The 25 Best Things to Do in Annapolis, MD

Annapolis isn't your typical state capital. As you stroll down its brick-lined streets, the salty breeze from the Chesapeake Bay whispers tales of seafaring adventures and colonial intrigue. This charming city, dubbed "America's Sailing Capital," effortlessly blends its rich maritime history with a vibrant, modern spirit.

Picture this: sailboats dotting the harbor, their masts swaying gently against a backdrop of 18th-century buildings. The U.S. Naval Academy stands proudly, a testament to the city's enduring nautical legacy. But Annapolis offers more than just pretty views and history lessons. From savoring freshly shucked oysters to exploring hidden alleyways, this compact city packs a punch that'll leave you yearning for more.

Ready to chart your course through Annapolis? Let's dive into the 25 best things to do in this captivating coastal gem. Trust us, by the end of this list, you'll be plotting your escape to Maryland's capital faster than you can say "ahoy, matey!"

Tour the U.S. Naval Academy

Step onto the hallowed grounds where future naval officers are forged. The U.S. Naval Academy isn't just a school; it's a living piece of American history. As you wander past impressive Beaux-Arts buildings and perfectly manicured lawns, you'll feel the weight of tradition in every step.

Don't miss the stunning Naval Academy Chapel, with its iconic dome visible from across the city. Inside, you'll find the crypt of John Paul Jones, the "Father of the American Navy." The on-site museum brings naval history to life with interactive exhibits and artifacts that'll make you feel like you've set sail through time.

Key Information:

• Location: 121 Blake Rd, Annapolis, MD 21402
• Hours: Daily, 9 AM - 5 PM (Guided tours available)
• Admission: Free (Valid photo ID required for visitors 18+)

Why Visit: Experience the precision and pride of America's naval tradition firsthand.

Insider Tip: Time your visit to catch the midshipmen's noon meal formation – a impressive display of military discipline and precision.

Explore the Maryland State House

When you walk into the Maryland State House, you're not just entering a government building – you're stepping into a page of American history. This stately structure, topped with its distinctive wooden dome, has witnessed more than its fair share of pivotal moments. It's the oldest state house still in legislative use and even served as the nation's capitol for a hot minute back in the 1780s.

Inside, you'll find a perfect blend of working government offices and museum-worthy exhibits. Keep your eyes peeled for the room where George Washington resigned his commission as commander-in-chief of the Continental Army. It's like a real-life "National Treasure" set, minus Nicolas Cage.

Key Information:

• Location: 100 State Cir, Annapolis, MD 21401
• Hours: Daily, 9 AM - 5 PM
• Admission: Free

Why Visit: Stand where history happened in America's oldest state capitol in continuous legislative use.

Insider Tip: Check out the Old Senate Chamber, recently restored to its 18th-century glory. It's like time travel, but without the pesky paradoxes.

Stroll Through Historic Annapolis

Lace up your comfiest shoes and prepare for a journey through time. Historic Annapolis is a living museum where every brick and cobblestone has a story to tell. As you meander down narrow streets with names like Pinkney and Cornhill, you'll feel like you've stumbled onto the set of a period drama.

Keep your camera ready as you pass by colorful Georgian and Victorian homes, their facades a rainbow of historical hues. Stop by the Paca House and Garden for a glimpse into 18th-century high society, or peek into quirky shops housed in buildings older than the nation itself.

Key Information:

• Location: Downtown Annapolis
• Hours: Always open (individual attractions may have specific hours)
• Admission: Free to explore (some historic homes may charge admission)

Why Visit: Experience one of the best-preserved colonial towns in America, where history lives on every corner.

Insider Tip: Join a guided walking tour for the inside scoop on Annapolis' juiciest historical gossip and hidden architectural gems.

Set Sail on the Chesapeake Bay

You can't come to America's Sailing Capital without, well, sailing! The Chesapeake Bay is your aquatic playground, and there's no better way to experience it than with the wind in your hair and the sun on your face. Whether you're a seasoned sailor or can barely tell port from starboard, there's a sailing experience for you.

Hop aboard a sleek schooner for a sunset cruise, or channel your inner pirate on a family-friendly adventure. For the more hands-on types, sailing lessons are available. Who knows? You might discover your sea legs and a new passion all in one trip.

Key Information:

• Location: Various departure points around Annapolis Harbor
• Hours: Vary by operator, but typically run from April to October
• Price: $40-$100+ per person, depending on the type and length of sail

Why Visit: Experience the thrill of sailing on one of America's most beautiful bodies of water.

Insider Tip: Book an early morning sail for the best chance of spotting dolphins playing in the bay.

Feast on Blue Crabs at Cantler's Riverside Inn

If you leave Annapolis without cracking into a pile of steamed blue crabs, did you even visit? Cantler's Riverside Inn is the local go-to for this messy, delicious Maryland tradition. Perched right on Mill Creek, this no-frills joint serves up some of the best crabs in town, fresh from the Bay to your table.

Arm yourself with a mallet, roll up your sleeves, and prepare to get your hands dirty. The sweet, succulent crab meat is worth every bit of effort. And if you're not up for the full crab-picking experience, their crab cakes are legendary too.

Key Information:

• Location: 458 Forest Beach Rd, Annapolis, MD 21409
• Hours: Mon-Thu & Sun 11 AM - 10 PM, Fri-Sat 11 AM - 11 PM
• Price: $$-$$$

Why Visit: Experience a true Maryland crab feast in a waterfront setting that screams "local favorite."

Insider Tip: Go for the all-you-can-eat option if you're feeling particularly crabby (hungry, not grumpy).

Visit the Annapolis Maritime Museum

Housed in the last remaining oyster-packing plant in Annapolis, the Maritime Museum is your gateway to understanding the city's deep connection to the Chesapeake Bay. This isn't your typical stuffy museum – it's a hands-on journey through Annapolis' maritime heritage.

Climb aboard a recreated oyster boat, try your hand at tonging for oysters (without getting wet), and learn about the Bay's delicate ecosystem. The museum's crown jewel is the Thomas Point Shoal Lighthouse exhibit, where you can experience what life was like for lighthouse keepers in the Bay.

Key Information:

• Location: 723 Second St, Annapolis, MD 21403
• Hours: Tue-Sun 10 AM - 3 PM
• Admission: Adults $7, Seniors $5, Children $3

Why Visit: Gain a deeper appreciation for Annapolis' maritime culture and the Chesapeake Bay's ecology.

Insider Tip: Time your visit for one of their "Tides and Tunes" summer concerts for great music with a waterfront view.

Kayak Spa Creek

Want to see Annapolis from a different perspective? Grab a paddle and hit the water! Kayaking Spa Creek offers a unique vantage point of the city's waterfront and a chance to get up close and personal with the local wildlife. As you paddle past historic homes and underneath the Spa Creek Bridge, keep your eyes peeled for ospreys diving for fish or turtles sunning themselves on logs.

Don't worry if you're a kayaking newbie – the creek is calm and perfect for beginners. Plus, there are plenty of rental shops that offer quick lessons to get you started.

Key Information:

• Location: Various launch points, including Truxtun Park and Annapolis Canoe and Kayak
• Hours: Daylight hours, rentals typically available from May to October
• Price: Rentals from $20/hour or $60/day

Why Visit: Experience Annapolis' beauty from the water while getting a bit of exercise.

Insider Tip: Paddle to the end of Spa Creek to find a hidden rope swing – a perfect spot for a quick dip on a hot day.

Discover History at the William Paca House and Garden

Step back in time at the William Paca House, a Georgian mansion that's been meticulously restored to its 18th-century glory. William Paca, one of Maryland's four signers of the Declaration of Independence, built this elegant home as a testament to his wealth and status. Today, it stands as a beautifully preserved peek into colonial high society.

While the house itself is impressive, the real star of the show is the two-acre garden out back. Descend the terraced landscape, past precisely trimmed topiaries and colorful flowerbeds, to the charming summer house reflected in a fish-shaped pond. It's an oasis of tranquility in the heart of bustling Annapolis.

Key Information:

• Location: 186 Prince George St, Annapolis, MD 21401
• Hours: Mon-Sat 10 AM - 5 PM, Sun 12 PM - 5 PM
• Admission: Adults $12, Seniors $10, Children $6

Why Visit: Experience the luxurious lifestyle of a Founding Father in a beautifully restored 18th-century setting.

Insider Tip: The garden is at its most spectacular in late spring when the peonies are in full bloom.

Shop and Dine on Main Street

Main Street is the beating heart of Annapolis, a lively thoroughfare that perfectly blends historic charm with modern vitality. This is where locals and visitors alike come to shop, dine, and soak in the city's vibrant atmosphere. As you stroll down the brick-paved street, you'll find everything from quirky boutiques and art galleries to cozy cafes and upscale restaurants.

Don't miss Kilwin's for some mouthwatering homemade fudge, or pop into The Spice & Tea Exchange to awaken your senses. When hunger strikes, grab a table at Preserve for farm-to-table delights with a modern twist.

Key Information:

• Location: Main Street, Downtown Annapolis
• Hours: Most shops open 10 AM - 6 PM, restaurants often open later
• Price: Varies by establishment

Why Visit: Experience the heart of Annapolis' shopping and dining scene in a picturesque historic setting.

Insider Tip: Visit on a warm evening when the street comes alive with outdoor dining and live music.

Relax at Quiet Waters Park

Need a break from the hustle and bustle of downtown? Escape to Quiet Waters Park, a 340-acre oasis just a short drive from the city center. This sprawling park offers something for everyone, from serene walking trails and gardens to more active pursuits like kayaking and stand-up paddleboarding.

Art lovers will appreciate the rotating exhibits at the Visitor Center gallery, while families can let the kids loose on the expansive playground. In winter, the park even transforms its outdoor pavilion into an ice skating rink, perfect for channeling your inner Olympic figure skater (or Bambi on ice – no judgment here).

Key Information:

• Location: 600 Quiet Waters Park Rd, Annapolis, MD 21403
• Hours: Daily 7 AM - dusk
• Admission: $6 per vehicle

Why Visit: Enjoy a slice of nature and outdoor recreation just minutes from downtown Annapolis.

Insider Tip: Rent a tandem bike and pedal through the park's six miles of paved trails for a fun, active way to explore.

Explore the Banneker-Douglass Museum

Tucked away in the heart of Annapolis, the Banneker-Douglass Museum offers a powerful journey through African American history in Maryland. Housed in the former Mount Moriah African Methodist Episcopal Church, this museum packs a lot of impact into a relatively small space.

From the contributions of Benjamin Banneker and Frederick Douglass to the struggles and triumphs of the Civil Rights movement, the exhibits here tell stories that are both deeply personal and universally important. Don't miss the beautiful stained glass windows, a reminder of the building's past life as a church.

Key Information:

• Location: 84 Franklin St, Annapolis, MD 21401
• Hours: Tue-Sat 10 AM - 4 PM
• Admission: Free

Why Visit: Gain insight into Maryland's African American history and culture through engaging exhibits and programs.

Insider Tip: Check their calendar for special events and lectures that dive deeper into specific aspects of African American history and culture.

Catch a Show at Rams Head On Stage

When the sun goes down, Annapolis' nightlife heats up, and there's no better place to experience it than Rams Head On Stage. This intimate venue has hosted everyone from local up-and-comers to national acts, all in a setting so cozy you'll feel like you're at a private concert in someone's living room.

With just 300 seats, there's not a bad spot in the house. Whether you're into rock, jazz, blues, or folk, you're sure to find a show that gets your toes tapping. And with a full menu and bar available, you can make a whole night of it.

Key Information:

• Location: 33 West St, Annapolis, MD 21401
• Hours: Vary by show, box office open Mon-Sat 11 AM - 7 PM
• Price: Varies by performance, typically $25-$75

Why Visit: Experience live music in an intimate setting that's become an Annapolis institution.

Insider Tip: Join their mailing list for advance notice on ticket sales – popular shows sell out fast!

Visit the Thomas Point Shoal Lighthouse

Standing proudly in the Chesapeake Bay, the Thomas Point Shoal Lighthouse is a true icon of Annapolis. This hexagonal, screwpile lighthouse has been guiding ships safely through the Bay since 1875, and it's the last of its kind still in its original location. While you can admire it from afar on many boat tours, nothing beats setting foot on this National Historic Landmark.

Tours are limited and book up quickly, but they're worth the effort. You'll boat out to the lighthouse and climb up into the keeper's quarters, getting a firsthand look at what life was like for the lighthouse keepers who once called this isolated outpost home.

Key Information:

• Location: Thomas Point, Chesapeake Bay (boat access only)
• Hours: Tours run on select Saturdays, June through October
• Admission: $80 per person

Why Visit: Step inside a piece of maritime history and enjoy unparalleled views of the Chesapeake Bay.

Insider Tip: Bring a camera with a good zoom lens – the lighthouse is a favorite hangout for local ospreys and cormorants.

Attend the Annapolis Boat Shows

If you're a boat enthusiast (or just like to pretend you are), time your visit for one of Annapolis' world-famous boat shows. Held in October, these back-to-back events – the United States Sailboat Show and the United States Powerboat Show – transform the city's harbor into a floating metropolis of gleaming vessels.

From sleek sailing yachts to luxurious power cruisers, you'll find every type of boat imaginable. Even if you're not in the market to buy, it's a spectacle worth seeing. Climb aboard shiny new boats, check out the latest marine gadgets, and dream about your future life as a sea captain.

Key Information:

• Location: City Dock, Annapolis
• Dates: Two weekends in October (check website for exact dates)
• Admission: Adults $20-$35, depending on the day

Why Visit: Experience the largest in-water boat shows in the world right in the heart of Annapolis.

Insider Tip: Visit on Preview Day for a less crowded experience and first dibs on show specials.

Enjoy a Pint at Galway Bay Irish Restaurant

In a city with such strong maritime roots, it's no surprise that Annapolis knows how to pour a proper pint. Galway Bay Irish Restaurant brings a slice of the Emerald Isle to Maryland's capital, complete with dark wood interiors, hearty pub grub, and an impressive selection of Irish whiskeys.

While the Guinness here flows as freely as the Chesapeake, don't miss their house-made Irish Egg Nog, available year-round. It's so good, they bottle and sell it across the state. Pair it with some bangers and mash or fish and chips for the full Irish experience.

Key Information:

• Location: 63 Maryland Ave, Annapolis, MD 21401
• Hours: Mon-Thu 11 AM - 12 AM, Fri-Sat 11 AM - 2 AM, Sun 10 AM - 12 AM
• Price: $$

Why Visit: Experience authentic Irish hospitality and cuisine in the heart of Annapolis.

Insider Tip: Visit during their weekly Irish music sessions for a lively atmosphere that'll have you tapping your feet.

Paddle to Honeymoon Bridge

For a peaceful escape just minutes from downtown, grab a kayak or stand-up paddleboard and make your way to Honeymoon Bridge. This hidden gem, tucked away in Quiet Waters Park, is a charming wooden footbridge that spans a narrow part of Harness Creek.

The paddle there is half the fun, taking you through serene waters where you might spot herons fishing or turtles sunning themselves on logs. Once you reach the bridge, tie up your vessel and take a stroll. It's a popular spot for, you guessed it, honeymooners, but it's just as magical for any romantic outing or peaceful solo adventure.

Key Information:

• Location: Harness Creek, accessible via Quiet Waters Park
• Hours: Park hours (7 AM - dusk)
• Price: Park admission $6 per vehicle, kayak rentals available

Why Visit: Enjoy a peaceful paddle and discover a hidden romantic spot in Annapolis.

Insider Tip: Pack a picnic to enjoy on the small beach near the bridge – it's the perfect spot for a scenic lunch.

Browse the Annapolis Bookstore

Bibliophiles, rejoice! The Annapolis Bookstore is a book lover's paradise, housed in a charming 18th-century building on Maryland Avenue. This isn't your average bookstore – it's a labyrinth of literary treasures, with rooms upon rooms filled with both new and used books.

Get lost among the shelves, curl up in one of the cozy reading nooks, or join one of their frequent author events or book clubs. And don't miss the secret garden out back – it's the perfect spot to crack open your new purchase with a cup of coffee from the in-store café.

Key Information:

• Location: 53 Maryland Ave, Annapolis, MD 21401
• Hours: Mon-Sat 10 AM - 8 PM, Sun 10 AM - 5 PM
• Price: Varies (used books offer great deals!)

Why Visit: Discover literary treasures in a historic setting with tons of character.

Insider Tip: Check out their rare book room upstairs for some truly unique finds.

Visit the Kunta Kinte-Alex Haley Memorial

At the heart of Annapolis' City Dock, you'll find a powerful tribute to both the resilience of the human spirit and the importance of storytelling. The Kunta Kinte-Alex Haley Memorial marks the spot where Kunta Kinte, ancestor of author Alex Haley and protagonist of the groundbreaking novel "Roots," was brought to America on a slave ship in 1767.

The memorial features a bronze statue of Alex Haley reading to children of diverse ethnicities, surrounded by plaques that tell Kunta Kinte's story. It's a moving reminder of a difficult past and a call to celebrate the cultural diversity that has shaped America.

Key Information:

• Location: 1 Dock St, Annapolis, MD 21401
• Hours: Always open
• Admission: Free

Why Visit: Reflect on an important part of American history and the power of knowing our roots.

Insider Tip: Visit at night when the memorial is beautifully lit, offering a different perspective on the powerful sculptures.

Catch a Game at Navy-Marine Corps Memorial Stadium

Even if you're not a die-hard sports fan, catching a Navy football game is an experience not to be missed. The atmosphere at Navy-Marine Corps Memorial Stadium is electric, with midshipmen marching in formation and the Naval Academy mascot, Bill the Goat, rallying the crowd.

But it's not just about the game. The stadium itself is a memorial to fallen Navy and Marine Corps personnel, with arches naming significant battles and campaigns. It's a unique blend of athletic excitement and solemn remembrance that you won't find anywhere else.

Key Information:

• Location: 550 Taylor Ave, Annapolis, MD 21401
• Hours: Varies by game schedule
• Price: Varies, typically $25-$50 per ticket

Why Visit: Experience the thrill of college football combined with naval tradition and history.

Insider Tip: Arrive early to tailgate with locals and enjoy the pre-game festivities.

Explore Sandy Point State Park

Just a short drive from downtown Annapolis, Sandy Point State Park offers a perfect escape to nature. With its sandy beaches, picnic areas, and hiking trails, it's a favorite spot for locals and visitors alike to enjoy the Chesapeake Bay.

Take a dip in the bay, cast a line from the fishing jetty, or simply relax on the beach with views of the iconic Bay Bridge. In the winter, keep an eye out for the "polar bear plunge," where brave (or crazy) souls take a dip in the frigid waters for charity.

Key Information:

• Location: 1100 East College Parkway, Annapolis, MD 21409
• Hours: 6 AM to sunset, year-round
• Admission: $4 per person in-state, $6 per person out-of-state

Why Visit: Enjoy beach activities and stunning Bay views just minutes from Annapolis.

Insider Tip: Visit on a weekday to avoid the weekend crowds, especially in the summer.

Sample Local Flavors at the Annapolis Farmers Market

Get a taste of the local bounty at the Annapolis Farmers Market. Held year-round, this market brings together the best of what local farmers, bakers, and artisans have to offer. From fresh Chesapeake seafood and organic produce to homemade jams and artisanal cheeses, it's a feast for the senses.

Chat with the vendors to learn about their products and get tips on how to prepare them. It's not just about shopping – it's about connecting with the local community and understanding the rich agricultural heritage of the Chesapeake region.

Key Information:

• Location: Riva Road and Harry S. Truman Parkway
• Hours: Saturdays 7 AM - 12 PM (April-December), 9 AM - 12 PM (January-March)
• Price: Free admission, bring cash for purchases

Why Visit: Experience the local flavors and meet the people behind Annapolis' food scene.

Insider Tip: Arrive early for the best selection, especially for popular items like fresh eggs and seasonal produce.

Take a Ghost Tour of Annapolis

As night falls, Annapolis takes on a different character. The colonial-era streets, dimly lit by flickering lamps, set the perfect stage for tales of the supernatural. Join one of the city's popular ghost tours for a spine-tingling journey through Annapolis' haunted history.

From the ghost of a Frenchman said to haunt the Maryland Inn to the spirit of an enslaved woman at the William Paca House, you'll hear stories that will make you see the city in a whole new light. Whether you're a believer in the paranormal or just enjoy a good story, these tours offer a unique and entertaining way to explore Annapolis after dark.

Key Information:

• Location: Various starting points in downtown Annapolis
• Hours: Usually 8 PM or 9 PM, check with tour operators
• Price: Around $20 per adult

Why Visit: Discover Annapolis' spooky side while learning about its history in an entertaining way.

Insider Tip: Bring a camera – you never know what might show up in your photos!

Visit the Hammond-Harwood House

Step back in time at the Hammond-Harwood House, one of the finest examples of Anglo-Palladian architecture in the country. Built in 1774, this Georgian mansion offers a glimpse into the lives of wealthy colonists on the eve of the American Revolution.

The house is renowned for its exquisite woodcarvings, plasterwork, and original furnishings. Don't miss the incredible collection of paintings by Charles Willson Peale and his family. The guided tours are informative and engaging, bringing the house's history to life.

Key Information:

• Location: 19 Maryland Ave, Annapolis, MD 21401
• Hours: Tue-Sun 12 PM - 5 PM (Apr-Dec), Fri-Sun 12 PM - 5 PM (Jan-Mar)
• Admission: Adults $10, Seniors $9, Students $6

Why Visit: Explore one of America's best-preserved colonial homes and its impressive art collection.

Insider Tip: Ask about the secret drawer in the game table – it has a fascinating story!

Enjoy Craft Beers at Forward Brewing

Annapolis might be known for its history, but it's not stuck in the past. Case in point: Forward Brewing, a modern craft brewery that's making waves in the local beer scene. Located in Eastport, just across the bridge from downtown, this small-batch brewery offers a rotating selection of innovative brews.

From crisp lagers to hop-forward IPAs and experimental sours, there's something for every beer lover. The taproom has a laid-back, friendly vibe that perfectly captures the spirit of Eastport. Grab a flight to sample a variety of brews, or settle in with a pint and watch the sailboats go by.

Key Information:

• Location: 418 Fourth St, Annapolis, MD 21403
• Hours: Wed-Thu 4 PM - 9 PM, Fri 3 PM - 10 PM, Sat 12 PM - 10 PM, Sun 12 PM - 8 PM
• Price: $$

Why Visit: Taste innovative, locally-brewed beers in a casual, waterfront setting.

Insider Tip: Try their beer slushies in the summer – they're refreshing and uniquely delicious!

Explore the Annapolis Arts District

For a taste of Annapolis' creative side, head to the Annapolis Arts District. This vibrant neighborhood, centered around West Street, is home to a diverse array of galleries, theaters, and public art installations.

Start at the Annapolis Collection Gallery to see works by local artists, then catch a show at the Annapolis Shakespeare Company. Don't miss the colorful murals scattered throughout the district – they make for great photo ops. If you're lucky, you might catch one of the district's events, like the monthly First Sunday Arts Festival.

Key Information:

• Location: West Street and surrounding area
• Hours: Vary by venue
• Price: Many galleries are free to enter, event prices vary

Why Visit: Immerse yourself in Annapolis' thriving arts scene and support local creatives.

Insider Tip: Visit during the First Sunday Arts Festival (May-November) to enjoy live music, art vendors, and street performances.

Structuring Your Annapolis Trip for a 3-Day Itinerary

Now that we've explored the best things to do in Annapolis, let's put it all together into a manageable 3-day itinerary. This plan will help you make the most of your visit, balancing must-see attractions with time to soak in the city's unique atmosphere.

Day 1: Historic Annapolis and Naval Traditions

Start your Annapolis adventure with a deep dive into the city's rich history and naval heritage.

• Morning: Begin with a tour of the U.S. Naval Academy. Don't miss the impressive Chapel and the Naval Academy Museum.
• Lunch: Grab a bite at Chick & Ruth's Delly, a local institution known for its oversized sandwiches named after politicians.
• Afternoon: Explore the Maryland State House and take a stroll through historic downtown, including a stop at the Kunta Kinte-Alex Haley Memorial.
• Evening: Enjoy dinner on Main Street, followed by a ghost tour for some spine-tingling fun.

Day 2: Maritime Adventures and Local Flavors

Today's all about experiencing Annapolis' connection to the water and its culinary scene.

• Morning: Start with a sailing trip on the Chesapeake Bay. For a more active option, try kayaking on Spa Creek.
• Lunch: Head to Eastport for lunch at a waterfront restaurant like Chart House or Boatyard Bar & Grill.
• Afternoon: Visit the Annapolis Maritime Museum to learn about the city's oyster industry, then explore the quirky shops and galleries of Eastport.
• Evening: It's time for a traditional Maryland crab feast at Cantler's Riverside Inn.

Day 3: Arts, Culture, and Relaxation

Wrap up your visit with a mix of culture and outdoor enjoyment.

• Morning: Start your day at the Annapolis Farmers Market (if it's a Saturday), then explore the Annapolis Arts District.
• Lunch: Enjoy a quick lunch at Galway Bay Irish Restaurant.
• Afternoon: Spend a relaxing afternoon at Quiet Waters Park. Rent a bike or simply enjoy the walking trails and art galleries.
• Evening: Catch a show at Rams Head On Stage to end your trip on a high note.

Remember, this is just a suggested itinerary. Annapolis is a city that rewards wandering, so don't be afraid to stray from the plan if something catches your eye. Each day offers opportunities to mix and match activities based on your interests, energy levels, and the weather.

Also, keep in mind that some attractions might have different operating hours or require advance booking, especially in the off-season or due to current health guidelines. Always check the official websites or call ahead to confirm details.

Most importantly, take time to soak in the atmosphere of this charming city. Sit on a bench by the harbor, chat with locals, and enjoy the laid-back vibe that makes Annapolis special. Whether you're a history buff, a sailing enthusiast, or just looking for a relaxing getaway, Annapolis has something for everyone.

Indulge in Ice Cream at Annapolis Ice Cream Company

No trip to Annapolis is complete without a scoop (or two) from the Annapolis Ice Cream Company. This local favorite churns out small-batch, homemade ice cream in a variety of creative flavors that change with the seasons.

From classics like vanilla and chocolate to unique concoctions like Apple Pie or Peanut Butter Oreo, there's a flavor to satisfy every sweet tooth. The shop's prime location on Main Street makes it the perfect spot for an after-dinner treat or a mid-afternoon pick-me-up.

Key Information:

• Location: 196 Main St, Annapolis, MD 21401
• Hours: Sun-Thu 11 AM - 10 PM, Fri-Sat 11 AM - 11 PM
• Price: $

Why Visit: Taste some of the best homemade ice cream in Annapolis in a charming, local shop.

Insider Tip: Try the "Skipjack," a flavor that changes daily – it's always a delightful surprise!

Shop at Midnight Madness

If you're visiting Annapolis during the holiday season, don't miss Midnight Madness. This beloved local tradition transforms downtown Annapolis into a festive wonderland, with shops staying open late and offering special deals.

Stroll down Main Street, Maryland Avenue, and West Street, all decked out in twinkling lights and holiday decorations. Street performers, carolers, and the scent of hot cider add to the magical atmosphere. It's the perfect opportunity to find unique gifts while soaking in Annapolis' small-town charm.

Key Information:

• Location: Downtown Annapolis
• Dates: Two Thursdays in December (check website for exact dates)
• Admission: Free

Why Visit: Experience Annapolis at its most festive and magical while getting some holiday shopping done.

Insider Tip: Park at the Navy-Marine Corps Memorial Stadium and take the free shuttle downtown to avoid parking hassles.

Take a Water Taxi Ride

See Annapolis from a different perspective by hopping aboard one of the city's water taxis. These charming boats offer not just transportation, but a unique tour of the harbor and surrounding waterways.

Cruise past the Naval Academy, get up close to massive yachts, and enjoy unobstructed views of the Annapolis skyline. The captains are often long-time locals who can share fascinating stories and point out landmarks you might otherwise miss.

Key Information:

• Location: Various pickup points around Annapolis Harbor
• Hours: Seasonal, typically 9 AM - 11 PM in summer
• Price: $3-$8 per person, depending on the route

Why Visit: Enjoy scenic views of Annapolis from the water while learning from knowledgeable local captains.

Insider Tip: Take the water taxi to Eastport for dinner – it's a fun and memorable way to get to some of the city's best restaurants.

Final Thoughts on Annapolis

Annapolis may be small in size, but it's big on charm, history, and maritime culture. From its colonial past to its vibrant present, Maryland's capital offers a unique blend of experiences that make it a standout destination on the East Coast.

Whether you're sailing on the Chesapeake Bay, strolling through historic streets, indulging in fresh seafood, or immersing yourself in naval tradition, Annapolis has a way of capturing your heart. Its walkable size makes it easy to explore, while its depth of attractions ensures you'll never run out of things to do.

As you plan your visit, remember that Annapolis shines in every season. Summer brings warm days perfect for sailing and outdoor concerts. Fall offers crisp weather ideal for ghost tours and boat shows. Winter transforms the city into a holiday wonderland. And spring bursts with blooming gardens and the excitement of naval academy graduations.

No matter when you visit, take the time to engage with the locals. Annapolitans are proud of their city and always ready to share their favorite spots or a good story. Sit at a bar in Eastport, chat with a shopkeeper on Main Street, or strike up a conversation with a midshipman – these interactions often lead to the most memorable experiences.

Before you leave, take a moment to stand by the water's edge and look out over the Chesapeake Bay. Feel the breeze, listen to the call of seagulls, and watch the sailboats glide by. In that moment, you'll understand why Annapolis has captivated visitors for centuries and why it continues to be a treasure of the Chesapeake.

So pack your boat shoes (or just comfortable walking shoes), bring your sense of adventure, and prepare to fall in love with Annapolis. From its rich history to its vibrant culture, from its maritime heritage to its culinary delights, Annapolis is ready to welcome you. Who knows? You might just find yourself planning your return trip before you even leave.