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By Huuk Team

Road trip from Charleston to Leesburg

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ITINERARY

7h 41m384 miles18 stops
1
Frothy Beard Brewing Company
1401 Sam Rittenberg Blvd Ashley Landing, Charleston, SC 29407-5031
2
The Black Fedora Comedy Mystery Theatre
164 Church St, Charleston, SC 29401-3125
Live theatre featuring clean comic whodunit shows, volunteer audience participation, a la carte appetizers, homemade desserts, and drinks -- at the downtown City Market. “Uproarious entertainment” - Thrillist.com
3
Edmondston-Alston House
21 E Battery St, Charleston, SC 29401-2740
Constructed nearly 200 years ago, circa 1825, the Edmondston-Alston House presents a unique history of the people, both free and enslaved, who lived and labored on this property. Its collection of furniture, silver and decorative arts, largely original to those who owned the house, constitutes a rich, complex history of Charleston in the 19th century. Commanding a magnificent view of Charleston Harbor, the Edmondston-Alston House has witnessed many historic moments in the port city’s history. One of the oldest houses along the High Battery, it withstood the American Civil War, the Earthquake of 1886, and numerous hurricanes; it has survived to share a piece of Charleston history.
4
Sea Glass Therapeutic Massage
2544 Ashley River Rd, Charleston, SC 29414-4617
Located in the West Ashley section of Charleston, Sea Glass Therapeutic Massage offers Swedish, therapeutic, deep tissue, couples and hot stone massage. If you prefer massage at your own location, we will be happy to come to you. Travel and setup fee applies for mobile massage.
5
Cathedral of St. John the Baptist
222 E Harris St, Savannah, GA 31401-4616
The oldest Roman Catholic church in Georgia.
6
Coastal Georgia Botanical Gardens
2 Canebrake Rd, Savannah, GA 31419-9298
A unit of University of Georgia Extension, CGBG is a historic property with trees and farm buildings dating to the 1920s, 30s and 40s, when "the Bamboo Farm" was an active USDA Plant Introduction Station. Today, new gardens and paths are being developed and installed. By increasing the plant diversity on the 51-acre property, CGBG aims to bring people in touch with the wonders and beauty of the plant world. Admission charge, free parking and amenities include a Gift Shop and two public restrooms on site. Among the gardens to enjoy include the Woodland Shade Garden, Whiet Garden, Water Garden, Garden for All Abilities, Orchid House, Mediterranean Garden, Rose Garden and Judge Arthur Solomon Camellia Trail. Numerous cold-hardy palms, bamboo species and camellia species are highlights in our botanical collection.
7
Regal River City Marketplace Stadium 14
12884 City Center Blvd River City Marketplace, Jacksonville, FL 32218-7216
8
Downtown Cigar Lounge
11 N Ocean St, Jacksonville, FL 32202-3311
Location in the heart of downtown Jacksonville in a 101 year-old historic building. We are home to a diverse selection of premium hand-rolled cigars from various regions and a variety of wines, beers and specialty drinks . DCL is not only about cigars we are also a gallery displaying the artwork of local artists.
9
Underbelly
113 E Bay St, Jacksonville, FL 32202-3414
Located in the heart of Downtown, in Jacksonville's "Elbow District", Underbelly isn't just a building and a stage where people come to enjoy music. It's much bigger than that. It's not the paint on the walls. It's not the brick, wood, and nails that hold it all together. It's not the lights or the electricity that define it. Underbelly is a garden. A place for people, regardless of who you are or what you do, to just leave it all at the door for a small while. It's a place for humans. People wanting to be just that. Surrounded by others that feel the same to come together for however long it may be, to be here and now - no more, no less. It's a place where the best musicians unite to create moments that exist nowhere else. Isn't that what it is all about? Finding those moments of magic that will stay with you forever? Well, that's what we sell. We sell magic in all sizes. So come with many, come with none, it doesn't matter. Because when you're here, you're home.
10
Depot Park
200 SE Depot Ave, Gainesville, FL 32601-7004
Depot Park is a signature city park in downtown Gainesville providing a space for unique public outdoor enjoyment. Depot features a children's adventure play area with a custom splash pad of waterfalls, water soakers, and ground jets. A water's edge promenade hosts special events like food truck rallies, art festivals, and musical performances. The park is fully staffed and free of charge.
11
Young's Paso Fino Ranch
7950 NW 80th Ave, Ocala, FL 34482-1112
12
Marion Theatre
50 S Magnolia Ave, Ocala, FL 34471-1153
13
Ocala Palms Golf & Country Club
5174 NW 26th St, Ocala, FL 34482-3250
14
Teatro Martini
6400 Carrier Dr, Orlando, FL 32819-8260
When the sun goes down at the circus, the acts get hotter, the laughs get bigger, and everything gets a whole lot crazier. Award winning acts from around the world will amaze and astound while the best of the best perform on the stage and all around you. Laugh till you can’t breath, watch till you can’t believe, and celebrate what happens when you finally get to see Teatro Martini. Located in Orlando, Florida, in the heart of I-Drive, this highly interactive show features circus performers from around the world including comedy magician, clowns, acrobats and performing puppies!
15
1001 Transportation
6401 Time Square Ave Cu-20 #1022, Orlando, FL 32819-9118
Airport Transportation Affordable flat rate Orlando & Miami ground transportation with over 20 years of combined experience. Our chauffeurs have earned an excellent reputation for exceptional standard of safety, reliability and professionalism Transportation in Orlando & Miami Florida.
16
The Legends Walk Course
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
17
Island H2O Water Park
3230 Inspiration Dr, Kissimmee, FL 34747
Island H2O Water Park is your place for family fun! Tube slides, raft riding & splash zones, plus luxury cabana rentals at a sprawling water park.
18
Corpus Christi Catholic Church
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
Customize this Trip

OVERVIEW

1
Start:Frothy Beard Brewing Company
Charleston, South Carolina·
4.5
(86) review
1401 Sam Rittenberg Blvd Ashley Landing, Charleston, SC 29407-5031
2
The Black Fedora Comedy Mystery Theatre
Charleston, South Carolina·
4.5
(993) review
Live theatre featuring clean comic whodunit shows, volunteer audience participation, a la carte appetizers, homemade desserts, and drinks -- at the downtown City Market. “Uproarious entertainment” - Thrillist.com
164 Church St, Charleston, SC 29401-3125
3
Edmondston-Alston House
Charleston, South Carolina·
4.5
(992) review
Constructed nearly 200 years ago, circa 1825, the Edmondston-Alston House presents a unique history of the people, both free and enslaved, who lived and labored on this property. Its collection of furniture, silver and decorative arts, largely original to those who owned the house, constitutes a rich, complex history of Charleston in the 19th century. Commanding a magnificent view of Charleston Harbor, the Edmondston-Alston House has witnessed many historic moments in the port city’s history. One of the oldest houses along the High Battery, it withstood the American Civil War, the Earthquake of 1886, and numerous hurricanes; it has survived to share a piece of Charleston history.
21 E Battery St, Charleston, SC 29401-2740
4
Sea Glass Therapeutic Massage
Charleston, South Carolina·
5.0
(9) review
Located in the West Ashley section of Charleston, Sea Glass Therapeutic Massage offers Swedish, therapeutic, deep tissue, couples and hot stone massage. If you prefer massage at your own location, we will be happy to come to you. Travel and setup fee applies for mobile massage.
2544 Ashley River Rd, Charleston, SC 29414-4617
5
Cathedral of St. John the Baptist
Savannah, Georgia·
5.0
(9819) review
The oldest Roman Catholic church in Georgia.
222 E Harris St, Savannah, GA 31401-4616
6
Coastal Georgia Botanical Gardens
Savannah, Georgia·
4.0
(96) review
A unit of University of Georgia Extension, CGBG is a historic property with trees and farm buildings dating to the 1920s, 30s and 40s, when "the Bamboo Farm" was an active USDA Plant Introduction Station. Today, new gardens and paths are being developed and installed. By increasing the plant diversity on the 51-acre property, CGBG aims to bring people in touch with the wonders and beauty of the plant world. Admission charge, free parking and amenities include a Gift Shop and two public restrooms on site. Among the gardens to enjoy include the Woodland Shade Garden, Whiet Garden, Water Garden, Garden for All Abilities, Orchid House, Mediterranean Garden, Rose Garden and Judge Arthur Solomon Camellia Trail. Numerous cold-hardy palms, bamboo species and camellia species are highlights in our botanical collection.
2 Canebrake Rd, Savannah, GA 31419-9298
7
Regal River City Marketplace Stadium 14
Jacksonville, Florida·
4.5
(9) review
12884 City Center Blvd River City Marketplace, Jacksonville, FL 32218-7216
8
Downtown Cigar Lounge
Jacksonville, Florida·
4.5
(9) review
Location in the heart of downtown Jacksonville in a 101 year-old historic building. We are home to a diverse selection of premium hand-rolled cigars from various regions and a variety of wines, beers and specialty drinks . DCL is not only about cigars we are also a gallery displaying the artwork of local artists.
11 N Ocean St, Jacksonville, FL 32202-3311
9
Underbelly
Jacksonville, Florida·
3.5
(9) review
Located in the heart of Downtown, in Jacksonville's "Elbow District", Underbelly isn't just a building and a stage where people come to enjoy music. It's much bigger than that. It's not the paint on the walls. It's not the brick, wood, and nails that hold it all together. It's not the lights or the electricity that define it. Underbelly is a garden. A place for people, regardless of who you are or what you do, to just leave it all at the door for a small while. It's a place for humans. People wanting to be just that. Surrounded by others that feel the same to come together for however long it may be, to be here and now - no more, no less. It's a place where the best musicians unite to create moments that exist nowhere else. Isn't that what it is all about? Finding those moments of magic that will stay with you forever? Well, that's what we sell. We sell magic in all sizes. So come with many, come with none, it doesn't matter. Because when you're here, you're home.
113 E Bay St, Jacksonville, FL 32202-3414
10
Depot Park
Gainesville, Florida·
5.0
(94) review
Depot Park is a signature city park in downtown Gainesville providing a space for unique public outdoor enjoyment. Depot features a children's adventure play area with a custom splash pad of waterfalls, water soakers, and ground jets. A water's edge promenade hosts special events like food truck rallies, art festivals, and musical performances. The park is fully staffed and free of charge.
200 SE Depot Ave, Gainesville, FL 32601-7004
11
Young's Paso Fino Ranch
Ocala, Florida·
4.0
(9) review
7950 NW 80th Ave, Ocala, FL 34482-1112
12
Marion Theatre
Ocala, Florida·
4.5
(90) review
50 S Magnolia Ave, Ocala, FL 34471-1153
13
Ocala Palms Golf & Country Club
Ocala, Florida·
4.5
(9) review
5174 NW 26th St, Ocala, FL 34482-3250
14
Teatro Martini
Orlando, Florida·
4.5
(960) review
When the sun goes down at the circus, the acts get hotter, the laughs get bigger, and everything gets a whole lot crazier. Award winning acts from around the world will amaze and astound while the best of the best perform on the stage and all around you. Laugh till you can’t breath, watch till you can’t believe, and celebrate what happens when you finally get to see Teatro Martini. Located in Orlando, Florida, in the heart of I-Drive, this highly interactive show features circus performers from around the world including comedy magician, clowns, acrobats and performing puppies!
6400 Carrier Dr, Orlando, FL 32819-8260
15
1001 Transportation
Orlando, Florida·
5.0
(98) review
Airport Transportation Affordable flat rate Orlando & Miami ground transportation with over 20 years of combined experience. Our chauffeurs have earned an excellent reputation for exceptional standard of safety, reliability and professionalism Transportation in Orlando & Miami Florida.
6401 Time Square Ave Cu-20 #1022, Orlando, FL 32819-9118
16
The Legends Walk Course
Kissimmee, Florida·
4.0
(96) review
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
17
Island H2O Water Park
Kissimmee, Florida·
3.5
(96) review
Island H2O Water Park is your place for family fun! Tube slides, raft riding & splash zones, plus luxury cabana rentals at a sprawling water park.
3230 Inspiration Dr, Kissimmee, FL 34747
18
Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867

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FAQ
Frequently Asked Questions
What's the driving distance between Charleston and Leesburg?
The distance is 384 miles
What's the travel time between Charleston and Leesburg?
The driving time can vary depending on traffic conditions, but it is typically 7h 41m mins in normal traffic
What are some of the best cities to visit between Charleston and Leesburg?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Leesburg?
There are plenty! Here are some stops you shouldn’t miss on your way to Leesburg
What’s the weather like in Leesburg?
The weather in Leesburg is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Leesburg in January
Weather in Leesburg in February
Weather in Leesburg in March
Weather in Leesburg in April
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Weather in Leesburg in July
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Weather in Leesburg in October
Weather in Leesburg in November
Weather in Leesburg in December
Interested in a detailed plan for your time in Leesburg?
Plan your dream Leesburg trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Leesburg
A 2-day itinerary in Leesburg
A 3-day itinerary in Leesburg
A 4-day itinerary in Leesburg
A 5-day itinerary in Leesburg
A 6-day itinerary in Leesburg
Where else can I travel to if I'm starting my trip in Charleston?
We have a lot of great trip options for Charleston! See the links below for all the itineraries we created for you