Snowbirds head south in October and home in April. We’ll drive your car to Florida in the fall and back to New York in the spring. You fly down, you fly home, and the car is waiting in the driveway at both ends.
Call Cubs Drive Your Car to Florida at 917.756.1088 to get a quote before the season rush begins.
When to book your snowbird car transport
For an October or November pickup heading south, book by late August. For an April or May return heading north, book by early February. Earlier is always better, and there is no such thing as too early. We take bookings a year out.
Those two windows are when our calendar fills and we get busy.
This guide covers the full season month by month, what to expect on both legs of the trip, how delivery works inside a gated Florida community, and what to have ready when you call.
The snowbird booking calendar
| Your pickup window | Book by | How busy it gets |
|---|---|---|
| Late September to early October | Early August | Light. Widest choice of dates. |
| Mid-October to mid-November | Late August | Heaviest southbound stretch of the year |
| Thanksgiving week | Early October | Tight. Fewer working days. |
| December to January | Six weeks out | Moderate |
| February | Six weeks out | Light. Easiest window we have. |
| Mid-March to April | Early February | Heaviest northbound stretch |
| May | Late March | Moderate. Tail end of the return season. |
Book ahead of these dates and you pick your day. Book inside them and we work with what’s open.
Why the fall and spring windows fill first
Florida gains close to a million seasonal residents every winter. The University of Florida’s Bureau of Economic and Business Research has tracked this migration for decades, and the pattern has held: the state’s population climbs about 5 percent between October and April, then drops back.
Almost all of that movement happens in two eight-week stretches. Our drivers are on the road constantly during those weeks, and a single New York to Florida run takes two to three days including the return flight.
The math is simple. There are only so many pickup days in October. Booking early costs you nothing. It just means you name the date instead of choosing from what’s left.
Southbound (Driving from NY to FL): October and November
Most of our southbound snowbird customers leave between the first week of October and Thanksgiving. Cold weather in the Hudson Valley and upstate New York moves people earlier some years than others.
Book by late August for anything in this window.
If you have flexibility, late September is the easiest week of the fall. Availability is wide open and you’re ahead of the crowd by two weeks.
Still deciding where you’re headed? Our guide to snowbird destinations in Florida covers the Gulf Coast, the Atlantic side, and the central retirement communities.
Northbound (Driving from FL to NY): March through May
The return trip runs on a different rhythm. Most snowbirds head home between mid-March and early May, with a heavy cluster right after Easter and Passover.
Book by early February for an April pickup. Florida gets warm fast in April. Heat, humidity, and the start of bug season push a lot of people north at the same time, which is why the spring window compresses more than the fall one.
We break down the timing in detail in our guide to when snowbirds leave Florida.
Two windows most people overlook
Late September. Two weeks ahead of the rush. Same warm arrival, none of the competition for dates.
February. If you’re a late arriver or you split your season into two shorter stays, February is the quietest month on our calendar all winter.
Both windows give you first pick of pickup days and more room to shift if your plans move.
Booking around your flight
We work backward from your flight date so your car is sitting in your Florida driveway when you land, not three days later.
Tell us your flight when you book. If you don’t have it yet, give us your best estimate and update us when you do.
Plans change. Flights get moved. Closings get delayed. Call us as soon as you know and we’ll work with you to change the pickup time.
Someone needs to be there at both ends. A neighbor, a family member, or a property manager works. Plenty of our customers have a son or daughter hand over the keys in New York while they’re already in Florida waiting for the delivery.
Delivery inside a gated community
This is where a driveaway service and a car shipping company part ways.
Most large Florida retirement communities have gate access rules, and many restrict commercial vehicles on interior roads. The Villages, Sun City Center, and a good number of the Naples and Boca Raton communities either turn away a 75-foot car carrier at the gate or send it to a meeting point half a mile away.
Your car is not a commercial vehicle. One of our drivers pulls up in your sedan or SUV, checks in at the gate the same way any visitor does, and parks it in your driveway. No meeting point, no shopping center handoff, no calling a neighbor to come pick you up.
Two things make gate access go smoothly:
Add the driver to your community’s visitor list. Most gate systems let you register a guest online or by phone a day ahead. Give them the driver’s name and your delivery date.
Tell us about any access quirks when you book. Gate codes, call boxes, a guardhouse that closes at 8pm, a driveway that’s hard to spot after dark. Small details, but they save a phone call at the gate.
If you’re not sure what your community requires, a call to your HOA office before you leave New York clears it up in five minutes.
Book both directions at the same time
Most of our customers use us for both legs. Booking them together locks in your return date before the spring window fills.
You don’t need to know your exact return day in October. A rough week is enough to hold the slot, and we’ll firm it up as the date gets closer.
What to have ready when you call
Your pickup address in New York, New Jersey, or Connecticut.
Your Florida drop-off address, including the community name if it’s gated.
Your preferred pickup date or a rough window.
Your flight date, if you have it.
Who will be present at pickup and at delivery.
What’s going in the car. Golf clubs, winter clothes, boxes, whatever you want. Pack it as full as you like as long as the driver can see out the back.
That’s the whole conversation. Most quotes take five minutes on the phone.
Before pickup day, our guide on how to prep your car for the trip walks through the short checklist.
When driving yourself makes more sense
We’re not the right call for everyone, and it’s worth saying so.
You enjoy the road trip. Some people look forward to it. Stops in Charleston, family in Virginia, a few days on the road. If that’s you, drive it.
You’re already making stops along the way. If the drive south is half the trip, a driver doesn’t help you.
The car stays in Florida year-round. Some snowbirds buy an inexpensive second car and leave it in the driveway all summer. If the vehicle is worth less than a couple of round trips, that math works.
You’re hauling more than fits in the car. A roof box and a trailer full of furniture is a moving job, not a driveaway job.
Curious what the drive actually involves? We wrote up how long the trip from New York to Florida really takes, including where most people stop overnight.
Frequently asked questions about booking car transport
How far in advance should I book?
Book by late August for an October or November pickup, and by early February for an April return. Outside those two windows, six weeks is plenty. We take bookings up to a year ahead, and earlier never hurts.
Can I book too early?
No. We hold dates as far out as you want to plan. A lot of our repeat customers book next October before they’ve even flown home in the spring.
Do you drive the car back to New York in the spring?
Yes. We handle both legs, and most of our customers use us for both. Booking them together holds your spring date before that window fills.
What if my flight or travel dates change?
Call us. We move pickup dates regularly. The more notice you give us, the easier it is to slot the new date without changing anything else.
Can you deliver inside a gated community?
Yes. A driver pulls in with your car and checks in at the gate like any visitor. Add the driver to your visitor list ahead of time and give us any gate codes when you book.
Do I need to be there for pickup and delivery?
Someone does, but it doesn’t have to be you. A neighbor, family member, or property manager can hand over or receive the keys at either end.
Can I leave personal items in the car?
Yes. Load it up. The only limit is that your belongings can’t block the driver’s view.
Where in Florida do you deliver?
Orlando, Tampa, Sarasota, Naples, Fort Myers, Boca Raton, Fort Lauderdale, Miami, and points between. See our pickup locations for the northern end of the route.
Pick your date before the season does
The snowbird calendar has barely moved in fifty years. Season starts in October and runs through April or May, the same way it did when your parents were doing it. What changes is how quickly the good pickup dates disappear once everyone starts calling at once.
Two dates to write down: late August for a fall pickup, early February for a spring return. Hit those and you name your day.
Call or text us at (917) 756-1088, or send us your dates and we’ll get you a price the same day. We pick up across New York, New Jersey, and Connecticut.