Family Travel in Key West

Family Travel in Key West

Key West is a Caribbean island in the Continental U.S. and a great option for families By: Samantha Davis-Friedman
<p>Families will love visiting Dry Tortugas National Park. // © 2014 Samantha Davis-Friedman</p><p>Feature image (above): Key West is the southernmost...

Families will love visiting Dry Tortugas National Park. // © 2014 Samantha Davis-Friedman

Feature image (above): Key West is the southernmost point in the U.S.  // © 2014 Key West BusTour

Related Content

The Details

Casa Marina Resort

Dry Tortugas National Park


Harry S. Truman Little White House

Hungry Tarpon Restaurant

Mangrove Mike’s

Pigeon Key Foundation

Robbie’s of Islamorada

Sunset Celebration

The Ernest Hemingway Home and Museum

The Southernmost Point

There’s something for everyone in the southernmost U.S. city of Key West, Fla. This family-friendly destination offers waterfront activities such as kayaking, stand-up paddleboarding, snorkeling and glass-bottom boat rides; historical sights like Hemingway House and Truman’s Little White House; and vibrant nightlife along Duval Street and in Mallory Square.

A Scenic Drive and Great Stops
Considered to be one of the top scenic drives in the U.S., the Overseas Highway stretches 113 miles from the Florida mainland all the way to Key West. The picturesque roadway is built on what remains of Henry’s Flagler’s Florida East Coast Railway. Dubbed “Flagler’s Folly” by critics at the time, the completed project later became known as “The 8th Wonder of the World.” 

The railway was built from 1905 to 1912, but in 1935, a hurricane destroyed more than 30 miles of track. During the repairs, much of the rails were converted to highways, but ruins of the railroad can still be seen along the drive.

A great midway stop between Miami and Key West is Islamorada. Depending on the time of day, families can check out the “best breakfast in the Keys” at Mangrove Mike’s or enjoy a delicious lunch on the waterside deck of Hungry Tarpon Restaurant. In addition, kids and adults can feed the 100 or more giant tarpons that gather around the dock at Robbie’s Marina. A highly prized Florida Keys game fish, the tarpon dates back to prehistoric times.

Another interesting stop on the way to Key West is Pigeon Key. One of the most historically significant islands in the chain, this is where the 400 workers who built the Overseas Railway were housed in the early 1900s. Today, the island boasts a museum that holds artifacts from Flagler’s Railroad and offers daily guided historic tours.

Noteworthy Sights
Key West offers families two ideal photo opportunities: the buoy marking the exact southernmost spot and the mile marker zero sign where U.S. Route 1 both begins and ends, depending on which way one is traveling.

Between these two sights is the Hemingway House and Museum. Visitors can see where iconic American writer Ernest Hemingway lived and worked and spot the famous polydactyl (six-toed) cats that roam the house and gardens; many of the animals are descendants of a six-toed cat given to Hemingway by a ship’s captain.

A few blocks from Hemingway House is Harry S. Truman Little White House. It was originally the naval command headquarters during the Spanish-American War, World War I and World War II, and the building later served as the winter White House of President Harry S. Truman. 

Today, Truman Little White House is a museum as well as a retreat and place of government business for our nation’s leaders. Both the Hemingway home and Little White House are open seven days a week, 365 days a year.

Extraordinary Excursion
For Key West travelers who want a unique experience, the day trip to Dry Tortugas National Park and Fort Jefferson should not be missed. Departing from Key West onboard the high-speed catamaran Yankee Freedom, visitors travel 70 miles across open water to one of the most unique and spectacular national parks in the U.S. 

Once at Dry Tortugas National Park, tourists can explore historic Fort Jefferson, a 19th century fort, and enjoy swimming and snorkeling in the crystal blue water surrounding the island. Agents should note that this is a full-day excursion that departs at 7:30 a.m. and returns at 5:30 p.m.

When the Sun Goes Down
At the end of each day, Key West hosts a lively Sunset Celebration at Mallory Square Dock. Here, local artists and street performers gather with tourists to watch the sun sink into the Gulf of Mexico. After dark, families can walk to Key West’s “main drag,” Duval Street. Running shore to shore from the Gulf of Mexico to the Atlantic Ocean, the street is just over a mile in length and is lined with shops, bars and restaurants.

The saying goes that good things come in small packages. With a laid-back attitude and a place in American history, Key West offers sun, fun, the beauty of the Caribbean and even a little bit of education. For such a small package, this family vacation is hard to beat.



Getting There: The trip to Key West along the 120-mile long Florida Keys by car takes about four hours from Miami along the scenic Overseas Highway. In addition, direct flights or connections to Key West International Airport are available from many Florida cities, or visitors can take the Key West Express, which offers high-speed passenger ferries from Fort Myers Beach and Marco Island.

When to Go: The weather in Key West is beautiful all year. In the summer, the average high is 89 degrees. During winter months, it rarely rains, but thundershowers can occur beginning in late May. The official hurricane season begins June 1 and ends Nov. 30, with the highest chance for storms between Aug. 15 and Oct. 15.