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By Huuk Team

Road trip from Leesburg to Winston-Salem

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Show more (4+)

ITINERARY

11h 31m598 miles26 stops
1
MetroWest Golf Club
2100 S Hiawassee Rd, Orlando, FL 32835-6307
MetroWest Golf Club, voted the best golf course in Orlando, is located just minutes away from Universal Orlando Resort. The club provides a fair, yet demanding challenge to make a pleasurable golf experience for players of all skill levels.
2
Marion Theatre
50 S Magnolia Ave, Ocala, FL 34471-1153
3
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.
4
The Legends Walk Course
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
5
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!
6
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.
7
Ocala Palms Golf & Country Club
5174 NW 26th St, Ocala, FL 34482-3250
8
Lake Rianhard
701 Front St Em frente a Market Street, Celebration, Orlando, FL 34747-4915
9
Corpus Christi Catholic Church
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
10
Young's Paso Fino Ranch
7950 NW 80th Ave, Ocala, FL 34482-1112
11
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.
12
The Brumos Collection
5159 San Pablo Rd S, Jacksonville, FL 32224-1823
The Brumos Collection imparts a sweeping story of automotive development through racing. More than a technical tale, the exhibition reveals the very soul in these machines-cars inspired by their predecessors, developed by masters, tested in competition and celebrated in history. Remarkable vehicles spanning three centuries show the collaborations and rivalries that changed the automotive world.
13
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.
14
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.
15
Regal River City Marketplace Stadium 14
12884 City Center Blvd River City Marketplace, Jacksonville, FL 32218-7216
16
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.
17
Cathedral of St. John the Baptist
222 E Harris St, Savannah, GA 31401-4616
The oldest Roman Catholic church in Georgia.
18
Studio Cellar
912 Lady St The Vista, Columbia, SC 29201-3106
19
The Sleepy Poet Antiques Mall
4450 South Blvd, Charlotte, NC 28209-2673
20
Sugar Creek Brewing Company
215 Southside Dr, Charlotte, NC 28217-1727
Sugar Creek Brewing Co. Bringing Belgian-inspired beer to the Carolinas and beyond, Sugar Creek Brewing Company combines the watchful eye of a Trappist Monk with the technical precision of nuclear engineering to craft fresh, full-flavored beers that are immensely satisfying and intensely drinkable. Using unique combinations of aromatic yeast strains, domestic and imported hops and award-winning malt varietys, Sugar Creek infuses traditional recipes with modern tastes and techniques to create beer that nourishes both mind and body. Sugar Creek Tap Room Mon-Wed: 4pm - 9pm Thursday: 4pm - 10pm Friday: 2pm - 10pm Saturday: 11am- 10pm Sunday: 12pm - 8pm Tighten the ropes and raise the sails, the Sugar Creek Brewing Co. Tap room is where your exploration begins! We have constructed a large taproom and private event room and staffed it with kind, courteous and knowledgeable beertenders. On tap you will find all of our year-round beers as well as seasonal and small-batch releases. Beers are available by the glass, 4 oz. Tasting flights, and growler fills via our Pegas CrafTap growler filler. The taproom is open for exploration seven days a week! Sugar Creek Private Event Room Adjacent to our taproom is our 1700 sqft private event room, complete with a private outdoor patio, private bar, and overhead projector. Private events are available seven days a week, for parties as small as 15 people. In addition to offering a full range of our favorite beers, Sugar Creek is happy to provide food services or accommodate outside catering.
21
Bojangles' Coliseum
2700 E Independence Blvd, Charlotte, NC 28205-6925
Located in Charlotte, NC - Since 1955, Bojangles' Coliseum has hosted concerts, family shows, conferences, sports events, and Charlotte Checkers hockey.
22
Wooden Robot Brewery
1440 S Tryon St Suite 110, Charlotte, NC 28203-4262
23
JDL Fast Track
2505 Empire Dr, Winston Salem, NC 27103-6709
24
Recreation Billiards
412 W 4th St, Winston Salem, NC 27101-2805
25
Salem Lake
1001 Salem Lake Rd, Winston Salem, NC 27107-1571
26
Lam Museum of Anthropology, Wake Forest University
Palmer Hall, Carroll Weathers Drive, Winston Salem, NC 27109
Discover North Carolina's only museum dedicated to the study of global cultures. Explore stories of humanity, from ancient archaeological sites to the celebrations and struggles of today. Learn about peoples around the world through their everyday and ceremonial objects, and visual arts. Changing exhibits highlight the Museum's collections of nearly 30,000 archaeological and ethnographic artifacts from more than 350 cultures and 90 countries. Admission is free.
Customize this Trip

OVERVIEW

Leesburg to Winston-Salem
1
Start:MetroWest Golf Club
Orlando, Florida·
3.0
(96) review
MetroWest Golf Club, voted the best golf course in Orlando, is located just minutes away from Universal Orlando Resort. The club provides a fair, yet demanding challenge to make a pleasurable golf experience for players of all skill levels.
2100 S Hiawassee Rd, Orlando, FL 32835-6307
2
Marion Theatre
Ocala, Florida·
4.5
(90) review
50 S Magnolia Ave, Ocala, FL 34471-1153
3
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
4
The Legends Walk Course
Kissimmee, Florida·
4.0
(96) review
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
5
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
6
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
7
Ocala Palms Golf & Country Club
Ocala, Florida·
4.5
(9) review
5174 NW 26th St, Ocala, FL 34482-3250
8
Lake Rianhard
Celebration, Orlando, Florida·
4.5
(95) review
701 Front St Em frente a Market Street, Celebration, Orlando, FL 34747-4915
9
Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
10
Young's Paso Fino Ranch
Ocala, Florida·
4.0
(9) review
7950 NW 80th Ave, Ocala, FL 34482-1112
11
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
12
The Brumos Collection
Jacksonville, Florida·
5.0
(9) review
The Brumos Collection imparts a sweeping story of automotive development through racing. More than a technical tale, the exhibition reveals the very soul in these machines-cars inspired by their predecessors, developed by masters, tested in competition and celebrated in history. Remarkable vehicles spanning three centuries show the collaborations and rivalries that changed the automotive world.
5159 San Pablo Rd S, Jacksonville, FL 32224-1823
13
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
14
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
15
Regal River City Marketplace Stadium 14
Jacksonville, Florida·
4.5
(9) review
12884 City Center Blvd River City Marketplace, Jacksonville, FL 32218-7216
16
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
17
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
18
Studio Cellar
Columbia, South Carolina·
5.0
(9) review
912 Lady St The Vista, Columbia, SC 29201-3106
19
The Sleepy Poet Antiques Mall
Charlotte, North Carolina·
4.5
(93) review
4450 South Blvd, Charlotte, NC 28209-2673
20
Sugar Creek Brewing Company
Charlotte, North Carolina·
4.5
(98) review
Sugar Creek Brewing Co. Bringing Belgian-inspired beer to the Carolinas and beyond, Sugar Creek Brewing Company combines the watchful eye of a Trappist Monk with the technical precision of nuclear engineering to craft fresh, full-flavored beers that are immensely satisfying and intensely drinkable. Using unique combinations of aromatic yeast strains, domestic and imported hops and award-winning malt varietys, Sugar Creek infuses traditional recipes with modern tastes and techniques to create beer that nourishes both mind and body. Sugar Creek Tap Room Mon-Wed: 4pm - 9pm Thursday: 4pm - 10pm Friday: 2pm - 10pm Saturday: 11am- 10pm Sunday: 12pm - 8pm Tighten the ropes and raise the sails, the Sugar Creek Brewing Co. Tap room is where your exploration begins! We have constructed a large taproom and private event room and staffed it with kind, courteous and knowledgeable beertenders. On tap you will find all of our year-round beers as well as seasonal and small-batch releases. Beers are available by the glass, 4 oz. Tasting flights, and growler fills via our Pegas CrafTap growler filler. The taproom is open for exploration seven days a week! Sugar Creek Private Event Room Adjacent to our taproom is our 1700 sqft private event room, complete with a private outdoor patio, private bar, and overhead projector. Private events are available seven days a week, for parties as small as 15 people. In addition to offering a full range of our favorite beers, Sugar Creek is happy to provide food services or accommodate outside catering.
215 Southside Dr, Charlotte, NC 28217-1727
21
Bojangles' Coliseum
Charlotte, North Carolina·
4.0
(98) review
Located in Charlotte, NC - Since 1955, Bojangles' Coliseum has hosted concerts, family shows, conferences, sports events, and Charlotte Checkers hockey.
2700 E Independence Blvd, Charlotte, NC 28205-6925
22
Wooden Robot Brewery
Charlotte, North Carolina·
4.5
(97) review
1440 S Tryon St Suite 110, Charlotte, NC 28203-4262
23
JDL Fast Track
Winston Salem, North Carolina·
4.0
(9) review
2505 Empire Dr, Winston Salem, NC 27103-6709
24
Recreation Billiards
Winston Salem, North Carolina·
4.0
(9) review
412 W 4th St, Winston Salem, NC 27101-2805
25
Salem Lake
Winston Salem, North Carolina·
4.5
(97) review
1001 Salem Lake Rd, Winston Salem, NC 27107-1571
26
Lam Museum of Anthropology, Wake Forest University
Winston Salem, North Carolina·
4.0
(9) review
Discover North Carolina's only museum dedicated to the study of global cultures. Explore stories of humanity, from ancient archaeological sites to the celebrations and struggles of today. Learn about peoples around the world through their everyday and ceremonial objects, and visual arts. Changing exhibits highlight the Museum's collections of nearly 30,000 archaeological and ethnographic artifacts from more than 350 cultures and 90 countries. Admission is free.
Palmer Hall, Carroll Weathers Drive, Winston Salem, NC 27109

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FAQ
Frequently Asked Questions
What's the driving distance between Leesburg and Winston-Salem?
The distance is 598 miles
What's the travel time between Leesburg and Winston-Salem?
The driving time can vary depending on traffic conditions, but it is typically 11h 31m mins in normal traffic
What are some of the best cities to visit between Leesburg and Winston-Salem?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Winston-Salem?
There are plenty! Here are some stops you shouldn’t miss on your way to Winston-Salem
What’s the weather like in Winston-Salem?
The weather in Winston-Salem is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Winston-Salem in January
Weather in Winston-Salem in February
Weather in Winston-Salem in March
Weather in Winston-Salem in April
Weather in Winston-Salem in May
Weather in Winston-Salem in June
Weather in Winston-Salem in July
Weather in Winston-Salem in August
Weather in Winston-Salem in September
Weather in Winston-Salem in October
Weather in Winston-Salem in November
Weather in Winston-Salem in December
Interested in a detailed plan for your time in Winston-Salem?
Plan your dream Winston-Salem trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Winston-Salem
A 2-day itinerary in Winston-Salem
A 3-day itinerary in Winston-Salem
A 4-day itinerary in Winston-Salem
A 5-day itinerary in Winston-Salem
A 6-day itinerary in Winston-Salem
Where else can I travel to if I'm starting my trip in Leesburg?
We have a lot of great trip options for Leesburg! See the links below for all the itineraries we created for you