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Every once in a while, I get some crazy idea that actually comes to fruition. I mean I always have crazy ideas floating around in my head, but sometimes they actually turn into a fun adventure! Like when I decided we do that New York to Florida drive. And back of course!
Because, why not? Right.
No seriously, this trip was super fun and an awesome adventure! And we saved a ton of money by driving. I know many families do this road trip – from New York or the Northeast down to Disney, Universal Orlando or other parts of Florida. So, I am so excited to share my guide to help you plan your New York to Florida drive!
Best Tips for Your New York to Florida Drive
JUNE 2020 UPDATE: Considering driving from New York (or the tri-state area) to Florida in the time of COVID-19? We just did it – and here is my post all about road tripping during the coronavirus pandemic, and what crossing into Florida looked like (spoiler – there was no checkpoint looking for random NY’ers on our drive down).
Why do the New York to Florida Drive?
Driving to Florida is long. From our house on Long Island, to my parent’s condo in North Naples, it is exactly 1,285 miles. Google maps predicts around 20 hours if you drive straight through.
Of course you could totally take your time! A 21-day road trip from New York to Orlando sounds divine!
I have done this drive two other times, in my pre-kid days. This winter’s voyage was the first time we did the drive as a family and the longest road trip my kids (age 6 & 9) have been on. In the end it was so worth it as we arrived in our favorite spot in Florida – Naples has the best beaches, great outdoor dining and so many unique things to do.
I will start by saying, we did have a great time. The kids were super well behaved on the drive and it honestly went better than I expected. I should also preface this article by saying I love to drive. I am fairly convinced I missed my calling as a long-haul truck driver. And I am the only driver in my family.
Yes, the entire 2,600-mile round trip drive was done completely by me.
Which I probably wouldn’t have any other way. Hubby does not drive, and he only rode with us on the way down. Because he had to return to work, he flew back home from Ft. Myers, and we stayed another week in Florida and then four days in North Carolina.
Now I do love driving, but this trip, especially with one driver, takes time. Let’s be honest, you can fly from New York to Florida in under three hours! So, driving down is not something I plan on doing every time we head south. But for this particular trip, driving made a lot of sense.
CHECK OUT MY BEST TIPS FOR SURVIVING LONG HAUL FLIGHTS
My kids had off from school for President’s week, which most schools in the Northeast do. We always use this February break to head to Naples, to get some sun and visit my parents. We stay with them so we don’t have to worry about expensive, peak season accommodations.
Unfortunately, since all the schools in the area are off during this holiday week, the airlines JACK up the prices to fly out of the New York area! It’s really criminal what they charge to get away during the school break.
To travel from New York to Florida, and not have kids miss school, you are looking at airfare of $600-$800 a ticket. It’s really insane.
Plus, a rental car since my parent’s sedan does not fit 6 people!
On top of all that, we had a family reunion in North Carolina the weekend after the break. For this trip, it made sense to do the New York to Florida drive – allowing us to stay in Florida for a week, with a four day stop in North Carolina on the way home.
NY To Florida Drive: Itinerary
Planning your perfect New York to Florida road trip takes some planning. I did some initial research and put some thought into how the drive was going to go. Since I have done both this drive before, and have road-tripped from New York to North Carolina with small children, I knew I did not want to over plan. I knew it would be best to be flexible depending on how things were going and how I was feeling.
The plan was to leave New York after school on Friday, the last day before vacation and arrive in Orlando by Saturday night. That would allow us to visit with my cousin for two whole days. There is so much to do in Orlando and we could spend time with her elementary age kids that Sunday and holiday Monday – since they did not have the whole week off.
The plan was to then head to Naples on Tuesday morning, with a stop for the day at Siesta Key beach. We would then have a week to spend in Southwest Florida.
Driving to Florida from NY
Long Island to Petersburg, VA (386 miles)
I am such a careful planner. I think and overthink many aspects of a trip – and this was no exception! I’m usually great at thinking through all the angles, BUT one big mistake I made was waiting until 3pm on a Friday afternoon to the hit the road. Let me re-phrase that – leaving at 3PM ON A FRIDAY – BEFORE A LONG WEEKEND – WHEN ITS RAINING.
In retrospect, I should have pulled the kids out of school an hour earlier, but since they were missing so many days for this two-week trip I waited until afterschool to leave. Once we hit the highway all ready to go, we sat in bumper to bumper traffic for two hours.
Which really put us behind where I thought we would stop for the night.
So, my first tip is – don’t leave the New York City area during rush hour. Especially on a Friday!
But luckily, after that first two hours (where we drove about 30 miles) the rest of the trip – literally, was traffic free!
The plan for the first night was to drive as far as possible, with a target stopping time of around midnight. We told the kids that dinner would be at a rest-stop and quicker than other meals on the road.
NOTE: We had a cooler with drinks and snacks, but we stopped for meals. With only one driver, it would have been too much to try to eat meals in the car.
That night, we stopped for dinner at the Chesapeake House in Maryland. The stretch of I-95 between Staten Island and Washington, DC is littered with rest areas. These are super convenient for gas, food, snacks and restrooms. Not always the healthiest food choices (fast food, food court set up) they do make for an easy road-side stop.
At the Chesapeake house, baby girl and hubby had Wendy’s and little man and I opted for Pizza Hut. Clean restrooms, a variety of food choices and one gas fill-up later, we were then on our way to drive as far as possible before stopping for the night.
The plan was to drive for 7-8 hours, building in a 1-2 hour buffer for dinner and traffic, making midnight a realistic stopping time. However, I did not want to pre-book a hotel because I wanted the flexibility to stop if I was tired, or keep going if we were making good time.
We do both Marriott and Hilton points, so we wanted to stop at either a Residence Inn Marriott or at a Hampton Inn. I wanted the hotel we stopped at to provide a complimentary breakfast so would not have to drive around looking for food in the morning. So before leaving home, I went on google maps and mapped out hotels South of Richmond, VA. I noted the names, addresses, and phone numbers of hotels on a 200-mile stretch of I-95. In this region they were all Hampton Inn’s which is part of the Hilton Honors rewards network.
I had hoped to make it to Roanoke Rapids, NC but with the delays due to traffic we only made it to Petersburg, Virginia.
If you have ever driven down I-95 on the east coast, there are blue signs at every exit noting what gas stations, food options and hotel accommodations are available. A few years back, we were driving from Sesame Place in Pennsylvania to Raleigh, North Carolina and were prepared to stop for the night just south of Washington, DC. We saw a sign for a hotel and pulled off the highway. It was full (it was the summer and around midnight). We then pulled into another hotel and they did not have any more cribs available! So, on we pressed, now tired and annoyed until we found a hotel at the next exit – which if I remember, was like 10 more miles down the highway!
Lesson learned, and this time, when we realized that Petersburg, Virginia was going to be our stopping point for the night, hubby used the notes I had gathered to call the hotel to confirm room availability and the rate for the night. That way, when we rolled up to the lobby, it was just shy of midnight, we were able to head right to our room!
ROAD TRIP PRO-TIP: If you are road tripping, and its late and call ahead to the hotel and ask the front desk to send someone to make-up the pull-out couch or to set up a pack and play (If you will be using one). We have done this before. Makes it much easier to transition a sleepy kid from the car, and into the hotel if there isn’t a pause to make up a bed!
PACKING PRO-TIP: If you are stopping for one night as part of a longer road trip, pack one bag for what you will need to bring into the hotel with you. For each family member, pack PJs, clothes for the next day, toiletries, phone chargers and medications. Don’t forget your nightlight and sound machine! For us, all this fit nicely in our Vera Bradley duffle. We also brought our computers, iPads and headphones into the hotel with us.
Petersburg, VA to Orlando, FL (735 miles)
The first night in the hotel I realized it was hard for me to go from being so alert and driving, to laying down and falling asleep. I had trouble settling in, so I did not get the best night of sleep. We had about 10 hours of driving ahead, so I tried to balance sleeping in and taking it easy in the morning, with having to get up and get rolling. I decided to have a long, hot shower followed by breakfast, by myself, in the hotel lobby.
We stayed at the Petersburg Hampton Inn where they offer complimentary breakfast. After eating, we packed up the car and hit the road. We left the hotel around 9:45am with the goal of not stopping until we hit the best of the tourist attractions on the drive from New York to Florida – South of the Border!
South of the Border is a fun I-95 roadside attraction located at the border of North Carolina and South Carolina. SOTB is a glorified rest stop with food, bathrooms, gas stations and little trinket stores. At SOTB you can also find a hotel, RV camping ground, an aquarium and mini-golf!
FUN FACT: This picture, which I use for my profile pic across my social media channels was taken at the Waffle House at South of the Border. My sister took this pic when we drove to Florida in January 2008.
As you drive south along I-95, for over 100 miles before you reach SOTB you will see the goofiest signs advertising the stop! Honestly, it’s a great place to stretch, use the facilities, and buy stuff you never knew you wanted!
Driving from New York to Florida where to stop is up to you, but SOTB is one not to miss. After heading south past SOTB, you hit a stretch of highway with not much. At this point in the day, we wanted to take a pause from the car and have a sit-down lunch. We stopped for about an hour at a Ruby Tuesday in South Carolina. This gave me a chance to re-caffeinate (yeah for unsweetened southern tea) and hit the salad bar for something healthy!
As you drive down this part of I-95 from Virginia to Florida, most of the “rest-stops” include just restrooms and vending machines. At each exit, you will see the blue signs advertising which gas/hotel/food options are available. After this trip, I was listening to this episode of the Vacation Mavens podcast where they talk about apps you can use to check out what is available at each exit! Wish I would have known about this sooner.
After lunch, we kept heading south through South Carolina and Georgia. We crossed the Florida State line as the sun was setting! It was so cool to see the temperature gauge in the car rise with each passing stretch of road!
We were super excited to have entered Florida, however, if you look at the map, Florida is a really long state! From the FL/GA line, it’s still 3 hours to Orlando! But of course, crossing into Florida felt like a big milestone!
We were poised to get to Orlando pretty late, so for dinner that night, we stopped at a Cracker Barrel in St. Augustine, Florida. We don’t have Cracker Barrel in New York so it’s such a road trip staple for us! And Cracker Barrel has something for everyone – you can get breakfast anytime and there is the fun store to shop in. A good incentive for the kids to behave in the restaurant and eat their meal – the promise of being able to pick out a candy in the Cracker Barrel store!
After dinner, we hit the road for the last stretch to Orlando. For this part of the ride, I recommend that you have some change or small bills with you. There are several tolls in the Orlando area – and unlike all the other tolls on the New York to Florida drive, these DO NOT TAKE EZ PASS (Just the Florida sunpass).
Last year, while driving from Naples to Orlando I got stuck without 75 cents in exact change at one of the unmanned toll booths! I had to take an envelope and send in a check for SEVENTY-FIVE cents to pay the fare!
Luckily all tolls were paid, and in the Daytona area, we left I-95 behind to cut across the state. After a long day of driving, we rolled into my cousin’s South Orlando condo at 11pm!
Orlando, FL to Naples, FL (189 miles)
Orlando was not our final destination in Florida. After two days of fun with family – lots of time by the pool and a trip to Wild Florida, we had three more hours to drive to our final destination of North Naples.
We had originally planned to leave Orlando on a Tuesday morning, stopping for the day at Siesta Key – a place I have been desperately wanting to visit! However, on Monday little man came down with that awful stomach bug that had been going around this winter. He missed Wild Florida and once he got back up and running, we decided to spend that day in Orlando instead of at the beach.
That night, we felt okay with taking him in the car for the ride. I think he ended up sleeping most of the way.
I’ve done the Orlando-Naples drive MANY times, and google maps usually recommends you go down Route 17 instead of on the interstate. I have to say, for the few extra miles you will drive, I highly recommend taking I-75 – especially if you are driving at night. Last year I drove those backroads after a long day at LEGOLAND Florida – and it was a little unnerving to be in the middle of nowhere. Also, the restrooms, gas and restaurants were few and far between if you take Route 17.
The drive from Orlando to Naples was pretty uneventful. We went at night and arrived in SW Florida around 10pm. The kids were excited to see their grandparents and even though I LOVE being on the road, it was nice to be able to stay in one place for week and unpack our car and bags.
As a family, the New York to Florida drive was a fun adventure. You should definitely check out my post about the best road-trip gear, but for most of the ride, the kids watched this DVD player with these headphones, while I listened to hours upon hours of podcasts! I was proud of myself for getting us all there and I was so proud of my little ones for mostly behaving on the ride and embracing the adventure! Sometimes the journey really is as fun as the destination!
Driving from NY to Florida is not something I want to do everyday, but we did save a ton of money by driving to Florida.
Click here to read more about Walt Disney World with a Baby
Heading to Florida – Then check out:
How to get a day pass to the Hyatt Regency Coconut Point
The Ultimate Guide to New Smyrna Beach
Getting Back Home: Driving from Florida to New York
Oh and in case you are wondering, we did a great job on the reverse – driving from Florida to New York! We left Naples early on a Thursday morning. But not too early. I knew it would be a long haul from to drive from Naples to North Carolina (12 hours), so we made a reservation to stay the night at a Hampton Inn in South Carolina.
The next day we had four hours left to go to Raleigh, North Carolina. We had a wonderful family reunion and then heading home in one shot on a Sunday morning. Of course we hit traffic when we arrived back in the New York City area, but that is to be expected!
Driving from New York to Florida in One Day
January 2020 UPDATE: Last January, my aunt and I drove from New York to Orlando in one day. We left Long Island at 4am and arrive at her condo in Southeast Orlando at 11:45PM. The trip total is 1,127 miles and google maps puts the travel time at 16 hours, 11 minutes.
Leaving Long Island at 4am was great in that we got out of the New York area way before any traffic began to build. But, when we hit the Baltimore/DC area, we did hit all their rush hour traffic ( around 7:30AM). This was a weekday, and really unavoidable.
The MD/DC traffic was the only traffic we hit the entire way. The rest of the drive was smooth sailing, just long. We tried to minimize the stops, but we were driving in a small Jeep SUV with a 12-gallon gas tank, so we stopped for gas way more than I would have though.
Otherwise, we took about a 45 minute Cracker Barrel lunch break in southern North Carolina, with the rest of the food and snack stops being just fast food. We did have two drivers, and no kids with us, so most of the drive was pretty painless.
The worst part was the last three hours. After a long day of driving, we crossed into Florida around 8PM. I was so excited – we were finally in FLORIDA! But… if you are heading to Orlando, its still another THREE HOURS to Orlando! This was a mental drain after a long day, but we made it to Orlando safe and sound right before midnight!
Have you done the road trip from NY to Florida? Another long road trip? Leave me a comment and tell me your best tips for driving to Florida!
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I love road trips! I always say I am going to go to Florida before my husband but then I get nervous to drive by myself the entire way. I think I could do it now that I read this!
honestly, the kids were almost better with one driver – they know mom is driving and they really can’t be asking for stuff every 5 minutes.
Sounds like a successful road trip… once you got past that initial rush hour traffic anyways! And to do ALL of the driving yourself? I am super impressed! I learned a ton from your Pro Tips. I never would have thought to call ahead to a hotel and ask them to make up the extra bed or set up a pack-and-play.
yes, I love to drive!!!!
I love that you posted this! We are actually going to try a FL to NY road trip soon!
We leave Saturday for a Georgia to Maine road trip! While not exactly the same route, much of it will be the same. We’re taking two weeks, so I’m excited about what we’re going to have time to see 🙂
that is awesome! How long is that ride?
I lived in Upstate Ny and used to do that trip about three times a year. However, now that we are emptynesters we fly all the time. These bones can’t take it like they used to. The best times of our lives was when we would travel together. Great conversations, but that was also before cell phones to. We always loved SOTB too! Time goes by so fast enjoy all the memories you can make!
Road Trips can be great fun – or not, depending on how well you plan. I love that you have got some really practical tips and tricks to make the trip easy and manageable. You are a machine driving that distance!
Wow, you are a super mom! I do not think I could do that long of a drive with children. We just did a 13-hour drive to North Carolina from Michigan. That was plenty enough for me and I did not have children, just my husband. I am so glad you survived 🙂 with a safe and happy trip!
Wow, you drove 2600 miles!!!! Amazing. I can never do that you are superwoman. None the less I love to go for long distance travel by road. I liked some of your tips like calling the hotel in advance.
I have done quite a lot of road trips, but usually leave in time to stop along the way for sights and experiences. One thing is certain though, it always takes longer than planned, haha!
yeah this wasn’t really that type of trip Since it was February, I wanted to get down to Florida as quick as possible!
Sometimes making the drive just makes much more sense. We did the drive to Florida when I lived in North Carolina when we went to Disney. So much better of an experience!
yeah from NC its not that bad!
Wow, that’s awesome that you did all the driving! I would definitely get irritated and need to swap after a while haha! But seriously, this sounds like a really fun road trip. I always read about Route 66 or a trip up the West coast so this makes for a nice change 🙂
We used to do a similar drive from Michigan to Florida almost every year. My mom doesn’t like long-distance drives, so my dad would do almost the whole 20 hours behind the wheel. And we drove straight through only stopping to use the bathroom and eat! I don’t know how he managed.
I could not do that. I know I would get tired. And/or the first few day of vacation I’d be shot. Plus by driving you save so much money over flying (4 people + a rental car) so I think one night in a not-so-expensive hotel you still come out ahead.
Oh, my goodness. This is a drive that I don’t know if I’m up for. How awesome for you all!!
That is a long trip! Well done! I really like the pack and go idea. We’ve recently adopted this idea and it has helped so much. Why bring every single item AND sleepy kids into a hotel when we really only need pajamas and our toiletries?
I know, I don’t LOVE leaving a ton of stuff in the car – but we take in valuables, but I try to park in a well-lit part of the parking lot etc.
Long drives are always fun! Loved reading your travelogue.
Wow, that’s one long road trip from NY to Florida but you made it look quite effortless! Well done!
What a well organized trip you did! This is awesome. That would be a super fun road trip to take, lots of great stops, and nice work with planning for the kiddos. That’s always my ammo….key stops and plenty of healthyish snacks!
South of the Border is so much fun! Definitely, a must stop! Your tip on packing fruit is perfect. Great way to make sure you are getting fruit which can be tough when in a time crunch and wanting to make it to a destination by a certain time.
Podcasts are a road trip must!!!! Sounds like you all had a ton of fun. I’m about to head out for my summer adventures, and this time I’m packing grapes because they look delicious in your photo.
I cant stand tolls!!!I avoid them like the plague, but a pitstop to any car dealer gets you a free toll pass for future reference.
Sounds like a beautiful drive! I’ve done the drive from Ohio to Florida before. But Virginia, the Carolinas, Georgia? Beautiful states!
They are – I kinda wish I spent more time in SC – like savannah or Charleston, but I was worried about the weather being iffy and we wanted to get right to the warm, Florida weather.
Sometimes the trip driving is so much more fun than flying! Your trip sounds just like that! I bet the kids enjoyed it too ✌️
We are heading to Disney in about two weeks, and after reading this, I’m ready to pack up my van! We’ve never flown to Disney. In fact, my eight-year-old has never flown. What can I say; we’re road trip kind of people. I look forward to all the unique things along the journey.
My husband does 99% of the driving because he likes to. We try to stop for the night in time for a sit-down dinner and a hotel swim for the kid. We also like chain hotels with decent breakfasts like Hampton Inns. Holiday Inn Express is another favorite.
It’s cool that you stopped at Cracker Barrel. That is usually our first lunch stop on any road trip. We love stretching our legs while looking around. We’ve also thrown in stops at Walmart or Target just for a break.
This is a great post! I’m even more excited to get going now!
Have a great trip!!!!!!!
We’ve had to mail in a check at a toll road before! Since then I carry rolls of coins!! We are headed out this weekend for a long road trip. I should check out that app for the Exits!!
I know! I wish I had know – we just went off the blue signs. Along I-95 MOST exits have amenities.
This sounds so fun. It made me think back to the road trips we took as kids. At the time, the drive seemed awful, but in retrospect, we created such great memories!
This is so detailed, I love it! And oh my how the mini bag of immediate necessities has saved me before – there’s nothing worse than arriving tired and realising everything you need is buried under everything else 😂
All great info – thanks for sharing! I’m from Long Island, too, and currently live in MD, so I do that drive frequently and I totally feel your pain about all that NY traffic!
oh wow! yeah the NY -> DC part of the trip is the worst!
Oh my, you are brave! To drive all this without a co-pilot to switch if needed… You go girl!
This sounds like a very nice road trip though. Too bad I only visit the States for a week or so and can’t really enjoy much road tripping around the country, as flying most of the times is such a time-saver
I’d say you might be crazy, but maybe more like a crazy genius! It’s a beautiful lesson to teach your kids that the journey is part of the adventure!!
I don’t know how you managed…the four hour drive from Charleston to my hometown is too much for me. But a serious road trip is on my travel list.
I am impressed with all that driving! I love doing road trips. Since I am American and my husband is British, I drive when we are in places where they drive on the right and he drives when we go to places they drive on the left. We usually try to do a maximum of 6 hours driving per day. We know we can do that so we can feel comfortable booking a place to stay in advance. I would be nervous that knowing my luck nothing would be available.
My husband and I have been dreaming of a road trip in the Us for a while now. And yeah, we would start it in New York and go South to Florida. Saving this post!
I love road trips and would love to see Florida and NYC – thanks for the helpful guide 🙂
How I miss road trips after growing up taking them. My parents were meanderers. If something caught their attention it was pull over and everyone out. Your details make me want to tackle this drive but I’m a west coast gal. It sounds like getting out of the metro NY area is as harrowing as getting through Los Angeles too.
yes! we did San Fran to anaheim last year and yes, LA traffic was BAD!
Makes me want to go on a road trip!
Now that we live up here, we may have to drive down to FL to visit family instead of flying… You broke the drive up pretty well.
its long, but the price is right!
We have driven from Canada to Florida a few times and many think we are crazy, but we love it. Wow for you doing all the driving yourself! We split in and it can still be tough. Great post!
Really useful, given that we do about half of this drive but use a similar route for family holidays.
But my favorite part? “This picture, which I use for my profile pic across my social media channels was taken at the Waffle House at South of the Border.” Epic!
I am literally LOL = yes, I love this pic. it was a special trip with my sister. Thanks for checking out my post!
How funny that I came across your story. I too, am from the Long Island area and am planning on driving down with my two kids (aged 12 and 9) during President’s Day week. My husband is unable to get out of work, but I too love to drive and love long road trips, so I thought this would be a great little adventure for us.
do it! It will be great! Such an adventure! And such a money saver for sure!
Thanks for sharing. nice road trip really inspired me.
Hi, what is the best route to take from Long Island to Orlando, but avoiding Washington completely? Thanks!
hmmm – could take 495 AROUND DC – we have done this also. Lately the GPS has been taking me through DC on Baltimore Wash Parkway to 395 – def traffic if you hit it at the wrong time as we have when going to NC last month. Otherwise, going to the west maybe smaller roads, but it looks like staying on the highway you would be very out of the way ( would probably off-set the time you would save by avoiding traffic!)
Wonderful tips. I will be taking many of your suggestions for our future Disney trip from Carmel, NY!
FYI: There is a Cracker Barrel in Fishkill, NY, a few minutes from our home in Carmel. For perspective, Carmel is only about 1 hour from the Bronx and 1.15 hours from Manhattan. We are a lake town filled with city commuters! So if you ever want to come to Splashdown beach Water Park in Fishkill (instead of Slplish Splash in Long Islsnd), you can have dinner at Cracker Barrel! 🙂
okay this is crazy because I was just talking about wanting to come down to splash down one day this summer! Yay for cracker barrel!
Thanks for these helpful tips! Road is an art form, a challenge, and adventure!Promising tips! I must try. I purposely under pack.
Thanx for share such informative article, It’s really awesome.
Thanks planning a nearly identical trip with two kids this February. Will pull them out of school early Friday before Presidents Day after reading this!
Please reach out if you have any questions. We are looking at plane tickets and its ugly out there – good luck!
Your article was so helpful! We are contemplating a trip from Long Island to see family in Fort Lauderdale. Love the rest stop, hotel, and restaurant suggestions!
oh thank you! Good luck! I just did this trip again early Jan 2020, I need to update my article!
The blog is really well written with all information given in great detail.This article will be really helpful for all who want to explore new places in US via road.Thanks for sharing this!
I stumbled across this blog while looking up information for our road trip (NYC to Orlando). With 3 adults (2 drivers) and 4 children, i’m looking to be practical as possible.
four kids is tough but with two drivers, should be great!
I am about to take this trip with my 4 year old niece and a 2 year old labradoodle. Pray for me.
no worries! You got this!!!!!