Are you thinking about how to plan a road trip to Florida? It may take longer than flying, but there are a lot of advantages. It’s much easier to bring the family dog. You can bring your favorite pillow. You don’t have to deal with the hassles of the airport or cram everything into one bag. You can spend even more time with your friends and family. And you won’t have to rent a car when you get to your final destination.

Are you thinking about planning a road trip to Florida? Our road trip planner should help you get the most out of your Southwest Florida vacation. We’ll give you some tips, tell you about fun places to stop on the way to Florida and help you plan a Florida Gulf Coast road trip itinerary and the vacation of a lifetime. 

People have been driving to Florida and Sanibel and Captiva Islands for vacations and road trips for decades. Families often travel to the same place each year, which makes it even more special. Family road trips were a tradition many looked forward to before air travel became the standard. It meant summer (or spring or winter) vacation was coming and you were headed for somewhere warm and relaxing. This road trip planner should help you get the most out of your Southwest Florida vacation. We’ll give you some tips, tell you about fun places to stop on the way to Florida and help you plan a Florida Gulf Coast road trip itinerary and the vacation of a lifetime. The islands are waiting for you. The first step is getting there!

Driving Vs. Flying to Florida

Driving Vs. Flying to Florida

If you’re asking yourself ‘Should I drive or fly to Florida?’ we can tell you that there are many perks to driving to Florida for your vacation vs. flying.

It depends on where you’re coming from, but driving to Florida is normally less expensive. For example, if you’re wondering about the cost of driving from New Jersey to Florida, says that at current gas prices a round trip will cost about $167. That’s far less than a round trip plane ticket! It will also give you more money to spend on things to do. Having your own vehicle will give you the option to explore the surrounding area and nearby towns. Discover downtown Naples or get on Island Time and visit Sanibel and Captiva Islands. The choice is yours!

Driving vs. flying to Florida is also better if you’re traveling with young kids or older friends and family members. Driving gives you more freedom to attend to your baby or toddler’s needs and more freedom to do things like stop and change diapers. You also won’t have to worry about them bothering anyone else. Flying on a plane and dealing with the demands of getting through the airport can sometimes be too overwhelming for older adults. If this sounds like you or someone you know, driving to Florida may be the most comfortable option.

Driving to Florida for your vacation is also ideal if you’re going to be staying for longer than a week. While some of our vacation destinations, like Captiva Island, are walkable, you’ll be glad to have the freedom of having your own vehicle. You also won’t have to pay the airport to house your car in a lot or parking garage, rely on someone to drop you off and pick you up, and you can use those fees and the ones you’d accrue from renting a car on a fun outing for you and your loved ones instead. How about a dolphin sightseeing cruise on Sanibel Island?

Driving Vs. Flying to Florida

Driving to Florida

Another reason to drive to Florida for your next Sanibel or Captiva Island vacation is that there are a lot of really interesting and unique places to see on your way to Southwest Florida. Whether you’re traveling via U.S. 41, I-75 or you’re taking road roads; it takes at least six hours to get to Southwest Florida from the Sunshine State’s border.

Here are 5 places you don’t want to miss along the way:

  1. St. Augustine
  2. Legoland (for the kids)
  3. Dali Museum featuring works of Salvador Dali
  4. Cape Canaveral
  5. Ocala National Forest

St. Augustine

This is the oldest city in the U.S. It’s near the Florida-Georgia border and Jacksonville. It’s easiest to get here if you’re using I-95, an interstate that runs along the country’s East Coast. St. Augustine is dotted with Spanish colonial architecture and it’s known for its lighthouse and Fountain of Youth attractions. It feels like you’ve stepped back in time, especially when you’re in the historic district. It’s a magical place.


This is an interactive theme park near Orlando. It has more than 50 rides, attractions and shows. It’s dedicated to all things Legos. The kids love it and the adults will secretly love it, too.

Dali Museum

Step into the wonderfully weird world of artist Salvador Dali. The museum is a beautiful waterfront building in the heart of St. Petersburg and features over 2,400 works from Dali.

Cape Canaveral

This is the hub of the Kennedy Space Center. You’ll find it halfway between Miami and Jacksonville. Learn about the history of space exploration and the Race to the Moon.

Ocala National Forest

This beautiful national landmark is located north of Orlando. It’s the southernmost forest in the U.S. and it features the globe’s biggest contiguous sand pine scrub forest. There are also more than 600 rivers, lakes and springs. While you’re in town, consider enjoying a meal at one of Ocala’s best restaurants. We offer vacation rentals in Ocala, too!

Stay in a Luxury Vacation Rental

Stay in a Luxury Vacation Rental

Now that you’ve decided to drive to Florida and you know how to plan a road trip to Florida, we can help you find the perfect luxury vacation rental. Wake up with picture-perfect views of the sunrise and watch the sunset over the Gulf of Mexico. Walk to the beach and enjoy endless days of relaxation. Staying in one of our beachfront vacation rentals is the best way to end a road trip to Florida.

If a Southwest Florida vacation sounds like what you need in your life, any of our Vacation Planning Advisers can help you plan the trip of a lifetime. We have vacation rentals in all eight areas of Southwest Florida, including popular Sanibel and Captiva Island destinations. Feel free to browse our vacation rentals if you already have a place in mind you’d like to stay. If you’re not sure, we can help narrow it down for you.

Helping our guests plan the trip of a lifetime is what we do best!