Road Trip to Key West: Winter Getaway in Florida

Some winter getaways are so magical that you never forget them. And if you are fortunate enough to go back again, you will feel the wonder all over again. Key West is home to Ernest Hemingway’s Home and Museum and his cats (descendants), The Southern Most Point and Sloppy Joe’s.

Getting there is pretty easy. You can fly, drive, take a cruise, ride ferries or even sail on your own boat to get there. There are three main highways in Florida. If you are going on a road trip to Key West you will eventually drive on one of the most scenic views in America on the 110 mile Overseas Highway also known as US1.

Your drive will take you to an area surrounded by the Gulf of Mexico and Atlantic Ocean with sandy beaches, quiet sleepy towns, natural plants and mangroves, palm trees, areas that are rich in history and legend and possibly sunrise or sunset depending on the time of the day.

The southern section of US 1 is part of “the old national road” that starts in Maine and travels down the East Coast to Florida. (Source: America’s Byways)

Key West is a year-round vacation place but its peak season is during the North American winter months, that is Christmas to Easter. Through Travelmath’s calculator’s driving distance and driving time, we found out it takes 3 hours 21 minutes to drive and it is 160 miles from Miami to Key West.

The truth is, Key West is closer to Havana, Cuba compared to Miami. It is only 90 miles to Cuba’s capital city. If there were a flight service from Havana to Key West (like before), it would only take 13 minutes.

Once you arrive into Key Largo on US1 from Miami, you can instantly sense the islands paradise feel. It is as if you are transported into a whole new world. Suddenly the city pressure is no longer with you. Instead you are greeted with a laid-back tropical paradise atmosphere.

Highlights of your road trip from Key Largo to Key West
Florida Keys is divided into Upper Keys, Middle Keys and Lower Keys.

Key Largo
Key Largo is located at the Upper Keys and your first stop before heading to Key West. A perfect place for diving, exploring John Pennekamp Coral Reef State Park and having a meal at a local restaurant that serves the “Catch of the Day.”

Grassy Key and Marathon
Grassy Key and Marathon at the Middle Keys area are famous for their marine and wildlife. Check out the Dolphin Research Center, Museum of Natural history of the Florida Keys and The Turtle Hospital.

The Seven Mile Bridge
Next is crossing The Seven Mile Bridge. This world’s longest segmental bridge has 39 expansion joints and an amazing drive with blue skies above meeting turquoise water below. You will also see the remains of the Old Seven Mile Bridge.

Key West
Key West was once owned by Spain and housed a large population of Cuban immigrants who opened up cigar-making factories and were involved in fishing and sponge gathering industries as well. It has a diverse culture and the natives are called Conchs.

In the historic Old Town are old Victorian homes that house restaurants, guesthouses, specialty stores and art galleries. Certain parts of the Old Town looks like Bahamas. Interestingly, roasters do roam the streets here.

Ernest Hemingway Home and Museum
This is one museum not to be missed. Ernest Hemingway had traveled all over the world and had lived in Key West in the early 1930s to 40s. His memorabilia are displayed here along with many of Hemingway’s cats roaming around the compound. In his home office (a separate building), see his travel trunks and typewriter sitting in one corner along with his chair and desk.

Seafood and Conch
Lobster, shrimp, assorted fish, stone crab, clams and conch should be included in your dinner while you are there. The conch is in almost every restaurant with conch fritters being the most popular. No one should leave Key West without trying out at least once.

Key West offers plenty of water sports including diving and fishing, historic sites, island cuisine, beautiful sunrise and sunset, most of all the Florida sunshine all year round. But the best time without the humidity would be in winter. It is definitely a great getaway for your family this winter.

How to get there
Whether your road trip starts from North East, Mid West or South, there are three major highways that merge to US1. I-95, I-75 and I-10 will take you to Florida. But only US1 will take you to Key West.

For all your road trip guides, please use Travelmath’s calculators to help you out.

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