Discover Charleston on a personalized private walk with Pineapple Tour Group. Led by expert guides, these tours immerse you in the city’s history and charm, tailored to your interests. Perfect for all travelers seeking a genuine experience. Join a bespoke journey through Charleston’s most captivating streets and stories, and experience the city like a local during this intimate outdoor adventure.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
1.5–2 hours
Fitness Level
Accessible for most visitors, requiring only regular walking ability
Wildlife
History
Charleston’s streets like Meeting Street have hosted significant events dating back to colonial times, shaping the city’s storied past.
Conservation
Local guides emphasize preserving Charleston’s historic architecture and green spaces, advocating for sustainable tourism practices.
Pineapple Tour Group
Discover Charleston on a personalized private walk with Pineapple Tour Group. Led by expert guides, these tours immerse you in the city’s history and charm, tailored to your interests. Perfect for all travelers seeking a genuine experience. Join a bespoke journey through Charleston’s most captivating streets and stories, and experience the city like a local during this intimate outdoor adventure.
Pineapple Tour Group curates guided experiences across Charleston, with a focus on historic plantations, Battery-era homes, and tailored private excursions. Offerings include Magnolia Plantation & Gardens — featuring the Magnolia House, the Audubon Swamp Garden, and the poignant “From Slavery to Freedom” tour — as well as the Life on the Battery: The Edmondston-Alston House Walking Tour and a dedicated visit to Middleton Place. The company operates a 90-minute Daily Bus Tour that runs in air-conditioned comfort while guides recount 300 years of Charleston history. Private Bus and Private Walking Tour options are available for groups seeking a personalized itinerary; private experiences are led by historians or knowledgeable guides and are customized to each group’s interests. Pineapple Tour Group emphasizes accurate historical interpretation and high guest satisfaction through experienced guides, reliable transportation, and well-paced itineraries. Tour descriptions highlight major sites and allow guests to choose half-day or full-day formats where applicable. Safety, accessibility, and clear scheduling information are provided at booking to ensure smooth arrivals and departures. Pineapple Tour Group serves first-time visitors and returning travelers who want deeper insight into Charleston’s architecture, gardens, and social history. Each tour balances visual landmarks with contextual storytelling to create memorable, educational visits that respect the significance of the places featured.
Tours Offered
7
Varied routes across Charleston and plantations
Daily Departure
Daily
90-minute daily bus tour available
Private Tours
Available
Customized by expert historians
Historic Sites
Magnolia, Middleton, Edmondston
Iconic Charleston landmarks included
Select daily bus departures, private tours, or full-day plantation visits — secure preferred dates and guide options now.
Wear comfortable shoes
Streets are historic cobblestones; comfortable footwear makes for a more enjoyable walk.
Bring a water bottle
Stay hydrated as the tour can cover several city blocks, especially in warmer months.
Check the weather forecast
Tours run rain or shine; dress appropriately for the weather to stay comfortable.
Arrive early
Punctuality ensures you get the most out of your personalized experience.
Comfortable walking shoes
Ensures comfortable exploration over uneven city streets.
Water bottle
Helps stay hydrated during the walk, especially in warm weather.
Sun protection (hat, sunscreen)
Protects against sun exposure during sunny days.
summer
Camera or smartphone
Capture the colorful architecture and charming scenes along the tour route.