The Ultimate 3 Day Key West Itinerary (With a Map of Key West)

Are you planning your ultimate Key West vacation but not sure where to start? Keep reading!

In this 3 Day Key West itinerary, I cover all the details you need to know to plan your dream vacation to Key West. I’ll go over the best areas to stay and different hotel options, the top restaurants to check out, and all the fun activities you need to do!

Plus, I’ve organized it all into 3 perfect days so you don’t need to do any more planning or research!

In my opinion, 3 days is the perfect amount of time to spend in Key West for first-timers. 3 days gives you the opportunity to soak in the atmosphere, explore the main sites, and go on 1-2 excursions if you wish!

So whether you’re a history buff, a nature enthusiast, or simply seeking the perfect beachside retreat, this Key West itinerary is designed to make the most of your time in the Conch Republic!

Note: This post contains affiliate links. If you click an affiliate link or book through an affiliate program, I receive a small commission at no cost to you!

The Ultimate Key West Itinerary: 3 Days in the Conch Republic

Where to Stay in Key West

Before we dive into this Key West itinerary, let’s talk about where to stay in the famous Key West!

Key West is only 4 miles long, so you might be thinking… how many places can there possibly be to stay? The answer is… a lot!

Key West has a few diverse neighborhoods, but the first decision you’ll need to make is whether you prefer the historic charm of Old Town or the modern amenities of New Town. These two areas split Key West down the middle: the eastern half and the western half.

Most people want to stay in Old Town to be near the action, but there are pros and cons to both areas, which I’ll dive into in the next sections!

Staying in Old Town Key West

For those seeking a slice of Key West’s rich history and vibrant atmosphere, Old Town is the ideal choice. This area is known for its charming streets lined with Victorian-style houses, art galleries, and boutique shops.

When staying in Old Town, you’ll be steps away from the iconic sites. You can explore the Hemingway Home and Museum, soak in the vibrant energy of Mallory Square, and party the night away on Duval Street, then walk back to your accommodation!

Here is a list of the top Old Town Key West hotels, but you can also check out your options on the map above! Old Town has tons of vacation rental and B&B options as well as typical hotels!

Almond Tree Inn (Moderate)
Ocean Key Resort (Moderate/Luxury)
The Mansion on the Sea (Moderate/Luxury)
Pier House Resort & Spa (Moderate/Luxury)
Marquesa Hotel (Luxury)
Casa Marina Key West (Luxury)

If you’re staying in Old Town, I recommend skipping the rental car. You’ll be able to access everything you need via walking or biking. Parking in Old Town can be difficult and expensive, so it’s better not to have a car!

However, if you plan to visit other Keys during your stay, you’ll definitely need a car! I recommend doing an epic road trip from Key Largo to Key Wes t so you can experience all the Keys have to offer!

Staying in New Town Key West

If you’re driving into the Keys, New Town is the first area you’ll come across. It’s where the airport is located, along with most of the “chain” hotels. This area is characterized by wider streets, modern conveniences, and a quieter ambiance compared to the lively energy of Old Town.

New Town provides a more relaxed environment, making it an excellent choice for those looking to unwind after a day of exploration. It’s also convenient for those who prefer to have modern amenities at their fingertips.

Hotels in New Town also tend to be a bit cheaper than those in Old Town!

Even though it’s a bit further away from the main Key West attractions, you still may not need a car if you’re staying in New Town.

This is because most of the hotels in New Town have free shuttles to Old Town that run multiple times a day. These shuttles make it easy to visit Old Town without having to worry about parking, or drinking and driving!

Here is a list of the top hotels to check out in New Town Key West!

Havana Cabana at Key West (Budget/Moderate)
Parrot Key Hotel & Villas (Moderate)
Margaritaville Beach House (Moderate)
The Perry Hotel and Marina (Moderate)
Hilton Garden Inn (Moderate)

How to Get to Key West

If you’re planning a Key West vacation, you’re going to need to know how to get there! There are a couple of options when it comes to traveling to Key West.

The Key West International Airport (EWY) is extremely convenient to fly into. It’s located right in the heart of New Town and just minutes away from Old Town. If you have the option, I highly recommend flying into Key West.

However, you may find that flights into EWY can be a little pricey. While there are direct flights from around the country, it is still a small airport, which tends to mean higher prices. Airlines like Silver and Allegiant often have cheap, direct flights though, so check to see if they fly out of your home airport!

The other option is to of course: drive! If flight prices into Key West Airport are too high, you can look into Miami Airport (MIA) or Fort Lauderdale Airport (FLL) and then make the drive down to Key West.

I touch more on this in my Ultimate Florida Keys Travel Guide, but I highly recommend this route so you can experience ALL of the Keys, not just Key West. The best option is to fly into Miami, rent a car, and make the drive from Miami to Key West.

Once you arrive in Key West, you can drop off your rental car and fly out of the Key West airport, so you don’t have to drive the length of the Keys twice!

Key West Map

Lastly, before we get into this Key West itinerary, here is a detailed map of Key West! It includes all of the restaurants, bars, and landmarks mentioned in this itinerary, plus more!

Make sure to save this map of Key West to your own Google Maps so you can access it during your trip!

Day 1: Brunch, Historic Sites & a Sunset Celebration

Blue Heaven + Exploring Old Town

Today is your first full day in Key West! Welcome to paradise!

Start your morning by heading straight to Blue Heaven, one of the most popular restaurants. They open at 8am, and I recommend getting there as close to opening as possible. If you show up later in the morning, be prepared to wait!

I highly recommend getting the Lobster Eggs Benedict and a slice of their GIANT Key Lime Pie!

After breakfast, it’s time to walk around Old Town Key West and explore the historic sites. There are a ton of things to do in the area, so you can choose a few (or all!) of them to fill your morning. Here are a few options!

Climb to the top of the Key West Lighthouse
Snap a picture at the Southernmost Point
Tour Ernest Hemingway’s Home & Museum
Explore the Key West Butterfly and Nature Conservatory

There are also some great lunch spots around this area, including The Lobster Shack, the Seaside Cafe at the Mansion, and Louie’s Backyard!

Beach Relaxation & Sunset Views

In the afternoon, head over to Fort Zachary Taylor State Park, a 19th-century fort and park located on the southern edge of Key West. Starting at $4.50 per person, the park is a great place to spend an afternoon.

There is a beautiful beach within the park where you can swim, lounge, and even snorkel! Plus, you can explore the fort’s grounds and learn about the incredible Civil War history.

To finish off your day, make your way to Mallory Square and witness the famous Sunset Celebration. This is the most famous place to watch the sunset in Key West, so if you want a front-row seat, arrive early!

Around sunset, Mallory Square comes alive with food vendors, street performers, music, and more. It’s the perfect way to finish off your first night in Key West.

Day 2: Ocean Adventures & Duval Street

A Morning Ocean Adventure

On Day 2 of this Key West itinerary, it’s time to get out on the water. You have a couple of options!

If you’re feeling adventurous, I highly recommend visiting Fort Jefferson at Dry Tortugas National Park. a former military installation approximately 60 miles west of Key West in the middle of the ocean.

To get here, you either need to take the 3-hour Yankee Freedom ferry or book a seaplane. (The latter is very pricey!!). Both options book up pretty far in advance, so I recommend looking at your options as soon as possible! You can read more about visiting here.

Fort Jefferson is one of the coolest places I’ve ever visited! The fort was never finished, but it was used during the Civil War and even held prisoners.

You can spend the day walking around the fort and enjoying the scenery. Plus there are incredible beaches and clear water surrounding the fort that you can snorkel and swim in. You can even camp here if you’re into that!!

If Fort Jefferson doesn’t sound like your cup of tea, there are plenty of other ocean adventures to be had locally in Key West. Here are some options!

No matter which you choose, you are sure to see some incredible marine life and have a great time on the beautiful Key West water! For breakfast before, head to the Cuban Coffee Queen!

A Night on Duval Street

In the evening, head back down to Old Town and grab dinner at one of the fabulous restaurants nearby. If you want to be on the water, I highly recommend Hot Tin Roof at the Ocean Key Resort. This is a great spot if you can’t get enough of those Key West sunset views! You can also grab pre-dinner drinks at Sunset Pier!

There are also some incredible restaurant options along Duval Street, including Blackfin Bistro, Kaya Island Eats, and Nine One Five.

After dinner, it’s time to check out the famous nightlife in the area and maybe do the “Duval Crawl”. This is the nickname for bar-hopping along Duval Street, as you will be crawling by the end!

Some of the most famous bars on Duval include Hog’s Breath Saloon, Sloppy Joe’s, the Bull and Whistle Bar, and the Smokin’ Tuna Saloon.

If dive bars aren’t your thing, don’t worry! There are other nighttime options on Duval Street. You can grab an incredible, adult-friendly dessert at the legendary Better Than Sex restaurant. Another option is to see a drag show at Aqua Nightclub or La Te Da! Or you can just wander down the street and appreciate the chaos.

Day 3: Bikes, Beach, & a Sunset Cruise

Biking to the Beach

On the last day of this Key West itinerary, start your morning by renting bikes and exploring the south side of Key West. There are plenty of places to rent bikes from, but I highly recommend Eaton Bikes! They will even drop off the bikes at your hotel for you.

Key West is extremely bike-friendly, so don’t worry about following a particular route, just make your way towards Smathers Beach. There’s a beautiful bike and walking path along A1A in front of the beach you can check out!

Once you’re ready to rest, head onto the gorgeous Smathers Beach, one of the only sprawling white-sand beaches in the entire Florida Keys! This man-made beach actually had white sand imported from the Bahamas, and it does not disappoint! It’s one of my favorite free things to do in Key West!

Shopping and Sunset Cruise

In the afternoon, head back down to Old Town and explore any other sites you missed on your first day. Around Mallory Square, there’s the Key West Aquarium, the Truman Little White House, and the Maritime Museum!

It’s also fun to explore Duval Street during the day! There are many great boutiques and souvenir shops to check out. Make sure to stop in Kermit’s Key Lime Pie Shoppe for another slice of Key lime pie!

In the evening, it’s time to close out your last night in Key West by embarking on a sunset cruise! As you already know, the sunsets in Key West are jaw-dropping, and the best way to see them is from the water on a sunset sail.

There are tons of different Key West sunset cruises to choose from, including dinner cruises, open bar cruises, and cruises with a dance floor! They typically last between 2 and 3 hours and will take you around Key West and Sunset Key as the sun sinks into the ocean.

You can check out my complete guide to Key West Sunset Cruises here to compare prices and help pick the perfect one for you!

Final Thoughts

That wraps up my perfect 3 Day Key West itinerary. As you can see, Key West is more than just an island destination; it’s a kaleidoscope of history, culture, and natural beauty that is sure to leave you wanting more!

And 3 days is the perfect amount of time to spend in Key West to be able to see and do it all. If you follow this 3 day itinerary, I guarantee you’ll have an incredible time!

Don’t forget to check out my other Florida Keys blog posts to help plan your epic adventure!
25 Epic Things to Do in Key West
Best Time to Visit the Florida Keys
Key Largo vs Key West