Orange and white vintage car parked infront of hotel with palm trees and orange umbrellas

Florida Road Trip Itinerary – 2 Weeks in the Sunshine State

by Madam ZoZo

See the best America’s Sunshine State has to offer in 2-weeks with this Florida road trip itinerary. James and I tested this route over the winter period to escape our first Midwest freeze. It is a medium-paced itinerary taking in Florida’s most famous and lesser-known attractions, compiled from a lot of research and recommendations.

Disclosure: I may earn compensation from the purchase of any product or service linked on this website, at no extra cost to you. I only link to products I use and love, therefore feel comfortable recommending.

Day 1

Fly to Florida, pick up your hire car and drive west to Crystal River. We suggest flying to Orlando as the most central location to the beginning and endpoints.

If you arrive in Crystal River with time to explore, you might like to wander through the Crystal River Archaeological State Park. The Park encompasses 61-acres including remnants of pre-Columbian Native American inhabitance.

NOTE: If you’re not travelling during peak Manatee season (late-Spring and Winter), you may choose to stay in Orlando and visit one of the many theme parks and/or skip right to Day 3. If you’re visiting during peak vacation periods, make sure you pre-purchase your tickets to the most popular park – such as Walt Disney World’s Magic Kingdom – which are known to sell out.

Driving distance: 97mi (157km)

Day 2

For your best chance at swimming with the Manatees, it’s generally recommended to book an early morning tour. The warm-blooded mammals spend winters in the natural spring systems, like those around Crystal River, where temperatures stay a consistent 72°F (approx 22°C). Don’t be fooled, 72°F is still chilly and you are going to need that wetsuit most tour companies offer. Also, manatees are a threatened species, therefore please heed the video all tour operators are required by State to show at the start of your excursion. Touching the animals is forbidden, but you can take plenty of pictures – so pack your waterproof camera. After your swim, take time for lunch in town before driving to St Petersburg (Tampa Bay).

Driving distance: 95 mi (153km)

Day 3

Spend your morning at the Salvador Dali Museum enjoying the work of both Dali himself and temporary exhibitions featuring other artists. You will need 2-3 hours to take in the unique building, garden and collection. Have lunch in St Petersburg before setting off to Everglades City.

Driving distance: 193mi (311km)

Crystal River viewed from the Crystal River Archaelogical Park
Manatee mother and calf swimming side by side
Swimming with manatees
The geodesic glass bubbles of the Salvador Dali Museum
The fun interactive garden at the Dali Museum

Day 4

Experience the tropical wetlands of the Everglades with a morning airboat ride. Drive eastward towards Florida City on the Tamiami Trail observing the varied landscape and abundant wildlife such as alligators and birds. Stop and stretch your legs along the way at the Shark Valley Visitor Centre, with a walk or cycle around the heart of the freshwater wetland.

Driving distance: 93mi (150km)

Day 5

Spend a day exploring the eastern side of the Everglades via the Royal Palms entrance to the National Park. The Visitors Center there can provide information on the various walks available and the current conditions of the trails. We visited during an extended wet season, and found many tracks were still closed due to flooding.

We also recommend a stop at Robert is Here, to cool off with one of their fresh fruit smoothies.

Driving distance: 26mi (42km) return from the centre of Florida City to Royal Palms Visitor Center. Local driving distance depends on accommodation location and chosen activities.

Day 6

Drive the full length of the Florida Keys to Key West, stopping at any points of interest along the way. Take the afternoon to wander around town, visit Hemingway’s Home, and take a photo at the southernmost point of continental U.S. (almost). Finish the day with dinner and drinks on Duval Street.

Driving distance: 126mi (202km)

Alligator sun baking in the mud, on the edge of the water
Wildlife spotting in the Everglades
Front of air boat passing between mangroves into a channel of water
Air boating in the Everglades
The Everglades' River of Grass
Hiking in the Everglades
Exterior front view of Hemingway's home in Key West with citrine shutters and arched windows
Hemingway's former home, Key West
Marker for the southernmost point in the continental USA (accessible by the public)

Day 7

Take a boat to the Dry Tortugas and spend a day languishing in your tropical surrounds and exploring by snorkel. You will need to book your ferry ticket well in advance or you risk missing out like we did :-(.

Day 8

Drive back north to Miami and get acquainted with the iconic South Beach by participating in an evening food and architecture tour on foot.

Driving distance: 164mi (265km)

Day 9

Dive deeper into South Beach’s art deco gems with an audio tour from the Miami Design Preservation League. Alternatively, relax on the beach and soak up some sun. Replenish with lunch, perhaps at one of the local cafes or restaurants introduced to you during the previous night’s tour. Spend the afternoon exploring “Little Havana” Calle Ocho or Biscayne Bay.

Driving distance: Local driving around greater Miami depends on the location of your accommodation.

Tropic Cinema, Key West, Florida, U.S.A.
Exterior of bar with large lettering reading "Sloppy Joe's Bar"
Sloppy Joe's - Hemingway's favourite Key West bar
White-washed art deco hotels with palm trees and a vintage car
Art deco dreams on South Beach
People queuing outside La Esquina De La Fama restaurant on corner in Calle Ocho
People queuing outside La Esquina De La Fama restaurant on Calle Ocho
Black and white lighthouse against blue sky
Cape Florida Lighthouse at Key Biscayne
Cuban men playing dominoes in Calle Ocho
Cubans playing dominoes in Maximo Gomez Park

Day 10

Before leaving Miami. spend the morning at Wynwood Walls taking in the work of talented street artists and muralists. Drive to Cape Canaveral, stopping in Vero Beach for lunch and maybe a swim.

Driving distance: 213mi (344km) Wynwood Walls to Cape Canaveral, using the scenic route from Vero Beach north.

Day 11

Enjoy a full day at NASA’s launch complex – Kennedy Space Center. This includes the astronaut hall of fame, Saturn V Rocket, launch pads, launch control and Space Shuttle Atlantis.

Driving distance: Local driving distance depends on accommodation location.

Day 12

Drive north to the Spanish colonial town of St Augustine. The nation’s oldest city was founded by Pedro Menendez in 1565, with remnants of its long history remaining preserved for education and enjoyment.

Driving distance: 126mi (42km)

Maya Hayuk piece at Wynwood Walls
Ben Eine's "Boring" at Wynwood Walls, Miami
Space Shuttle Atlantis on display at Kennedy Space Center
NASA at Cape Canaveral
NASA Vehicle Assembly Building

Day 13

Take a morning ferry to Fort Matanzas, which historically guarded the southern river access to St Augustine. The afternoon is best spent leisurely roaming the St Augustine historic district, including Castillo de San Marcos, the oldest masonry fortress in the U.S. St Augustine looks it’s most romantic in the evening when the colonial architecture is lit up like Christmas year round.

Driving distance: Local driving distance depends on accommodation location.

Day 14

Visit the Fountain of Youth Archaeological Park for a local history lesson and drink from the spring that provided early explorers mineral water refreshment.

Driving distance: Local driving distance depends on accommodation location.

Day 15

Return to Orlando or continue north to Jacksonville for your flight home.

Driving distance: 125mi (201km) to Orlando International Airport OR 51mi (82km) to Jacksonville International Airport

Castillo de San Marcos
Ponce de Leon's Fountain of Youth Archaeological Park
St Augustine historical reinactments

Florida road trip map

I hope you have a blissful 2-weeks in Florida with this road trip itinerary. If you have any feedback, questions or recommendations to share with us, please drop a comment below.

Peace, love and inspiring travel,

Madam ZoZo

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