Connecticut, Massachusetts and New England to the Keys
New England drivers have a long tradition of heading south when the leaves fall, and many want their car to follow. In-N-Out Keys is a veteran-owned, family-operated interstate carrier and broker that ships cars from Connecticut, Massachusetts, and across New England to the entire Florida Keys.
From the Nutmeg State and the Bay State to the Overseas Highway
Connecticut and Massachusetts send some of the most devoted winter residents to the Keys. Whether you own a second home in Islamorada, work seasonally in Key West, or are relocating for good, shipping the car saves several days of highway driving and a lot of wear on the vehicle. A New England to Keys drive can top 1,500 miles, and the Boston-area start is even longer.
We handle these moves as an interstate carrier and broker, lining up the right carrier for the long haul, and as a direct carrier for all of Florida, we take care of delivery down the islands ourselves. That keeps the last, most complicated stretch in experienced hands.
Where we pick up in New England
- Connecticut — Greenwich, Stamford, Norwalk, Hartford, New Haven, Bridgeport, Waterbury, and the Gold Coast and shoreline towns.
- Massachusetts — Boston, Cambridge, Worcester, Springfield, the North and South Shores, and Cape Cod.
- Elsewhere in New England — Rhode Island, New Hampshire, Vermont, and Maine are common origins as well. If yours is not listed, ask.
Narrow streets and tight driveways are common in New England towns, and large car haulers need space to maneuver. If yours is a tricky location, we will suggest a nearby parking lot or large intersection that makes loading easy.
Timing the trip around snow and the snowbird season
The New England snow season shapes shipping. Late fall is when snowbirds send cars south, and spring is the return trip, so both periods are busy. In deep winter, storms can delay pickups, and haulers avoid icy back roads. If you can, book your pickup two to three weeks ahead and stay flexible on the exact date. Delivery windows are estimates, not promises. We will give you a realistic one for your trip.
Many New England owners ship south in the fall and back north in the spring. If that is you, read our seasonal shipping page and the snowbird door-to-door guide for round-trip planning, and our Northeast snowbird route post for how the corridor works.
Protecting your car from salt and winter
New England cars often carry months of road salt, and open haulers expose a vehicle to weather on the trip south. Washing the car before pickup, including the underside if you can, gives the driver a cleaner view when documenting condition. If the car is a classic, a convertible, or a newer luxury model, consider an enclosed trailer. Our open versus enclosed guide explains the tradeoffs, and our exotic and classic page covers extra-careful handling.
How the process works
- Request a quote using our quote page: pickup ZIP, delivery address in the Keys, vehicle, and your target date.
- Confirm the booking and the pickup contact.
- Prepare the car. Clean it, photograph it, leave about a quarter tank, remove E-ZPass and personal items.
- Pickup. The driver inspects and loads the car, and you get a copy of the bill of lading.
- Delivery in the Keys. You or your representative inspects the car and pays on delivery.
Cost and payment
The main drivers of price are distance, season, the vehicle’s size, whether you choose open or enclosed transport, and how flexible you are on dates. Our cost guide explains each. We would rather quote you a real number after hearing the details than guess in advance.
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.
Starting elsewhere on the East Coast? See our pages for New Jersey and Pennsylvania, or our general out-of-state shipping page. On the Keys side, we deliver to Key Largo, Islamorada, and Key West.
Get a Free Quote →Call (754) 714-2439
Frequently asked questions
Do you ship cars from Connecticut and Massachusetts to the Florida Keys?
Yes. We arrange pickups across Connecticut, Massachusetts, and the rest of New England, with delivery to the entire Florida Keys.
What is the best time to ship from New England?
Late fall and spring are the busiest, so book early. Winter storms can delay pickups. Stay flexible if you can.
Can you pick up from my driveway in a small New England town?
Usually. If a large carrier cannot get in, we will agree on a nearby lot or larger street.
Should I ship open or enclosed?
Open is the standard and most economical option. Enclosed is worth considering for classic, convertible, or luxury cars, and for protection from salt and weather.
Can I ship the car both ways for the season?
Yes. Many owners ship south in the fall and north in the spring. Ask us about planning both legs.
How is payment handled?
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.
Related pages
- Car shipping to the Keys from out of state
- Seasonal auto shipping for snowbirds
- Northeast snowbird route
- New Jersey to the Florida Keys
- Pennsylvania to the Florida Keys
- Open vs. enclosed shipping
- How much does it cost?
- Request a free quote
In-N-Out Keys LLC · USDOT 4120018 · MC 1583555 · Veteran-owned and family-operated · Interstate carrier and broker, and a direct carrier for all of Florida · Serving the entire Florida Keys · (754) 714-2439
