5 road trips to take from Miami this winter

25 Sep 2026 3 min read Smartweb Infotech

From the Keys to Orlando: five drives we love, and the best car for each one.

Winter is the best time to drive out of Miami. The heat softens, the roads clear and the coastline looks its best. Here are five trips we recommend to our renters, with the car that fits each and a few tips from people who have done them many times.

1. Miami to Key West: the Overseas Highway

Distance: about 270 km each way, 3.5 hours without stops. Best car: a convertible or a comfortable sedan such as the Camry.

The drive over 42 bridges is one of the most famous in the country. Leave early to beat the traffic in Florida City, stop in Islamorada for fresh fish, and take the Seven Mile Bridge in the afternoon light. Stay overnight in Key West, because the sunset at Mallory Square deserves the extra day. Tip: keep your toll device on, and book parking in Key West ahead.

2. Miami to Orlando: theme parks and back

Distance: 380 km, about 4 hours. Best car: an SUV like the Kia Sportage or the Ford Explorer.

Families love this one, and the extra luggage space helps once the souvenirs start piling up. Turnpike tolls add up, so rent the toll device with the car and avoid fines. If you are staying a week, choose our weekly rate: it works out well below the daily price.

3. Miami to the Everglades and Naples

Distance: 250 km loop across the Tamiami Trail. Best car: any comfortable car; the roads are flat and straight.

Drive west on the Tamiami Trail through the Everglades. Stop for an airboat ride, look for alligators from the boardwalks at Shark Valley and have lunch at a roadside stand. Continue to Naples for the pier and a relaxed seafood dinner, and return via Alligator Alley. Fill up before the trail: stations are few.

4. The Gold Coast: Miami to Palm Beach

Distance: 120 km each way, just over 1.5 hours. Best car: the Camaro or the BMW 5 Series, for a drive in style.

Take A1A rather than the highway: it hugs the ocean through Fort Lauderdale and Boca Raton. Stop at Las Olas Boulevard for coffee and walk the Worth Avenue shops in Palm Beach. It is an easy day trip and a good excuse for a special car.

5. Miami to Fort Myers and Sanibel Island

Distance: 270 km each way. Best car: the electric Nissan Leaf or a hybrid, since the route has plenty of charging points.

Sanibel's beaches are known for shell hunting. Walk the shoreline at low tide, rent bikes to explore the island, and stay for the sunset. The causeway is toll-paying, so keep a few dollars or your device ready.

Before you set off

  • Check the fuel or charge level at pick-up and note it in the agreement.
  • Add an additional driver if the trip is long; sharing the driving makes it safer.
  • Keep our roadside assistance number in your phone.
  • Return the car with the same fuel level to avoid refuelling fees.

Planning one of these trips? Book your car online, or call us for help choosing.

S
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Smartweb Infotech
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