Filter Tours
33 Available Tour Excursions 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!
Price: $235.00
Duration: 1 hours
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
Price: $39.00
Duration: 2 hours
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.
Price: $26.00
Duration: 1 hours
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.
Price: $46.00
Duration: 1 hours
Take a pleasant walking tour through the beautiful historic center of Annapolis, specially designed for the US 250th Anniversary. Discover the fascinating role Annapolis played in the fight for and achievement of American independence! We will begin along the city dock and harbor that received many founding fathers in the 1700's, admiring the view to the Chesapeake Bay and wider world. We'll see two Georgian mansion built in the 1770's, as well as the iconic Maryland State House, 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 also explore the campus of St. John's College, which dates back to 1696, and talk about other Annapolis customs and traditions, as well as bars, restaurants, and more. All questions are welcome!
Price: $235.00
Duration: 1 hours
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!
Price: $40.00
Duration: 1 hours
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.
Price: $32.00
Duration: 1 hours
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
Price: $28.00
Duration: 1 hours
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.
Price: $35.00
Duration: 1-2 hours
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
Price: $34.00
Duration: 0 hours
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.
Price: $52.00
Duration: 1 hours
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.
Price: $46.00
Duration: 1 hours
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.
Price: $80.00
Duration: 3 hours
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
Price: $34.00
Duration: 2 hours
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.
Price: $46.00
Duration: 1 hours
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.
Price: $26.00
Duration: 1 hours
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.
Price: $157.00
Duration: 8 hours
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.
Price: $29.00
Duration: 2 hours
Key Info for Visitors
- Currency: USD
- Languages: English
- Climate: Humid subtropical
- Timezone: America/New_York
- Population: Approximately 40,000
- Best Time to Visit: best time to visit Annapolis is during spring and fall when the weather is mild.
- Visa Requirements Visitors from the US do not need a visa. International visitors from visa waiver countries (such as the EU, UK, Australia, Japan, and others) can enter under the Visa Waiver Program for up to 90 days with an ESTA approval. Citizens of other countries typically require a B-2 tourist visa. Always check current US entry requirements before travel.
About Annapolis
Annapolis, the capital of Maryland, is a charming waterfront city steeped in colonial history and maritime tradition. Its well-preserved 18th-century architecture, cobblestone streets, and scenic harbor create a uniquely atmospheric setting. Annapolis is famous as the home of the United States Naval Academy, where visitors can tour the impressive campus and learn about naval history. The city’s vibrant downtown is filled with boutique shops, art galleries, and cozy cafes, all within walking distance of the waterfront. Annapolis is also renowned as the sailing capital of the US, hosting major regattas and offering ample opportunities for boating and waterfront dining. The city’s rich history is evident in landmarks like the Maryland State House, the oldest state capitol still in continuous legislative use. With its blend of history, culture, and nautical charm, Annapolis offers a distinctive East Coast experience that appeals to history buffs, food lovers, and outdoor enthusiasts alike.
Annapolis Tours & Experiences
- Top Attractions: Highlights of Maryland
- Duration Range: Custom Durations
- Group Size: Intimate Groups
- Difficulty Level: Easy to Moderate
- Recommended For: Visit in spring or fall for pleasant weather and fewer crowds. Pack comfortable shoes for walking on cobblestone streets. Dress is generally casual, but slightly more formal attire is appreciated at upscale restaurants. Tipping is customary (15–20% at restaurants). Safety is generally good, but take normal precautions in crowded areas. Credit cards are widely accepted, but carry some cash for small vendors.
Average Tour Price: $65
Lowest Price Tour: $50
Highest Price Tour: $220
1. Choose Your Tour
Browse our curated selection of tours and select your perfect adventure.
2. Check Details
Review tour inclusions, duration, and meeting points carefully.
3. Book Online
Complete your booking securely with instant confirmation.
4. Enjoy Your Experience
Join the tour and create unforgettable memories in Annapolis.
Important Tour Information
- Bring comfortable walking shoes and appropriate clothing
- Check tour cancellation and refund policies
- Arrive at the meeting point at least 15 minutes early
- Carry valid identification and tour booking confirmation
Top Attractions
United States Naval Academy: A prestigious military academy with a museum, historic chapel, and stunning waterfront campus. Maryland State House: The oldest state capitol in continuous legislative use, featuring significant Revolutionary War history. City Dock: The lively heart of Annapolis, lined with boats, restaurants, and shops, perfect for strolling and people-watching. William Paca House and Garden: A beautifully restored 18th-century mansion with period gardens, offering a glimpse into colonial life. St. Anne’s Church: A historic Episcopal church with striking architecture and a peaceful churchyard, dating back to the late 1600s.
Popular Activities
Sailing and boating are central to Annapolis life, with charters, lessons, and regattas available. Walking tours explore the city’s colonial history and maritime heritage. The Annapolis Maritime Museum offers exhibits on the Chesapeake Bay. Dining along the waterfront is a must, with fresh seafood and local specialties. Seasonal festivals, such as the Annapolis Boat Shows and Maryland Renaissance Festival, provide lively cultural experiences.
Frequently Asked Questions
Local Food & Cuisine
Annapolis is famous for its Chesapeake Bay cuisine, especially Maryland blue crabs, crab cakes, and creamy crab soup. Oysters, rockfish, and other seafood are local staples. Try Smith Island Cake, Maryland’s official dessert. Notable restaurants include Cantler’s Riverside Inn for crabs and Vin 909 for creative American fare. Waterfront dining is popular, with many establishments offering views of the harbor.
Getting Around
Annapolis is easily reached by car from Baltimore (30 minutes) and Washington, DC (45 minutes). Baltimore/Washington International Airport is the closest major airport. Within the city, walking is ideal for the historic district. Public buses and taxis are available, but a car is useful for exploring the wider region. Parking can be challenging downtown; use public garages or park-and-ride options.
Travel Tips
Visit in spring or fall for pleasant weather and fewer crowds. Pack comfortable shoes for walking on cobblestone streets. Dress is generally casual, but slightly more formal attire is appreciated at upscale restaurants. Tipping is customary (15–20% at restaurants). Safety is generally good, but take normal precautions in crowded areas. Credit cards are widely accepted, but carry some cash for small vendors.
Culture & Customs
Annapolis has a relaxed, maritime-influenced culture with a strong sense of history and community. Locals are friendly and proud of their city’s heritage. Respect for naval and military traditions is important. Major events include the Annapolis Boat Shows, Fourth of July celebrations, and the Kunta Kinte Heritage Festival. Politeness and a laid-back attitude are the norm.
About The Author
Calvin has loved travel and adventure since first visiting Los Angeles with a suitcase in 1992 at the age of 20. He ditched the suitcase and got a backpack pretty fast.
He hates leaving after any trip and has to console himself by writing and sharing articles on it. You can find and connect with him on linked in here.
Likes
Travel, Gaming, Scuba Diving, Skiing and anything to do with water.
Dislikes
Exact luggage sizing police and being tired in an airport and many more..