Last updated on June 5, 2024 by Stefano Ferro, founder of MEL365, following extensive travelling in Florida, Keys & Miami

2 or 3 days in Key West based on your type of holiday

2 or 3 days in Key West will be enough time to have a great overview of the island.

In this guide, I have included 5 itineraries for 2 or 3 days in Key West with daily details for couples, families, active travellers, beach lovers or a bit of everything.

There is not much point in suggesting a romantic sailing trip to a family with 3 active kids. You get the point.

Without further ado, let’s get started

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2 or 3 days in Key West – in a nutshell

Is 2 or 3 days in Key West enough to see the island and its many attractions?

The quick answer is yes, especially if you have 3 days. You will love it. 

Do you have some spare days? Why not venturing in the other islands of the Florida Keys. 

There are 4 major islands (Key Largo, Islamorada, Marathon and Big Pine Key), all with the own character and things to do that I have described in my guides to a 5 days itinerary in the Florida Keys and 7 days itinerary too.

In this guide you will see a detail day-by-day plan for every type of trip, with the third day marked as optional (skip it if you are just 2 days on the island).

In this map below, I have highlighted the 5 areas of Key West where you will be likely to spend most of your time

Best places to stay in Key West
Best places to stay in Key West – 5 great areas
  • 2 or 3 days in Key West for couples: Key West can be such a romantic island to spend 2 or 3 days with your partner. You can experience some of the best sunset in the world, either from the popular Mallory Square or the more secluded Historic Seaport. Or why not paddling a SUP board at sunset time following the west coast or a lovely sunset cruise. Plenty of options. And for the day so many activities, besides the dreamy beaches around. Read more below on a 2 or 3 days in Key West for couples with a suggested daily plan
  • 2 or 3 days in Key West for families: this is a great island for kids with plenty of activities for the little ones and a few beaches to build sand castle and swim around, always in warm water. In 3 days you will be able also to experience some snorkeling in a shallow lagoon to see a plethora of fish. Read more below on a family itinerary
  • For beaches: Key West has some of the best beached in the Florida Keys. My suggestion for the people doing 3 days is to organise a trip to a beach outside Key West, in either Islamorada or Marathon Island. It can be done by car or public transportation.  Read more below on a 3 days beach itinerary in Florida Keys
  • For sport and action: Key West has some of the best water activities in the Keys and possibly Florida. You should also contemplate organising a parasailing session, if you are an adrenaline junk, such a great fun and gorgeous view too. SUP at sunset is also another top experience. Read more below for the history 3 days plan
  • For a bit of everything: spend one day enjoying water sports in the sea, one day experiencing the island and, if you have a third day, why not going dolphin watching in a little lagoon. Read below for more details

For great peace of mind, most, if not all, the organised activities suggested in this post have a free cancellation policy up to 24 hours from the experience.

I usually book all in advance, especially if visiting on a busy period like the school holidays. Then, if my plan changes, I cancel what I do not need anymore. Easy.

And, if you have 1 or more days, check out other 7 itineraries from 4 to 7 days in Key West.

3 days in Key West for couples

Create lasting memories with your partner by going on an adventure together.

The island of Key West has a lot to offer, from beaches to dolphins and romantic cruises.

The following is a plan you can follow to make the most of your 2 or 3 days in Key West

Day 1

Let your romance soar with a Parasailing Flight with your partner.

Enjoy the thrill of flying through the air while looking down on the blue emerald waters of the sea – and you can even fly at the same time.

You can start when it is convenient for you at the Fury booth on the pier behind Opal Key Marina.

Departures are every hour, however, book well in advance (you can always cancel free of charge up to 24 hours before starting)

Get hands-on with the marine life at the Key West Aquarium in the afternoon.

Sunset time?

Watch the famous Gulf of Mexico sunset over Key West as you enjoy a two-hour cruise aboard “The Party Cat” with live music and an open bar.

Day 2

Time to hit the beach!

Smathers Beach offers you a therapeutic experience with its rolling waves. Be sure to use sunscreen while at the beach, the sun can be quite strong.

Kayaking, tubing, and windsurfing are just a few of the activities available, if in the mood.

Would you rather not get wet?

Catch this Old Town Trolley that runs through a 12-Stop Hop-On Hop-Off Tour to see and experience the most of Key West

Is there any energy left?

If you want to experience the sights and sounds of the city, a 3-hour guided Food Tasting and Cultural Walking Tour is a great addition to your diary.

Watch the sun setting at Mallory Square, one of the most popular spots. You will not be alone

Day 3 (optional)

You can’t go wrong with a Catamaran Tour with Snorkeling & Water Activities to end your 3 days in Key West.

During your trip, you will enjoy great sailing, snorkeling at a reef, and finally you will arrive at a water park.

This is where the fun begins, with inflatable castles and the possibility to use a kayak or stand-up paddleboard (SUP) for a local exploration trip.

Sunset time? 

For an exciting adventure, take a sunset party cruise and dance the night away.

This is one of the best ways of experiencing the Caribbean nightlife by the sea.

Accommodations and experiences for couples:

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

2 or 3 days in Key West for families

Key  West is such a great place to spend your holiday with the family.

The kids will love the beach and the many activities running on the island.

Here is a plan for 2 days with an optional third, if you are so lucky to have an extended break.

Day 1

Start your holiday in Key West visiting the island with this Hop-On/Off island tour on the Old Town Trolley that stops in 12 locations, nearby the most iconic spots.

The tour includes also a complimentary ticket to the Sails to Rails Museum in the Historic Port area, a lovely boutique museum showing the history of Key West and the Caribbean transportation.

You will feel suddenly in a time machine. 

Don’t miss also a visit to the Butterfly And Nature Conservatory. Try to do it as a first thing in the morning to avoid the crowd and see more butterfly, usually very active in the early part of the day.

Plan to spend also some time at the Fort Zachary Taylor Historic State Park.

Take a few photos of the gorgeous park, explore the Fort, and see the cannons

For a cheap dinner, go to Mr Z’s (take away but you can eat there too) in Duval Street, otherwise walk to Simonton Street, a block up, for the Sarabeth’s restaurant/cafe.

Day 2

This is gonna be a great day in the sea.

What a better start than taking a morning catamaran cruise that includes snorkelling and a breakfast buffet.

In the afternoon, enjoy an interactive experience with marine life at the Key West Aquarium and a spectacular sunset at Mallory Square.

Alternatively, you can sign up for an all-inclusive full-day Watersports Adventure Tour, which will provide you with everything from jet skis to kayaks to parasailing, one of the best day experiences to have in Key West

Day 3 (optional)

Enjoy the third day in Key West on one of many beaches on the island.

The most popular beach is probably Smathers Beach, being also the longest and widest in Key West.

You have also the possibility to rent a canoe or a SUP to have some fun with the kids

Other two smaller beaches are Higgs Memorial Beach and Dog Beach, where you can do some easy snorkeling along the little pier.

Both have plenty of shadow, which is great for those hot days.

Are you not too keen on spending the whole day at the beach?

Enjoy the sunset and street performances at Mallory Square, where it will feel like a carnival. This is the most popular spot on the island at dusk.

Accommodations and experiences for families:

Snorkelling trip from Key West
Snorkelling trip from Key West

3 days in Key West for beaches

Are you looking forward to some sun and sand?

This plan will allow you to choose from several beaches to visit during your trip.

I have listed also a few options in other islands of the Florida Keys, which may work great especially if you are driving down from any other place in Florida.

Day 1

If you are traveling from Miami to Key West by car, take a pit stop at Harry Harris Beach and Park in Key Largo.

The parking is free and you will experience less people on weekdays.

Check out the sheltered cove, go snorkeling in the bay, and have a picnic on the beach.

Come with the whole family – it’s great spot for kids.

Alternatively, if you are in Key West, have a walk to Smathers Beach

There are plenty of palm trees and space on Key West’s longest beach.

The soft sand makes it also the perfect place for a stroll.

This is a typical Caribbean beach, however, it must be said that unfortunately on a few days, you can encounter seaweed and seagrass in the water.

Day 2

You have three options for day 2.

Drive or take a local bus to Sombrero Beach on Marathon Island.

Sombrero Beach is one of the largest beaches in the Keys, with calm waters, beach volleyball and restrooms. Such a chilled out spot.

Pets are also welcome there, perfect if you are traveling with your dog.

Alternatively, enjoy a full day of watersports aboard a double-decker catamaran.

From parasailing to jet skiing to kayaking, there are 12 different watersports you can try out on this action-packed day. 

With lunch and beers included, the day tour is a great deal

And finally, in case you want to just seat and relax, head to one, or both, of these two beaches.

  • South Beach (Close To The Center): known for its clear shallow waters, very family-friendly. Kayaking, paddle boarding, snorkeling, and other water sports are available as well. It is usually a calm and beautiful beach, but it can get crowded during the Island’s peak seasons.
  • Dog Beach: Every pet owner should know about this hidden gem. It’s a tiny beach but so convenient. This is the kind of beach that you and your furry friend will enjoy together. Dogs can play freely in both the water and sand.

Day 3 (optional)

Spend your last day at Fort Zachary Taylor Historic State Park Beach.

Start out by visiting the Fort Zack Army fort and learning more about its history, then hit the beach to swim, snorkel, and fish.

The area has been set up with picnic tables under the trees and a lot of room if you want to be on the sand or out in the water.

Take water sandals with you to make your life easier in the water (there are a few rocks in the sea).

The Higgs Memorial Beach Park on the west side of the island has another nice beach, although it is smaller.

Accommodations and experiences:

An empty and beautiful Smathers Beach in Key West
An empty and beautiful Smathers Beach in Key West

Three days of sport & action

Key West is an awesome place for sport and action. There are so many things you can do, including, of course, an early morning run around the island (10 miles) for the fully motivated active people.

If you are driving a car to Key West, I also suggest stopping at Keys Cable Park in Marathon Island, where you can do some wake boarding between a couple of cold beers, all with some live music in the background.

Day 1

Start your holiday with a bike tour of the island.

You have two possibilities here. You can rent and DIY to save some money (BikeMa and Fury are both good shops to hire a bike) or you can join an organised tour with a guide.

The advantage of the second option is that you will be guided through the iconic places and hidden gems of Key West that you might miss otherwise.

Once finished with the cycling and lunch, head to Paddlin’ Madeleine, just outside Key West, for a 2 hours paddleboard (SUP) tour.

I highly suggest contacting the owner to agree on the starting time (sunset is usually the best time because the paddling is on the west side of the island)

Day 2

Enjoy an early walk to the Fort Zachary Taylor State Park and the old center, up to Mallory Square.

Book your parasailing session just before lunch, for an injection of adrenaline and, of course, a unique view of Key West and the Caribbean Islands.

The afternoon is reserved for this energetic Jet Ski Island Tour, a 28 mile (45 km) ride in turquoise water around the island.

Furthermore, the second rider is free, making this a great package for friends or couples that want to ride together.

Day 3 (optional)

An action-packed Caribbean vacation would not be complete without this full-day Watersports Adventure Tour that includes sailing, snorkeling, kayaking, parasailing, jet skiing, and many more sports you would expect from such a beautiful place.

As a side note, breakfast and lunch are included in this tour.

Accommodations and experiences:

Strolling through the old streets of Key West is an experience by itself
Strolling through the old streets of Key West is an experience by itself

For a bit of everything

In this itinerary you will get to experience a bit of everything, from beaches to sport activities and, why not, a few interesting museums and iconic places you should visit.

Day 1

Start your stay on a high with this all-inclusive all-day Watersports Adventure Tour that will take you snorkelling in the Caribbean sea, paddling a SUB or riding a jetski in the calm water around Key West and finally enjoy your time in a water castle.

This is the ultimate experience for adults and kids alike.

If you have still some energy left, walk down to Mallory Square, the sunset center of Key West with such a great happening vibe.

You will have a wide selection of bar and restaurants beside the possibility of seeing a few street performers.

Day 2

Explore the island by riding your bike (renting facilities at BikeMa and Fury or join an organised tour with a guide).

Great attractions that you should not miss are:

If riding the bike is not your thing, take this Hop-On/Off island trolley tour instead.

The ticket lasts 24 hours and they have frequent runs, a much better option than driving your car around the island.

This tour includes also a free ticket to the lovely Sails To Rails Museum, which makes this package a bargain.

For sunset, go on a SUP tour just outside Key West with Paddlin’ Madeleine, the best way to close the day in an active way.

Day 3 (optional)

This is a day dedicated to the sea and the dolphins.

Join this eco tour for watching the bottlenose dolphin in their natural habitat.

Then move to a lagoon where you can do some snorkelling in shallow water.

The trip lasts around 3 hours and you will be offered a complimentary drink on the way back (beer, wine, etc). A great way to end your water experience.

Take the afternoon off at one of the many beaches around.

What is the best one?

Many locals will tell you Smathers Beach. But have a check also at Higgs Beach, just 500 meters west.

Close your holiday with a Party Cat Sunset 2-hour sail

Accommodations and experiences:

Sunset in Marathon Island
Sunset on Marathon Island
The tropical beach of Dry Tortugas, reachable by boat from Key West
The tropical beach of Dry Tortugas, reachable by boat from Key West
The iconic Alligator Reef Light House of Islamorada
The iconic Alligator Reef Light House of Islamorada
Another lovely beach in Islamorada
Another lovely beach in Islamorada
Islamorada has some amazing beaches to explore
Islamorada has some amazing beaches to explore
Another sunset on the lovely Islamorada
Another gorgeous sunset on the lovely Islamorada
Coast along the Key Largo, in the north of the Florida Keys
Coast along the Key Largo, in the north of the Florida Keys
South, North, East, West....The Florida Keys are far away from the business time in the cities
South, North, East, West….The Florida Keys are far away from the business time in the cities
It's not uncommon to spot iguanas in the Florida Keys
It’s not uncommon to spot iguanas in the Florida Keys
The old bridge connecting the Keys
The old bridge connecting the Keys
One of the new 42 bridges connecting the Florida Keys
One of the new 42 bridges connecting the Florida Keys
Sailing is another great thing to do in the Florida Keys
Sailing is another great thing to do in the Florida Keys
The best way to close this post....with another beautiful sunset
The best way to close this post….with another beautiful sunset sailing and drinking
Stefano Ferro - MEL365.com Founder and Editor

About the Author

Stefano is a seasoned travel expert and the visionary founder of MEL365.com, a leading travel website with traffic across 6 continents. With a rich background in the travel industry, Stefano spent four pivotal years at Amadeus Travel Distribution System, gaining invaluable insights into travel technologies and distribution.

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