Key West and the Overseas Highway Private Tour with Driver: From Miami to Mile Marker 0

How do you get to Key West by car from Miami?

Start with the road. The Overseas Highway is a single main route through a chain of islands, with the Atlantic on one side and the Gulf of Mexico on the other, and for long stretches there is nothing to turn onto. That is its charm and its constraint. A breakdown or a crash on one bridge can slow the entire chain, and there is no parallel road to take instead.

The history gives it a shape. Henry Flagler's Overseas Railroad reached Key West in 1912, a hurricane wrecked it in 1935, and the highway that opened in 1938 reused much of the railway's path. When you cross a long bridge today, you are often driving beside or over the old line.

Behind the booking sits a worldwide desk that answers at any hour and a Florida operator from our directory that is licensed, insured for commercial work and vetted. For the whole drive you have one point of contact, one confirmation and one invoice, with the booker fixing the fare ahead of payment.

Price & book your ride

The honest question: one day or two

Four hours each way is eight hours of driving, and Key West is a place to be in, not a place to photograph through a window. Here is how the choices compare.

• A one-day round trip from Miami leaves roughly three hours on the island if you depart early, and it is only sensible when there is no alternative. It tires the passengers and the driver.
• One night in Key West is the practical minimum. You drive down in the morning, have a full afternoon and evening in Old Town, sleep, and return in the late morning after the early traffic has cleared.
• A one-way drive and a flight back works well. Key West has its own airport, and the short flight returns you to Miami in under an hour. This turns a day trip into a pleasant outing with no return drive, and the desk can arrange the car in one direction.
• A driving week through the Keys uses the chauffeur to link stops, which the next section describes.

If you can spare only one day, take the one-way plus flight option or add a hotel night. The extra cost of a night is lower than the cost of spending the whole day in a car.

The drive in sections

Mile markers are small green signs along the roadside, counting down toward Mile Marker 0 at Key West. They are the way locals give directions, and the useful way to plan stops.

The mile marker numbers are approximate and drawn from long-standing practice, so treat them as a guide, not a schedule. The Florida Keys tourism board's page lists the highway's bridges and scenery, and the road signs are the authority on the day.

The speed limits are not generous. They change often, they are lower around the towns, and they drop on Big Pine Key, where the road is posted to protect the small Key deer. A chauffeur obeys them, which is part of why the drive is estimated at four hours and not three.

Reading the traffic

The Keys have three predictable traffic problems.

1. Friday afternoon and Saturday morning southbound. Weekenders from Miami fill the road. If you can, leave on Thursday or very early on Friday.
2. Sunday afternoon and evening northbound. The return is the busiest of the week. A Monday morning departure from Key West is easier.
3. Incidents. With one road, a single crash can close a lane for hours. The driver watches live traffic and tells you early, and a flexible schedule absorbs the delay.

Hurricane season, roughly June through November, adds another consideration. The Keys can be evacuated for storms, and because there is one road out, evacuation orders come early. Check forecasts and local guidance before you book, and keep the booking terms in mind: the cancellation terms on your confirmation apply as stated.

Arriving in Old Town

Old Town Key West is a small grid of narrow streets, many of them one-way, with limited curbside space and paid parking that fills. The best plan for a private car is the simplest: drive to the hotel, unload, and leave the car with the driver for the afternoon, or release the driver until the evening.

If you are not staying overnight, the driver will drop you near the middle of Old Town, then wait at a nearby lot or loading area. Give them a pickup time and a mobile number. In the middle of the day, cruise ships in port and weekend crowds make the center very busy, and walking is faster than driving for most of the distance.

Duval Street is the main spine, running across the island from the Gulf side to the Atlantic, with bars, shops and live music. The Florida Keys tourism board describes it as busy at night. For a quiet start, go in the morning.

Two hours in Old Town, and a full afternoon

If you have two hours, choose a short list.

• The Southernmost Point, the painted marker at the island's southern end, is the most photographed spot. Go early, before the line forms.
• The Ernest Hemingway Home and Museum is open daily, with walk-in visits from nine in the morning to five in the afternoon according to its website. The grounds are home to cats, some of them descendants of a six-toed cat given to Hemingway by a ship's captain. The home runs tours, and its official site lists rates and tours.
• Mallory Square at sunset, where street performers gather and the sunset is a social event.

With a full afternoon, add a meal on Duval Street or the waterfront, a walk through the quieter lanes, and time on the water. The tourism board highlights diving and snorkeling over coral gardens and a wreck, and fishing for tarpon, sailfish and snapper. Dive and snorkel trips are run by licensed operators and are booked separately from the driver.

Stops that suit a chauffeured drive

The advantage of a driver on the Overseas Highway is that you can say yes to a stop without worrying about the next fifty kilometers. Some stops work better than others.

• Key Largo and Islamorada are the dive and snorkel centers of the upper Keys. Boat trips are run by licensed operators and need a morning start, so they suit the drive down, not the return. Book them separately and give the driver the departure time.
• A roadside lunch in Islamorada or Marathon splits the drive neatly. The restaurants are on the water, and the pace is unhurried.
• Bahia Honda State Park is a beach and a view of the old railway bridge in the lower Keys. Check the park's hours and entry arrangements before you go, as they are set by the state.
• Big Pine Key is where speed limits drop for the Key deer. The deer are protected, and the driver will slow without being asked.

Choose two stops, not six. The road looks short on a map and long in the car, and a plan that tries to do everything arrives in Key West after dark.

Sun, water and what to carry

The Keys are bright, and the glare off the water is strong from late morning. Bring sunglasses, a hat and sunscreen, and a light shirt for the sun. Carry a small day bag with a towel, because many beach and boat stops need one. Water and chargers are on board in most vehicles, so bulky items can stay in the luggage area. The Luxury SUV is the usual choice for a family with dive gear, and the fleet page shows the other classes.

Mobile coverage is generally good along the highway but can be weaker in places, so download your hotel details and your driver's contact before you leave. If you are traveling in hurricane season, check the National Weather Service forecast on the day.

Ways to reach Key West compared

A rental car is a sound choice for a group that wants to dive, kayak and move as it pleases. A flight is the quickest way to arrive. The chauffeur is best for a relaxed outbound drive with stops, a hotel handover, and a return that is already arranged.

The Everglades, South Beach and the start of the road

The Keys begin where the mainland ends. Homestead and Florida City sit at the head of the Overseas Highway and beside the park entrance covered in our Everglades National Park guide, so a combined route is practical: the Everglades on the way down or on the way back. For the Miami end of the trip, see the South Beach guide, the Little Havana guide and the Vizcaya Museum and Gardens guide.

The Miami limo service page covers the city, and pickups at the airport are explained in the Miami International Airport guide. If you are joining from Fort Lauderdale, see the Fort Lauderdale airport guide. The wider network is set out in the North America directory, and the private tours with driver page covers drives that string stops together.

For official information, Visit the Florida Keys is the tourism board's page for Key West, and visitflorida.com covers the state. A tourism office that wants chauffeured transport for its visitors can open a trade account with LimousineWorldwideDirectory.com.

A two-day chauffeured plan

1. Day 1, 8:00 am: Depart your Miami hotel or the airport. Stop at Key Largo or Islamorada for a coffee and a short walk.
2. Midday: Lunch in Marathon, then cross the Seven Mile Bridge.
3. Mid-afternoon: Arrive at the hotel in Old Town, with the driver released until the next morning.
4. Evening: Walk to Mallory Square for sunset and dinner.
5. Day 2, late morning: Depart for Miami after breakfast and after the first rush has cleared. Allow four hours or more, and add a buffer if a flight is waiting.

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