Best Tours & Activities in Annapolis

IMPORTANT UPDATE (3/11/26): The Naval Academy is not currently letting visitors on the Yard for security reasons. Tours currently will focus on the Harbor and colonial downtown. Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor. 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!

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

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!

The Hidden History Pub Crawl is a tour through Annapolis' scandalous past. Sip on a beverage while entertained by stories of historical conspiracies, murder, riots and forgotten tales as your guide brings to life the city’s juiciest stories. With different stories every night, this is the most intriguing experience for Annapolis twisted history. The Hidden History Pub Crawl is a 2-hour Pub Crawl tour (approx. 1/2 mile) into some of the storied taverns of Annapolis. Spending about 20-30 minutes at each location, you'll relax with a cocktail while learning some of our most interesting and colorful history through the tales of our taverns. We will visit three bars on each crawl - locations visited may include some of the following: Middleton Tavern Rams Head Tavern Federal House Dock Street Bar & Grill Drummer's Lot at the Maryland Inn Harry Brownes Galway Bay Drinks are not included in this! This tour is limited to Adults (21+) ONLY! No children.

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.

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.

During The Historic Annapolis Food Tour, you will enjoy a series of dishes from restaurants in downtown Annapolis while weaving through historic sites. The tour lasts approximately 3.5 hours.

The only Haunted Pub Crawls permitted inside the oldest and most haunted pubs in Historic Downtown Annapolis. Enjoy a 2-hour guided adventure on our haunted pub crawl. Drink in the history, but try not to crawl out the door! Clink glasses with a long-dead barmaid, a "working girl" who'll fall for you, a ghost whose beer has a head even though he doesn't! Join us as we walk from pub to tavern to bar and into the same watering hole, and thru the same streets and alleys as our Founding Father! Hear tales so spooky, "they'll scare ya sober!", lol! Scary? Yes...because they are real! You'll spend about 30 mins at each bar, and your guide will give you plenty of time to purchase a drink or cocktail and then tell you the haunted tales of that location and those nearby. No stories will be told until all guests have their drinks. You'll have time to order and enjoy your drink, use the restroom, and hear the haunted tales! Then on to the next pub, possibly with a stop in the church graveyard!

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

The original 90-min Annapolis Ghost Tours are the only tours created by our owner, noted local Maryland historian, and author of "Haunted Annapolis". Don't be fooled by national chains pretending to be locally owned and run. Take a nighttime ghost walk through the historic downtown district on a spine-tingling journey into Annapolis’ dark and troubled history. Follow your local guide during this 1.5-hour tour to meet some of the more spirited residents and visiting some of the most horrific haunted sites. Choose from one of various seasonal departure times when you book. NOTE: 7pm & 8pm tours are family friendly if children are present. Language and content toned down accordingly. 9pm tours are considered adult tours, suitable for older children and teens, however there may be some profanity used for effect and adult subject matter.

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.

Embark on this Annapolis ghost tour and step back in time as you stroll through the historic district. Your guide will share chilling tales of hauntings at iconic buildings. Discover the restless spirits said to haunt Middleton Tavern, a historic site with numerous ghostly encounters. Throughout the evening, you'll traverse haunted ground, feeling the eerie presence of the spirits rumored to inhabit these locations. This mile-long trek will take you to some of the most haunted and historic sites in Annapolis, including the James Brice House, with its dark past, and the John Brice II House, where former inhabitants are said to still make their presence felt. This walking tour offers an entertaining and immersive experience into Annapolis's haunted history. Perfect for history buffs, or anyone seeking a thrilling evening, this tour promises to captivate and chill. Join us to uncover Annapolis's ghostly past and the spine-tingling stories that have been passed down through generations.

Get ready to discover why Let’s Roam is the ultimate in app-led adventure hunt excitement! Picture this: strolling through Annapolis, hitting up all the iconic landmarks and uncovering hidden gems, all while tackling trivia questions and conquering challenges with your squad. Whether you’re collaborating with your crew or engaging in some friendly competition, every step is a chance to learn something new and make unforgettable memories. Let’s Roam Adventure Hunts aren’t just for any day — they’re perfect for bachelorette parties that need some spice, birthday celebrations that deserve a twist, or corporate team building events that demand teamwork and laughs. The best part? Each player gets to dive into their own interactive role, with challenges tailored just for them. So, grab your friends, family, or colleagues, pick your roles, and get ready for an epic adventure through Annapolis. Let the games begin — and let the good times roll with Let’s Roam!

Set on the Chesapeake Bay at the mouth of the Severn River, the picturesque town of Annapolis features some 17 miles of shoreline. This makes it the perfect home of the United States Naval Academy—and thousands of other boating enthusiasts. But there’s much more to this place than just sailing. On this tour, we’ll examine the Revolutionary roots of Annapolis and meet some of the founding fathers who lived and visited here. We’ll explore the town’s role in America’s dark history of slavery and the Civil War, while also highlighting the miraculous accomplishments of free Black Marylanders in the eighteenth and nineteenth centuries. NOTE: This is a self-guided outdoor walking tour. Your purchase does not include entrance to any attractions highlighted on the tour.

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.

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.

Embark on a thrilling adventure in Annapolis! Unravel the city's rich history, from its days as the US capital to its vibrant present. Discover the tales of Princess Anne, Abraham Lincoln, and Duke Ellington. Marvel at the city's architectural wonders, learn about the oldest living people in Maryland, and even snap a selfie with your favorite statue. Uncover secrets of the past and solve riddles that will challenge your mind. This is Annapolis like you've never seen it before! With no set schedule, enjoy the freedom to explore at your own pace using a user-friendly app. Suitable for families, friends, and couples, this unique experience redefines sightseeing in Anaheim.

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.

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.