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By Huuk Team

Road trip from Kissimmee to Chesapeake

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Show more (3+)

ITINERARY

14h 36m773 miles14 stops
1
Corpus Christi Catholic Church
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
2
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.
3
American Girl Orlando
8001 S Orange Blossom Trl, Orlando, FL 32809-7654
Discover a place like no other, where lifelong memories are made, time together counts, and girls can be girls! Enjoy casual dining in the Bistro, where dolls are always welcome.
4
Daytona Escape Rooms Code to Escape
119 S Palmetto Ave, Daytona Beach, FL 32114-4387
Looking for something different to do in Florida? Enjoy one or more of our rooms for your next conference or seminar! Have your next party with us! Code To Escape offers a unique, fun activity for friends or family. We are Florida's number one life escape room game also. Boring conferences, seminars? Make them exciting with these team building escape room exercises. Teams of 2 - 12 people will hav
5
News-Journal Center at Daytona State College
221 N Beach St, Daytona Beach, FL 32114-3321
6
Boot Hill Saloon
310 Main St, Daytona Beach, FL 32118-4436
7
Peabody Auditorium
600 Auditorium Blvd, Daytona Beach, FL 32118-4247
8
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.
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
Cathedral of St. John the Baptist
222 E Harris St, Savannah, GA 31401-4616
The oldest Roman Catholic church in Georgia.
11
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.
12
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
13
O'Connor Brewing Co.
211 W 24th St, Norfolk, VA 23517
The brewery is located at 211 W. 24th Street in the new Railroad district of Norfolk, situated next to the historic Ghent neighborshood and just a mile or two from Downtown. The Tasting Room and Production facility share a 35,000 sq. foot mid-century modern historic building. Free parking is available in their private lot or street parking is free along 24th and 23rd street. O’Connor beer drinkers come from all walks of life, but what brings them together is a love of the small, simple joys in life. The pleasure of being outdoors, relaxing on the beach with friends, having dinner with family after a day of hard work, and of course, enjoying a fresh, flavorful beer. Customers appreciate the O’Connor brand for its approachability and authenticity. They value its independent spirit, that it remains family owned and operated, and its support of the local community. And their loyalty has established it as a mainstay brand with 10 years of sustained success.
14
The Mariners' Museum and Park
100 Museum Drive, Newport News, VA 23606
Curate your Mariners’ Experience! From inspiring stories of mariners who risked it all for freedom to true tales of man conquering the wild seas, our indoor galleries will spark curiosity, wonder, and an appreciation for our shared maritime heritage. Explore over 90,000 square feet of gallery space and discover your connection to our shared maritime heritage. Admission to the Museum is only $1 per person. Add some outdoor adventure to your day in our 550-acre Park which offers visitors a quiet and serene place to walk, hike or run amongst rolling woodlands. Our Park features the award-winning five-mile Noland Trail that surrounds the 167-acre Mariners’ Lake. The Park is free and open to the public.
Customize this Trip

OVERVIEW

1
Start:Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
2
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
3
American Girl Orlando
Orlando, Florida·
4.5
(98) review
Discover a place like no other, where lifelong memories are made, time together counts, and girls can be girls! Enjoy casual dining in the Bistro, where dolls are always welcome.
8001 S Orange Blossom Trl, Orlando, FL 32809-7654
4
Daytona Escape Rooms Code to Escape
Daytona Beach, Florida·
4.5
(98) review
Looking for something different to do in Florida? Enjoy one or more of our rooms for your next conference or seminar! Have your next party with us! Code To Escape offers a unique, fun activity for friends or family. We are Florida's number one life escape room game also. Boring conferences, seminars? Make them exciting with these team building escape room exercises. Teams of 2 - 12 people will hav
119 S Palmetto Ave, Daytona Beach, FL 32114-4387
5
News-Journal Center at Daytona State College
Daytona Beach, Florida·
4.5
(9) review
221 N Beach St, Daytona Beach, FL 32114-3321
6
Boot Hill Saloon
Daytona Beach, Florida·
4.5
(90) review
310 Main St, Daytona Beach, FL 32118-4436
7
Peabody Auditorium
Daytona Beach, Florida·
4.5
(96) review
600 Auditorium Blvd, Daytona Beach, FL 32118-4247
8
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
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
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
11
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
12
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
13
O'Connor Brewing Co.
Norfolk, Virginia·
4.5
(97) review
The brewery is located at 211 W. 24th Street in the new Railroad district of Norfolk, situated next to the historic Ghent neighborshood and just a mile or two from Downtown. The Tasting Room and Production facility share a 35,000 sq. foot mid-century modern historic building. Free parking is available in their private lot or street parking is free along 24th and 23rd street. O’Connor beer drinkers come from all walks of life, but what brings them together is a love of the small, simple joys in life. The pleasure of being outdoors, relaxing on the beach with friends, having dinner with family after a day of hard work, and of course, enjoying a fresh, flavorful beer. Customers appreciate the O’Connor brand for its approachability and authenticity. They value its independent spirit, that it remains family owned and operated, and its support of the local community. And their loyalty has established it as a mainstay brand with 10 years of sustained success.
211 W 24th St, Norfolk, VA 23517
14
The Mariners' Museum and Park
Newport News, Virginia·
5.0
(959) review
Curate your Mariners’ Experience! From inspiring stories of mariners who risked it all for freedom to true tales of man conquering the wild seas, our indoor galleries will spark curiosity, wonder, and an appreciation for our shared maritime heritage. Explore over 90,000 square feet of gallery space and discover your connection to our shared maritime heritage. Admission to the Museum is only $1 per person. Add some outdoor adventure to your day in our 550-acre Park which offers visitors a quiet and serene place to walk, hike or run amongst rolling woodlands. Our Park features the award-winning five-mile Noland Trail that surrounds the 167-acre Mariners’ Lake. The Park is free and open to the public.
100 Museum Drive, Newport News, VA 23606

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Kissimmee and Chesapeake?
The distance is 773 miles
What's the travel time between Kissimmee and Chesapeake?
The driving time can vary depending on traffic conditions, but it is typically 14h 36m mins in normal traffic
What are some of the best cities to visit between Kissimmee and Chesapeake?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Chesapeake?
There are plenty! Here are some stops you shouldn’t miss on your way to Chesapeake
What’s the weather like in Chesapeake?
The weather in Chesapeake is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Chesapeake in January
Weather in Chesapeake in February
Weather in Chesapeake in March
Weather in Chesapeake in April
Weather in Chesapeake in May
Weather in Chesapeake in June
Weather in Chesapeake in July
Weather in Chesapeake in August
Weather in Chesapeake in September
Weather in Chesapeake in October
Weather in Chesapeake in November
Weather in Chesapeake in December
Interested in a detailed plan for your time in Chesapeake?
Plan your dream Chesapeake trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Chesapeake
A 2-day itinerary in Chesapeake
A 3-day itinerary in Chesapeake
A 4-day itinerary in Chesapeake
A 5-day itinerary in Chesapeake
A 6-day itinerary in Chesapeake
Where else can I travel to if I'm starting my trip in Kissimmee?
We have a lot of great trip options for Kissimmee! See the links below for all the itineraries we created for you