Walking Tours

A Walk Through Charleston

Here’s a little-known secret: Some of Charleston’s best sites can’t be accessed by a bus or even a carriage – only by foot. Walking tours are one of the best ways to explore.

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Our most popular and diverse tour, A Walk Through Charleston, is a comprehensive overview of Charleston history through the centuries. Charleston was founded in 1670 and quickly developed into the most cosmopolitan seaport on the continent. Come walk with us and learn about bawdy taverns & pirates, heroic patriots, the grandeur of antebellum architecture, the devastation of the Civil War, and much more. History will come alive as we stroll through the historic streets and gardens of the “Holy City”.

A Walk Through Charleston

Here’s a little-known secret: Some of Charleston’s best sites can’t be accessed by a bus or even a carriage – only by foot. Walking tours are one of the best ways to explore.

logo green - Pineapple Tour Group

Our most popular and diverse tour, A Walk Through Charleston, is a comprehensive overview of Charleston history through the centuries. Charleston was founded in 1670 and quickly developed into the most cosmopolitan seaport on the continent. Come walk with us and learn about bawdy taverns & pirates, heroic patriots, the grandeur of antebellum architecture, the devastation of the Civil War, and much more. History will come alive as we stroll through the historic streets and gardens of the “Holy City”.

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Starting and ending at the Edmondston-Alston House, take an hour-long guided walking tour South of Broad Street and learn not only about the area’s rich history but about the extended Alston family during the years before the Civil War. Your experience will conclude with a 30-minute tour of the Edmondston-Alston House. Constructed in 1825, the house commands a magnificent view of Charleston Harbor and 90% of the home’s furnishings were originally owned by the family. This is the only walking tour in Charleston that includes a tour of a historic house; VIP access to the Edmondston-Alston House.

Life on the Battery: The Edmondston-Alston House Walking Tour

Charleston’s history and unique way of life can be greatly attributed to its location on a small peninsula bounded by two rivers. The southern tip of this peninsula, known as the Battery, has become one of the city’s most treasured sites and no visit to Charleston would be complete without touring this historic district.

Life on the Battery: The Edmondston-Alston House Walking Tour

Charleston’s history and unique way of life can be greatly attributed to its location on a small peninsula bounded by two rivers. The southern tip of this peninsula, known as the Battery, has become one of the city’s most treasured sites and no visit to Charleston would be complete without touring this historic district.

logo green - Pineapple Tour Group

Starting and ending at the Edmondston-Alston House, take an hour-long guided walking tour South of Broad Street and learn not only about the area’s rich history but about the extended Alston family during the years before the Civil War. Your experience will conclude with a 30-minute tour of the Edmondston-Alston House. Constructed in 1825, the house commands a magnificent view of Charleston Harbor and 90% of the home’s furnishings were originally owned by the family. This is the only walking tour in Charleston that includes a tour of a historic house; VIP access to the Edmondston-Alston House.

Charleston for Morons Comedy Walking Tour

Over 350 years of Lowcountry history in just 75 minutes!

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This laugh-out-loud comedy walking tour is 50% history – 50% Comedy – 100% fun. This is the only tour in Charleston hosted by not one, but two hilarious tour guides. That’s right two guides for the price of one. Walk through historic downtown Charleston past iconic landmarks and breathtaking scenery while your two guides make you laugh with a comedy history tour that even a moron can enjoy. Highlights of the tour include Waterfront Park, Rainbow Row, Four Corners of Law, the Dock Street Theatre and Philadelphia Alley.

Charleston for Morons Comedy Walking Tour

Over 350 years of Lowcountry history in just 75 minutes!

logo green - Pineapple Tour Group

This laugh-out-loud comedy walking tour is 50% history – 50% Comedy – 100% fun. This is the only tour in Charleston hosted by not one, but two hilarious tour guides. That’s right two guides for the price of one. Walk through historic downtown Charleston past iconic landmarks and breathtaking scenery while your two guides make you laugh with a comedy history tour that even a moron can enjoy. Highlights of the tour include Waterfront Park, Rainbow Row, Four Corners of Law, the Dock Street Theatre and Philadelphia Alley.

“I’ve taken many of the city tours over the years and I think this is the best. They give a tremendous amount of information, much of which you don’t get on other tours. Highly recommend.”

Glen A. | TripAdvisor

“I’ve taken many of the city tours over the years and I think this is the best. They give a tremendous amount of information, much of which you don’t get on other tours. Highly recommend.”

Glen A. | TripAdvisor

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We cannot wait to make your Charleston memories special!