Road trip from Sarasota to Chesapeake
All Category
Outdoor Activities
Nature & Parks
Shopping
Fun & Games
Concerts & Shows
Museums
Nightlife
Show more (4+)
All Category
Outdoor Activities
Nature & Parks
Shopping
Fun & Games
Concerts & Shows
Museums
Nightlife
Sights & Landmarks
Boat Tours & Water Sports
Food & Drink
Reset
Show less
ITINERARY
16h 21m860 miles17 stops
1
Gizella Kopsick Arboretum
2
WestShore Plaza
3
University of South Florida Botanical Gardens, Tampa
4
Marion Theatre
5
Ocala Palms Golf & Country Club
6
Ocala Civic Theatre
Ocala Civic Theatre has been uplifting, inspiring, and entertaining our community for more than 70 years. Founded in 1950, OCT is one of the largest community theatres in the state and serves 65,000 local residents each season. We are able to present professional-quality live performances thanks to the talents and dedication of our volunteers, staff, and guest designers. In addition, OCT’s Education & Enrichment programs reach more than 1,000 learners of all ages year-round through skill-building and performance classes. Celebrating 70 Years of OCT History! Our story began on March 3, 1950 at the first organizational meeting of The Marion Players, a group of young people who decided Ocala needed a “little theatre.” They had a wide variety of theatrical talents and experience, and they all shared a deep desire to provide the highest quality entertainment for local audiences.
7
Young's Paso Fino Ranch
8
Depot Park
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.
9
The Brumos Collection
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.
10
Underbelly
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.
11
Downtown Cigar Lounge
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.
12
Regal River City Marketplace Stadium 14
13
Cathedral of St. John the Baptist
The oldest Roman Catholic church in Georgia.
14
Edmondston-Alston House
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.
15
The Black Fedora Comedy Mystery Theatre
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
16
O'Connor Brewing Co.
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.
17
The Mariners' Museum and Park
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:Gizella Kopsick Arboretum
St. Petersburg, Florida·
4.5
(97) review
901 N Shore Dr NE, St. Petersburg, FL 33701-2052
2
Start:WestShore Plaza
Tampa, Florida·
4.0
(99) review
250 WestShore Plaza, Tampa, FL 33609-1918
3
Start:University of South Florida Botanical Gardens, Tampa
Tampa, Florida·
3.5
(98) review
4202 E Fowler Ave, Tampa, FL 33620-5150
4
Start:Marion Theatre
Ocala, Florida·
4.5
(90) review
50 S Magnolia Ave, Ocala, FL 34471-1153
5
Start:Ocala Palms Golf & Country Club
Ocala, Florida·
4.5
(9) review
5174 NW 26th St, Ocala, FL 34482-3250
6
Start:Ocala Civic Theatre
Ocala, Florida·
4.5
(81) review
Ocala Civic Theatre has been uplifting, inspiring, and entertaining our community for more than 70 years. Founded in 1950, OCT is one of the largest community theatres in the state and serves 65,000 local residents each season. We are able to present professional-quality live performances thanks to the talents and dedication of our volunteers, staff, and guest designers. In addition, OCT’s Education & Enrichment programs reach more than 1,000 learners of all ages year-round through skill-building and performance classes. Celebrating 70 Years of OCT History! Our story began on March 3, 1950 at the first organizational meeting of The Marion Players, a group of young people who decided Ocala needed a “little theatre.” They had a wide variety of theatrical talents and experience, and they all shared a deep desire to provide the highest quality entertainment for local audiences.
7
Start:Young's Paso Fino Ranch
Ocala, Florida·
4.0
(9) review
7950 NW 80th Ave, Ocala, FL 34482-1112
8
Start: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.
9
Start: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.
10
Start: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.
11
Start: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.
12
Start:Regal River City Marketplace Stadium 14
Jacksonville, Florida·
4.5
(9) review
12884 City Center Blvd River City Marketplace, Jacksonville, FL 32218-7216
13
Start:Cathedral of St. John the Baptist
Savannah, Georgia·
5.0
(9819) review
The oldest Roman Catholic church in Georgia.
14
Start: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.
15
Start: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
16
Start: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.
17
Start: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.
CHECKLIST
GPS device or app
Download Offline Map
Car charger and portable battery
Water bottles and snacks
Travel pillow and blanket
Sunglasses and sunscreen
First-aid kit
Trash bags
Hand sanitizer and wet wipes
Driver’s license and vehicle registration
Cash and cards
Camera or smartphone
Unlock Effortless Travel Planning
Create your dream trip in minutes by this prompt. Try now!
EXPLORE MORE
Discover Exciting Road Trip Inspirations
Sarasota to Tulsa
1,219 miles
22h 48m
14 stops
Outdoor ActivitiesToursShoppingNature & ParksMuseums
Sarasota to Allentown
1,140 miles
21h 48m
25 stops
Outdoor ActivitiesToursShoppingFun & GamesNature & Parks
Sarasota to Dayton
1,010 miles
18h 49m
21 stops
Outdoor ActivitiesToursShoppingMuseumsSights & Landmarks
Sarasota to Fresno
2,716 miles
48h 34m
41 stops
Outdoor ActivitiesToursShoppingNature & ParksSights & Landmarks
Sarasota to Charleston
483 miles
9h 34m
32 stops
Outdoor ActivitiesToursNature & ParksShoppingFun & Games
Sarasota to Cape Coral
79 miles
1h 38m
14 stops
Nature & ParksToursNightlifeOutdoor ActivitiesSpas & Wellness
EXPLORE OTHER
Check Out Different Road Trip Options
Little Rock to Spokane
1,986 miles
34h 25m
21 stops
Fun & GamesTraveler ResourcesNightlifeConcerts & ShowsShopping
Omaha to Wilmington
1,357 miles
25h 33m
29 stops
Boat Tours & Water SportsToursFun & GamesShoppingOutdoor Activities
Santa Ana to Manchester
3,034 miles
54h 27m
55 stops
Outdoor ActivitiesMuseumsTraveler ResourcesNature & ParksConcerts & Shows
Portland to Lakeland
3,048 miles
53h 51m
44 stops
Nature & ParksSights & LandmarksWater & Amusement ParksOutdoor ActivitiesFun & Games
Champaign to Peoria
95 miles
1h 51m
27 stops
MuseumsSights & LandmarksNature & ParksOutdoor ActivitiesFun & Games
Fayetteville to Arlington
353 miles
6h 39m
11 stops
Sights & LandmarksSpas & WellnessShoppingNature & ParksFun & Games
FAQ
Frequently Asked Questions
What's the driving distance between Sarasota and Chesapeake?
The distance is 860 miles
What's the travel time between Sarasota and Chesapeake?
The driving time can vary depending on traffic conditions, but it is typically 16h 21m mins in normal traffic
What are some of the best cities to visit between Sarasota 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 Sarasota?
We have a lot of great trip options for Sarasota! See the links below for all the itineraries we created for you