Top Annapolis Art & Culture

Step back in time on this 2-hour guided walking tour through the beautifully preserved Historic District of Annapolis, Maryland. Visit the Maryland State House, once the capitol of the United States, and explore a colonial kitchen and dining room inside a stunning Georgian mansion. Stroll past iconic landmarks including St. Anne's Parish, the Hammond-Harwood House, the Paca House, and the lively Annapolis City Dock. Hear the fascinating story of the friendly rivalry between the U.S. Naval Academy and St. John's College, two institutions that have shaped the character of this unique city. Along the way, your guide will bring everyday colonial Maryland life to vivid detail, from the merchant class to the working poor. Covering less than a mile on foot, this tour is an accessible and immersive introduction to one of America's most historic cities.

Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor and US Naval Academy. We'll see the Georgian mansions, the iconic Maryland State House, and much more as you learn the fascinating story of the town. We'll see where the Treaty of Paris was signed (bringing to a conclusion the Revolutionary War) and where General Washington resigned as general, thus becoming the "greatest man in the world" and the "American Cincinnatus. " We'll explore the campuses of two institutes of learning that have shaped American culture. We'll walk along the city dock, harbor, and see the view to the Chesapeake Bay and wider world. I'll also share personal and family stories along the way, to add a personal dimension to the tour. I welcome all questions and special interests for our tour!

Annapolis Walking Tours provides entertaining and informative tours throughout historic Annapolis. This tour is wonderful for people of all ages and involves approximately 2 miles of walking at a relaxed pace with frequent stops. Cobblestone pathways and uneven brick roads are present throughout; please wear comfortable walking shoes and bring appropriate rain gear/ umbrellas in case of rain. Annapolis is the sailing capital of the world; we go outside rain or shine! Tours are offered on the weekends. Additional times may be available with advanced notice. What should you bring? A camera Comfortable shoes Cash (for personal expenses) Important information: Punctuality is important and appreciated. Kindly be at the meeting spot ten minutes before the stated meeting time. The tour guide will wait a maximum of ten minutes before proceeding on the tour.

As an historic city, Annapolis has plenty of haunts. Explore Annapolis oldest and most-ghosted neighborhood on this tour of the historic downtown district, where hundreds of years of history were made. While you walk to neighborhood sights like the Maryland State House and haunted graveyards, your guide shares stories of purported paranormal activity and the real stories behind each.

Some history-focused city tours can feel stale. Spice up your visit to Annapolis on this guided tour that combines history with food. Visit historic sites and hear fascinating stories while enjoying a series of dishes from downtown restaurants, which may include a tavern frequented by Washington, Jefferson, and Franklin, and a local lobbyists' favorite lunch spot.

Take a pleasant walking tour through the beautiful historic center of Annapolis, specially designed for the US 250th Anniversary. Discover the fascinating role Annapolis played in the fight for and achievement of American independence! We will begin along the city dock and harbor that received many founding fathers in the 1700's, admiring the view to the Chesapeake Bay and wider world. We'll see two Georgian mansion built in the 1770's, as well as the iconic Maryland State House, where the Treaty of Paris was signed (bringing to a conclusion the Revolutionary War) and where General Washington resigned as general, thus becoming the "greatest man in the world" and the "American Cincinnatus. " We'll also explore the campus of St. John's College, which dates back to 1696, and talk about other Annapolis customs and traditions, as well as bars, restaurants, and more. All questions are welcome!

Sit back and relax on this up-close-and-personal cruise of Annapolis's waterways and scenic city shorelines on one of Watermark's 26-foot, open-aired vessels. Your captain will welcome you aboard for this intimate cruise from Annapolis Harbor and up Spa Creek, with stunning views of the U.S. Naval Academy, an abundance of boats of all size, a healthy dose of nature -- all with a recorded narration of historic facts and tidbits of Annapolis's colonial roots, its one-time ship-building might, and more.

Hear about Annapolis’s ghostly past with the help of a tour guide who’ll share historical spooky stories. From the spirits said to haunt Middleton Tavern to the dark past of James Brice House, you’ll explore a side of the city most tourists never see. Even though the subject matter may be dark, your tour leader will make sure you’re suitably creeped out, but still having fun.

If you are looking for a tour that goes beyond the typical tourist attractions, join this pub crawl that introduces you to lesser-known aspects of Annapolis history. Visit some of the city's most historic taverns and find out which was the most popular brothel and which one of the founding fathers was chased from.

Step into Annapolis's rich colonial past on a guided walking tour through the Historic District, led by a guide dressed in authentic colonial attire. Discover the history and heritage of the Maryland State House, the oldest continuously operating state capitol in the United States, where pivotal moments such as George Washington's resignation as Commander of the Continental Army and the ratification of the Treaty of Paris helped shape American history. Stroll past elegant mansions, historic homes, and landmarks while learning about the influential leaders, merchants, and signers of the Declaration of Independence who helped define Colonial Annapolis. Blending culture, history, and heritage, this family-friendly experience offers an engaging introduction to one of America's most significant colonial cities.

Paint an iconic landmark in the heart of Annapolis' historic district with a local award-winning watercolorist and teacher. Take home a piece of original art and learn a new skill. Make unique, creative memories. Book as a group or come as an individual. This activity takes place outdoors. Kids ages 8 years and up are invited!

Paint charming architecture in the heart of Annapolis' historic district with a local award-winning watercolorist and teacher. Take home a piece of original art and learn a new skill. Make unique, creative memories. Book as a group or come as an individual. This activity takes place outdoors. Kids ages 12 years and up are invited.

Discover the haunted history of Annapolis on a captivating evening ghost tour. Travelers wander through narrow streets alongside a knowledgeable guide dressed in period attire while hearing tales of supernatural occurrences and unexplained phenomena. This family-friendly walk explores haunted sites and local folklore, delving deep into the city's rich culture and historical legacy. Departing from Main Street, this guided experience offers a memorable glimpse into the lingering legends of Maryland's capital.

Discover the profound legacy of African American history in Maryland on an enlightening two-hour walking tour in Annapolis. Starting near Market House Park, journey through time to encounter significant landmarks such as the Alex Haley statue and the Maryland State House while learning about the vital contributions of historic figures including Harriet Tubman, Frederick Douglass, and Thurgood Marshall. Led by a knowledgeable guide in period attire, this experience delves into the local history, culture, and stories of the Underground Railroad, with tour proceeds directly supporting the Kunta Kinte-Alex Haley Foundation to enhance community heritage.

This private walking tour offers a calm and comfortable introduction to historic Annapolis at an easy pace. You explore the city as residents once did, along flat streets and quiet waterfront paths shaped by daily life and civic tradition. Clear storytelling brings forward the voices of merchants, lawmakers, families, and sailors who defined early Annapolis. Your walk begins near the harbor where trade and community met. The route continues through peaceful public spaces with time to pause, sit, and enjoy the surroundings. Stories focus on early American governance, maritime heritage, and local customs explained in a relaxed and engaging way. This experience suits travelers aged 50+ who value culture, history, and thoughtful narration without rushing. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Discover the quirky tales and unusual stories of Annapolis on this engaging walking tour. Led by a colonial-attired guide, explore fascinating anecdotes including the Russian sailor's grave in the Annapolis National Cemetery and the Confederate captain who never conceded defeat. Perfect for those curious about the unconventional side of history, this tour reveals the city's hidden gems and eccentric past. Ideal for adults and middle school-aged children, the tour takes place at 188 Main Street, Annapolis, MD. - Duration: 1 hour and 15 minutes - Suitable for adults and children aged 12 and older - Tours run on the second Saturday of each month - Learn about unique historical figures and events in Annapolis

Explore the eerie side of Annapolis with the Spirits & Spirits tour, blending a captivating walking tour through the Historic District with a thrilling cruise on the haunted waterways. Listen to spooky stories from your Ghost Guide, uncover nautical myths, and indulge in beverages available for purchase during the cruise. Perfect for those seeking a unique blend of history and ghostly tales in a fun atmosphere. This tour is suitable for adults and private tours can be arranged upon request. - Combination of a guided walking tour and a scenic ghost cruise. - Hear chilling tales from expert Ghost Guides while exploring Annapolis's Historic District. - Enjoy a variety of beverages and snacks available for purchase once on the boat. - Tours available on select dates, departing from 188 Main Street, Annapolis.

Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining, boutique shops, and historic sites. Guests enjoy a complimentary non-alcoholic beverage during the cruise before spending around three hours ashore exploring the town before the return journey to Annapolis. Admission to the Chesapeake Bay Maritime Museum is included, making this sightseeing day trip an ideal way to experience Maryland's rich maritime history.

Paint an iconic sailboat in the heart of Annapolis' historic district with a local award-winning watercolorist and teacher. Take home a piece of original art and learn a new skill. Book as a group or come as an individual. This activity takes place outdoors. Kids ages 10 years and up are invited.

Skip traditional walking tours and uncover some of Annapolis’s landmarks as you follow along this app-led scavenger hunt of the city. You and your team have a series of objectives to figure out and items to find, while you learn the history of Annapolis. This is a fun event for birthday parties, team building events, or even bachelorette parties. Challenge yourself and each other.

This private walking tour introduces historic ghost stories through the calm streets of Annapolis at a relaxed and comfortable pace. You explore the city where colonial history and long-shared legends quietly intersect. Storytelling focuses on documented events, respected local traditions, and the people who shaped early America. Beginning near the Maryland State House, you hear how politics, power, and personal lives left traces still discussed today. Around Church Circle, stories reflect faith, daily life, and the rhythm of an 18th-century town. Near the William Paca House, refined society and private lives reveal another layer of Annapolis history. The walk concludes by the City Dock, where maritime life and waterfront legends complete the experience. This tour is designed for travelers who value history, and storytelling without haste. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Embark on a spectacular, six-mile, narrated cruise from the Annapolis Harbor, past the U.S. Naval Academy seawall and along the banks, wetlands, and waterfront homes of this protected river. As you take in the great outdoors and rich history of the region, this 1-hour-and-30-minute excursion showcases why Annapolis remains a top destination for nature and maritime heritage enthusiasts alike.

Uncover the rich history of Annapolis on this engaging tour, showcasing Colonial Annapolis, the Maryland State House, and the U.S. Naval Academy. Guided by a knowledgeable colonial-costumed expert, wander through the historic district and delve into the city's 18th-century Golden Age. Stand in the Maryland State House, where pivotal moments in American history unfolded, including George Washington's resignation. Discover the U.S. Naval Academy's storied past and the life of midshipmen on the Yard. Perfect for history buffs and families alike, this tour offers a comprehensive view of Annapolis’ unique culture and heritage. - Enjoy a guided stroll through historic Annapolis with a colonial-costumed guide - Visit the Maryland State House, the oldest state capitol in continuous use - Explore the U.S. Naval Academy and learn about midshipmen life - Suitable for all ages with a focus on cultural and historical experiences