Annapolis is a city that invites exploration, whether by water, on foot, or through its haunted past. Its compact downtown, filled with historic buildings and lively waterfronts, makes it ideal for a variety of tours. We particularly love the Annapolis Harbor and U.S. Naval Academy Cruise for its relaxed 40-minute boat ride offering views of majestic sailboats and the Naval Academy’s iconic buildings. The Historic Walking Tour delivers a 2-hour deep dive into the city’s storied past, with stories about Washington, the Treaty of Paris, and the State House that truly bring Annapolis to life. For an eerie twist, the Haunted Annapolis Tour offers ghost stories rooted in real history, perfect for those who enjoy a spooky story with their sightseeing.
Annapolis is especially well-suited for those interested in American history, maritime culture, or just a relaxed day exploring a charming waterfront town. Its compact size makes in-depth tours manageable, and many experiences include notable landmarks like Ego Alley, the Maryland State House, and the Naval Academy. Whether you prefer a scenic cruise, a walking tour, or a ghostly adventure, Annapolis offers a variety of options to suit your interests and schedule.
1. Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise
At number 1, this 40-minute cruise offers a relaxed way to see the Annapolis Harbor and the U.S. Naval Academy. The boat tour is perfect for those short on time but eager to get a feel for the waterfront life, historic buildings, and sailboats bobbing in the harbor. The recorded narration provides interesting insights about the Naval Academy’s history and the city’s maritime heritage. This cruise is an affordable option at $30 per person, with consistently high ratings (4.7/5 from 115 reviews). It’s especially good for travelers who want a quick overview with scenic views, without the hassle of walking or long tours. Expect to see the stunning waterfront, learn about Annapolis’s naval connections, and enjoy a breezy ride. It’s a great warm-up or a quick break in your day.
Bottom line: A great choice for first-time visitors or those with limited time who want a scenic overview with educational tidbits.
2. Annapolis Historic Walking Tour at Harbor and Naval Academy
The 2-hour walk through Annapolis’s historic district ranks high for its depth and personalized storytelling. Led by a passionate guide, the tour hits highlights like Ego Alley, the Maryland State House, and the Naval Academy, including the Chapel and the Crypt of John Paul Jones. The guide, Michael, gets rave reviews for being knowledgeable, engaging, and accommodating, even in bad weather. The tour costs $235 per group (up to 10 people), which makes it excellent value for a private, in-depth experience. It is particularly suited for history lovers who appreciate stories about Washington’s resignation, the Treaty of Paris, and the architecture of Georgian mansions. Walking at a leisurely pace, you’ll soak in the charm of the streets and learn about the city’s role in American history.
Bottom line: For those who want a small-group, comprehensive look at Annapolis’s landmarks and stories, this tour hits the mark.
3. Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
For travelers intrigued by the spooky side of history, the 1-hour haunted tour offers ghost stories rooted in real events. Explore sites like Middleton Tavern and the James Brice House, where spirits are said to linger. The stories focus on local legends, such as the ghost of Roland in Middleton Tavern and restless spirits in historic homes. The tour features lively narration and a mix of historical facts and supernatural tales. Rated 4.5/5 from 83 reviews, many find it both entertaining and chilling. It’s perfect for history buffs who enjoy a spooky twist, or groups looking for a memorable night activity. The tour balances chilling stories with sightseeing, making it a fun, slightly eerie experience.
Bottom line: A fun, spooky way to experience Annapolis’s dark side, best suited for those who enjoy ghost stories intertwined with history.
4. Colonial Annapolis, State House & U.S. Naval Academy Tour
This 135-minute guided walk covers Annapolis’s most iconic landmarks, including its State House and the U.S. Naval Academy. It combines outdoor exploration with historical narration, giving you a well-rounded view of the city’s origins and significance. Guides share stories about key events like Washington’s resignation and the signing of the Treaty of Paris. The route winds through charming streets lined with colonial architecture and historic sites, providing a rundown. With a 4.8/5 rating from 34 reviews, it’s a popular choice for those wanting a deeper understanding of Annapolis’s evolution over four centuries. The tour balances education with scenic strolling, making it ideal for history enthusiasts who want a longer experience.
Bottom line: Perfect for travelers seeking a thorough, story-rich introduction to Annapolis’s historic district.
5. Historic Annapolis Food Tour
For something more flavorful, the 3.5-hour food tour combines history with cuisine. Visiting historic spots like taverns once frequented by Washington and Jefferson, you sample dishes at local eateries while learning their stories. Highlights include stops at historic restaurants and insider tips on where locals dine. This tour is rated 4.5/5 from 34 reviews and costs $80 per person. It’s perfect if you want a taste of local flavors alongside fascinating stories—think of it as a culinary history lesson with a side of good eats. Participants rave about the knowledgeable guide, Caroline, and the delicious stops, which keep everyone satisfied and engaged.
Bottom line: Great for food lovers or anyone wanting to combine sightseeing with flavorful bites.
6. Annapolis: Maryland State House Tour
This 75-minute tour of the Maryland State House features a period-attired guide revealing the building’s pivotal role in American history. As the oldest legislative building in continuous use, it’s where the Treaty of Paris was signed, and George Washington resigned his commission. The tour explores the architecture, grounds, and stories of notable Marylanders like Thurgood Marshall. Rated 5/5 from 6 reviews, it offers an intimate look into Maryland’s political history. It’s ideal for history buffs interested in American governance and architecture, with plenty of time to absorb the significance of this historic site.
Bottom line: An engaging, compact tour that immerses you in Maryland’s political milestones.
7. Outdoor Painting Activity with a Local Artist in Annapolis
Unleash your inner artist with this outdoor watercolor class led by a talented local painter. The 1.5-hour activity includes all materials and takes place in the scenic surroundings of Annapolis’s historic district. Participants learn basic watercolor techniques while capturing a local landmark, making it ideal for creative types or families. The guide, Em, is praised for her approachable teaching style, and the experience ends with taking home your own artwork. Rated 5/5 from 4 reviews, it’s a fun, relaxed way to connect with the city’s scenery and create a memorable souvenir. Kids aged 8 and up are welcome, making this suitable for families or small groups.
Bottom line: A unique, hands-on experience perfect for aspiring artists or those wanting a fun, artistic break.
8. The Original Haunted Pub Crawl by Annapolis Ghost Tours
For a lively evening, this 2-hour ghost-themed pub crawl combines history with drinks. Visit historic pubs like Middleton Tavern and Reynolds Tavern, with stories about their haunted pasts. The guide shares tales of ghostly barmaids, spirits, and paranormal activity while you enjoy a drink at each spot. Rated 4.5/5 from 12 reviews, it’s a fun, social way to experience Annapolis’s haunted side. The tour is flexible for those who want to sip and listen, making it ideal for groups seeking a quirky night out with a supernatural twist.
Bottom line: Perfect for night owls wanting a mix of drinks, history, and ghost stories.
9. Amazing Annapolis Scavenger Hunt
Turn discovery into a game with this citywide scavenger hunt lasting about 2 hours. Solve clues, complete challenges, and learn about landmarks like the Old Fox bookstore and historic homes—all while racing against other teams. The hunt is app-led, with options for car or walking routes, making it flexible for different fitness levels. Rated 4.5/5 from 7 reviews, it’s a fun activity for families, friends, or team-building groups. It encourages interaction with local businesses and hidden corners of Annapolis, making it a lively, competitive experience.
Bottom line: An active, game-based way to see the city and learn its secrets.
10. Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
This 2-hour pub crawl is a spirited mix of drinks and ghost stories. Visit historic taverns like Middleton Tavern and the Maryland Inn, hearing tales of spirits and murder from Annapolis’s haunted past. The guide shares chilling stories while you sip on drinks you purchase along the way. Rated 4.5/5 from 7 reviews, it’s perfect for those who love a good ghost story with their evening cocktails. It’s a casual, fun way to explore the haunted side of the city while enjoying some local libations.
Bottom line: Best for night owls who want ghost tales and drinks in a historic setting.
11. Hidden History Pub Crawl of Historic Annapolis
The only pub crawl focusing on lesser-known facts about Annapolis, this 2-hour experience visits historic taverns with stories about long-lost brothels and famous personalities chased out of town. With a 5/5 rating from just 1 review, this tour appeals to curious travelers interested in the city’s darker, less-publicized side. Drink specials at some stops add to the fun, and the guide provides local tips for further exploration.
Bottom line: A niche tour for those wanting to uncover Annapolis’s secret stories and enjoy some local brews.
$30.00 per person
12. The Original Walking Ghost Tour by Annapolis Ghost Tours
This 1.5-hour walk explores Annapolis’s most haunted neighborhoods, with stories of paranormal activity tied to historic sites. The guide shares tales of ghostly residents and the city’s darker episodes, making it an engaging alternative to standard sightseeing. Rated 4.0/5 from 27 reviews, it’s suitable for those who enjoy a mild scare intertwined with history. The tour visits key locations like haunted graveyards and the State House, with plenty of atmosphere to keep your curiosity piqued.
Bottom line: Ideal for ghost enthusiasts wanting a spooky stroll through Annapolis’s haunted streets.
13. Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
This 2-hour pub crawl combines storytelling about murder and mayhem with visits to historic taverns. The tales include ghostly bootleggers and sailors, with opportunities to try drinks like the Oyster Shooter. The guide crafts a lively experience with stories about the city’s notorious spirits. With a 4.2/5 rating from 6 reviews, it’s suited for those who want a bit of everything—drinks, history, and ghostly legends.
Bottom line: A spirited way to explore Annapolis’s darker legends with drinks in hand.
14. Annapolis: Round Trip Cruise to St. Michaels
For a relaxing day trip, this 7.5-hour round-trip cruise across Chesapeake Bay takes you to St. Michaels. You explore the town at your own pace, visit the Chesapeake Bay Maritime Museum, and enjoy scenic views from the boat. The cruise includes a complimentary beverage and showcases the maritime heritage of the region. It’s ideal for those who want a leisurely escape from land-based sightseeing, combining scenic sailing with cultural exploration.
Bottom line: Perfect for cruising enthusiasts and lovers of maritime history seeking a scenic, low-stress day trip.
15. Self-Guided Scavenger Hunt: Annapolis Red Bricks & Blue Views
This app-led scavenger hunt encourages independent exploration of Annapolis’s landmarks. The 2-hour challenge involves solving clues and completing challenges at sites like historic streets and unique local spots. It’s a budget-friendly option at just over $12 per person, making it accessible for families or small groups. Many users appreciated the fun learning experience and the chance to discover hidden corners they might miss on a traditional tour.
Bottom line: An engaging, interactive way to see the city at your own pace and challenge yourself and your friends.
$12.31 per person
16. Annapolis: Electric Boat Rental – Duffy Sun Cruiser – 10ppl
This eco-friendly boat rental allows you to cruise Annapolis’s waterways quietly and comfortably. The Sun Cruiser fits up to 10 people and is perfect for celebrating a special occasion or just relaxing on the water. With a rental price of $212 per group, it offers a unique, customizable experience. Passengers can enjoy spectacular waterfront homes, the sunset, or just the peaceful glide through the bay at a leisurely 5 MPH. It’s ideal for those who prefer independence and want a memorable, personalized outing.
Bottom line: A flexible, scenic way to enjoy Annapolis’s water views with friends or family, especially if you love being on the water.
$212 per group up to 10
How to Choose the Best Tour for You
Choosing between these options depends on your interests, schedule, and budget. For a quick, scenic overview, the Annapolis Harbor Cruise offers a lovely introduction. History enthusiasts might prefer the Colonial Annapolis Tour, while food lovers will enjoy the Historic Food Tour. If you’re after a spooky evening, the Haunted Annapolis Tour or Boos & Booze Pub Crawl are fun picks. For more active explorers, the Scavenger Hunt offers a lively challenge, and those with more time can consider the Round Trip Cruise to St. Michaels to enjoy a day on the water.
Remember to book early, especially for popular tours, and consider the time of year—spring and fall often provide the best weather and scenery.
To sum it up, Annapolis’s variety of tours makes it easy to tailor your visit to your interests. Whether you’re fascinated by naval history, haunted tales, or just want to relax on a boat, there’s a perfect experience waiting for you. For those seeking a immersive experience, the Historic Walking Tour or the Harbor Cruise are excellent choices, while adventure seekers might enjoy the Scavenger Hunt. To make the most of your trip, plan ahead and secure your bookings early—these tours tend to fill up quickly during peak seasons.