Florida Keys itinerary 4 or 5 days – itineraries with things to do based on your type of holiday

This archipelago offers some of the most beautiful beaches in the United States and some of the best diving and snorkelling in the country.

But can you experience it all with a Florida Keys itinerary of 5 days, or even less 4 days.

Let me be honest with you. You need more time.

In saying that, if you plan well in advance, you will be surprised at the number of things you can do and the number of places you can take in throughout your 4 or 5 days in the Florida Keys.

This guide will help you plan your itinerary to suit your interests, whether you are looking for romantic spots, a family vacation, the best beach time or just a bit of everything..

Now let’s get started

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Florida Keys itinerary 4 or 5 days – in a nutshell

I recommend not changing accommodations more than once, if you are only staying for four or five days in Florida Keys.

In this way, you do not have to pack and unpack or check in and out of hotels or Airbnbs, which can be time consuming.

Below is a map of the archipelago, along with the islands and attractions that I will describe in this post.

I have added an optional day (day 5) to every plan I describe in this post in case you want to trim the Florida Keys itinerary of 5 days down to just four, or if you just want to relax for one day.

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 5 days for couples: with 4 or 5 days, I would suggest splitting your stay between Key West and Big Pine Key. In Key West you will find plenty of activities, bars and restaurants. In Big Pine Key, you will find seclusion and privacy on a romantic beach literally for yourself. Read more below on a full romantic itinerary
Florida Keys itinerary 4 or 5 days for families: With children, I would suggest staying in one accommodation only, and exploring from there. I well know the hustle to move bags, sports gear and toys with kids 🙂 The island of Marathon is the perfect spot for a family trip. You can enjoy the beaches and nearby activities for a relaxing time with your kids. Furthermore, you could take a day trip to Islamorada or Key West for a snorkeling adventure or swimming with the dolphins. Read more below on a family itinerary
For sport and action: The two best islands to be based are Key Largo, for some of the best diving in the Florida Keys, and Key West where you will find plenty of sport and action. On the road from Key Largo to Key West you find also one of the most exciting places in the Florida Keys. Read more below for the 4/5 days plan
For a bit of everything: split your stay between Marathon Island and Key West to enjoy the best attractions that Florida Keys can offer, including unique Scuba Diving or crocodile spotting. Read below for more details
Main attractions in the Florida Keys: Are you just interested to the attractions and experiences of the archipelago? Check out my extensive post on 33 things to do in Florida Keys.

Florida Keys itinerary 5 days for couples

My recommendation would be to book your first part of the stay in Big Pine Key and then move to Key West.

Seclusion and privacy are guaranteed on Big Pine Key, with romantic beaches literally for you

Key West offers lots of opportunities for entertainment, bars, and restaurants.

Day 1 (overnight in Big Pine Key)

Start your trip by exploring the waters and having a picnic at Ramrod Swimming Hole.

It’s a hidden gem where you can spend an entire day relaxing at.

There’s plenty of fish, and you can go swimming and snorkelling.

Check into the Deer Run on the Atlantic, a private adults-only B&B beachfront that’s a favourite for couples.

Mark your first night here with a themed dinner for you and your significant other, relax in a jacuzzi and bond away from the work and obligations of your day-to-day life in this 4 Palm rated resort.

Day 2 (overnight in Big Pine Key)

Visit the 9,200-acre National Key Deer Refuge Nature Center – and it’s best to get there in the morning to see lots of deer as they stroll about.

In saying that, even around midday, drive down Key Deer Blvd to the Blue Hole and you will be able to spot a few.

Today’s beach time will be spent on Horseshoe Beach, a protected snorkeling place with clear waters, plenty of marine life including starfish, urchins and fish species.

As the night sets in, drive to the No Name Pub along Watson Boulevard, an old school bar.

Those dollar bills stapled on walls and the ceiling, and well wishes hang all over by patrons, are testament to how incredible the spot is.

From hot tuna dip appetisers, burgers, fried shrimp and loads of seafood, Bloody Marys and pizzas – there’s plenty to dig into, capped with great service and a nice island atmosphere.

Day 3 (overnight in Key West)

It is time to move to Key West and explore the underwater world with your significant other.

Different snorkelling tours are available to pick from, like

the Key West Double Dip aboard the Fury catamaran;
dolphin watching and snorkeling in the Key West National Wildlife Refuge or
the round-trip catamaran ride allowing you to explore Florida Keys Reef

For the evening, hop aboard “The Party Cat” and catch the famed Key West sunset as you enjoy open air live music, tropical food buffet and open bar.

After dinner, head to the upper deck and dance to your heart’s delight.

Day 4 (overnight in Key West)

Beach games and water sports – get it all on this day at Smathers Beach.

Swimming, kayaking, fishing, diving and snorkelling excursions – a few facilities at the beach make it easy to engage in any of the activities.

This time watch the sun setting over the Gulf of Mexico while on a state-of-the-art party catamaran.

Loads of snacks, live music, free drinks from ice cold margaritas and beer to wine and champagne – you get it all on this cruise.

Day 5 (optional day in Key West)

Have a picnic on the Fort Zachary State Park beach.

It’s a spot to enjoy the sun n’ sand – as well as the views.

Take this day to relax and cosy up with your partner.

Still around for another night?

Then meet up with other revellers to take on a sunset sail – but now on the 105-foot schooner America 2.0.

Sit back with your loved one and experience the “Green Flash” sunset phenomenon as you glide through the sea.

Accommodations and experiences:

Hotels in Big Pine Key: Deer Run on the Atlantic (romantic, secluded, free kayaks & bikes), The Barnacle B&B (on the water), Sunshine Travel Trailer (1BR, a unique experience)
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: Key West Fury Catamaran, dolphin watching and snorkeling, round-trip catamaran ride at the reef, “The Party Cat” for sunset, 105-foot schooner America 2.0

Paddling on a SUP north of Key West on another magical sunset

Florida Keys itinerary 5 days for families

It would be best to stay in a single accommodation when traveling with children, and explore the area from there.

The island of Marathon is the perfect place for a family vacation, considering the hustle and bustle of moving bags, sports gear, and toys.

Day 1

Kickstart your trip by bringing your family face-to-face with dolphins at the Dolphin Research Center.

Watch them play and engage in their interactive programs – from simply shaking the fins to outrightly swimming with them.

A family favourite with the Dolphin Dip, where you get on a submerged platform, give the dolphins back rubs or flipper shakes, then break into a dance.

For your first night, hang out by the waters and enjoy the full moon at Sparky’s Landing.

This waterfront spot is packed with loads of seafood and live music sets the ambience.

Enjoy entertainment from the local musicians, and if you arrive early in the evening, you can catch their happy hour specials.

Day 2

No trip to the Keys is complete without cruising on the Seven Mile Bridge – if only just for the panoramic views.

The historic structure dates to the early 1900s, and gives you magnificent views.

Spend the day at Sombrero Beach where there is something for everyone – swimming, picnics, beach games like volleyball, playgrounds for kids, and it is even pet friendly.

What about some trivia with the family when the night sets in?

Head out to Havana Jack’s Oceanside that’s set right on the ocean with great sunset views.

If your trip falls on a Tuesday, this is the spot to be for trivia night, which will be great to do with the grown-ups.

The live music every night makes it a relaxing spot to hang out with your loved ones.

Day 3

Head over to Florida Keys Aquarium Encounters to get hands-on with dolphins, stingrays and other marine life – and you can even swim with them for the extra thrill.

Thereafter, visit the Turtle Hospital for you and the kids to learn about the welfare and rehabilitation of the sea turtles.

Spend the rest of the day at the beachside Curry Hammock State Park camping – and be sure to catch the sunset.

Day 4

Tour and culture day!

Visit Pigeon Key for a walk through history at the island’s museum, and delve more into marine science at the Pigeon Key Foundation & Marine Science Center.

At Crane Point Museum, Nature Center and Historic Site you’ll get deeper into the area’s cultural and natural history, covering both that of the wildlife and the indigenous people of the region.

There’s a pirate ship built for kids to explore, too.

Day 5 (optional day)

It’s time to drive to the popular Key West for a morning snorkeling tour on the world’s third longest coral reef.

The tour comes complete with breakfast and mimosas.

Drive back to Marathon and on the way stop at the Bahia Honda Key seafront state park, peaceful and snugly.

It’s got views and great activities like kayaking.

For this evening, head to Lorelei’s Restaurant and Cabana Bar in the Islamorada.

Sure, it’s not quite inside Marathon, but it can give your family a unique experience on your visit to the area.

The restaurant is located right on the water.

There are plenty of sitting areas for groups and since the tables are set close to the water, you can get right up during the dinner and check out the boats.

Live music, great food, and even the occasional treats like a magician’s performance – the kids will love it.

Visit the marina just next door and gift shop to check them out as you wait for seats in case you arrive and find it packed, or even when you just want to stretch your legs.

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: Morning snorkeling tour leaving from Key West

Four or 5 days of sport & action in Florida Keys

Split your stay between the two most active destinations in the Florida keys: Key Largo and Key West

Key Largo is the place to be for scuba diving, even if you are a newbie or you just want to try it out. If you can, make it to the very famous statue of Christ of the Abyss, magnificent.

Key West is surely the best base for any kind of sport activities and exciting experiences.

On the way, from Key Largo to Key West, stop for some wake boarding in Marathon.

Day 1 (overnight in Key Largo)

Drive your way to the first accommodation in Key Largo.

Check out the Florida Keys Visitor Centre for the latest news and happening in the area. Always a great source of information.

Then it’s time to swim with the dolphins at the Dolphin Plus Bayside.

It is not certainly a budget option, but surely unique.

Then go to the Rainbow Reef Dive Center to get ready for the day after.

I highly suggest contacting them days or even better weeks in advance to book your dive.

Do you still have some spare time?

Head to the interesting Crocodile Lake National Wildlife Refuge for a visit or to the Far Beach for a swim.