The Perfect 4 Day Key West Itinerary

We spent an amazing 4 days in Key West. Well, any time in Key West is amazing, right? The Kimpton Key West hosted us for a fun time. We explored all of their properties and tried a few new places for dinner. Along the way, I learned a few things I thought I would share about our Key West itinerary.

First off, let’s talk about planning an itinerary… do it, but don’t overdo it. Leave space in the day for random stuff. You are on vacation, after all, not every second of every day needs to be planned. Plan for an island time experience.

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Getting to Key West

key west airport arrival terminal

How do you get to Key West? There are really three ways… by car, by plane and by ferry.

A lot of airlines now offer direct flights into Key West. Or, you can fly into Miami International Airport and experience the Key West Road trip. If you have never done this, I would plan it at least once. Plan to make stops along the way. Check out the Everglades National Park, Key Largo, and other cool spots along the overseas highway. Did you know there are 11 National Parks in Florida? Two can be found in the Keys (the Everglades and the Dry Tortugas)

The Ultimate Road Trip from Miami to Key West

Along the Overseas Highway, you will notice everything is marked by mileage, with Mile Marker Zero being in Key West.

Rather take a ferry? Check out the Key West Express.

So… with the ground rules set… let’s see how to explore Key West, enjoy some downtime, AND have an amazing time in just 4 days.

The Beginning

Ok.. we planned this on purpose, we arrived very early in Key West. This meant we traveled with very little sleep, but that’s ok.

Side note, I booked our plane tickets directly with the airline. So, they set the schedule, departure/arrivals, and time for the layover. BUT, their itinerary only allowed for 25 minutes from touchdown to take off on our layover down. Might work, if you aren’t 10 minutes late leaving …. but, we managed to make the connecting flight, so all good. But, next time, I will ensure we have plenty of time between connections.

kevin and michele on an airplane

We always travel with carry-on only. It just makes the trip that much easier. Plus, for 4 days… you really don’t need that much stuff. Once we land it’s straight to the hotel. For this visit, we headed to Winslow’s Bungalows. This Kimpton property is just amazing.

Winslow’s Bungalows

Located at 725 Truman Ave, you are fairly close to everything. If you get tired of walking you can always take an Uber or the free Duval Loop bus. If you are taking a cab from the airport to the hotel, you may want to let them know it’s the Kimpton on Truman instead of Winslow’s Bungalows. The reason is these properties used to be part of the Historic Key West Inns, but now are part of the Kimpton family.

This property used to be the Chelsea House and Key Lime Inn. Kimpton has combined them into one property now known as Winslow’s Bungalows.

Here’s a bit of quick history about the property…..

  • It’s named after the famous painter and summer Key West resident Winslow Homer
  • Has 3 pools, an outdoor bar, and vibrant gardens
  • 85 guestrooms including 2 deluxe suites and is Kimpton’s largest Key West hotel
  • The room designs pay homage to the property’s past owners including an Army officer, an Irish steamboat Captain, and a circus performer
  • On the property is Maloney House, where the first mayor of Key West lived. He planted an amazing fruit grove that is still used by the hotel today.
  • The property has 3 stand-alone bungalows to accommodate guests wanting a bit more privacy
  • The property is very pet friendly. They offer Henry’s dog treats to their dog guests
  • If you want to try the famous Key West bagel made by Goldman’s, they are offered at breakfast (they are very very yummy)
  • Music is played at the pool bar
  • The old Blue Parrot Inn is across the street and is now part of this property. They have 11 rooms and their pool is called the serenity pool because they don’t play music and it offers a zen tranquil feeling

Day 1

They didn’t have our room ready yet, remember we arrived early (before checkout). But, that was ok. They held our luggage so we could head off to have breakfast and a much needed cocktail to start the vacation off. Our breakfast of choice? Blue Heaven of course.

After breakfast, it was time to head back to the hotel and enjoy a bit of pool time. Best way to cool off and refresh after a day of traveling.

As you can see, our room was, perfect. Winslow’s Bungalows offers great spaces to relax and enjoy Key West. Not too far from the heart of Duval Street, this place offers three pools and an amazing pool bar.

Fully refreshed, we head out to explore. First stop… the Mile Zero sign. No vacation in Key West is complete without a picture in front of the Mile Zero sign.

Needing a place to cool off, we then headed over to the Custom House. This place offers rotating exhibits all about Key West and those who influenced Key West. Always a great stop. Some the coolest and best things can be found in their gift shop.

Now, it’s time for dinner. A favorite stop of ours is Sloppy Joe’s. I know, I know, it can be a bit touristy, but I still love this place. The food is always good, the drinks are poured strong and they offer live music. Who could ask for more?

Speaking of live music, plan a stop at the Smokin’ Tuna, one of the best places in Key West for music. They have an outdoor courtyard that offers shade and cold adult beverages.

Most of the time I suggest sunset celebration at Mallory Square, but this night, we opted for a different perspective. Sunset from the top of Schooner Wharf. This is the perfect place to see the harbor, enjoy a cold beverage and listen to live music.

Day 2

Today, hubby heads off to enjoy a morning out on the water fishing. Me… well, I do what I love to do while in Key West, I head out for a morning walk. Who doesn’t love a morning walk around Key West? I love to look at the historic homes that are scattered all over this small island. It’s one of the great things about the Island, they have kept the charm and preserved its history.

Historic Walking Tour

When I get back, it’s time for breakfast. I head down this wandering path at Winslow’s and partake in their complimentary breakfast. It’s a basic continental breakfast. It’s served in the bar area. Enjoying my second (and maybe third) cup of coffee, I did a bit of work. Caught up on a few emails, and, worked on this blog post. At the bar, is a great spot to work. I don’t spend too much time working… after all, there is a lot more to see and do before Kevin returns from his fishing trip.

Kevin returned after a successful fishing trip, and we then set out for the next adventure. Kimpton Hotels hosted us for a tour of their Lighthouse property. This place is very cool Across the street from the Hemingway House, it offers a great view of the lighthouse and they have a very nice bar.

Not staying at the Lighthouse? No worries, the bar is open to the public, Plan to stop in and enjoy this place. The bartender is engaging and can mix many amazing cocktails. We had the best time trying the house specialties. We actually couldn’t decide which ones we liked best. It’s ok to like them all, right?

While in Key West, it seems to always be cocktail time. With that in mind, we had time before our dinner reservations and headed over to General Horseplay. This place is known for their cocktails and fun Happy Hour. It’s a great place to start off an evening.

For dinner… we were hosted by Poke in the Rear. Don’t overlook this place. It was, one of the best dinners we had while on Island.

Day 3

Today we have a quick bite of breakfast and then head out to explore the streets of Key West. Being married to a photographer, I spend a lot of time wandering around. But, I wouldn’t have it any other way. We saw roosters, flowers, palm trees, and stickers. All my favorites.

Grabbed a cold brew from Cuban Coffee Queen and walked around the Historic Seaport.

Heard the band starting to play at Sunset Pier… which means we are stopping to listen and enjoy a cold beverage. Here’s where I would insert the idea of having free time built into your Key West itinerary. If you “had” to be somewhere … you might miss out on an awesome view, cold beverages, and amazing live music.

A few more stops for pictures and then we are heading back to Winslow’s Bungalows. Not only do they have a great pool bar and pool area, but they offered a free tasting of Mutiny rum. It was yummy and the story was just as interesting.

We didn’t have any dinner plans to speak of so we “thought” we would head over to Mallory Square and enjoy sunset and then play it by ear. I think that’s a great way to spend any evening in Key West, at least one night. No particular plans and let the evening unfold.

Well, as we walked by Little Pearl and saw they had two chairs open at the bar… and we hopped on the chance to eat at Little Pearl. This place offers a tasting style menu and is worth every penny if you can get a reservation.

Day 4

We have a later flight, also planned on purpose, which gives us almost a full day to play in Key West. What is always fun to see is the “guest” ships that dock at Mallory Square. On this day we were able to see the USCGC Eagle. This 295-foot, three-masted barque is used as a training vessel for future officers of the United States Coast Guard. This is also known as “America’s Tall Ship” and is the largest tall ship flying the Stars and Stripes and the only active square-rigger in US service. Very, very cool to see in Key West.

Then it was off to lunch at First Flight. This is the Southernmost microbrewery and they offer a great courtyard seating area and a wonderful menu.

Afterward, we head off to the airport to head home. As per usual, we grab a last vacation cocktail and share a frozen Key Lime pie on a stick (dipped in chocolate).

We tried new places for food and drinks and had plenty of down time to relax. That’s what makes the perfect vacation… a perfect balance.


I get it, we didn’t do much on this trip. But, we had a really good time. If this seems a bit too slow for you, then check out these ideas:

  • Take a guided tour – a food tour, a walking tour, a ghost tour (see our recommendations here)
  • Take the ferry (or seaplane) out to the Dry Tortugas National Park – be sure to book this one in advance as it sells out quickly.
  • Head out on the water to snorkel the coral reefs
  • Go up the Keys for a day trip and see Bahia Honda State Park, sea turtles, or the Key Deer on Big Pine Key.
  • 3 Reasons Smathers Beach is the best
  • Visit one of the 18 museums on the island… like the Truman Little White House

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