Old Town is the heart of Key West: tin roofs, picket fences, gingerbread porches and streets that were laid out long before anyone imagined a car carrier. It’s a beautiful place to live. It’s also one of the trickiest places in the Keys to deliver a vehicle. Here’s how car delivery to Old Town Key West actually works, and how to make yours smooth.
Why Old Town Is Different
Many Old Town streets are narrow, lined with parked cars and shaded by big trees. Some lanes are one-way, and some are barely wider than a golf cart. A full-size car carrier is long, tall and heavy. It needs room to pull over, room to drop a ramp and clearance overhead for branches and wires.
That means the truck can’t always stop right in front of your house. That’s normal here, and planning for it is part of what we do every week.
What Gets in the Way
- Width. Parked cars on both sides can leave a single narrow lane.
- Height. Low limbs and overhead lines can block a loaded top deck.
- Turning room. Tight corners can stop a long rig from getting onto a block at all.
- Traffic and timing. Busy hours near Duval Street make stopping harder.
How We Plan the Final Approach
Before delivery day we look at your address and ask a few questions: Is there a driveway? Is the street one-way? Is there a spot nearby where a truck can safely pull over? Then we pick one of three approaches:
- Door-to-door when the street allows it.
- A nearby side street or corner a short walk from your home.
- A meet spot with plenty of room to unload safely.
As a direct carrier for all of Florida, we handle the Keys leg ourselves, so the person planning your delivery knows these streets.
Popular Meet Spots
When a home just isn’t reachable, the most common choice is the old Sears center lot on North Roosevelt Boulevard. It’s a popular meeting spot and one of the only large parking lots on the island, which gives a carrier room to unload without blocking traffic. From there it’s a short drive into Old Town.
Military families often use the same lot. Our Military PCS to Key West page explains how that works for base moves.
We’ll confirm the exact spot and time with you before the truck arrives, so nobody is circling the block.
Tips for a Smooth Old Town Delivery
- Give us the full address and any access notes. Gates, alleys, and which side of the street you’re on all help.
- Keep your phone on. The driver will call when getting close.
- Have someone ready. If you can’t be there, name the person receiving the car.
- Know where the car will park. Old Town parking is tight, so have a plan for after delivery.
- Do the inspection in daylight. Walk around the car before you sign.
Moving into an Old Town cottage? Our Moving to Key West guide covers the rest of the move. Shipping a golf cart for getting around the neighborhood? See golf cart shipping to Key West.
Paying at Delivery
We prefer COD whenever possible, and it works well for Keys deliveries. 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.
Frequently Asked Questions
Can the truck deliver right to my Old Town house?
Sometimes. It depends on street width, overhead clearance and turning room. If it isn’t safe, we’ll meet you at a nearby corner or a larger lot.
Where is the usual meet spot?
The old Sears center lot on North Roosevelt Boulevard is a popular choice because it’s one of the only large parking lots on the island.
Will you tell me ahead of time if we need a meet spot?
Yes. We review your address before delivery day and confirm the plan with you, so there are no surprises.
Does it cost more to deliver in Old Town?
Your quote is based on your full route and vehicle. Tell us your address when you request a quote so we can plan the final stretch.
Book Your Old Town Delivery
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.