Top Annapolis Tours, Sightseeing & Cruises

Explore Annapolis' vibrant past on this unique historical pub crawl. Over two hours, discover how drinking influenced the city and the nation while enjoying recommended drinks at each stop. From rebels to rum-runners, each location reveals fascinating stories paired with a drink that defines the era. Perfect for whiskey enthusiasts and history buffs alike, this tour offers a relaxed atmosphere to toast the past and enjoy the present. Dress comfortably as you stroll through downtown, rain or shine, and prepare for a fun evening immersed in tipsy history. - 2-hour historical pub crawl through downtown Annapolis - Discover how drinking shaped Annapolis' history - Enjoy recommended drinks at each stop, not included in the price - Limited walking involved; dress for comfort and the weather

Cruise through history on the Annapolis Harbor & USNA Cruise. This narrated cruise offers insights into the U.S. Naval Academy and Annapolis' rich maritime heritage while enjoying stunning views of the Chesapeake Bay Bridge. Perfect for families and history buffs alike, this cruise is a cherished local tradition that uncovers the beauty and significance of this historic seaport. - Narrated cruise around Annapolis Harbor and U.S. Naval Academy - Learn about the history and significance of the region - Enjoy picturesque views, including the Chesapeake Bay Bridge

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.

The Thomas Point Lighthouse is the most iconic lighthouse in Maryland. View this National Historic Landmark on a narrated cruise into the Chesapeake Bay. Not just for lighthouse enthusiasts, everyone loves it during this 1-hour-and-30-minute excursion that blends history, sightseeing, and the great outdoors into a memorable maritime adventure.

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

Step aboard a classic vessel for a scenic Chesapeake Bay Bridge cruise. As you depart the dock in downtown Annapolis, you will pass along the seawall of the United States Naval Academy and out into open water. As you approach the Bay Bridge, keep an eye out for local wildlife, including osprey, eagles, rays, and even the occasional dolphin, while enjoying great outdoors sightseeing. Then, marvel at the twin spans of the bridge, one of the largest over-water structures in the world. Sit back and relax with a soft drink, beer, or wine available for purchase, and enjoy the sights on this 90-minute journey.

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.

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.

Come on to our Haunted Pub Crawl Tour in Annapolis! Enjoy some liquid courage while hearing ghostly tales of Annapolis' most historic haunts and drinking hotspots. Take a Boo's and Booze Haunted Pub Crawl for genuine stories, scares, and delicious drinks in the historic district, with up to 2 hours of ghostly fun with the city's spirits and Spirits. Price does not include drinks or tastings.

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.

Put a ghoulish twist on your night out with a haunted pub crawl through historic Annapolis. Visit three bars over the course of the night, each with a ghost story behind it that will scare you sober. Drinks available at your own purchase.

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.

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

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!

Celebrate the holiday season with a delightful 45-minute cruise along Spa Creek, guided by Captain Santa or Mrs. Claus. This family-friendly adventure includes hot cocoa served by an onboard elf and cozy blankets to keep warm as you enjoy the festive sights. A portion of the proceeds supports Historic Annapolis, making this a jolly way to give back while creating cherished family memories. Perfect for families and holiday enthusiasts, the cruise offers private bookings for larger groups. Reserve your tickets in advance for this limited-capacity experience. - 45-minute festive cruise along Spa Creek with holiday characters - Enjoy complimentary hot cocoa and cozy blankets on board - Supports Historic Annapolis with a portion of proceeds - Perfect for families and private group bookings available for up to 21 passengers

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

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.

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.

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.

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.

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.

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.

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.