Annapolis Tours

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.

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.

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.

The best part of this tour is the down-home hospitality Sam tries to deliver with every ride. There is no real set schedule, so we have a bit more flexibility in how we do things. Sam will help you from the time you first write to the time she hugs you goodbye at the last stop and beyond if you're traveling to anywhere else that she is familiar with. Get to know other travelers and share once in a lifetime experiences along the way.

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!

This Tour is NOT just a Wine Tour but also History and Nature Tour. One hour from Halifax is Wolfville & Grand Pre National Historic Site the first stop on Tour. Explore the natural beauty of the Annapolis Valley & Nova Scotia’s Wine Country. You will visit Fox Hill Cheese as well as three Award winning Vineyards including Planters Ridge, 1365 Church Street Vineyard & Luckett's where you can try Nova Scotia's finest wine Tidal Bay. You will also see stunning Views & Vistas of the Bay of Fundy from Blomidon Look-off. We also will visit Halls Harbour to SEA the Highest Tides in the World and a great spot for a lunch. Lobster Maybe!…Bring your Eagle Eye as we pass Sheffield Mills a large Bald Eagle Nesting area and then your tour will continue traveling into the heart of the Annapolis Valley through a 400-year-old village of Wolfville. Your Clean, Safe and Comfortable Tour Vehicle will be a Ford Transit 350 XLT High Roof 14 Passenger Van with 4 Guests Minimum to 10 Guests Maximum.

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.

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!

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!

Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor and U. S. 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! The tour has excellent photo opportunities by the water and at historic buildings. All my tours can be customized upon request.

Let us take you on an adventure through Navy culture and heritage. Historic Annapolis is Americas' sailing capital and home to the US Naval Academy, nestled along the Chesapeake region. We will help explore the sites, sounds and taste of "Nap Town". Annapolis has been rated as one of the most beautiful towns in America by Conde Nast Traveler. From historic buildings like the Maryland Statehouse to colonial homes and the vibrant downtown district of shops and restaurants, there's lots to love in Annapolis. Not to mention views of Chesapeake Bay and a stroll on the grounds of the Naval Academy.