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Discover Annapolis’ history and flavors on this 3.5-hour guided food tour, visiting historic sites and enjoying delicious dishes at local eateries.
The Historic Annapolis Food Tour offers a compelling blend of history and cuisine for those visiting this charming city. Priced at $80 per person and lasting approximately 3 hours and 30 minutes, this tour is designed for curious travelers who appreciate a well-rounded experience. It departs from the Visit Annapolis & Anne Arundel County at 26 West Street and ends back at the same meeting point, making it convenient for visitors staying nearby. What makes this tour stand out is its carefully curated mix of historic landmarks and local eateries, including a tavern once frequented by Washington, Jefferson, and Franklin, and a favorite lunch spot of Maryland lobbyists. The tour’s mobile ticket feature ensures smooth entry, and with most bookings happening 27 days in advance, it’s clear that this experience resonates well with visitors seeking an authentic taste of Annapolis.
While the tour is notably popular and highly rated, with a 4.5/5 rating from 34 reviews and 94% recommending it, it’s worth noting that the walking pace involves roughly 6-7 km, including some time inside restaurants, so guests should be comfortable with moderate activity levels. The tour is suitable for most travelers, and the limited group size of 12 allows for personalized interaction. It’s an ideal choice for those wanting to combine historical insight with culinary delights in a manageable, well-organized setting.


The tour begins at the Visit Annapolis & Anne Arundel County Visitor’s Center at 26 West Street. From there, the guide leads visitors through the heart of the city, highlighting key historic sites such as the US Naval Academy. The tour emphasizes lesser-known stories about Annapolis’ past, making history feel lively and engaging.
One notable stop outside of the Hammond-Harwood House involves discussing its architectural and historical significance. The guide offers insights into the building’s past, providing context that enriches the walk through Annapolis’ streets. This stop, like others, combines historical narration with visual appreciation of the city’s well-preserved architecture.
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The US Naval Academy is a central part of the tour. The guide explains its importance to the city and the nation, giving a glimpse into Annapolis’ military history. The walking pace allows ample time to absorb details while enjoying the scenery.
Throughout the tour, visitors learn little-known stories and interesting facts that often escape typical sightseeing. For example, outside the Hammond-Harwood House, the guide describes architectural details and historical anecdotes that bring the location alive. This approach turns what might be a straightforward walk into an engaging story session.

The tour features a multi-course progressive meal at several locally owned restaurants, with each stop showcasing what chefs are known for in Annapolis. Expect delicious dishes culminating in dessert at the end, ensuring no one leaves hungry. The stops have been carefully chosen for their authenticity and quality, with notable mentions such as Harry Brown’s, which offers Maryland crab soup, crab empanadas, oysters, and local beers.
One of the restaurant experiences includes sampling Maryland-style cuisine, such as crab dishes, which visitors find particularly satisfying. The food stops are spaced out to keep the energy high, with the guide sharing culinary history alongside the food, making each bite meaningful.
Guests frequently praise Carolyn, the guide, for her knowledgeable narration, friendly demeanor, and ability to connect with the group. She shares stories about Annapolis’ history, mixed with humor and local tips, encouraging further exploration after the tour ends.
Many reviews highlight how Carolyn’s storytelling makes the experience both educational and enjoyable. Her restaurant choices are also highly appreciated, as they reflect local favorites and offer a true taste of Annapolis. She ensures the pace remains comfortable, with most of the time spent indoors for food and inside walking.
The tour starts at 1:00 pm, making it suitable for a leisurely afternoon activity. It is near public transportation, and the meeting point is easily accessible. The group size is capped at 12 travelers, fostering an intimate atmosphere. It’s recommended to arrive hungry, as the meal is filling and ends with dessert.
Guests are advised to note any food allergies or restrictions at the time of booking, as accommodations can only be made if noted beforehand. The tour is rain or shine, so participants should dress appropriately for the weather and comfortable shoes for walking.
The 3 hours 30 minutes of the tour include walking, stopping, and dining, with most walking covering around 6-7 km. The pacing has been praised for being manageable and well-balanced between sightseeing and eating.
While some find the initial walk before the first food stop slightly long (about an hour), most appreciate the thorough exploration of Annapolis’ historic district. The inside stops ensure there’s a good balance between outdoor walking and indoor dining.

This food and history tour distinguishes itself through its focus on local culinary traditions and lesser-known stories. The mix of walking, storytelling, and tasting creates a dynamic experience that appeals to history buffs and food lovers alike. The personalized approach of the guide and the quality of food at each stop are frequently highlighted as key strengths.

Some guests note that walking for about an hour before the first food stop might be longer than expected. It’s advisable to wear comfortable shoes and be prepared for moderate activity. Also, most reviews emphasize that the food stops could be more refined, with some suggestions for more diverse desserts or specialty cocktails.
As with any tour involving food, allergy or dietary restrictions need to be communicated in advance to ensure proper accommodations. The cost of $80 per person is considered acceptable for the value, considering the multiple stops and rich historical content.
The Historic Annapolis Food Tour offers a well-rounded experience combining stunning architecture, fascinating stories, and delicious local cuisine. Ideal for visitors who want to maximize their time in Annapolis with a guided, engaging activity, this tour provides insights that go beyond typical sightseeing.
While the moderate walking and length of time spent walking should be considered by those with mobility concerns, most participants find the tour manageable and rewarding. The knowledgeable guide, authentic food experiences, and historic landmarks make this a worthwhile choice for first-time visitors and repeat explorers alike.
“It's a walking tour. Very deliciously, filling tour! Caroline was so knowledgeable about Annapolis and her restaurant choices were perfect.”
Is the tour suitable for children or families?
The tour is generally suitable for most travelers, including families, especially those comfortable with moderate walking and indoor dining. The focus on history and food makes it engaging for a wide age range.
Are dietary restrictions accommodated?
Yes, accommodations can be made if allergies or restrictions are listed at the time of booking. It’s best to communicate specific needs early.
What should I wear for the tour?
Comfortable shoes are recommended due to the walking involved. The tour runs rain or shine, so appropriate attire for weather conditions is advised.
Can I participate if I have limited mobility?
The tour involves moderate walking over several stops; participants should assess their comfort level with this. Most activities are inside restaurants once the walking portion is completed.
What is the best time to take this tour?
The 1:00 pm start makes it ideal for a midday activity. It’s best to book in advance, especially during peak seasons, as the tour tends to fill up 27 days ahead.
Is gratuity included?
No, tour guide gratuity is not included in the price and is at the discretion of your.