Florida Keys itinerary 3 days – five options with things to do based on your type of holiday

It can be quite difficult to plan an itinerary for 3 days in Florida Keys.

Florida Keys is a 137.3 square miles (356 sq km) archipelago with over 1700 islands and 42 bridges connecting the keys.

The following article provides all you need for enjoying an itinerary for three days in the Florida Keys, no matter if you’re a beach lover, a family or a couple looking for a romantic getaway, an action & sport person or just want to do it all.

Let’s get started without further ado

You can read also

Florida Keys itinerary 3 days – in a nutshell

With only three days in Florida Keys, you won’t be able to see everything in the archipelago, as you might imagine.

My recommendation is to stay either in Key West or one of the other keys.

I would not suggest moving between two accommodations, as this will eat up in your short available time

Best islands to stay in Florida Keys — Best 5 islands to stay and visit in Florida Keys – Check out my shared Google Map that you can use on your trip

Florida Keys itinerary 3 days for couples: Key Largo is surely the best destination if you are after a full on diving 3 days experience, however, if this is not the case, then you should stay in Key West and explore from there, with activities, beaches, bars and restaurants literally next door. Read more below on a full romantic itinerary
Florida Keys itinerary 3 days for families: Marathon is a great destination to be based for a family trip. You will find beaches for a relaxing time and nearby activities to take your kids too. Moreover, you could drive to the nearby Islamorada for more options or Key West for a snorkelling fun-day tour. Read more below on a family itinerary
For beaches: This is a hard choice one. There are so many beaches around. In saying that, Key West offers some of the best beaches in the Florida Keys, easy to access, all mostly within walking distance of the old centre. However, I suggest driving one day out of Key West to experience other beaches in Marathon, Islamorada or the secluded Big Pine Key. Read more below on a 3 days beach itinerary in Florida Keys
For sport and action: Although Key Largo has some of the best diving in the Florida Keys, I suggest staying in Key West and from there, drive to Marathon for an adrenaline day and experience two days of sports in and around town, with plenty of fun in the water. Read more below for the history 3 days plan
For a bit of everything: Marathon Island, right in the center of the Florida Keys is the perfect base to explore the area, from Key West and its many activities to Key Largo and its unique Scuba Diving or crocodile spotting. Read below for more details

In this post I suggest also a few organised tours and trips.

I usually book all well in advance, especially if travelling during the school holiday.

Then I cancel what I don’t need or if I change my plans (free of charge up to 24 hours prior to the experience), a great peace of mind.

Florida Keys itinerary 3 days for couples

If you want to create special memories with your loved one, bond and go on exciting adventures together.

With beaches, dolphins, and romantic cruises, Key West has it all. Base yourself there to experience all

Here is how you can plan your three days there:

Day 1 (night in Key West)

Start things on a high – literally, with Parasailing Flights for you and your significant other.

Get that adrenaline rush as you take to the skies and look down the emerald blue sea waters – and you can even fly at the same time.

Meet at the Fury booth on the pier behind Opal Key Marina, and departures are every hour – so you can start at a time convenient to you.

In the afternoon, head on over to the Key West Aquarium and get hands on with the marine life.

End your day on “The Party Cat” 2-hour cruise with some live music and an open bar as you watch the famous Key West sunset over the Gulf of Mexico .

Day 2 (night in Key West)

Beach time!

Spend your day at Smathers Beach and enjoy the therapeutic rolling waves- and remember to bring your sunscreen with you.

Plenty to do here, from kayaking, tubing, and even learning to windsurf.

Don’t want to get wet?

Go into the kayak and sail around the harbour as you check out the marine life.

Still have some energy?

Then a 3-hour guided Food Tasting and Cultural Walking Tour will be a great addition to your diary as you explore the sights and sounds of the city.

Day 3 (night in Key West)

What better way to tie off your 3 days Florida Keys itinerary than with a Catamaran Tour with Snorkeling & Water Activities.

You will get to do some amazing sailing, great snorkelling at the reef and finally you will arrive at a water park.

And this is when the fun begins, with an inflatable castle and the possibility of taking a kayak or a SUP to paddle around.

For sunset, you have two options.

Stay local and go to the Mallory Square, the most popular place to watch the sun going down.

Otherwise, close the trip off with a Sunset party cruise by Catamaran where you get to dance the night away.

One of the best way to experience the Caribbean nightlife by the sea.

Accommodations and experiences:

Hotels in Key West: Simonton Court Historic Inn (in the heart of Key West, meters from Mallory Square), The Mermaid & The Alligator (great value, a little paradise)
Airbnb in Key West: Barbary Beach House (1BR right in front of the best beach), The Laureate (1BR, great value)
Organised experiences in Key West: Parasailing Flights, The Party Cat Sunset 2-hour sail, Food Tasting and Cultural Walking Tour, Catamaran Day Tour with Snorkeling & Water Activities , Sunset party cruise by Catamaran

Another lovely old house of Key West — Lovely colonial old house in Key West

Florida Keys itinerary 3 days for families

Marathon is packed with aquariums, dive centres and dolphin encounters – and of course the sandy beaches, colourful reefs and clear waters for your family to enjoy.

Marathon Island is the best place to find your accommodation and explore from there. Let’s get on with it:

Day 1 (night in Marathon)

Go on a scenic drive across the Seven Mile Bridge connecting Little Duck Key and Knight’s Key.

While at the Knight’s Key, visit the Dolphin Research Center and interact with dolphins, sea lions, and check out the tropical birds.

Spend your afternoon on Sombrero Beach.

Have a picnic with your family, play some beach volleyball, watch the kids enjoy the clear waters and get wet yourself too – and you can even go fishing!

Day 2 (night in Marathon)

Interact with marine life at Florida Keys Aquarium Encounters through guided tours and touch tanks – and for the family members willing to get wet, go snorkelling in the coral reef.

Alternatively, drive to Key West and sign up for the Dolphin Watch and Snorkel Eco Tour, where you’re taken to natural habits of bottlenose dolphins, with a professional guide accompanying you.

Your family will be safe on the aquatic journey atop the catamaran as you check out the turquoise waters of Key West.

Day 3 (night in Marathon)

Start your day with a visit to the kid-friendly Crane Point Museum and Nature Center, where even the little ones as young as 6 get to enjoy interpretative displays of sea animals, from turtles to whales.

Head on over to Captain Hook’s Marina & Dive Center and pick up equipment for a day with the waters – from scuba and snorkelling gear, right up to chartering a boat.

Alternatively, drive to Key West and take the 12-Stop Hop-On Hop-Off Bus Tour and explore the different points of interest at your own pace.

Tickets last for an entire day, and there are frequent pick-ups at each of the 12 stops, such a great fun for kids

Accommodations and experiences:

Hotels in Marathon: Courtyard by Marriott (view and pool to die for), Seascape Resort & Marina (bargain, free kayaks, amazing pool)
Airbnb in Marathon: Skipjack Marina (1Br up to 4 people), Indigo Reef Resort (3Br up to 7 people)
Organised experiences: Dolphin Watch and Snorkel Eco Tour, 12-Stop Hop-On Hop-Off Bus Tour in Key West