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Annapolis Tours
All Annapolis Tours & Excursions in 2026
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19 results
Best Seller
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.
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Historic Annapolis Walking Tour - Small Group Guided Tour
1 hour 30 minutes to 2 hours
Free Cancellation
from
$35
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.
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Historic Annapolis Food Tour
3 hours 30 minutes
Free Cancellation
from
$80
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!
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Annapolis Historic Walking Tour: Harbor and Colonial Downtown
2 hours
Free Cancellation
from
$235
Per group
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.
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Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
2 hours
Free Cancellation
from
$29
Special Offer
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.
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Annapolis Highlights Self-Guided Walking Audio Tour
1 to 2 hours
from
$4
$5
Per group
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
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Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis
2 hours
Free Cancellation
from
$30
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.
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Ashes and Apparitions of Annapolis Ghost Tour
1 hour
Free Cancellation
from
$26
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.
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Operator reviews
Annapolis Colonial and Maritime History Walking Tour
2 hours
Free Cancellation
from
$39
Uncover some of Annapolis’s landmarks as you follow along this app-led scavenger of the city. You and your team will 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.
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Awesome Scavenger Hunt: Annapolis Red Bricks & Blue Views
2 hours
Free Cancellation
from
$15
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.
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The Original Haunted Pub Crawl by Annapolis Ghost Tours
2 hours
Free Cancellation
from
$31
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.
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Hidden History Pub Crawl of Historic Annapolis
2 hours
Free Cancellation
from
$30
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.
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Private Historic Ghost Stories Walking Tour in Annapolis
2 hours
from
$492
Price varies by group size
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.
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Private Cultural Walking Tour of Historic Annapolis Waterfront
2 hours
Free Cancellation
from
$579
Price varies by group size
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!
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Outdoor Painting Activity with a Local Artist in Annapolis
1 hour 30 minutes
Free Cancellation
from
$95
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.
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Amazing Annapolis Scavenger Hunt
2 hours
Free Cancellation
from
$20
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.
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Outdoor Watercolor Class in Annapolis the Sailing Capital of USA
1 hour 30 minutes
Free Cancellation
from
$95
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.
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Urban Sketching and Painting Activity in Old Town Annapolis
1 hour 30 minutes
Free Cancellation
from
$95
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.
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The Original Walking Ghost Tour by Annapolis Ghost Tours
1 hour 30 minutes
Free Cancellation
from
$26
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.
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Annapolis Scavenger Hunt Interactive Walking Activity
2 hours
Free Cancellation
from
$35
Per group
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