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Things to do in: Key West

by Patrick O'Halloran
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Key West

Key West or the ‘Conch Republic’ as the locals like to refer to it is a unique port of call. It has a laid-back, free-spirited and quirky charm. We love visiting this small little town located on the southernmost tip of Florida.

There is a lot to see and do within its 7 square miles. Its geographical position gives it a unique flavour. Think Deep South meets the Caribbean. In fact, Key West’s charms are so varied that I am sure there is something to be enjoyed by almost every type of cruiser no matter their age or interests.

Ships docks in one of 3 locations:

  • Mallory Square (usually smaller ships)
  • Pier B
  • Outer Mole Dock

Key West is fairly compact and easy to walk around. However, beware of the humidity. I recall one occasion being there and feeling absolutely drained after about an hour. Make sure you keep hydrated.

That said the opportunities to hydrate yourself in Key West are plentiful, especially if it’s of the alcoholic kind. There seems to be a bar on every corner and the infamous Duval Street bars seem to have happy hours throughout the day. They cater to all manner of folk. There is a famous saying in Key West that you won’t know if the person next to you in a bar is penniless or a billionaire.

Old Town Key West, which occupies the western half of the island, is where most of the tourist attractions are located. However, I would suggest exploring beyond the usual touristy hangouts of Duvall Street and Mallory Square although they are still worth your time.

If you are only there for a few hours and want to see as much as you can in as short a time as you can then we can highly recommend the Key Lime Bike Tours as an ideal excursion when you are in port.

One word of warning is that all the bikes used are the traditional kind in that they have no handbrakes. Yes, I had the same thought too. How the heck do you stop. They do have brakes of course. You engage the brake by simply backpedalling. Strange but you quickly get the hang of it. Before you set off on your trip you have the chance to practice in a large yard where you pick up the bikes.

The guides are an amazing and fun source of knowledge for all things Key West. When we did the bike ride our guide was an expert on the different architectures you can find there. We learnt so many interesting and surprising things about Key West. Did I say Key West is very flat? Perfect for all things pedal powered.

We visited all of the following on our trip

Mallory Square


The heart of Key West if you like. It’s located on the waterfront in the Old Town. It’s also the location of the traditional sunset celebration. Unfortunately for cruise ship passengers you will most likely have boarded or even departed Key West by sundown so will miss this torchlit festival that happens every evening.

When we visited in Brilliance of the Seas we departed around sunset time so it was a real treat. A flotilla is small boats and yachts all jockeyed for positions to get a unique view of the evening sky. We enjoyed cocktails on the pool deck as we sailed slowly out of port.


Hemingway’s House


Located at 907 Whitehead Street this was the home to one of America’s most respected authors. He lived here for around 10 years and wrote some of his best work here. It’s a beautifully preserved house and the museum makes it well worth your time.

The house is also home to around 50 polydactyl, or six-toed cats. It’s not hard to spot them as they seem to run the place.

Southernmost Point


Probably one of the most iconic photo stops in Key West. This concrete buoy marks the most southerly point of continental USA. The fact that it’s not actually the southernmost point (that would be the beach area of Fort Zachary National Park) is unknown or matters little to most.

It’s still a great spot for a photo.

Key West Lighthouse


The second lighthouse to stand here. The first being destroyed during the hurricane of 1846. An event that created a need for a new cemetery (see Key West Cemetary below) You can climb to the top for some stunning views of Key West and the ocean.

Key West Seaport

One of the best things you can do for free in Key West is to take a walk along Key West Bight otherwise known as Key West Seaport.  

In the past, it was the place to find the Shrimpers, Spongers and Turtle Traders but now the waterfront is home to some very nice restaurants and bars. A perfect place for something to eat or to enjoy a drink or two. Enjoy a Conch Fritter and a beer if you can.

There are still plenty of boats to see at the seaport, from small fishing vessels to millionaires yachts and if you’re lucky and old Schooner.

Key West Cemetery


Located in the heart of the old district is Key West Cemetery. Founded in 1847, after the hurricane of the previous year washed away the old one. It’s a fascinating place to visit and if you have a good guide it really comes to life. So to speak.

A word of warning if you have an aversion to anything reptilian the local iguanas seem to love this place as they use the myriad of gravestones and tombs as their personal radiators. I find them fascinating so it was a treat for me.

In addition to the above we visited:

Presidents Gates – This gate was built in 1906 has over the years have welcomed Presidents: Harry S. Truman, Dwight D. Eisenhower, John F. Kennedy.

Mile Marker Zero – One of the most popular places for a photo. MMZ marks the start/end of US1 that stretches all the way from Key West up to Maine.


Dog Beach – Yes dogs have their own beach in Key West. It’s the only place they can go unleashed and not get into trouble. It’s fun seeing them frolic in the surf.

At the end of the tour, we even got to finish off with a slice of the amazing key lime pie at Kermit’s Cafe Kitchen. After all that cycling you’ve earned it.


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