Key West Itinerary: 2 Days of Fun and Relax in Paradise!

Whenever we plan a trip to Florida, we always make sure to add at least a road trip from Miami to Key West to our schedule. No matter what.
Yet while looking around for things to do, we realized there was no Key West itinerary that included all the stuff we enjoyed. So  we wrote one with all the places we go to on the island when we decide to stay for a couple of days!

Are you looking for a getaway to a tropical paradise? Look no further than Key West! Just off the southern tip of Florida, this laid-back island is the perfect place to spend a weekend away and escape the hustle and bustle of everyday life. Whether you’re a nature lover, history buff, or just looking for a simple beach vacation, Key West has something for everyone. Here’s a guide to help you make the most of your weekend getaway to this beautiful island.

Day 1: Exploring Key West’s Historic Side

Key West has a fascinating history that you won’t want to miss.
Take a walk through the historic streets of Old Town and admire the charming pastel-colored houses with their stunning architecture.

We found out through experience that even the Key West Cemetery can be a super interesting place to visit.
Especially if you’re planning to visit Florida and the Disney Parks for Halloween.
Make sure you visit the Key West Cemetery – you will not regret it, I promise!

The island has seen its share of famous residents, like Ernest Hemingway and Robert Frost.
No itinerary would be complete without taking some time to explore the former homes of these great writers.

Let me offer a few ideas on interesting things to do in Key West on your first day.

Visit the Ernest Hemingway Home & Museum

The Ernest Hemingway Home & Museum is a beautifully preserved Spanish colonial-style house.
Hemingway lived in Key West from 1931 to 1939: you’ll be transported back in time to the era when he wrote some of his most famous works.

Explore the rooms where Hemingway penned classics like “For Whom the Bell Tolls” and “The Old Man and the Sea“.
Admire his personal belongings, including his writing desk and typewriter, which still sit untouched.

Wander through the lush gardens that inspired him and even meet some of his feline companions – descendants of his beloved six-toed cat.

Yes: being a cat lover, as you might guess from many of my posts, I was ecstatic to see so many cats!

They even sit by the ticket booth, waiting for guests.
You can take as many pictures of them as you want.
We sure did and some are printed on our walls: the perfect postcards from our trip to Miami and Key West!

Opening times: The Museum is open everyday from 9:00am to 5:00pm.

Tickets: Adults – $18; Children – $7; Children 5 and under can visit the Museum for free.

Take a Historic Conch Train Tour

The Key West’s historic Conch Train Tour is a fantastic addition to any Florida Keys itinerary.
It’s a must-do also if you’re only planning to explore Key West for a couple of days!

The old town trolley tour lasts about 75 minutes, so it’s the perfect way to get acquainted with the history of Key West, its architecture and local lore.

The Conch Train takes you through the charming streets of Key West, including iconic spots like Mallory Square, Duval Street, and Hemingway’s House. 

We found it an engaging and informative experience.
Our guide provided a ton of fascinating insights into the island’s past and present.

What makes it a great addition to the perfect weekend in Key West is that it offers a comprehensive overview of the island. We used it as a starting point to plan further exploration.

Starting point: 303 Front Street Depot – The tour ends behind the same Depot, in Mallory Square.
When does it run:  From October 23, 2023: first tour starts at 9:15am; last tour departs at 4:15pm.
It’s closed the last Saturday in October due to the Fantasy Fest.
Tickets: You can buy discounted tickets for the Key West Conch Train Tour by clicking here. 

Stroll Down Duval Street

When you stay in Key West for a weekend, a leisurely stroll down Duval Street is an absolute must. After all, this is not just any street. 

Duval Street is the Key West beating heart. It will be an unforgettable experience!

Duval Street is full of an eclectic mix of shops, restaurants, bars, and historic sites. You can start by exploring the unique boutiques that line the street, offering everything from quirky Florida souvenirs to stylish clothing. 

If you’re an art enthusiast, you’ll find galleries showcasing the work of local artists, which can make for a delightful cultural detour.

One of the highlights of Duval Street is its lively atmosphere.
It’s where the action happens, especially in the evenings. 

We found street performers, live music, locals dressed in costumes who tried to scare us tourists.
Yes, Aldo almost jumped out of his skin with just a “Boo” from someone who was hiding behind a bush!

Be sure to check out Sloppy Joe’s Bar, a famous spot that was once frequented by Ernest Hemingway.
The history of the place is as intoxicating as its drinks!

As you walk around, you will easily notice a ton of dining spots.
Start looking for the perfect one where you can have dinner, right after the sunset celebration in Mallory Square.

We reserved a table at Two Friends Patio Restaurant a couple of hours before dinner, as it looked quite crowded already.
It’s a great place to go if you want to try local delicacies like conch fritters, crab cakes or coconut shrimps.
As an added bonus, at night there’s almost always live music so it will be a fun evening for sure!

Experience the Sunset Celebration in Mallory Square

As the sun descends over the Gulf of Mexico, Mallory Square comes alive with vibrant energy.

Every evening, this waterfront gathering becomes the main place to go if you want to enjoy the Key West essence.
You’ll find street performers, artisans and food vendors. 

We decided to drink an ice-cold juice while waiting for the sunset and… wow.
It’s no wonder that people from all around the world gather to witness the sky painted in hues of orange and pink as the sun dips below the horizon!
The locals actually refer to this incredible natural show as the “Key West sunset“.

The Sunset Celebration is the perfect way to end day one of your Key West weekend.
It perfectly encapsulates the spirit of the island as a celebration of life, nature and the local culture.

Don’t miss the chance to be a part of this amazing tradition!

Day 2: Adventure and Relaxation

Your second day itinerary revolves almost entirely around the ocean.
The State of Florida is famous because of its gorgeous beaches: let’s make sure we thoroughly enjoy them!

Oh, I hope you packed a ton of sunscreen: you’re going to need it!

Snorkeling, Water Sports and some tan

Wake up early and head to one of Key West stunning beaches to catch the sunrise.
Watching the sun gradually paint the sky with vibrant hues of orange and pink is a magical experience that will start your day off on the right foot. 

If you’re like me and tend to wake up a bit like a zombie, grab a cup of coffee from a local café, then find a cozy spot on the sand to enjoy the tranquil beauty of the moment.
I swear it’ll help!

No trip to Key West is complete without spending some time adventuring at its beautiful beaches. From the crystal-clear waters to the soft sandy shores, and the fishes swimming around the coral reef. All of it can be considered as one big instagrammable spot. 

A bit like shooting in Miami.
There’s no way you’ll get a bad picture!

You can take a dip in the refreshing ocean, go for a snorkeling session or simply relax on a beach towel and soak up the sun.

In case you’re an adventurous person like Al, you’ll be happy to know that there are a ton of water sports in Key West.
From reef snorkeling to parasailing, to jet ski tours and eco-kayak adventures, there’s no way you’ll get bored!

Some people think they can just “swim” to the Key West Shipwreck.
But it’s not that simple anyway. There are nine ships along what is called the “Shipwreck Trail” and you will need to be an expert diver to even get close.
In my opinion the best way to go is to book a tour or get the help of an expert guide.

Would you prefer something easier?
Visit the Key West Shipwreck Treasure Museum!

Bonus: Relax at Fort Zachary Taylor Historic Beach

Many of you asked me about the best beaches on the island.
So let me be a bit more specific by telling you about the one we absolutely loved.

Fort Zachary Taylor Historic Beach can be considered one of the hidden gems in Key West.
It seamlessly combines history with natural beauty. 

You can explore the historic fort, which played a pivotal role in the Civil War, and admire the well-preserved cannons and fortifications.
Or just relax.

The crystal clear waters and sandy shores provide the perfect backdrop for relaxation and water activities like snorkeling.

Parking is available at the entrance.
With $6 per vehicle you’ll be able to safely park your car and enjoy a day at this amazing beach.
The experience is worth every penny!

What makes Fort Zachary Taylor Historic Beach truly unique is its ability to transport you back in time while offering a beach experience that’s second to none.
In our opinion there’s nothing else like it on the island.

Entrance fee: $6 per vehicle
Opening times: every day, from 8:00 am until sundown. For reference, you will be asked to leave by 5 pm.

Explore the Key West Lighthouse and Keeper’s Quarters Museum

On your second day in Key West, one of the historical gems not to be missed is the Key West Lighthouse and Keeper’s Quarters Museum.
This iconic structure stands tall and proud, offering a glimpse into the island’s maritime heritage.
I think it’s the best way to spend an interesting afternoon away from the crowds.

For reference, consider this is super close to the Hemingway Home and Museum.
So you can definitely add it to yesterday’s itinerary if you move the Conch Train Tour to the second part of your itinerary!

The adventure begins with a climb to the top of the lighthouse, which rewards you with breathtaking panoramic views of Key West and the surrounding turquoise waters. 

As you ascend, you’ll learn about the lighthouse’s rich history and its crucial role in guiding ships through the treacherous waters of the Florida Keys.

Next to the lighthouse, you’ll find the Keeper’s Quarters Museum, a beautifully preserved piece of history.
This is where you can explore the life of the lighthouse keepers and their families who braved the elements to ensure the light never went out.
It’s like stepping into a time capsule!

How long does it take: Consider at least 1 hour for the full tour.
Opening times: Monday to Sunday from 10:00 am to 5:00 pm. Last admission at 4:30 pm.
Tickets: Adults – $17; Children from 7 to 18 – $9; Senior/College ID/Locals/Retired Military – $13M; Children under 7 and active military can visit for free.

Go on an Evening Boat Cruise

Booking an evening boat cruise in Key West is an essential ingredient for an unforgettable weekend, whether you’re with your significant other or exploring solo.

As the sun dips below the horizon, these cruises offer a magical way to witness the enchanting twilight vistas over the Gulf of Mexico.

The gentle sea breeze, the colors painting the sky and the serene waters create a romantic ambiance that’s hard to beat.

It’s not just a journey: it’s a sensory experience, a moment of tranquility that lingers in your memory, making it the perfect way to cap off your Key West adventure.

This one here is the catamaran sunset cruise we tried and we loved every second!

While it can be a bit busy (here you can check the best time to visit Key West and Florida to avoid the crowds), it’s a very good deal.
Especially because you can keep your travel plans flexible with the free cancellation policy.

The cruise takes about two hours and as a bonus it offers an unlimited open bar, as well as delicious appetizers you can eat with your fingers (including veggie treats!).
As you watch the sunset, there will be live music: you can dance and have a ton of fun!

Click here to check rates and availability.

Optional Day Trips and Activities

I’m a big fan of having extra options wherever I go, for a number of reasons.
Maybe I don’t feel like doing something, maybe it’s raining, or maybe I just don’t want to go to the beach.

The following activities can be used as ideas for your next trip or to fill an extra day in case you have decided to spend 3 days in Key West instead.
I hope these can be useful!

Day Trip to Dry Tortugas National Park

In case you have a full day ahead, I think a visit to Dry Tortugas National Park is an absolute must when you’re in Key West, Florida.

You can easily catch a ferry from Key West to Dry Tortugas National Park.
Or a seaplane, that’s also an option!
It should take you a bit more than 2 hours to get there.

Once at Dry Tortugas, you can explore Fort Jefferson, a historic coastal fortress, snorkel in the crystal-clear waters, and relax on the pristine sandy beaches.

To make the most of your day trip, allocate at least 5-6 hours, including travel time, and be sure to make reservations in advance. 

It’s a memorable adventure that combines history, natural beauty, and marine wonder, all within a day’s reach from Key West!

Opening times: The park is always open. I suggest you always double check for sudden closures by checking the NPS website.

Tickets: $15 per person. The entrance fee is valid for 7 consecutive days. Visitors under 16 won’t have to pay for a ticket.

Discover Key West’s Culinary Delights: Key Lime Pie and More

Some extra time in Key West can definitely be used for a food tour.

The one we booked for ourselves lasted about 3 hours and it wasn’t just a food tour. It was also a cultural experience that we absolutely loved.

Our guide, Don, was a local who walked with us while telling us all about the way they actually cook traditional dishes on the island, how they pronounce “conch” and why it’s an absolute delicacy.

He stopped whenever we wanted to take pictures and he gave us tips on how to avoid the tourist traps on Duval Street that we actually still use whenever we go on a trip to Florida Keys.

The food tour includes 6 dishes from local eateries and family restaurants. The kind of places where the locals go to.
As a final gift we were also given an electronic guide with a ton of recommendations on where to eat in Key West, and an ebook with a collection of recipes to replicate the Key West signature dishes at home.

If you have enough time and you love some fun to go with your lunch, by all means, this is a tour you can’t miss!

Click to check out rates and availability.

See Key West Dolphins on an Eco-Tour

We visited the Florida Keys a number of times. So once, when we had a little free time, we decided to book a dolphin-watching cruise from Key West.
It was a lot of fun and an amazing way to spend half a day by doing something different.

In case you’re short on time, consider that this eco-tour will take at least 3 hours, but often it’s a bit more.

You will embark on a fast catamaran, to cruise the Gulf of Mexico, looking for sea flora and coral formations.
Until the first pod of bottlenose dolphins will start swimming and jumping all around the boat.

Seeing them free to have fun in the shimmering turquoise waters of the Gulf was absolutely amazing!
Make sure you bring your camera because you’ll want to take a ton of photos and videos!

The second part of the tour includes the Key West Wildlife Refuge, where you can snorkel in the shallow backcountry waters. 

Why did I mention “Eco-Tour“?
Because this is possibly the only local tour with a “Dolphin SMART” certification. It’s a US program that protects and promotes the responsible observance of dolphins.

Click here to check rates and availability.

Visit the Southernmost Point of the Continental U.S.

The Southernmost Point Buoy in Key West marks the southernmost point in the Continental United States.
Just 90 miles to Cuba!

You can reach the buoy easily, by foot. It’s located not too far away from the Key West Butterfly and Nature Conservatory.
So you can watch the butterflies first, and then you can go take a ton of pictures at the Southernmost Point of the Continental USA, all in max 1 hour!

Where to Stay and Eat in Key West

Best Hotels and Accommodations in Key West

A weekend in Key West means you’ll need to sleep on the island for at least a couple of nights.

I have 3 hotels I can recommend, which are all located in or near the Key West historic district.
Because the truth is that we always chose to spend the night in the Old Town!

While there are a ton of absolutely amazing hotels, these are the ones we personally tested and liked.

• Seascape Tropical Inn (within walking distance from many of the places I mentioned in this article)
• Hyatt Centric Key West Resort & Spa (beachfront and a 5 minutes walk from Mallory Square)
• The Duval House (Caribbean style, very nice for its rates)

Top Restaurants and Dining Experiences

At the end of the day, no trip to Key West would be complete without some classic Key West cuisine, am I right?

Here’s what we can easily recommend for a short weekend on the island.
Make sure you try some of the authentic Key West dishes such as the Key Lime Pie, conch fritters and even Cuban sandwiches!

• Two Friends Patio Restaurant for conch fritters after the sunset celebration in Mallory Square
• Kermit’s Key West Key Lime Shoppe for the best Key lime pie ever
• Key West Cuban Coffee Shop for Cuban sandwiches and cafecito
• Hot Tin Roof for a romantic dinner on the porch at sunset
• Kaya Island Eats for delicious fish tacos and Jamaican chicken wings

How many days do you need to visit Key West?

Key West is a tropical paradise tucked away in the southernmost tip of Florida.
Driving there from Miami is like finding a hidden treasure chest at the end of a wild goose chase.

Only instead of gold coins, you’ll be rewarded with crystal clear waters, vibrant sunsets, and a whole lot of margaritas!

But how many days should you spend in this slice of heaven?
Me and Aldo have been often enough to Key West that we think we can offer a few useful tips that might help you decide. 

Some would argue that you need at least a week-long escape to truly enjoy this gorgeous island.
According to our experience, 2 days in Key West are absolutely perfect.
For a number of reasons.

The first being the fact that the Florida Keys are amazing so you might want to consider exploring also the other islands.
Like Islamorada, which is one of our favorite places to be!

Key West is a place where you can rest, relax and enjoy the ocean.
But there’s so much more than that, especially if you, like us, are a fan of water sports and natural wonders. 

Why 2 days in Key West are a great idea

No matter what you choose to do for your weekend getaway to Key West, you’re sure to have an unforgettable experience.

With its sun-soaked beaches, warm waters, and rich history, this island paradise is the perfect place to unwind and escape everyday life.

So grab your sunglasses and sunscreen and get ready to explore this slice of paradise!

Enjoy Your Perfect Weekend Getaway!

Pin it for later!