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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: https://www.reefhousekeylargo.com/


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!


Although the huts are on a first come first serve basis, we never had a problem finding one available. However, it's never a bad idea to mark your spot early if you are planning on having full pool and beach day with your family.


The Reef House Cabanas are the perfect place to eat lunch by the pool and eat good food and drinks.

The Reef House of Key Largo is a beautiful place at night. Cabanas and Tiki Huts for laying out in the sun and relax in the evening.


  • Sports and Water activities: The resort offers guest services for kayaking, jet skis, fishing, snorkeling, and boating excursions.


  • Recreation: The resort also has an outdoor volleyball and basketball area, shuffleboard, and life size yard games like chess and connect 4 that is fun for the whole family.


The Reef House of Key Largo is family friendly with shuffleboards, lawn games.


The Reef House of Key Largo is our favorite place to snorkel, paddle board, and jet ski. The best Florida Keys travel guide.

  • Restaurants: Flipper's Pool Bar, Gus' Grill, Key Largo Dining, Breezer's Tiki Bar

We mostly ate at Flipper's Pool Bar which provides beach side service, but we did try a few nearby local restaurants this past stay that we fell in love with.


Our favorite local restaurants to try in Key Largo

Tower of Pizza- get the tropical pizza with banana slices, so yummy! https://www.towerofpizzakeylargo.com/

The Fish House- try their hogfish, amazing! https://fishhouse.com/



Day 2: Full day in Key Largo

Our 2nd day was a non traveling day, so we mostly hung out at the resort's beach and pool enjoying poolside drinks and food.


The nachos at Flipper's Pool Bar with blackened chicken and shrimp are unbelievable! This is not your usual soggy nacho dish, this is upscale luxury eating at it's best! So good, we got seconds!


At night we walked around the resort and played shuffleboard and volleyball while enjoying the pretty lights.


Helpful tip: If you are looking to float in the relaxing water, check out the local Walgreens or beach shops for pool rafts. These are easy to inflate and deflate and pack with you on the go. We used this one here throughout our Florida Keys island hopping vacation which provided a restful way to get our disabled son in the water with us. So worth it!

Florida Keys offers a lot of wheelchair friendly activities for the family. We love the Reef House of Key Largo's pool and food menu, and water activities.

Things to do near Key Largo

Theater of the Sea- dolphin show, bird show, turtles, seals and beach

John Pennekamp Coral Reef State Park- snorkeling, scuba diving, and glass bottom boat tours


Day 3: Boating Day in Islamorada

Islamorada is centrally located in the Keys and is surrounded by marinas, boats, and spectacular views making it our favorite place to stop and eat. According to Google, it is dubbed the fishing capital of the world with more fishing boats per square mile than any other place in the world.


On our past Florida Keys vacations we would stop and eat at Islamorada Fishing Company as we head down to Key West, but this time we wanted to try something new.


My hubby booked us a private charter through a google search that was wheelchair accessible and ended up being the highlight of our vacation!


What to do in Islamorada?

We booked our first fishing charter with Captain Mick Nealy. Wheelchair accessible pontoon boat.

Book a boating excursion

For special needs boating accommodations click here https://captainmickswateradventures.com/


We scheduled our very first private charter this past trip and had an incredible time. Captain Mick Nealy is associated with the Active Disabled Americans and has such a big heart for providing boating accommodations for the handicap. This charter is specifically designed for individuals in wheelchairs to be able to bring their wheelchairs on deck and enjoy the day fishing, swimming, and boating in the clearest blue waters signature of the Florida keys.


My son had the most amazing time learning so much from Captain Mick. Captain Mick took us through a bird sanctuary, a deserted island, and by a popular fishing spot where my son reeled in 10 snappers during our time out in the waters. We did a half-day excursion and found it to be one of the best things we had ever done for our son who is wheelchair-bound. We ate breakfast before we arrived on the charter and brought plenty of boat snacks, sunscreen, and drinks. Captain Mick had a large cooler filled with ice, so we were able to have cold drinks available.


Captain Mick with the Active Disabled Americans offers affordable charters for people with special needs in wheelchairs. He finds the best places to catch fish.

Captain Mick giving us a fishing boat tour in Islamorada. We visited a ship wreck and a bird sanctuary.

The boat is a fiberglass pontoon boat with a canopy for shade. Captain Mick provided the fishing poles, bait, snorkels, and life jackets so you basically don't need to bring anything other than towels, snacks, and drinks for your boating excursion.


Our charter ended at 4 pm. since we started a little later in the morning around 10 a.m. It was a super casual experience and designed to fit the needs and accommodation of the participants with special needs.


Since we ended at 4 p.m. we found that it was the perfect time to drive to our next destination for the night in Duck Key.


Where to stay in Duck Key?

Hawk Cay resort is a beautiful property to visit in Duck. This was one of our hotels we stayed at on our recent Florida Keys Vacation.

Hawk Cay Resort

For booking and resort information click here https://www.hawkscay.com/


Hawk Cay Resort ended up being a place we enjoyed the grounds for 24 hours as we made it our second pit stop before ultimately heading all the way down to Key West.


Hawk Cay Resort is more like a community vibe where you can rent golf carts to tour the island and have villas available as an option to sleep in if you didn't want to stay in the hotel. The pool area is large with a tiki bar restaurant and fun beach lagoon where you can paddle board and swim.


Next to the lagoon is the dolphin encounter pier where you can schedule hands-on dolphin experience. We opted not to do this as we had already done this experience before on another vacation.


However, if you really want to see the best dolphin show in the Florida Keys that out beats Seaworld, I highly recommend visiting the Theater of the Sea as mentioned above! Hands down the best dolphin show I've ever seen.


Amenities

Tennis Courts

Water Sports


Food Near By

Angler and Ale


We just ate at the poolside Tiki bar and it was pretty tasty and lovely service. The staff were so friendly and happy to help.


Day 4: The Drive into Key West

We left Duck Key right after check out which was at 11 am. We ate breakfast by the pool before getting on the road (the fewer stops the better sometimes). Especially during this point of the trip when it's mostly bridges and wildlife. The panoramic view from the world-famous 7-mile bridge is so serene.


There are definitely places to stop along the way from Duck to Key West, but there's something so special about the peaceful scenic drive to Key West and the exhilarating anticipation of getting to your next destination.


Where to stay in Key West?

Our favorite place to stay in Key West is the Pier House. It has it's own private beach.

The Pier House Resort

For booking and resort information click here https://www.pierhouse.com/


This was our second time staying at the Pier house and won't be our last. This is THE SPOT if you like a beach where you can actually go in the water. Most people don't know this about Key West, but there's not too many hotels there that offer beach amenities.


Since the island is mostly surrounded by marinas and boats, only a few hotels have access to a sandy beach. And from our many years of traveling to Key West, we have learned by trial and error which hotels are the best for beach access. Although the Southern Most Hotel is a top contender, the water there can unfortunately get murky and full of seaweed depending on the wind direction. We've stayed there a couple of times and really love the resort, but the beach can be a real bummer if it's churning up mucky seaweed.


However, we never came across this issue at the Pier House. The resort is located on the bay side of the island near Mallory Square and the Boardwalk Marina, so the wind direction is ideal for clean blue water.


The beautiful beach at the Pier House Resort in Key West. Live music and poolside food service.

Beautiful blue water at the Pier House in Key West. It has a floating dock fun to jump off of or sunbath.

Day 5-7: The best of Key West

Family things to do in Key West?

  • walk the boardwalk at the marina, we did this nightly post-dinner meals

  • visit Kermit's Key West Key Lime Shoppe

  • watch the sunset at Mallory Square

  • Tour Ernest Hemingway's house and pet the 6-toed cats

  • Visit the historical lighthouse

  • ride the conch train and tour the island

  • stand in line to take a picture at the famous mile post 0 buoy

  • schedule a boating excursion, snorkeling, sunset, fishing

  • Jet ski-if the water isn't choppy

  • Plan a beach day at Smathers beach, check wind direction for seaweed and schedule a day with the clearest water

  • Window shop and collect souvenirs on Duval Street

  • rent a golf cart and drive around to your favorite spots

  • rent bikes

  • visit the aquarium

  • try the Flying monkeys smoothies (non-alcohol choices are available for the family)

  • tour the Butterfly garden

  • satisfy your sweet tooth at Sugar Kingdom


We love to visit Hemingway's House and the six toed cats. Beautiful landscaping and tour.


The Best family-friendly Restaurants in Key West?


Blue Heaven restaurant in Key West.


How many days are needed for a Florida Keys vacation?

If you plan to island-hop and stay at different hotels on your way down to Key West, then I would recommend at least 5-7 nights.


If you plan to just take a few pit stops with no overnight stays, then 4 nights in Key West is doable to sightsee and capture the whole island. Plus, you can always plan to stop at different places on your way back home if you didn't get a chance to see and eat at all the places on your itinerary driving to Key West.


The three places I would highly recommend to visit on your way down to Key West are: the Theater of the sea, the Islamorada Fishing Company, and Robbie's in Islamorada.


These places are filled with adventure, clean bathrooms, great for walking around, easy to park, and wheelchair accessible.


What other hotels would you recommend for a family friendly vacation in Key West?

  • Southern Most Hotel

  • Rent a home off of Duval street

  • Margaritaville Beach House Key West


I hope you found this Key West travel guide to be resourceful as you plan your next family vacation in the Florida Keys. It's a beautiful peaceful place near and dear to our hearts and a place we believe you will enjoy as well..



"We could have gone anywhere we wanted to this summer. Anywhere in the world. But when I asked my kids... Kids, remember when I asked you where you wanted to go on vacation? What did you say?" - Clark Griswald


My Kids: "Florida Keys Dad!"