Which Annapolis Tours & Things To Do To Choose? We Rank The 15 Best

Annapolis isn’t just a pretty port town; it’s a lively hub packed with unique tours and experiences that reveal its maritime charm, storied past, and quirky side. Whether you’re craving a scenic boat ride, a walk through colonial history, or a spooky ghost story, Annapolis delivers.

We’re particularly fond of the Annapolis Harbor and U.S. Naval Academy Cruise, which offers a quick, 40-minute adventure that captures the essence of this waterfront city—sailboats, historic buildings, and vibrant activity all in one trip.

If a walking tour is more your style, the Harbor and Naval Academy Historic Walk combines history and architecture with engaging storytelling.

For those interested in ghost stories, the Haunted Annapolis Tour offers a spooky, fun way to explore the city’s dark past.

Annapolis’s variety of tours and activities makes it a perfect destination for history lovers, foodie adventurers, and even those seeking a thrill. From outdoor painting classes to maritime museum visits, the options are broad enough to satisfy almost any curiosity. To help you decide, we’ve broken down the top experiences available, highlighting what makes each stand out.

1. Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise

At number 1, this harbor cruise offers a perfect quick glimpse of Annapolis’s waterfront life. For just $30 per person, you’ll enjoy a 40-minute boat ride that showcases the U.S. Naval Academy, historic buildings, and the lively dockside scene.

The cruise features recorded narration sharing stories about the city’s maritime heritage and naval history, making it an easy way to get oriented with the area.

Several reviewers praise the friendly crew and the impressive views, especially the sight of sailboats and the academy’s iconic buildings. This tour is ideal for travelers short on time but eager to see the core of Annapolis from the water.

Bottom Line: A short, engaging introduction to Annapolis’s waterfront and naval history, perfect for first-timers or families looking for a relaxed activity.

2. Annapolis Historic Walking Tour at Harbor and Naval Academy

For around $235 per group, this two-hour guided walk is an excellent way to explore Annapolis’s historic center in depth. The tour covers Ego Alley, the Maryland State House, Hammond-Harwood House, and the Naval Academy—all while sharing fascinating stories from the city’s colonial days and early American history.

Guide Michael is highly praised for his knowledge and engaging storytelling, making the tour both educational and fun. Highlights include visiting the Crypt of John Paul Jones and seeing where General Washington resigned as commander.

This tour works well for small groups up to 10 people, offering a personalized experience. Its focus on historical sites combined with lively commentary makes it a strong choice for history enthusiasts or anyone wanting a meaningful look at Annapolis’s founding and development.

Bottom Line: An intimate, comprehensive look at Annapolis’s history, ideal for history buffs or groups seeking an immersive experience.

3. Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

If you like your history served with a side of spooky stories, this 1-hour tour at $24 per person is a perfect pick. It explores Annapolis’s haunted sites, from Middleton Tavern to James Brice House, sharing ghostly tales and eerie legends.

The tour walks past historic locations while narrating stories of spirits said to linger from the city’s dark past. The guide’s storytelling has earned praise, with visitors remarking on the chilling but fascinating narratives.

The tour is compact yet packed with spooky lore, making it suitable for families, history buffs, or anyone who enjoys a little ghostly fun. It’s a lively way to see the city while learning about its darker tales.

Bottom Line: A fun, slightly chilling experience that combines history and ghost stories—great for those who enjoy a spooky twist on American history.

4. Colonial Annapolis, State House & U.S. Naval Academy Tour

At around 135 minutes and $32 per person, this walking tour gives you a broad overview of Annapolis’s colonial roots and political significance. It visits the Maryland State House, the Naval Academy, and the charming streets of the historic district.

The tour provides insights into four centuries of history, including the signing of the Treaty of Paris and George Washington’s resignation as commander. Guests appreciate the well-paced itinerary and the opportunity to see key landmarks while hearing engaging stories.

This tour is best suited for travelers wanting an overview of the city’s architecture, political history, and colonial past without the need for multiple separate tours. It’s an excellent value for a comprehensive experience.

Bottom Line: A thorough, well-rounded walk through Annapolis’s colonial and political history, perfect for first-time visitors.

5. Historic Annapolis Food Tour

For $80 per person, this 3.5-hour guided tour combines history, architecture, and local cuisine. It takes you to historic landmarks and popular eateries, where you’ll sample dishes from restaurants with ties to figures like Washington, Jefferson, and Franklin.

The tour promises stories behind the food and the city’s culinary evolution, making it more engaging than a standard food walk. Reviewers highlight how knowledgeable the guide is and how much they enjoyed the variety of food stops.

Ideal for food lovers and history fans alike, this tour offers a tasty way to learn about Annapolis’s past while sampling local flavors. It’s also a great way to get restaurant recommendations for later.

Bottom Line: A deliciously different way to explore Annapolis’s history and cuisine in one memorable tour.

6. Maryland State House Tour

At just $24 for 75 minutes, this tour immerses you in the story of the oldest legislative building still in continuous use. Led by period-costumed guides, you’ll hear about Maryland’s role in American history, including the Treaty of Paris and George Washington’s resignation.

The tour covers the grounds and architecture, making it rich in detail for history enthusiasts. Visitors mention how engaging the guides are and how the tour deepens understanding of Maryland’s political legacy.

A great choice for those interested in government history and historic architecture, this tour pairs well with a walk through the city afterward.

Bottom Line: An insightful, well-led exploration of Maryland’s political history via its most historic building.

7. Outdoor Painting Activity with a Local Artist in Annapolis

Priced at $77, this experience pairs art with scenery. Led by an award-winning watercolorist, you’ll paint an iconic Annapolis landmark outdoors. The class is relaxed, with all materials provided, and suitable for ages 8 and up.

Reviewers note that Em, the instructor, is personable and knowledgeable, making the class accessible whether you’re a novice or more experienced. It’s a wonderful way to create a personal souvenir of your trip and learn a new skill in a scenic setting.

This activity is perfect for creative travelers or families wanting a hands-on experience. Keep in mind it’s outdoor and weather-dependent.

Bottom Line: A fun, artistic activity that leaves you with a keepsake, ideal for families and art lovers alike.

8. The Original Haunted Pub Crawl by Annapolis Ghost Tours

At $31, this 2-hour pub crawl takes you inside some of the city’s most haunted taverns. It’s a lively mix of history, ghost stories, and drinks, perfect for a fun night out. The tour visits three bars, sharing tales of spirits from Annapolis’s past, such as ghostly barmaids and legendary hauntings. The reviews highlight the guide’s engaging storytelling and the cozy, historic pubs.

A popular choice for groups seeking a mix of nightlife and storytelling, this tour offers a unique way to experience Annapolis after dark.

Bottom Line: A spirited night out with a spooky twist, ideal for those interested in both history and a good laugh.

9. Amazing Annapolis Scavenger Hunt

For $29, this 2-hour citywide scavenger hunt turns exploring Annapolis into a fun game. It guides you to landmarks, local businesses, and lesser-known spots, challenging you with clues and challenges.

Reviewers enjoy the mix of fun and education—one called it “great fun” and loved discovering new places. It’s suitable for team-building, parties, or families who want a flexible, interactive activity.

An excellent way to see the city through a competitive lens, this hunt keeps you moving and thinking.

Bottom Line: An active, engaging way to learn about Annapolis, especially for groups or families seeking a challenge.

10. Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

This 2-hour tour combines ghost stories and drinks for a spirited evening. For $27, you’ll visit four historic pubs while listening to tales of murder, ghostly sailors, and legends. The stops include Middleton Tavern and the Annapolis Jail, with plenty of time for drinks. Reviewers mention Ryan, the guide, as personable and knowledgeable, enhancing the experience.

Perfect for an evening of storytelling, drinks, and a little spooky fun, it’s suited for those who enjoy a lively night out with a haunted twist.

Bottom Line: A fun, social way to explore Annapolis’s haunted taverns with plenty of ghostly stories and drinks.

11. Hidden History Pub Crawl of Historic Annapolis

For $30, this lesser-known tavern tour offers a behind-the-scenes look at Annapolis’s secret stories. It visits historic bars like Rams Head Tavern and Harry Brownes, sharing tales of founding fathers and legendary establishments.

The small group size ensures a personalized experience, and drink specials add to the fun. One reviewer simply states, “Most bars offer drink specials,” making it an affordable and authentic experience.

Ideal for travelers who want a different angle on Annapolis’s drinking scene and history, this tour reveals stories most visitors never hear.

Bottom Line: An intimate, off-the-beaten-path pub crawl that uncovers the city’s hidden stories and legendary taverns.

12. The Original Walking Ghost Tour by Annapolis Ghost Tours

This 1.5-hour, free walking tour guides you through Annapolis’s most haunted neighborhoods. It focuses on paranormal stories and historic sites like the Maryland State House and haunted graveyards. Visitors mention Sarah, the guide, as very knowledgeable and personable. It’s a fun, spooky alternative to more conventional sightseeing, especially for those curious about Annapolis’s darker side.

A great choice for budget travelers or those interested in ghost stories, it’s a lively stroll into the city’s haunted corners.

Bottom Line: Free, entertaining, and spooky—perfect for ghost story enthusiasts or budget-conscious travelers.

13. Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

At $30, this tour promises tales of murder, ghostly figures, and historic hauntings while exploring Annapolis’s pubs. It’s a lively mix of storytelling and drinks, with stories about bootleggers, sailors, and the ghost of Roland. Visitors enjoy the immersive experience, feeling like paranormal investigators for an evening.

Ideal for those interested in history, spirits, and a night of storytelling, this pub crawl offers a spirited way to learn about Annapolis’s ghostly legends.

Bottom Line: An entertaining, spirited pub crawl with plenty of haunted tales and a lively atmosphere.

14. Annapolis: Round Trip Cruise to St. Michaels

For $157, this full-day cruise across the Chesapeake Bay takes you to St. Michaels, a charming historic village. The cruise includes a visit to the Chesapeake Bay Maritime Museum, and the leisurely ride offers scenic views. Guests enjoy exploring the town at their own pace, making it perfect for those who love maritime history and picturesque towns.

This trip is best suited for travelers who want a mix of cruise comfort and independent exploration. It’s a longer activity but offers a comprehensive taste of Maryland’s maritime culture.

Bottom Line: A full-day escape combining scenic cruising with free time in a historic town, ideal for leisurely travelers.

15. Self-Guided Scavenger Hunt: Annapolis Red Bricks & Blue Views

Costing just over $12, this app-led scavenger hunt is a budget-friendly, fun way to discover Annapolis. It guides you to landmarks, local businesses, and hidden spots, challenging you to solve puzzles and answer trivia.

Reviewers appreciate its engaging format and the chance to learn while exploring at your own pace. It’s great for birthday parties or team-building, and you can extend the fun with additional challenges for free.

Suitable for all ages, this activity encourages friendly competition and quick thinking.

Bottom Line: Affordable, interactive, and flexible—perfect for groups wanting a fun challenge with plenty of learning.

How to Choose Your Perfect Annapolis Tour

When selecting a tour, consider your interests and how much time you want to spend. For a quick introduction, the Annapolis Harbor and U.S. Naval Academy Cruise or the Ghost Tours are excellent options. If you’re more into history, the State House or Walking Tour provide immersive insights. Food lovers should consider the Historic Food Tour, while adventure seekers may prefer the Scavenger Hunt.

Budget-conscious travelers will find value in the free or low-cost options like the Ghost Walking Tour or Haunted Pub Crawl. Book early, especially for popular activities like the Paint & Create or Boat Cruises, to secure your spot.

Final Thoughts

From scenic boat rides and historic walks to ghost stories and culinary adventures, Annapolis offers a diverse array of tours and activities. For a quick, scenic introduction, the harbor cruise provides a lovely snapshot.

History enthusiasts will appreciate the State House and Walking Tour, while those seeking a thrill might enjoy the Ghost Tours. Foodies should not miss the Food Tour, which combines dining with storytelling.

Whatever your preference, Annapolis’s well-curated experiences promise memorable moments. Booking early is advisable, especially for tours with limited availability or special activities. Now, it’s time to pick your favorite and start planning your trip to this charming Maryland port.