Top Annapolis Tours, Sightseeing & Cruises - page 2

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

This murder mystery experience is a true whodunit with suspects, alibis and a twist ending. Every clue hides in something real: a plaque, a statue, a facade in downtown Annapolis. You will collect the evidence, piece together the case and accuse a suspect at the finale. We offer 24/7 customer support and built-in hints to guarantee that you never stay stuck. Also, the app will provide real historical facts and local legends about the landmarks you're visiting, making a learning experience as much as it's a fun one. The game can be played anytime, at any hour, and will take you ~90-120 minutes with optional cafe breaks. You can pause and resume whenever you want (even on another day). Total walking distance involved is about 1.5 miles and the game will end in the same area where it started, making it easy to fit into your day. It has intermediate difficulty and it's perfect for solo adventurers, couples, friends, families with older kids, or team-building events.

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.

Discover the history of Annapolis, Maryland in a fun way with a citywide scavenger hunt. Drive to nontraditional locations all around town (a car-free hunt is also available), getting to know landmarks, local businesses, and alternative spots. The goal is to solve clues, complete challenges, and answer questions to gain points and beat the other teams.

This lighthearted, adults-only, tongue-in-cheek, walking tour is presented by a guide in the character of a colonial indentured servant who works odd jobs day and night to make ends meet – colonial style. During your walking tour in Historic Annapolis, you’ll hear scandalous anecdotes and jaw-dropping tales about what went on inside Annapolis’ famed homes and taverns. Colonial Founding Fathers, Annapolis gentry, renowned portrait artists, and regular folk, too, were all up to their tricks! There was revenge, murder, spying, drinking, political discord, and pleasures of the night.

Welcome the holidays with Watermark's Christmas in the Capital Tour: Annapolis Traditions and State House Trees. Meet your period-attired guide inside our cozy office before embarking on your tour. Stroll with your colonial guide around Maryland’s capital city, trimmed in greenery for the season. Hear holiday traditions of times past and present as you walk by colonial mansions, Victorian homes, and quaint shops A highlight of the tour is the Maryland State House, with decorated Christmas trees representing the different counties of Maryland, presented by the Federated Garden Clubs of Maryland. The tour ends at Annapolis's grand Christmas tree at Market House Park. Take home the holiday cheer with a goody bag of treats including George Washington’s famed eggnog recipe!

Celebrate the holiday season with the Holiday Candlelight Stroll, a delightful 75-minute walking tour through Annapolis. Led by a period-attired guide, this tour takes you through Maryland’s capital, adorned in festive greenery. Learn about the rich holiday traditions as you pass by charming colonial mansions, Victorian homes, and quaint shops. The tour culminates at the grand Christmas tree in Market House Park, where you'll receive a goody bag featuring George Washington’s famous eggnog recipe. - 75-minute guided evening walking tour of Annapolis - Explore colonial and Victorian holiday traditions - Enjoy insights into local holiday traditions from your guide - Receive a goody bag at the end of the tour that includes George Washington's eggnog recipe

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 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 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.