Planning a Family Trip to the Florida Keys

By Shannon Gurnee
In Florida
January 10, 2022

Today, on Redhead Mom, I’m sharing a partnered guest post about planning a family trip to the Florida Keys.

Travel to the Florida Keys

Planning a family trip to the Florida Keys is a great way to relax, unwind, enjoy the beautiful scenery and do outdoor activities and setting up an LLC in Florida can provide a legal and financial structure for your travel business and protect your personal asset. For example, popular in the Florida Keys are fishing charters and boating. Below we talk about some of the specific things to keep in mind if you’re planning a trip to this top U.S. destination for your family. 

An Overview of the Keys

The Florida Keys are a 125-mile-long chain of islands. They’re south of the tip of Florida, and Key West, the southernmost of the Keys, is just 90 miles from Cuba. 

There is one road and 42 bridges connecting these islands. 

You can drive to the Keys from Miami or Fort Lauderdale if that’s where you fly into. 

Many people decide to stay at several Keys if it’s their first time to get a feel for all of them. For example, you can go to Key Largo, one of the uppermost keys, and from there head to Islamorada, the fishing capital of the U.S. Then, you can end your trip with Key West. 

Regardless of which of the particular keys you visit, you’ll probably do a lot of relaxing paired with plenty of watersports and fishing because those are things they’re all known for. So make sure to book a boat charter and bring along your best watersports and fishing accessories!

Key Largo is the Dive Capital of the World. As mentioned, Islamorada is the Sport Fishing Capital of the World. The Seven Mile Bridge at Marathon is one of the world’s longest segmented bridges. 

Key West was home to famed writers like Ernest Hemmingway and Tennessee Williams, and the Florida Keys Shipwreck Trail links nine underwater wrecks and artificial reefs that extend from Key Largo to Key West. 

When to Go

While there’s hardly a wrong time to go to the Keys, the winter through early spring tends to be best for a lot of people. These are the peak travel months in the area. It seldom rains in the winter, while the rainier season is in the summer. The temperatures are also mild and pleasant. For example, in January, the highs are usually in the 70s. 

In the summer, there are fewer tourists, and you might get better deals, but it’s hot and humid. You also have to think about hurricane season from June 1 through November 30. 

Must-Sees in the Keys

Some of the must-sees and must-dos in the keys include the following:

  • Duval Street: Duval runs from Mallory Square in Key West to the Southernmost Point marker. It’s the famed area in Key West with galleries, cafes, museums, and shops. You can people-watch, and there are often special events here. Duval Street is also home to the Ernest Hemingway Home and Museum. 
  • Bahia Honda State Park: This has one of the best beaches in the Keys and arguably one of the prettiest in all of Florida. There are two separate beach areas, and the park spans around 400 acres. You can take snorkeling boat tours, rent beach equipment, and there are concessions as well. 
  • Dry Tortugas National Park: Accessible only by boat or seaplane, Dry Tortugas National Park is 70 miles from Key West. It’s made up of an archipelago of seven islands, and it’s home to Fort Jefferson. 
  • Earnest Hemmingway Home and Museum: This is a must located in Key West. There are more than 40 cats who call the property home, and the museum includes Hemingway’s collection of Spanish furniture from the 17th and 18th centuries. 
  • John Pennekamp Coral Reef State Park: John Pennekamp is off Key Largo. It’s one of the best places for diving and snorkeling. There’s a small shell-covered beach as well. You can take glass-bottom boat tours to see the marine life under the surface if you aren’t a diver. 
  • Dolphin Research Center: The Dolphin Research Center is in Grassy Key. There are interactive programs, and you can learn more about the care of dolphins in the area. 
  • Turtle Hospital: In Marathon, the Turtle Hospital lets you get a first-hand view of what goes into rehabilitating injured sea turtles. The education center is open daily, and you can take 90-minute guided tours. 


There is so much to see and do for families in the Florida Keys that your biggest issue is going to be narrowing it all down when you’re limited on time. It’s a beautiful place, making for a great multi-generational travel destination. If you want a more energetic atmosphere, there’s always Key West, or you can choose one of the other keys for something laid back like Marathon. 

About Has 2236 Posts

Shannon Gurnee is the author of Redhead Mom formerly "The Mommy-Files", a national blog with a loyal following. She has a Bachelor's Degree in Marriage, Family, and Human Development with a Minor in Business Management. Shannon and her husband, Frank, have a large family with 6 awesome kids and love living on the Central Coast near San Luis Obispo, California, as well as traveling around the world. A full-time Social Media and Professional Blogger, Shannon also serves as a National Brand Ambassador for many well-known companies. Her blog focuses on motherhood, family fun activities, traveling, fashion, beauty, technology, wedding ideas and recipes while providing professional opinions on products, performances, restaurants, and a variety of businesses.

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