Since I was a kid and first saw the Florida Keys in the Arnold Schwarzenegger flick, True Lies, I have wanted to go there! So when I moved to Florida and my parents came to visit it was naturally on the top of the to do list.

I’ve since been back to Key West two more times and there is still so much more I want to do!

Getting To Key West

My trips to Key West have always been weekenders – typically leaving West Palm and the Treasure Coast after work on a Friday, then stopping for the night in Homestead. This allows me to beat the traffic and get down to Key West before lunch the next day. If you get stuck in the Saturday traffic, the trip takes much longer and you won’t enjoy yourself as much.


On our most recent trip to Key West, we stopped over in Islamorada at the Moorings Village and Spa. This is where the Netflix series, Bloodline is filmed (No, I’ve never seen it).

The House out of Netflix Series Bloodline

There is a no trespass sign so normally you can’t get down to the beach unless you are staying at the resort, but it was a quiet morning the day we were there! We asked some of the workers and they were quite happy to let us venture onto the beach.

Boat on the foreshore

Definitely a great photo opportunity!

Breakfast in Marathon

After an early start we stopped off at the Seven Mile Grill on Marathon Key for some brekkie before continuing on through the rest of the Keys. I ordered an omelette then helped Danielle finish her food. Full already and we haven’t even hit Key West!

Now that we’re full, let’s get back on the road. We eventually entered the lower Keys and crossed that last bridge onto Key West. After a quick spin around the island to get our bearings we checked into our accommodation.

Accommodation on Key West

Fairfield Inn

This particular time we stayed at the Fairfield Inn and Suites Key West at the Keys Collection. This was a simple, clean but comfortable hotel. They had a nice pool with an outdoor bar. To be honest, you probably don’t need much more than a bed at Key West as there is plenty of other stuff to do on the island. We paid about $240 for a room with two queen beds for one night. 

24 North Hotel

Similarly priced to the Fairfield Inn is 24 North Hotel. This hotel also has a great pool area and gym. It is also across the road from the Ocean so you may get an ocean view from your room. Both the Fairfield and 24 North are on the East end of the island, so a little further from the action, but they do offer free shuttles to Mallory Square which operate until 11pm.


My wife and I have also stayed in an Air BnB near the south West side of the island. This was walkable to downtown, although a decent stretch in the August heat.

Our AirBnB Key West

The room was cozy and quaint but did not include a pool or gym. We were able to stay there as we had a coupon, but it is usually $2-300 per night on a weekend.

The Southern Most Point…sort of

One of the compulsory activities when visiting Key West is to take a photo in front of the United State’s Southern Most Point. Except for Hawaii and Puerto Rico. So let’s say Southern Most Point on continental US. Except it’s on an island, not on the continent…and it’s not even the southern most point on the island – but you still have to get your photo there, ok?

The Southern Most Point

That being said, it was hot and there was a long line in front of the Buoy, so we just stood off to the side and took our photos. You’ll also find street vendors selling coconut water (still in the coconut) and snow cones. Seriously, that guy is a genius! Just about every tree on the island bears coconuts. So all he needs is a drill and a bunch of straws and he is making money! It was a most welcome refreshment in the heat.

The Southern Most House on Key West

Just a short walk away, you’ll find the Southern Most House. It is worth stopping in just for the view across the swimming pool. The house originally belonged to a judge before the Ramos-Lopez family took ownership in the late 1930s.

Key West Butterfly and Nature Conservatory

On an earlier visit to Key West, we stopped in at the Key West Butterfly and Nature Conservatory. Not too far from the Southernmost point, you’ll find this old mansion with a massive glass house out the back.

At $12 per person, it is reasonably priced. Once you get out the back you get lost in the colours of the butterflies and the flamingos, it is incredible!

A Butterfly at the Key West Butterfly and Nature Conservatory

You’ll wind your way through a lush garden, past ponds and trickling streams all in a climate-controlled habitat.

Key West Butterfly and Nature Conservatory

It is definitely worth just taking the time to enjoy the 50-60 varieties of butterfly.

The Fort and The Beach

Every time I’ve been to Key West, I have wanted to take the boat out to the Dry Tortugas. These islands are further West and home to Fort Jefferson – a fort, literally in the middle of the ocean. Unfortunately, it is a full day trip so we didn’t have time. We did however, make it to Fort Zachary Taylor. This fort is a historic landmark situated on the South West end of Key West. Entry to the Fort and beach is $6 for a vehicle.

Fort Zachary Taylor

The Fort was built after the War Of 1812 as part of a plan to defend the South East Coast. It was controlled by the Union during the Civil War, and played a role in WWI and WWII.

Iguana at Fort Zachary Taylor

Though the military guards are long gone, as you enter the Fort you’ll be greeted by its new inhabitants, some very large iguanas. If you are a history buff like me you’ll enjoy reading the placards and letting yourself drift back to an earlier time. 

Beach near Fort Zachary Taylor

It was a hot, humid day so after a walk around the Fort it was time to hit the beach. Though the beaches near the Fort are rocky (don’t expect wide sandy beaches on Key West), the water is super clear and perfect for snorkeling. Unfortunately we didn’t have our gear but getting into the water was refreshing all the same!

Related Post: Check out this post about when we went back to Key West on a cruise and snorkelled at Fort Zachary Taylor Historic State Park Beach.

Dining at Caroline’s on Duval

We’d worked up an appetite swimming so it was time to eat. There is no shortage of food choices on the island! One of the rules I have when visiting Key West is you must have Key Lime Pie with every meal. And that we did! To help us out, our hotel had given us coupons which give you a free slice of pie with any entree – make sure you get those!

The Key Lime Pie at Caroline’s was a welcome refreshment with a velvety cheesecake texture. Delicious!

A Key West Sunset at Mallory Square

Mallory Square is a favourite gathering location of Key West. Just a stone’s throw from downtown, Mallory Square is where many of the cruise ships pull in.

Cruise Ships at Mallory Square, Key West

It is the best place on the island to watch the sunset.

Key West Sunset

Around sunset, you will find street performers and other vendors catering for the crowds.

There is music, incredible colors and even a busking dog who will collect money as his owner plays the banjo. 

Key West Nightlife

The evening is when Key West comes alive. The sun has set, it is a little cooler and all the boats have returned port. Everyone is ready to eat, drink and share their tails from the day.

From Malory square we we walked along the water past all the restaurants. In the distance over the water you could see lighting in the storm clouds.  We made our way to the Waterfront Brewery for dinner.

Yes, we had a Key Lime Pie coupon for here as well! This pie was softer and cooler than Caroline’s (that may have been because we were sitting in air conditioning.) We were well and truly full after this. Not to mention, ready for bed. We rushed back to Mallory Square to catch the next shuttle back to the hotel.

The Little White House

The Little White House In Key West has a great deal of history. To this day it is an active presidential building, though it has been a while now since a president stayed there. Most famously the Little White House became the home for President Truman, where he worked from during the winter months.

The Little White House on Key West

President Truman had ended up in office unexpectedly, and within a few months had to make a decision on dropping atomic bombs on Japan. It goes without saying he was stressed and his health was ailing. What better cure than the island life of Key West? At the time the house was waterfront property.

On the tour we got to see his poker table, his bar, and even the presidential bathroom and bedroom, not to mention his desk – definitely a lot smaller than the one in the Oval Office I’m tipping. Much of the furnishings are the same as those that were in place during Truman’s time there. It was a short, but very insightful and historic tour. It will give you a glimpse into the personal life of President Truman.

Hemingway House

While we were learning about the 33rd President of the US and his tropical home away from home, Danielle was learning about one of the country’s great writers, Ernest Hemingway. He used to live on Key West and his home is now a museum.

Hemingway House

Hemingway lived on Key West with his 2nd wife, Pauline, until he eventually had an affair with a reporter in 1938. Until the affair, Hemingway had his own boxing ring in the back yard. His wife, so betrayed by his actions moved the boxing ring and replaced it with a swimming pool. Costing $20,000 back then ($350,000-$1,000,000 in today’s currency), Ernest was a little upset to say the least. That was the end of their marriage.

Hemingway's Pool

Today, 59 cats roam the property and are all descendants of Hemingway’s original cats. These aren’t just any normal felines. They are polydactyl cats – with extra digits on their paws. They even have their own vet. You’ll meet some of these cats on your tour. Take some time to enjoy the serenity of the yard and the pool.

Galleries and Shopping

If you run out of things to do, there are plenty of art galleries and shops to enjoy along Duval Street. Just walking around the island and taking in the atmosphere is a lot of fun.

There is incredible architecture in the colonial island style homes and you’ll come across plenty of chickens and iguanas in your explorations.

I just love strolling along and enjoying the slower pace of life – island life! There was definitely more to see but we needed to get on the road.

Island Fish Co

One of my traditions when visiting Key West is to stop in at the Island Fish Co in Marathon for lunch on the way home. One last island meal before getting back to all that’s waiting at home. Ironically the restaurant is on Fat Deer Key which is what you’ll be by the time you’re done.

Island Fish Co in the Florida Keys

I thought I’d be healthy after all this eating and got the Taco Salad – but it was ginormous so I think I cancelled out my good will. And of course, we were still in the Florida Keys, so we had to get Key Lime Pie! 

Island Fish Co Taco Salad

Island Fish Co has two options: the regular Key Lime Pie or the deep fried version – we had to try both! The deep fried version was delicious, crunchy on the outside and gooey on the inside. Their regular pie was just as tantalising. The base was cooked darker than the other pies we had over the weekend, which made it like an Anzac biscuit (for the Aussies out there). The filling was like a caramel slice texture.

Deep fried vs original Key Lime Pie

Each of the Key Lime Pies we tried over the weekend had their own slant. For me, the deep fried version was my favourite.

Next time we go back, I’d love to have more time to explore. I’d like get out on the water, go snorkelling and maybe make it out to the Dry Tortugas. What do you want to do in Key West?