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The Best of Key West: The Ultimate Florida Keys Family Travel Guide

The Best of Key West: The Ultimate Florida Keys Family Travel Guide

This past June my kids, hubby, and I kicked off the summer season with a relaxing 7 night family vacation in the Florida Keys. The Florida Keys is by far my family's favorite vacation spot that offers something for everyone. From laying out at the beach, snorkeling, shopping, to boating and fishing, the Florida Keys offers the best island hopping experience in the United States that are filled with both adventure and solitude making it the perfect (all in one) family vacation destination.

In my family travel guide, I will show you the best of Key West and all the perks that the Florida Keys have to offer. I will show you our favorite islands to visit, and wheelchair-friendly activities for everyone to enjoy together as you plan your next family vacation to Florida. With 7 years of experience traveling through the Keys, this is truly your Ultimate Florida Keys Family Travel guide.

What are the best family friendly Keys to visit?

The Florida Keys are so fun to visit because it consists of 1,700 islands featuring a historic overseas highway that takes you all the way down to the Southern Most part of the State in Key West.

It's arguably the best road trip you'll ever experience with incredible scenery, palm trees, blue water, beach shops, delicious restaurants, and family friendly excursions that will make your car ride super relaxing and memorable. My family has driven down the overseas highway since our son was 3 years old, and I can easily tell you it is captivating for all ages to enjoy.

Along the highway, you'll come upon the most popular Keys that are connected by bridges and are only a few minutes to a few hours apart from each other depending on what Keys you are wanting to explore. You can really sail through these islands in no time and get a lot of things checked off your itinerary without even having to stay over night if you are just planning to island hop from one Key to another.

Below is a list of my family's highly recommended islands to visit as you travel through the Florida Keys in driving order starting from Miami:

  1. Key Largo

  2. Islamorada

  3. Duck Key

  4. Marathon Key

  5. Big Pine Key

  6. Key West

Map of the Florida Keys

Florida Keys Itinerary: 7 night stay

Day 1: Arrived at Miami Airport at 9:30 am (2 hour flight from Virginia Beach, VA)

  • Depending on what state you are departing from, I would highly recommend scouting out affordable direct flights to Miami that will have you arriving in the morning or early afternoon. This will give you ample daylight time to drive to Key Largo to start your Florida Keys itinerary right away and be able to enjoy a full day in the Florida Keys.

  • We rented a Chrysler Pacifica van from Alamo as it offers sufficient room for our luggage and manual wheelchair at a reasonable price. Although my son does have a power chair, he mostly uses a manual chair especially for traveling as it's easier to fold and lift into vehicles. Traveling with a manual chair might be something to consider if ramps and special lifts are not available to you.

  • Also, we started including our handicap placard in our packing list and this has been a game changer when it comes to renting vehicles that are not marked with handicap permits and it makes parking at venues so much more convenient. In Key West, parking is free if you have a handicap permit.

Where to stay in Key Largo?

The Reef House in Key Largo. Favorite places to stay in the Florida Keys.

The Reef House Resort and Marina

For booking and resort information click here:

I cannot say enough good things about this resort. This was our second time staying here and we enjoyed it even more the second time! There landscaping is absolutely gorgeous and it looks so pretty lit up at night.

Besides the beautiful bay views and the landscaping, the resort is surrounded by local restaurants and small beach shops that are ideal for the whole family.

Resort Amenities:

  • Beach with sunset views. Most people talk about Mallory Square in Key West being the best place to catch the most amazing sunsets, but unfortunately, depending on the time of year and how the sun sets, the sunset views at Mallory Square can get blocked from an island that sits just yards away from the popular watching spot.

Here at the Reef House, it's just water meets the horizon that creates the best scene to watch the sky glow in gorgeous yellows, reds, and the prettiest shades of pinks.

  • Beach Huts and Palm trees: This resort offers enough beach huts and palm trees for shade, which makes it a fun protected place to lay out and enjoy the pool and beach all day in the hot Florida sun. Each beach hut comes with a table and outlet for charging your phones (and the best part is) they are free to use!