Sail, Sip, & Stroll: Your Guide to the Best Things to Do in Annapolis

Sail, Sip, & Stroll: Your Guide to the Best Things to Do in Annapolis


Welcome to Annapolis, Maryland! This charming city on the Chesapeake Bay is a sailor’s paradise, steeped in maritime heritage and brimming with nautical charm.

With its picturesque harbor, historic streets, and abundance of waterfront activities, Annapolis offers a delightful escape for visitors of all ages.

Whether you’re a history buff, a foodie, or an outdoor enthusiast, this charming Maryland city has something to entice you.

From sailing adventures and waterfront dining to exploring the United States Naval Academy and strolling through charming historic districts, this city is a treasure trove of experiences waiting to be discovered.

So, hoist the sails and let’s embark on a journey to uncover the best things to do in Annapolis!

Book your flight with Skyscanner to Annapolis and tour the historic United States Naval Academy, a landmark and service academy.

Soak Up the Maritime Atmosphere at City Dock

Winter Sunrise at Annapolis City Dock (Ego Alley)

Annapolis’ City Dock is the heart and soul of the city, where vibrant energy comes alive.

This busy waterfront hub is a popular gathering place for locals and tourists, offering stunning views of the Chesapeake Bay and a lively atmosphere that’s hard to resist.

Whether you’re a seasoned sailor or simply enjoy watching sailboats gliding by, City Dock is a must-visit destination.

What Makes City Dock a Great Place to Visit:

  • The dock’s location on the Chesapeake Bay provides breathtaking views of the water, sailboats, and the iconic Naval Academy. It’s the perfect spot to relax and watch the world go by.
  • City Dock is always buzzing with activity. Street performers, musicians, and artists often entertain the crowds, creating a festive ambiance.
  • A variety of restaurants and cafes line the dock, offering delicious seafood, refreshing drinks, and outdoor seating with harbor views.
  • Β You can go on a scenic boat tour or rent your own vessel to explore the Chesapeake Bay at your own pace.
  • Just across Spa Creek, you’ll find the quirky “Maritime Republic of Eastport,” a self-proclaimed micronation with its own unique traditions and events.

πŸ‘‰Stay in a waterfront hotel near the Naval Academy for easy access to tours and panoramic views of the Chesapeake Bay.

Things to Do at City Dock:

  • Watch the Wednesday Night Sailboat Races: Witness the excitement as sailboats compete in this popular weekly event.
  • Dine with a View: Enjoy fresh seafood and delicious cuisine at waterfront restaurants like Carrol’s Creek and Iron Rooster.
  • Take a Boat Tour: Embark on a Watermark tour for a narrated cruise around the harbor, offering insights into Annapolis’ maritime history.
  • Rent a Boat: Explore the Chesapeake Bay on your own terms by renting a sailboat, kayak, or paddleboard.
  • Stroll Along Ego Alley: This narrow waterway is a popular spot for boaters and offers a charming backdrop for a leisurely walk.
  • Visit the Annapolis Maritime Museum: Learn about the Chesapeake Bay’s maritime heritage through exhibits and educational programs.
  • Cross the Bridge to Eastport: Explore this charming neighborhood with its unique shops, restaurants, and quirky “Maritime Republic” spirit.

πŸ‘‰Find the best flights to Annapolis on Skyscanner and explore the Maryland State House, the oldest state capitol in continuous legislative use.

Explore History and Heritage at the United States Naval Academy


A visit to Annapolis would not be complete without experiencing the grandeur and tradition of the United States Naval Academy (USNA).

This iconic institution, often simply called “the Yard,” is not only a top attraction, but also a source of immense pride for the city.

Founded in 1845, the Naval Academy has a rich history and plays a vital role in training the future leaders of the U.S. Navy and Marine Corps.

The Naval Academy is steeped in history, with beautiful buildings, monuments, and landmarks that tell the story of the U.S. Navy.

What Makes the Naval Academy a Great Place to Visit:
  • The campus is a stunning example of Beaux-Arts architecture, with impressive buildings like Bancroft Hall (the largest college dormitory in the world) and the iconic Naval Academy Chapel.
  • Witness the disciplined routines of the midshipmen (students) and experience the unique atmosphere of this prestigious institution.
  • The USNA Museum offers fascinating exhibits on naval history, showcasing artifacts, ship models, and interactive displays.

πŸ‘‰Book a historic inn near the Maryland State House to immerse yourself in the colonial charm of Annapolis.

Things to Do at the Naval Academy:
  • Take a Guided Tour: Join a guided tour to learn about the history and traditions of the Naval Academy, and visit iconic landmarks like the Crypt of John Paul Jones, where the legendary naval hero is entombed.
  • Visit the Naval Academy Chapel: Marvel at the stunning architecture of this iconic chapel, known for its Tiffany stained glass windows and impressive dome.
  • Explore the USNA Museum: Dive into the rich history of the U.S. Navy through exhibits showcasing artifacts, ship models, and interactive displays.
  • Witness Noon Formation: If you time your visit right, you can witness the impressive Noon Formation, a daily tradition where the entire Brigade of Midshipmen assembles for inspection.
  • Attend a Sporting Event: Cheer on the Navy Midshipmen as they compete in various sports, including football, basketball, and lacrosse.

πŸ‘‰Use Skyscanner to plan your trip to Annapolis for sailing or kayaking on the Chesapeake Bay, a haven for water sports enthusiasts.

Wander Through Historic Downtown Annapolis

Downtown Annapolis

Step back in time as you stroll through the charming streets of historic downtown Annapolis.

With its brick sidewalks, cobblestone alleyways, and beautifully preserved colonial architecture, it’s easy to imagine yourself in the 18th century.

This vibrant district is a living museum, where history and modern life seamlessly intertwine.

What Makes Historic Downtown Annapolis a Great Place to Visit:
  • Annapolis served as the nation’s capital for a brief period, and its streets have been walked by the likes of George Washington and Benjamin Franklin.
  • The district boasts a remarkable collection of colonial-era buildings, many of which are open to the public.
  • With its quaint shops, inviting restaurants, and bustling street life, downtown Annapolis exudes a warm and welcoming ambiance.
  • The compact size of the historic district makes it perfect for exploring on foot, allowing you to discover hidden courtyards, secret gardens, and picturesque corners at every turn.

πŸ‘‰Find a cozy bed and breakfast close to downtown Annapolis for a comfortable stay within walking distance of shops and eateries.

Things to Do in Historic Downtown Annapolis:
  • Visit the Maryland State House: Explore the oldest state house in continuous legislative use, where George Washington resigned his commission as commander-in-chief of the Continental Army.
  • Tour the William Paca House and Garden: Step inside this beautifully restored Georgian mansion, once home to a signer of the Declaration of Independence.
  • Take a Walking Tour: Join a guided tour to delve deeper into the city’s history and architecture, or explore at your own pace with a self-guided map.
  • Stroll Along Main Street and Maryland Avenue: Discover unique shops, art galleries, and boutiques offering everything from souvenirs to locally made crafts.
  • Relax in a Historic Tavern: Enjoy a pint or a meal in one of the many historic taverns and pubs that dot the district.
  • Browse the Annapolis City Dock: Located at the end of Main Street, City Dock is a lively hub with shops, restaurants, and boat tours.
  • Visit the Banneker-Douglass Museum: Learn about Maryland’s African American history and culture at this museum, located on Franklin Street.

πŸ‘‰Secure your flight with Skyscanner and stroll through the charming streets of downtown Annapolis, filled with unique shops and restaurants.

Indulge in Annapolis’ Culinary Scene

Annapolis is a foodie’s paradise, boasting a diverse culinary scene that caters to every palate. 

No trip to Annapolis is complete without experiencing its vibrant food scene.

Here are a few local favorites to satisfy your cravings:

  • Fox’s Den: This Instagram-worthy pizza place on Main Street is known for its amazing, vibey atmosphere and delicious pizza. Don’t miss their creative cocktails! (Open for dinner only)
  • Bread & Butter: This casual spot serves up healthy breakfast, sandwiches, and salads, perfect for a quick bite or a leisurely meal by the water. Their chipotle chicken panini is a must-try!
  • Boatyard Bar & Grill: A popular hangout for locals, Boatyard Bar & Grill offers a diverse menu featuring fresh seafood, American classics, and more. It’s a great place to soak up the local atmosphere and enjoy a delicious meal.
  • Preserve: This trendy new American restaurant on Main Street is a top choice for foodies seeking innovative dishes and a stylish ambiance.
  • Carrol’s Creek Cafe: While the food is good, it’s the stunning waterfront patio that truly sets this seafood restaurant apart. Enjoy your meal with a breathtaking view of the harbor.
  • Chop Tank: This fish and crab house boasts an amazing rooftop deck overlooking the water, making it the perfect spot for happy hour drinks and appetizers.

πŸ‘‰Choose a boutique hotel near the Chesapeake Bay for convenient access to sailing, fishing, and water sports.

Discover Hidden Gems and Off-the-Beaten-Path Attractions

While Annapolis’s main attractions are definitely worth exploring, don’t miss the opportunity to stray from the touristy areas and discover some of the city’s hidden gems.

These lesser-known spots provide unique experiences and a deeper understanding of Annapolis’ rich history and natural beauty.

Annapolis Maritime Museum:

On the waterfront of Back Creek, Annapolis Maritime Museum celebrates the maritime heritage of the Chesapeake Bay through engaging exhibits, educational programs, and a working boatyard.

It is an excellent place to learn about the bay’s ecology, history, and the importance of preserving this vital ecosystem.

Quiet Waters Park:

Escape the hustle and bustle of downtown and find tranquility in Quiet Waters Park.

With miles of trails, a dog beach, a playground, and a variety of water activities, it’s the perfect spot for a family outing or a peaceful retreat.

πŸ‘‰Fly into Annapolis with Skyscanner and visit the Annapolis Maritime Museum to learn about the area’s rich maritime history.

Anne Arundel County:

South River in Anne Arundel County, Maryland

Venture beyond the city limits to discover the natural beauty and diverse attractions of Anne Arundel County.

Enjoy a scenic drive along the Chesapeake Bay, explore historic sites such as London Town and Gardens, and visit charming towns like Severna Park and Crownsville.

Banneker-Douglass Museum:

Delve into the rich history and culture of African Americans in Maryland at this state-of-the-art museum.

Explore exhibits on Harriet Tubman, Frederick Douglass, and Benjamin Banneker, and learn about their contributions to the state and the nation.

πŸ‘‰Secure a room close to the Annapolis Maritime Museum to explore the nautical history of the region effortlessly.

More Things to Do in Annapolis

Maryland State Capitol
  • Enjoy a Performance at Rams Head On Stage: This intimate venue hosts a variety of musical acts and performances throughout the year.
  • Shop for Unique Finds in West Annapolis: This neighborhood is home to a variety of independent shops and boutiques offering everything from antiques to handmade jewelry.
  • Take a Day Trip to the Chesapeake Bay Environmental Center: Explore this 510-acre nature preserve with trails, exhibits, and educational programs.
  • Catch a performance at Summer Garden Theater: Enjoy an evening of outdoor theater under the stars at this charming venue.
  • Dine al fresco on West Street: Experience the vibrant atmosphere of West Street, lined with restaurants offering outdoor seating and delicious cuisine.
  • Stroll through Snowflake Alley: Wander down this charming alleyway adorned with twinkling lights year-round, creating a magical ambiance day or night.
  • Cheer on the Navy Midshipmen: Experience the excitement of a Navy football or lacrosse game at Navy-Marine Corps Memorial Stadium. Go Navy!
  • Go for a nature walk at Jonas Green State Park: Take a leisurely stroll through this scenic park, admiring the diverse plant life and enjoying views of the Severn River.
  • Attend a music event at Eastport Yacht Club: Listen to live music and mingle with locals at this popular waterfront venue.
  • Indulge in fresh seafood on the Maryland Crab & Oyster Trail: Embark on a culinary adventure along this scenic trail, stopping at restaurants like Blackwall Hitch to savor delicious crab and oyster dishes.
  • Take a guided tour of the Maryland State House: Step inside this historic landmark and learn about its fascinating past and the role it plays in Maryland’s government.

πŸ‘‰Book through Skyscanner for a trip to Annapolis and enjoy a performance at the Annapolis Symphony Orchestra.

FAQs About Annapolis

Annapolis, Maryland
What is the best time of year to visit Annapolis?

The best times to visit Annapolis are generally spring and fall.

The weather is pleasant, and the crowds are smaller than in the peak summer season.

Spring brings blooming flowers and festivals, while fall offers beautiful foliage and crisp air.

However, Annapolis is a charming destination year-round, with each season offering its own unique appeal.

Is Annapolis a family-friendly destination?

Certainly! Annapolis warmly welcomes families.

The city provides a wide range of family-friendly attractions, such as the Chesapeake Children’s Museum, the Annapolis Maritime Museum, and Quiet Waters Park.

Numerous restaurants are child-friendly, and the historic downtown area is easily walkable, making it convenient for families to explore together.

πŸ‘‰Opt for accommodations near the Maryland Hall for the Creative Arts to enjoy local theater and art exhibitions.

How do I get to Annapolis from major cities?

Annapolis is easily accessible by car, train, or plane:

Car: Located about 30 miles east of Washington, D.C., and 25 miles south of Baltimore, Annapolis is a short drive from both cities.

Train: Amtrak offers service to the nearby BWI Airport and New Carrollton stations, with connecting options to Annapolis.

Plane: The closest airport to Annapolis is Baltimore/Washington International Thurgood Marshall Airport (BWI).

Where to stay in Annapolis?

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Annapolis offers a range of accommodations to suit every taste and budget. Here are a few standout options:

134 Prince:

This super cute, luxury boutique hotel feels like a bed and breakfast with its charming atmosphere and included breakfast.

It’s conveniently located near downtown Annapolis, making it easy to explore the city’s attractions.

Annapolis Waterfront Hotel:

As the name suggests, this hotel boasts a prime waterfront location in the heart of Annapolis.

Enjoy stunning views of the harbor and easy access to all the downtown excitement.

The Graduate Annapolis:

Consistently ranked among the top hotels in the area,

The Graduate Annapolis offers a stylish and modern experience with comfortable rooms and a lively atmosphere.

πŸ‘‰With Skyscanner, reach Annapolis and sample local seafood specialties at the annual Annapolis Crab Feast.

Set Sail for Your Own Annapolis Adventure

Annapolis, Maryland

From sailing adventures on the Chesapeake Bay to historical explorations and culinary delights, Annapolis offers a wealth of experiences for every type of traveler.

Whether you’re drawn to the city’s maritime heritage, its charming historic district, or its vibrant food scene, you’ll find plenty to love in this captivating destination.

So why not chart your course for Annapolis and discover the magic for yourself?

With its friendly atmosphere, diverse attractions, and abundance of activities, Annapolis is sure to leave a lasting impression.

Start planning your Annapolis adventure today and create memories that will last a lifetime.

πŸ‘‰Discover a family-friendly lodge near Quiet Waters Park for easy access to outdoor activities and picnics.

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