Annapolis might just be the East Coast's most underrated gem. With its sailboat-studded harbors, cobblestone streets, pastel-colored houses, and a rich swirl of colonial and maritime history, it's a solo travel dream. Whether you're craving coastal adventures, peaceful garden walks, or a dive into American history, Annapolis delivers with charm in every corner. Here's your go-to guide for the most delightful, safe, and unforgettable things to do in and around Annapolis, Maryland.

1. Visit the Maryland State House and Lawyers Mall

The Maryland State House is a must for history buffs and solo wanderers who love a good story with their sightseeing. As the oldest state capitol still in continuous legislative use, this gorgeous Georgian building has seen everything from George Washington resigning his military commission to the ratification of the Treaty of Paris. It’s free to enter, and the guided tours are short, informative, and filled with tons of information that you won’t get from a plaque.

Step outside onto Lawyers Mall, a tree-lined plaza dotted with statues and historic markers. It’s a peaceful place to sit and reflect, especially in the early morning when the crowds are low. Located in the heart of Annapolis’ historic district, it’s a perfect first stop before weaving your way into the rest of the city’s colonial charm.

2. Tour Annapolis Harbor by Boat

See Annapolis from its most iconic perspective: the water. Several boat tours depart from the Annapolis City Dock, including 40-minute harbor cruises, romantic sunset sails, and even history-themed voyages. For solo travelers, it’s a lovely way to relax, take photos, and hear stories from local guides about the city's maritime past. I rode the Watermark Annapolis Harbor & USNA Cruise in the afternoon and the team was so much fun! The captain even let me have a go at the wheel!

The Annapolis Harbor has been the heart of the city for over 300 years. You’ll cruise past the U.S. Naval Academy, charming waterfront homes, and busy marinas. Most tours run spring through fall, and tickets can be booked in advance or right on the dock.

3. Stroll the Annapolis Harbor on Foot

Not into boating? No worries. Walking along the Annapolis Harbor is just as magical—maybe even more so. As a solo traveler, this is your chance to slow down and really take in the city’s rhythm. Start at City Dock, where locals sip coffee and chat by the waterfront, and wander along Ego Alley as sailboats and yachts glide in and out like a slow-motion ballet.

There’s something grounding about hearing the creak of dock lines and the call of gulls while watching the water sparkle in the sun. Grab an iced latte from a nearby café and let yourself drift from boutique to bench to art gallery. One of the best parts? You can do it all at your own pace. No need to rush. Pause by the bronze Alex Haley statue for a moment of reflection, then meander past the shops and colonial brick buildings. Annapolis Harbor is a place that rewards you for showing up solo—it feels like it was made for quiet exploration and spontaneous joy.

4. Admire the Colorful Houses on Pinkney Street & Fleet Street

If you're looking for Instagram-worthy spots, this is it. Pinkney Street and Fleet Street are lined with colonial-era homes in shades of butter yellow, periwinkle, mint green, and coral. It's like walking through a pastel dreamscape, and yes—your camera roll will thank you. The houses look like they were plucked straight out of a storybook, with their crisp shutters, quirky door knockers, and flower boxes spilling over with blooms.

But this stroll isn’t just about the aesthetics. It’s about the vibe. There’s something deeply comforting in wandering down a quiet lane where history lives in the cracks of the brick and color is used unapologetically. Maybe you’ll find yourself chatting with a local tending their garden, or maybe you’ll just soak in the stillness and charm.

These streets are part of the historic downtown, just a few blocks from the City Dock, and they’re perfectly walkable. Reminder: these are people’s homes, so an extra long, unnecessary photo session is not recommended. Be quick and polite as you capture the beauty of the homes.

5. Tour the William Paca House & Garden

Step back into the 18th century at the William Paca House, a beautifully restored Georgian mansion that offers an intimate peek into early American life. Built by William Paca, a signer of the Declaration of Independence, the home is a living piece of history with original woodwork, antique furnishings, and stories that bring Annapolis’ colonial past vividly to life. The guided tours are small and personable—perfect if you're traveling solo and want to ask questions without feeling rushed.

But let’s talk about the garden, because it is truly the star of the show. Step through the back doors and you’ll find yourself in a two-acre, walled garden that feels like a secret world. Think: terraced paths, a lily pond, and quiet benches under arching trees. It’s the kind of place where you can journal, breathe, and feel completely at peace. Located right in the heart of downtown, it's a gentle escape from the bustle—ideal for solo travelers craving a moment of calm beauty. Don’t be surprised if you end up staying longer than planned.

6. Visit the U.S. Naval Academy

You don’t need to be military-minded to appreciate this legendary institution—trust me, the U.S. Naval Academy is far more than uniforms and marching bands. Stepping onto the grounds feels like walking into a living monument of American history and ambition. The guided tours are led by passionate midshipmen or expert guides who are informative, welcoming, and never overwhelming. You’ll walk past grand Beaux-Arts buildings, peek inside Bancroft Hall (the largest college dormitory in the country!), and even visit the Naval Chapel and the crypt of John Paul Jones, the father of the U.S. Navy.

But it’s not just about history—it’s about presence. There's something powerful about watching cadets in formation while sailboats glide across the water. The grounds are peaceful, immaculately kept, and surprisingly meditative. You’ll need a government-issued ID to enter, and while bags are limited, all you really need is your curiosity. Pro tip: wear comfy shoes—this place is bigger than it looks. And don't skip the gift shop, which is full of surprisingly cute Navy gear and women-owned local brands.

7. Soak Up the Sun at Sandy Point State Park

Just a 15-minute drive from downtown Annapolis, Sandy Point offers sandy beaches, shady picnic spots, and views of the iconic Chesapeake Bay Bridge. It’s a sweet solo escape for a morning swim, a lazy picnic, or a sunset walk. This spot is especially great if you're craving a nature break after a history-heavy day. Bring a book, wear your swimsuit, and don’t forget your camera—the views here are chef’s kiss.

8. Dinner at Cantler’s Riverside Inn

This waterfront crab house is where locals go to get messy with Maryland’s famous blue crabs. It’s casual, lively, and perfect for solo diners thanks to the communal tables and friendly staff. Even if you don’t want to crack crabs, there are other delicious options. Cantler’s is tucked away on Mill Creek, just a 10-minute drive from the historic district. Pro tip: go early to avoid long waits, and bring cash—some seating areas are cash-only.

9. Rent a Kayak in Back Creek

For a little active adventure with a peaceful twist, rent a kayak or paddleboard in Back Creek and let yourself drift into a different side of Annapolis. This hidden gem of a waterway, tucked just south of downtown in Eastport, is quieter than the main harbor, which means fewer boats and more serenity. Perfect for folks who want to connect with nature and explore at their own rhythm—no group schedules, no pressure.

Out on the water, you’ll paddle past marinas, charming waterfront cottages, and maybe even spot a blue heron or two stalking the shoreline. The water here is typically calm, so even beginners will feel comfortable. Most rental shops are super friendly and will give you a quick how-to if it’s your first time. Pack a waterproof pouch for your phone (photos, hello!), wear sunblock, and enjoy every minute of this gentle, scenic escape.

10. Crack Some Oysters at Boatyard Bar & Grill

This Annapolis favorite is all about the seafood, and their oysters are the main event. Grab a seat at the bar and strike up a convo with locals or just enjoy people-watching. Boatyard Bar & Grill is located in Eastport, a short walk across the Spa Creek Bridge. It has a laid-back vibe with nautical decor and a solid menu full of Chesapeake flavors.

11. Walk Around Quiet Waters Park

Need a serene moment away from people? Quiet Waters Park is your spot. With over 340 acres of trails, gardens, forests, and waterfront views, this peaceful retreat feels a world away from the city—yet it’s just a quick 10-minute drive from downtown Annapolis. Whether you're in the mood for a meditative walk, a sketching session under the trees, or simply some quiet time by the water, this place wraps you up in nature and calm.

You can wander at your own pace, stopping to admire outdoor sculptures in the art garden, journaling in the shade of a willow, or watching paddleboarders glide across the creek. The park even has a designated dog beach, which is great if you're missing your pup or just want to watch some joyful canine chaos. It's safe, uncrowded on weekdays, and absolutely made for introspective wandering. Bring a water bottle, a snack, and your favorite playlist—or just let the birds be your soundtrack.

12. Eat Ice Cream at Annapolis Ice Cream Company

Sometimes you just need a scoop (or three). This small-batch, local favorite serves up classic and quirky flavors, all made on-site. It’s perfect for a sweet solo treat while people-watching on Main Street. Located right in the heart of downtown, this spot often has a line—but it moves fast and is 100% worth the wait. Don’t skip their seasonal specials!

13. Grab a Coffee at Annapolis Market House

Part cafe, part foodie market, the Annapolis Market House is a great stop for a solo breakfast or afternoon pick-me-up. The open-air vibe and community tables make it easy to sit and stay awhile.

You’ll find it right at City Dock, steps away from the harbor. Grab a latte, maybe a pastry, and enjoy the energy of one of the most vibrant corners of Annapolis.

14. Check Out the Historical Statues Around Town

Annapolis is full of meaningful public art. History in Annapolis isn’t tucked away in museums—it’s right out in the open, woven into the sidewalks, parks, and plazas. As you explore the city, take time to pause at the historical statues and monuments that tell powerful stories of resilience, justice, and identity. One of the most moving stops is the Kunta Kinte – Alex Haley Memorial at City Dock, where a bronze sculpture of Haley reading to children honors the real-life descendant of an enslaved man brought through Annapolis. It’s not just art—it’s storytelling that roots you to place and purpose.

Just a few blocks away at Lawyers Mall, you’ll find the Thurgood Marshall statue, a tribute to the first African American Supreme Court Justice, who grew up nearby. These aren’t just photo ops—they’re spaces to reflect, connect, and learn.

15. Day Trip to Fort McHenry National Monument

If you love a good flag-waving moment or a deep dive into American resilience, Fort McHenry is calling your name. Located just an hour north of Annapolis in Baltimore, this star-shaped fort is where Francis Scott Key penned the lyrics to what would become “The Star-Spangled Banner” during the War of 1812. Walking through its gates feels like stepping into a living piece of patriotic history. You can watch reenactments, witness the daily flag-raising ceremony, and take a self-guided tour through barracks and bunkers once used to defend the Baltimore Harbor.

The views here are stunning—seriously, bring your camera. From the ramparts, you’ll see ships passing in the distance and the skyline of Baltimore across the water. Getting there is best by car, or you can take the MARC train and grab a quick rideshare. Pack a snack or picnic lunch, because the grassy areas along the water are perfect for spreading out a blanket and soaking it all in. Whether you’re here for the history or just the fresh air and perspective, Fort McHenry is a day trip that delivers on both heart and heritage.

16. Day Trip to Calvert Cliffs State Park

Want to hunt for 15-million-year-old fossils? Head an hour south to Calvert Cliffs State Park, where the past quite literally could wash up at your feet. The 1.8-mile hike to the beach is mostly flat, shaded, and wonderfully peaceful—perfect for someone who loves a mix of quiet woods and coastal wonder. You’ll hear birdsong, pass little streams, and maybe even catch glimpses of deer along the way. It's an easy trail with a big reward at the end: a dramatic stretch of shoreline backed by soaring fossil-rich cliffs.

The real magic happens at the water’s edge. Bring a sieve or just use your hands—this is where you can dig around for prehistoric treasures like ancient shark teeth and shell fossils. It’s best visited early in the day before crowds roll in. Pack a picnic, wear shoes that can handle a little mud, and give yourself permission to slow down and enjoy.

17. Dinner & Wandering in St. Michaels, MD

This charming harbor town is just over an hour from Annapolis over the William Preston Lane Jr. Memorial (Bay) Bridge and makes for a dreamy evening escape. Start your adventure with a scenic drive across the Eastern Shore—windows down, playlist on, and that sweet feeling of freedom only travel can bring. Once you arrive in St. Michaels, the mood shifts instantly: it’s slower, softer, and wrapped in maritime nostalgia. Grab dinner at one of the waterfront restaurants where fresh seafood is the star. I ate at Awful Arthur's Seafood Company (unfortunately closed in 2022).

After dinner, let your curiosity guide you through town. Grab a scoop of ice cream from Justine's Ice Cream Parlour and wander the main street then head to Muskrat Park on the harbor to watch the sky melt into twilight. The historic vibe here is rich, but never stuffy—just the kind of place where you can linger without feeling out of place.

18. Explore the Chesapeake and Ohio Canal National Historical Park

For a full-day outdoor adventure that blends natural beauty with American history, head about 50 miles west to the Chesapeake and Ohio Canal National Historical Park. This incredible greenway stretches for nearly 185 miles along the Potomac River, but don’t worry—you only need to explore a small stretch to feel like you've uncovered something special.

Start your journey at Great Falls (I visited the Maryland side), where you’ll walk about half a mile from the Great Falls Tavern Visitor Center to the overlook. The trail is short but scenic, and the reward? Sweeping views of the Potomac River as it crashes dramatically over jagged rocks. This area can get busy and parking is limited, so go early to enjoy the views with a little more serenity.

From there, head south to the Boathouse at Fletcher’s Cove to rent a bike for the afternoon. You’ll park in a nearby residential area and walk about 15 minutes to the boathouse tucked along the canal path. Rentals include bikes, kayaks, SUPs, and canoes—but for this visit, I went with a basic mountain bike, which was perfect for the smooth, mostly flat trail. I biked 12 peaceful miles north, finishing just north of the Great Falls area.

This section of the C&O Canal is wide, shaded, and wonderfully quiet. You’ll ride past charming lock houses, pause at footbridges, and maybe even spot turtles sunbathing on the canal banks. There’s no rush, no pressure—just space to breathe and move at your own pace. Bring plenty of water, sunscreen, and a snack (or two), and don’t forget your camera. The path is perfect for riders looking for reflection, movement, and a whole lot of beauty tucked between the trees.

A Great Time in Annapolis

Annapolis has that rare mix of charm, soul, and just enough edge to keep a solo traveler endlessly inspired. This isn't just a place to pass through—it's a destination to wander slowly, breathe deeply, and connect with history, water, and yourself.

You don’t have to be fearless to travel solo—you just have to be curious. And in Annapolis, your curiosity will be well rewarded. So go ahead: plan the trip, book the ticket, and show up for yourself. The harbor is waiting, and trust me—it looks even better when you’re walking into it on your own terms. Whether you're chasing history, sunshine, or just a little peace and quiet, Annapolis is your reminder that you don't need anyone else to have the adventure of a lifetime.

18 Wonderful Things to Do in Annapolis, Maryland