Winter in Key West goes fast. One week you are watching the sunset at Mallory Square, and the next you are packing up and thinking about the drive north. For a lot of seasonal residents, the easier answer is to fly home and let the car follow. This guide covers how to plan shipping a car out of Key West at the end of the season so it lands where you need it, when you need it.
Why the Trip North Is Different From the Trip Down
Most of what you read about Keys car shipping is about getting a vehicle to the island. We cover that in detail on our Ship a Car to Key West page. Going the other way follows the same road in reverse, but the planning is a little different.
When the season winds down, many snowbirds want to leave around the same weeks. Trucks heading up the Overseas Highway fill up, and the best spots go to people who booked early. If you know your flight date, that is the moment to request a quote.
The Two Legs of a Northbound Shipment
We are a direct carrier for all of Florida, so the first leg, from your Key West driveway to the mainland, is ours. For long routes out of state, the vehicle usually moves on to a separate interstate transporter for the trip north. That handoff is planned ahead of time so your car isn’t sitting and waiting.
When to Book
A simple rule: book as soon as you know your departure window. A few weeks of lead time gives us room to line up the right carrier for your route. Shorter notice is often possible, but your pickup date may have less flexibility.
- Know your window, not just one day. A pickup range of a few days makes it much easier to match you with a truck.
- Plan around your flight. Many owners schedule pickup a day or two before they leave so they can still get around town.
- Tell us about the delivery end. A gated community, a narrow street or a condo garage up north is worth mentioning up front.
Getting the Car Ready to Leave the Island
Salt air and a season of short trips around town can leave a car needing a little attention before a long haul. Before pickup:
- Wash it so the pickup inspection is easy to read.
- Take your own dated photos of every side.
- Remove beach chairs, parking passes, toll devices you don’t want used, and loose items.
- Leave about a quarter tank of fuel.
- Make sure the battery is strong if the car sat for long stretches over the winter.
If you are closing a rental, the pickup can happen at the property, or at a nearby spot that a truck can reach easily. In Old Town that often matters. See our guide to Old Town Key West car delivery and meet spots.
How Payment Works on Routes Leaving the Keys
We prefer COD (cash on delivery) whenever possible. Every carrier accepts COD, but not every carrier takes billed payments, so paying on delivery lets us line up the best carrier for your route.
Routes leaving the Keys are a bit different. Because a separate transporter usually handles the long-distance leg, payment may be split between the two parts of the trip. We work that out with each customer before anything is booked, so you know exactly who gets paid and when. Our post on why we prefer COD explains it in more detail.
Coming Back Next Season?
If you’ll be back in the fall, mention it when you book. Many seasonal residents ship south again before the winter rush, and it helps to get on our radar early. If you are making the Keys home for good, our Moving to Key West page covers the bigger move.
Heading somewhere specific like New York? Our New York to Key West route guide covers that corridor in both directions.
Frequently Asked Questions
How far ahead should I book shipping a car out of Key West?
As soon as you know your departure window. A few weeks of notice gives the most flexibility, especially when many seasonal residents are leaving at the same time.
Will the same truck take my car all the way north?
Not always. We handle the Keys and Florida leg directly. Long routes out of state usually use a separate interstate transporter, and we coordinate the handoff.
Can I pay on delivery when shipping out of the Keys?
We prefer COD whenever possible. On routes leaving the Keys, payment may be split because a separate transporter is used. We set this up with you before booking.
Do I need to be there at pickup?
You or someone you trust needs to be there to hand over the keys and sign the inspection. Tell us in advance if that will be a neighbor or property manager.
Plan Your Trip North
Tell us your vehicle, your pickup and delivery addresses, and your dates. Request a free quote online or call (754) 714-2439. We usually reply within the hour.
Key West Auto Shipping is run by In-N-Out Keys LLC (USDOT 4120018, MC 1583555), a veteran-owned, family-operated interstate carrier and broker and a direct carrier for all of Florida. Owner Steve Janowski is an Army veteran. We serve the entire Florida Keys. Learn more about us.