Every October the same conversation happens in garages from Sag Harbor to Southampton. The house is nearly closed. The flights to Palm Beach are booked. And somebody has to decide which of the cars comes along for the winter, and how.

It is rarely a simple answer, because a Hamptons garage rarely holds a single kind of car. Here is how seasoned seasonal residents think it through, one vehicle at a time.

The everyday SUV

This is the car that does the real work in Florida: the trips to Publix, the drive to the club, the airport runs when the grandchildren visit. It almost always makes the trip.

It is also the easiest one to move. A standard open car carrier, the two-level truck you see delivering to dealerships, handles it without fuss. Between New York and South Florida, recent prices on that kind of transport have run roughly $1,050 to $1,300 for a typical vehicle. The trip covers about 1,250 miles, and the truck usually spends three to five days on the road once the car is loaded.

The sensible move is to send it a few days before you fly, so it is waiting in the driveway in Palm Beach rather than arriving after you do.

The convertible

A convertible feels made for Florida, and it is worth bringing. The question is how it travels. An open carrier is perfectly safe for most cars, but it leaves the vehicle exposed to rain, grit, and whatever comes off the truck ahead for three days down I-95. For a soft top, or a car with paint you care about, many owners pay for a covered trailer instead. That typically adds around half again to the price of open transport.

The collector car

If the garage holds something rare, a vintage 911, an early Mercedes roadster, a Ferrari bought for the Palm Beach concours season, there is no real debate. It travels enclosed.

What matters more is the quality of the enclosed carrier. Look for three things. First, a hydraulic liftgate that raises the car level onto the trailer, so a low front end never meets a steep ramp. Second, soft straps that hold the car by the wheels instead of hooks near the suspension. Third, cargo insurance that actually covers the car’s value. Enclosed haulers commonly carry between $250,000 and $1 million in coverage, and you should ask for the exact figure in writing before the car leaves the drive.

The golf cart

In plenty of Palm Beach and Jupiter communities, the cart gets more use than any car. Owners who have customized one, with a lift kit, new seats, or a street-legal conversion, often prefer to bring their own rather than buy again. Carts can ride on the same trucks as cars, so it is worth asking about one when you book the rest of the move. Mention its size and whether it runs on batteries or gas, because that changes how it is loaded.

Two cars, one booking

If more than one vehicle is heading south, book them together. One truck, one pickup window, and one handoff is far simpler than coordinating separate carriers, and it means both cars arrive within the same few days rather than a week apart.

The car that stays behind

Not every car should go. A car kept in New York for spring visits, or one the house manager uses, can stay garaged. Put it on a battery tender, fill the tank, and ask your insurer whether storage coverage makes sense for the months it will sit.

Timing is the hidden cost

Whichever cars travel, the calendar shapes the experience as much as the trailer does. Southbound demand on the East Coast climbs from October through December, as the whole seasonal migration heads the same way at once. The best pickup dates fill early.

The return is even tighter. In March and April, with everyone heading north before Memorial Day, trucks leaving Florida are full, and the northbound leg often lands a tenth or so above what the identical trip cost in autumn. Booking the spring return while you are settling in for the winter, instead of in March, is the simplest way to avoid paying a premium.

A practical guide to snowbird car shipping lays out the seasonal timing, open and enclosed options, and pickup logistics for both legs of the trip.

Gates, hedges, and long trucks

One detail catches almost everyone the first time. A full-size car carrier runs about 75 feet, nearly the length of a tennis court, and it cannot squeeze down a privet-lined lane or through a guarded entrance in Palm Beach. Expect the handoff to happen at a nearby wider road or a commercial lot. If you are already in Florida when the car leaves, a house manager or neighbor can hand it over and sign the condition report for you.

A few final notes

Keep the trunk light. A set of golf clubs and a weekend bag are fine, around 100 pounds in total, but anything packed inside the car is not insured, so jewelry and art belong with you.

And if Florida is becoming your legal home rather than your winter one, plan for the paperwork. Once you establish residency, the state expects the car to be titled and registered there within 10 days.

Handled early, the car is the one part of the season nobody remembers. It leaves the Hamptons in October and is in the driveway in Palm Beach when you land.