Steal This Six-Day Florida Road Trip Itinerary For Your Next Vacation (Family-Friendly)

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Today I’m sharing a six day Florida Road Trip Itinerary with you that I hope you’ll steal for your next vacation! It was created specifically for families wanting to travel with their little ones by the Visit Florida team so you know it’s going to be good! We followed this same itinerary in May and had such an amazing trip!

We’re going to be exploring three different areas in Florida during this road trip so buckle up! Before we dive into the itinerary, let me share a little bit about each of the places we are going to explore.

St. Augustine

Florida’s Historic Coast, encompassing St. Augustine and Ponte Vedra Beach, holds the title of the oldest continuously occupied European settlement in the U.S., dating back to its founding by Spanish explorers in 1565. The area boasts a rich tapestry of cultural influences, including Native American, Greek, Minorcan, French, and British, which are evident in its diverse cuisine, unique architecture, vibrant shopping areas, and lively entertainment options. This destination is a paradise for food lovers, with a thriving dining scene that enhances its charming atmosphere. From arts and culture to nature, music, and entertainment, there’s always something exciting to explore and enjoy.


Kissimmee, Florida, is the perfect destination for your next getaway, offering a blend of exciting attractions, natural beauty, and vibrant local culture. Just minutes from world-famous theme parks like Walt Disney World and Universal Studios, Kissimmee also boasts stunning outdoor adventures, from airboat rides through the Everglades to hiking and zip-lining in lush landscapes. The area is rich in history and charm, with quaint downtown streets lined with unique shops and delicious dining options. Whether you’re looking for thrilling amusement park fun, serene nature experiences, or a bit of both, Kissimmee has something for everyone, making it an ideal spot for your next trip.

Central Florida

Central Florida’s Polk County is perfectly situated between Orlando and Tampa, making it an easy drive to top Central Florida attractions and the Gulf and Atlantic beaches. Polk County has something for everyone, from the newest attractions like LEGOLAND Florida Resort, Peppa Pig Theme Park Florida, and Florida Children’s Museum to historic sites like Bok Tower Gardens, Westgate River Ranch Resort (the Southeast’s largest dude ranch), and Frank Lloyd Wright’s 13 structures at Florida Southern College. With 554 freshwater lakes, you can enjoy great fishing, adventurous airboat eco tours, and exciting water sports. Plus, the area’s parks, preserves, and trails showcase Polk County’s natural beauty.

Day 1

Fly into the Orland Airport and pick up your rental car! You’ll then navigate north to St. Augustine! We recommend staying at The Local. The Local – St. Augustine is a 20 room digital hotel located in a prime location on Anastasia Island. Just a short walk to historic downtown. We really enjoyed the outdoor pool!

After getting settled in go grab dinner at Anastasia Kitchen  at Lighthouse Plaza. Then come back and enjoy the outdoor pool, lounging chairs, and some beverages on the deck! It’s the perfect time to help your little ones get out some wiggles before bedtime.

Day 2

Today is all about exploring St. Augustine! You’re going to start by getting tickets to the Old Town Trolley. I recommend parking at the Old Jail since there is free parking. The Trolley tour will take you to all the very best attractions in the downtown area. It is narrated and was very interesting to learn more about the history of this historic area. We stayed on the trolley for most of the way until we reached the Castillo de San Marcos. Built by the Spanish in St. Augustine to defend Florida and the Atlantic trade route, Castillo de San Marcos National Monument preserves the oldest masonry fortification in the continental United States and interprets more than 450 years of cultural intersections. 

After exploring, we walked across the street to the The Pirate & Treasure Museum. The St. Augustine Pirate & Treasure Museum offers an exciting and educational museum experience that transports you and your family back in time over 300 years to Port Royal, Jamaica, at the height of the Golden Age of Piracy. 

At this point, you’ve worked up an apeite so walk the three blocks to Meehan’s Irish Pub for lunch! They had great food and even offer a backyard for outdoor dining.

After lunch, get back on the Trolley at The Castillo de San Marcos. That is stop 17. You can then take the trolley back to the Old Jail, or if you have a little more time, you can get off at the Fountain of Youth Archeological Park and explore. This is where St. Augustine began. The location of the Timucuan Indian VIllage, Seloy, the FOY Park features multiple exhibits, demonstrations, interpretations, archeological finds, shows, reenactments, and activities can be found throughout the 15 beautiful acres.

For dinner that evening, definitely visit Salt Life Food Shack! It’s the perfect locale for beach goers to enjoy great dishes, cool drinks and the opportunity to catch up with family and friends.

Day 3

After an adventure packed day in St. Augustine yesterday, it’s time to pack up and leave to our next Florida destination our our road trip! But before you leave, make a quick stop the St. Augustine Alligator Farm where all 24 known species of crocodillia are one exhibit. Be sure to take the walk through the lagoon and spot hundreds of wading birds – an unforgettable site! They’ve even got a kids playground and sand pit on-site for little kids to enjoy!

It’s now time to say goodbye to St Augustine and start driving to Kissimmee, Florida! Travel south on A1A Scenic & Historic Coastal Byway. We recommend driving south to Palm Coast, then taking Palm Coast Parkway to I-95 south to I-4 and Kissimmee.

The next place you’ll be checking into is called Magic Village Views. This community is framed by contemporary architecture and lushly landscaped gardens and lawns, Magic Village Yards and Magic Village Views are concierge-style communities with upscale condos, exclusive services and unrivaled privacy and comfort that will turn your dream vacation into reality. We loved the outdoor pool and hot tub that was behind the clubhouse and having so much space in our condo was a dream when traveling with two kids!

After you’re drive, you may just want to spend some time enjoying the condo and the pool! But for dinner, you’re going to be stepping back in time to the 11th century and embarking on an unforgettable journey as you’ll be attending Medieval Times Dinner & Tournament that evening! You’ll get to dine on a four course dinner and watch two hours of entertainment like jousting, swordsmanship, hand-to-hand and combat! Note, if your little ones are sensitive to noise, you may want to bring headphones!

Day 4

After a good nights sleep at Magic Village Views, it’s time to head to Discovery Cove! Discovery Cove® is an all-inclusive day resort offering a unique experience where you can snorkel with thousands of tropical fish and rays, hand-feed exotic birds, and meet playful otters and curious marmosets. Relax and explore rocky lagoons surrounded by lush landscaping, tropical reefs, winding rivers, and white sandy beaches. Your visit includes prepared meals, snacks, beverages throughout the day, and all the swim gear you need! Pro-tip: Book yourself a day bed so you can have a little space to escape the sun or a nice place for your little ones to take an afternoon nap!

After spending all day swimming, you’ve for sure worked up an appetite so we recommend heading to Ford’s Garage at The Promenade at Sunset Walk. Ford’s Garage Kissimmee, situated at Promenade at Sunset Walk, is your go-to spot for burgers and beer. Everyone feels at home here, with its unique 1920s service station atmosphere that adds a nostalgic touch to your dining experience.

You’ll also find a mini train and an arcade at The Promenade at Sunset Walk both of which my kids really enjoyed!

Day 5

After an exciting previous day, take some time to enjoy your condo this morning! Since you have a kitchen, it might be nice to cook up breakfast at home before heading to our last destination during this Florida road trip!

The next destination that you’ll be enjoying as a family is Central Florida and your first stop is Bonnet Springs Park! Immerse yourself in the natural beauty of this 168-acre oasis perfect for family fun. This free park offers a variety of activities, and we suggest taking the tram to explore the entire area. Be sure to hop off and visit popular spots like the Crenshaw Canopy Walk. Don’t forget to grab lunch at The Depot Cafe.

Within the Bonnet Springs Park is the Florida’s Children’s Museum. We really liked the fact that they had both an outdoor and indoor area for the kids to enjoy. Note- your kids can get wet in the outdoor area so it might be a good idea to bring a change of clothes! I’d plan to spend at least an hour here since there are two floors with lots of different exhibits!

For dinner that evening, we have a couple of suggestions for you!

  • MOJO Federal Swine & Spirits (BBQ restaurant)
  • The Joinery (Trendy food hall with plenty of options for the whole family)
  • Tsunami Sushi & Hibachi (sushi and hibachi restaurant)

We personally visited the Joinery and had a fantastic meal that everyone enjoyed! Of course, grabbing ice cream before leaving.

Day 6

Today is your last day in Florida on our six day road trip and today you will be visiting Legoland! This was our very first experience at Legoland and we were blown away with our family-friendly it was! We now consider ourselves a Legoland family because of how amazing our first experience was. It’s designed especially for families with kids aged 2 to 12, although our one year old had fun too! Bursting with interactive rides, water attractions, and elaborate LEGO exhibits, it offers endless fun and creativity. Highlights include themed areas like LEGO NINJAGO World, Miniland USA, and the LEGOLAND Water Park. Our personal favorite area was the Legoland Movie World!

You’ll most likely spend the whole day here as there is so much to do (and eat!). That night, you’ll want to check-in to the Legoland Hotel! It’s right next to the park and SO COOL as it offers an immersive and playful experience for families. Designed with kids in mind, the hotel features themed rooms such as Pirate, Kingdom, Adventure, and LEGO Friends, each brimming with colorful LEGO decor and interactive features.

Guests can enjoy exclusive early access to the park, nightly entertainment, and a variety of kid-friendly amenities, including a heated pool, a disco elevator, and daily LEGO-building activities. The on-site restaurants serve delicious, family-friendly meals, making the LEGOLAND Hotel a perfect complement to your theme park adventure. We absoltley loved our stay here and definitely think it’s worth staying here!


That wraps up your six day road trip through Florida! You and your family got to see and experience St Augustine, Kissimmee, and Central Florida during your week vacation and hopefully made some beautiful memories along the way! I know myself and my family sure did while we did this same itinerary!

This article was sponsored by Visit Florida while all opinions remain our own.

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