'Real' Florida - Two Week Itinerary
'Real' Florida - Two Week Itinerary

'Real' Florida - Two Week Itinerary

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For most people, a trip to Florida = Disney World. But those people who spend their whole vacation battling the crowds and traffic in Orlando are missing out on the beauty and cultural experiences that the rest of the state has to offer. While you can definitely modify this itinerary to include a few days in the theme parks, this 2 week trip has been designed to hit all the highlights of 'real' Florida that the locals love. 

The best time of year to visit Florida is spring when it is hot and dry. Hurricane season runs from June 1st to November 30th during which time it is typical to get daily afternoon thunderstorms. This makes it difficult to make any plans ahead of time because you can't be sure when the rain will hit. Winter is a decent time of year to go but it might be a little too chilly to enjoy the beaches.

The public transportation system in Florida is not very good so this trip will require you to rent a car at the airport. 

Itinerary Overview

  • 696.2 mi
  • 12.8 h

Day 1: Fly into Jacksonville or Orlando

The closest airport to the first stop on the list is Jacksonville but the flights into this airport are limited. Orlando will have more options but it will require a little more driving. When you pick up your rental car at the airport, make sure to ask how they want you to pay for tolls roads. There are several toll roads in the state that no longer have booths. Tolls are paid with an e-pass or with toll-by-plate. 

Head to St. Augustine, the oldest city in the US, where you will spend two nights. This historic town has a number of quaint inns in addition to the usual chains. 

Day 2: St. Augustine

Spend the day exploring the colonial history of St. Augustine. Some things you can do are:

  • Walk St. George Street
  • Visit Castillo de San Marcos National Monument
  • Visit the St Augustine Lighthouse
  • Take a ghost tour

Make sure you protect yourself with sunscreen and drink lots of water. Florida is hot! On the day that we went to Castillo de San Marcos the national park service had put a sign up to warn us that the heat index was "Extreme Danger".

Stay another night in the city.

St. Augustine Lighthouse
St. Augustine Lighthouse
Castillo de San Marcos Heat Index

Day 3: Daytona

Drive south towards Daytona. If you happen to be in town when there is a NASCAR race, I highly recommend going for the experience. I especially recommend it for those who are not familiar with the sport at all. I don’t follow NASCAR and had never watched it on TV, but I found whole event so exciting in person. If there isn't a race going on, you could still go to the track and do the Richard Petty racing experience.

If none of that sounds appealing, there are some great spots to try surfing along the east coast, including Ponce Inlet, New Symrna Beach, and Cocoa Beach. The water on the Atlantic coast is rougher and colder compared to the Gulf of Mexico. If history is more your thing, check out Ponce de Leon Inlet Lighthouse. 

Stay the night close to Titusville or Cocoa.

Day 4: Kennedy Space Center

Spend most of today nerding out at Kennedy Space Center. Then in the late afternoon, get on the road and head west across the state towards Weeki Wachee where you will be going tomorrow. Stay the night close to Weeki Wachee Springs State Park, maybe in Brooksville or Spring Hill.

Day 5: Weeki Wachee Springs State Park

Prepare for a busy and active day. You will spend the morning kayaking down the Weeki Wachee river and the afternoon at the waterpark in Weeki Wachee State Park.

Head out early to the kayak rentals at Weeki Wachee Springs State Park. You must make a reservation ahead of time and you must book through the state park. Other companies offer rentals but only the kayaks rented from the state park are allowed to launch from the park. You will have four hours to paddle down the river and at the bottom, a shuttle will take you back to the park. In the beginning the current is strong so save your energy and don't paddle too hard. The current will get weaker as you go and it will be a lot more work at the end. Keep an eye out for manatees, which won't be difficult in the crystal clear spring water.

After getting the shuttle back, head inside the park itself where you will find Buccaneer Bay waterpark, the mermaid show, and a boat ride. The last mermaid show is at 3pm and the boat ride ends at 2pm, so make sure you start kayaking early enough to fit everything in.

You can either drive south and stay the night and your next stop or head back to the same hotel as last night.

Kayak Weeki Wachee Springs State Park
Manatee Weeki Wachee Springs State Park

Days 6-7: St. Petersburg

St. Petersburg is on the southern end of the Pinellas peninsula. On the west side are the beaches and on the east side is downtown. So for the next two nights you have the option of staying on the beach, where you will get beautiful views of the sunset, or in downtown, where you will have easy access to great restaurants and bars.

Wherever you decide to stay, spend at least one day relaxing on the beach. With it's powder white sand and warm water, St. Pete beach is frequently voted among the best in the world. On the other day, check out some of the museums in downtown St Petersburg, including the Salvador Dalí Museum and the Chihuly Collection.

The Tampa Bay area is an upcoming foodie destination so you will be spoiled for choice when it comes to dining. Restaurant hotspots include downtown St. Pete, Soho (S. Howard Ave.) in South Tampa, Armature Works in Downtown Tampa, and Ybor City. I suggest you dine out one night in downtown St Pete and one night in Ybor City.

Recommendation # 1: Annata Wine Bar in downtown St Pete

This restaurant and bar is one of my favorites for its amazing charcuterie boards and large wine selection.

Recommendation #2: Columbia Restaurant in Ybor City

You might have seen the Columbia Restaurant in St. Augustine but the Tampa location is the original. This is the place to go for an introduction to Tampa's Cuban culture. After dinner, walk down 7th Avenue and try out one of the cigar bars. From there you can head back to your hotel or keep the night going at one of the nightclubs.

Days 8-9: Sanibel Island

In the morning drive south through Sarasota and Fort Myers to Sanibel Island where you will spend two nights. The highlight here is of course the beaches. Spend the days relaxing on the sand, collecting shells, and cooling down in the water.  Other activities to consider include driving Wildlife Dr. in J. N. Ding Darling Wildlife Refuge, visiting the Clinic for the Rehabilitation of Wildlife Education Center, paddle boarding, or renting a boat. 

Day 10: The Everglades

There are two options to get from Sanibel Island to Miami: route 41 or I-75. I-75 is faster, but route 41 is much more scenic and will give you the opportunity to spend some time in exploring the Florida Everglades. There are two visitor centers that are easily accessible for a day trip: Gulf Coast in Everglades City or Shark Valley on route 41, closer to Miami. Near both visitors centers there are several companies that offer airboat tours into the Everglades. These tours are super fun, and I highly recommend taking one! 

Continue driving and spend the night in Miami.

Observation Tower Everglades City
Mangroves Airboat Tour Everglades City

Days 11-14: Miami

Finish up your road trip in Miami. There are endless things to do, but some places you might want to consider are:

  • Vizcaya Museum and Gardens
  • Bayside Marketplace
  • Wynwood Walls street graffiti
  • Little Havana
  • Frost Museum of Science
  • Miami Beach

Fly home from Miami International Airport.

Have some more time or don't want to spend so long in Miami? Consider taking route 1 the whole way to Key West, the southern most point in the continental US. If you are feeling adventurous, from here you can find tours to the historic Dry Tortugas National Park. 

About the Author

Author Photo

Lauren K.

Lauren works a regular 9-5 day job, but traveling and sharing her experiences is her passion. She prefers nature to the cities and her favorite vacations are ones that involve hiking in the mountains.



  • supal

    this is so good! I grew up in Florida and need to do most of these places! You got all the right bits!

  • Melissa

    Great post! I love how you give great suggestions for seeing the whole state!

  • Lekha Chellani

    Loved this blog. I like visiting Florida but so far have only explored Miami and Key West. Looking forward to St Augustine & Daytona on my next trip.

  • Chelsea

    This is amazing yet makes me kind of sad as we had a trip to Florida booked but had to cancel based on current events!

    In saying that, I will definitely use this list when we reschedule!

    I love that you fully advocate for going to quieter places that aren’t necessarily huge tourist spots.

    We are for sure going to Jacksonville, Daytona and Miami and will use this list to figure out the rest! I think I want to squeeze in the Everglades too!


  • Sarah Barthet

    This is so helpful! I’ve actually never thought to visit Florida because all I read about is Disney (which isn’t my thing) so it’s nice to get a fresh perspective!

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