
Oxford, one of Maryland’s oldest towns, is another hidden gem. Its quiet charm, scenic ferry rides, and cozy B&Bs make it perfect for a peaceful weekend away. You can also rent bikes and explore the flat, scenic trails connecting the waterfront villages.
For a more laid-back day trip, Tilghman Island offers a taste of authentic Chesapeake culture. Enjoy crab shacks, fishing charters, and sunsets that paint the horizon in gold.
2. A Cultural Getaway to Washington, D.C.
Less than an hour’s drive from Annapolis, Washington, D.C., offers an entirely different kind of weekend experience. Whether you’re an art lover, foodie, or history buff, there’s always something new to explore.
Spend a day wandering through the Smithsonian museums, all of which are free and world-class. The National Gallery of Art, the Museum of African American History and Culture, and the Air and Space Museum are perennial favorites.
If you’re visiting during spring or fall, D.C.’s parks come alive—especially during the National Cherry Blossom Festival in early spring. For an upscale culinary experience, try one of the Michelin-starred restaurants in the city’s revitalized neighborhoods like Shaw or The Wharf.
After a day of sightseeing, unwind at a rooftop bar overlooking the monuments, or take an evening cruise along the Potomac River for a dazzling view of the city lights.
Spend a day wandering through the Smithsonian museums, all of which are free and world-class. The National Gallery of Art, the Museum of African American History and Culture, and the Air and Space Museum are perennial favorites.
If you’re visiting during spring or fall, D.C.’s parks come alive—especially during the National Cherry Blossom Festival in early spring. For an upscale culinary experience, try one of the Michelin-starred restaurants in the city’s revitalized neighborhoods like Shaw or The Wharf.
After a day of sightseeing, unwind at a rooftop bar overlooking the monuments, or take an evening cruise along the Potomac River for a dazzling view of the city lights.
3. Baltimore’s Waterfront Adventures
Just a 40-minute drive from Downtown Annapolis, Baltimore makes for an easy and exciting weekend escape. The city’s Inner Harbor area is filled with attractions, including the National Aquarium, Harborplace shops, and Fells Point, a historic district lined with cobblestone streets and trendy restaurants.
Baltimore’s arts and food scene has blossomed in recent years. You can spend Saturday sampling local favorites like crab cakes at Thames Street Oyster House, then explore the street art and galleries in the Station North Arts District. Baseball fans might catch an Orioles game at Camden Yards, while music lovers can enjoy live performances at The Hippodrome or Rams Head Live.
For a quieter stay, consider booking a boutique hotel in Mount Vernon or Harbor East, where you’ll be close to both cultural attractions and the waterfront.
Baltimore’s arts and food scene has blossomed in recent years. You can spend Saturday sampling local favorites like crab cakes at Thames Street Oyster House, then explore the street art and galleries in the Station North Arts District. Baseball fans might catch an Orioles game at Camden Yards, while music lovers can enjoy live performances at The Hippodrome or Rams Head Live.
For a quieter stay, consider booking a boutique hotel in Mount Vernon or Harbor East, where you’ll be close to both cultural attractions and the waterfront.
4. Wine and Countryside in Virginia
If rolling hills and vineyard views sound like your idea of relaxation, head southwest to Virginia’s wine country, about 90 minutes from Annapolis. The Loudoun County Wine Trail is home to dozens of wineries, from boutique family-owned vineyards to grand estates.
Spend your days sampling award-winning wines and your evenings relaxing at cozy inns or elegant farmhouses. Favorites include Stone Tower Winery, known for its panoramic views, and Breaux Vineyards, which offers a touch of European flair.
In addition to wine tasting, the area’s towns like Leesburg and Middleburg offer charming downtowns filled with antique shops, bakeries, and upscale dining. Horse lovers can even time their visit with one of the region’s equestrian events or polo matches.
Spend your days sampling award-winning wines and your evenings relaxing at cozy inns or elegant farmhouses. Favorites include Stone Tower Winery, known for its panoramic views, and Breaux Vineyards, which offers a touch of European flair.
In addition to wine tasting, the area’s towns like Leesburg and Middleburg offer charming downtowns filled with antique shops, bakeries, and upscale dining. Horse lovers can even time their visit with one of the region’s equestrian events or polo matches.
5. Nature Escapes in Western Maryland
For outdoor enthusiasts, a weekend in Western Maryland is the perfect opportunity to reconnect with nature. Just a few hours from Annapolis, you’ll find Deep Creek Lake, a stunning mountain destination offering year-round recreation.
In summer, you can boat, kayak, or swim in the crystal-clear lake. Fall brings fiery foliage that makes for unforgettable hiking and scenic drives through Garrett County. In winter, head to Wisp Resort for skiing, snowboarding, and cozy nights by the fire.
If you prefer something closer to home, Patapsco Valley State Park (about 40 minutes away) offers excellent hiking, biking, and picnic spots along the river. It’s an ideal day trip for families or anyone looking for a dose of nature without venturing too far.
In summer, you can boat, kayak, or swim in the crystal-clear lake. Fall brings fiery foliage that makes for unforgettable hiking and scenic drives through Garrett County. In winter, head to Wisp Resort for skiing, snowboarding, and cozy nights by the fire.
If you prefer something closer to home, Patapsco Valley State Park (about 40 minutes away) offers excellent hiking, biking, and picnic spots along the river. It’s an ideal day trip for families or anyone looking for a dose of nature without venturing too far.
6. Historic Charm in Gettysburg and Harpers Ferry
History buffs will love the short trip to Gettysburg, Pennsylvania, less than two hours from Annapolis. Explore the Gettysburg National Military Park, where you can take guided tours of the battlefield and learn about one of the most pivotal moments in American history.
Alternatively, Harpers Ferry, West Virginia, combines history with breathtaking scenery. Nestled at the confluence of the Potomac and Shenandoah rivers, the town is filled with 19th-century charm and offers hiking trails with panoramic views—particularly the Maryland Heights Trail. After a day of exploring, unwind at one of the area’s cozy inns or craft breweries.
Alternatively, Harpers Ferry, West Virginia, combines history with breathtaking scenery. Nestled at the confluence of the Potomac and Shenandoah rivers, the town is filled with 19th-century charm and offers hiking trails with panoramic views—particularly the Maryland Heights Trail. After a day of exploring, unwind at one of the area’s cozy inns or craft breweries.
7. Coastal Retreats on Maryland’s Atlantic Shore
When you’re in the mood for ocean breezes and sandy beaches, the Atlantic coast is just a couple of hours away. Ocean City is a classic Maryland beach destination, with its lively boardwalk, family attractions, and seafood shacks. Spend the weekend swimming, biking, or watching the sunrise over the Atlantic.
For a more serene seaside escape, head to Assateague Island National Seashore, famous for its wild horses and pristine beaches. It’s a wonderful place for camping, birdwatching, or simply enjoying nature’s beauty in its purest form.
If you prefer a balance of beach and boutique charm, Rehoboth Beach, Delaware, offers stylish shopping, art galleries, and gourmet dining just over two hours from Annapolis.
For a more serene seaside escape, head to Assateague Island National Seashore, famous for its wild horses and pristine beaches. It’s a wonderful place for camping, birdwatching, or simply enjoying nature’s beauty in its purest form.
If you prefer a balance of beach and boutique charm, Rehoboth Beach, Delaware, offers stylish shopping, art galleries, and gourmet dining just over two hours from Annapolis.
Make Every Weekend Count
Whether you’re drawn to the energy of nearby cities, the tranquility of the countryside, or the adventure of the coast, there’s a world of experiences waiting just beyond Downtown Annapolis. These weekend getaways showcase the incredible variety of life within a few hours’ drive—from vineyards and mountains to beaches and bustling metros.
And if you’re ready to call this region home, The Tower Team can help you find your perfect base in Annapolis. Their local expertise, client-focused service, and deep understanding of the area make them the ideal partners for finding a property that fits your lifestyle and love of exploration.
Visit thetowerteam.com to start your journey—and enjoy the freedom to discover something new every weekend.
And if you’re ready to call this region home, The Tower Team can help you find your perfect base in Annapolis. Their local expertise, client-focused service, and deep understanding of the area make them the ideal partners for finding a property that fits your lifestyle and love of exploration.
Visit thetowerteam.com to start your journey—and enjoy the freedom to discover something new every weekend.