Florida Key West

If you drive two and a half hours down the Florida Keys, you will reach the cool town known as Key West. Don’t sleep on the drive down – you will miss some of the best views from the many bridges you cross. I saw dolphins swimming and some of the bluest waters you could ever imagine.

Here are some ideas on things to do in Key West if you are planning a weekend in Key West.

How to Get to Key West

Drive down to Key West for the weekend
Seven Mile Bridge

No matter how you get to Key West, you will have a great view. Plus, it will be a fun experience. So, figure out which works best for your itinerary. 

  • Plane – To get to Key West you can fly directly into the Key West International Airport. Find out which airport you can fly directly to Key West from.
  • Boat – There is also the option to take the Key West Express, a ferry from Fort Myers or Marco Island to Key West. The journey takes around 3.5 hours.
  • Drive – If you are visiting Key West as part of a road trip around Florida, you can fly into any Florida airport and drive down to the Keys. You will need to rent a car, you can do so with Expedia.

As you drive down the Florida Keys, follow your journey on a map and spot the names of each Key. Some of my favourites are Knockemdown Key, Upper Sugarloaf Key, No Name Key and Fat Deer Key!

What to Do in Key West for a Weekend?

Weekend in Key West, Florida

If you can manage it, I would recommend spending 3 days in Key West. It will give you enough time to see as much as possible and get a true feeling of the Florida Keys.

Given how far the drive is to Key West, I would not recommend spending only 1 night and 2 days in Key West if you have come by car.

The Key West Express ferry departs from mainland Florida in the morning and returns from Key West to Fort Myers in the evening. So, technically you could leave on Saturday morning and come back on Sunday evening. However, you would not have a full day, given the ferry takes 3.5 hours.

Best Attractions for a Weekend in Key West

Duval Street Key West

It may be hard to fit all the places I recommend into a weekend itinerary in Key West. However, I always like to have a long list of things to do in a destination to have plenty of options.

For example, if it rains, you will want some indoor activities to choose from. Or, perhaps you are feeling tired and want more relaxing options.

There are some places that I never managed to visit, but I would like to next time. Including, the Key West Butterfly and Nature Conservatory and the Key West Shipwreck Treasure Museum. Consider checking them out for yourself.

Duval Street

You need to make sure you take a stroll down Duval Street during your weekend in Key West. It is a well-known area in Key West and it is also where you will find many bars and restaurants.

You are bound to find your way on Duval Street at some point during your Key West weekend.

Boat Trip in Key West

Sunset boat ride in Key West
Sunset boat trip

One of the best parts of the Florida Keys is the remarkable water. I would recommend that you make the most of it by experiencing it by boat.

I went on a dolphin watching and snorkelling trip at sunset.

The dolphin watching was fantastic. I managed to see about eight dolphins all at once. Although dolphin sightings are not 100% guaranteed, the captain knew exactly where to go to get the best sightings.

On the way home, you watch the sunset and wait until it has set before you head back to land. You can also take this trip during the day.

Another option is a sunset sail in Key West.

Southernmost Point in Key West

Southernmost point in Key West
Southernmost Point

The Florida Keys mark the southernmost point in the continental US.

The Southernmost Point landmark is located in the Old Town of Key West.

There is a live webcam stream pointing at the sign so you can tell people back home to look out for you.

It can get quite busy, so expect to line up for a photo – unless you come outside of peak times. It is very touristy but a classic thing to do in the Florida Keys.

Key West Aquarium

Visiting the Key West Aquarium is a good activity when you need an afternoon off from being in direct heat. Even though the aquarium is small, you can spend a decent amount of time there because there are exhibits with feeding times and talks throughout the day.

Before you purchase a full-priced ticket for the aquarium, look to see if there is a coupon.

Fishing in Key West

Fishing is an activity I had always wanted to try. What better place than in the Florida Keys? Opt for half-day fishing trip, which allows you time to enjoy other activities in Key West during your weekend away.

During your fishing trip staff are on hand to help you catch your fish. You are allowed to keep the fish that you catch. The crew members can prepare it for you at the end so that you can cook it. Alternatively, many restaurants will cook the fish you caught in Key West.

Ernest Hemingway House

Hemingway's home, Key West
Hemingway’s home

You can visit the Ernest Hemingway home in Key West and have a tour around the property. You will need cash to pay for the admission fee. This museum is across the road from Key West Lighthouse.

I found it interesting because I had studied some of his work before but didn’t know much about Hemingway himself.

If you like cats, you should visit. Hemingway loved cats and there are over 40 cats that live at his house. They are all descendants of the original cat that lived there when he did.

I was surprised to learn that many of his cats have a gene that means they have an extra toe on their paws! Seeing these cats was the first time I had heard of such a thing, but it is more common than you would think.

I went at around 4:00 pm, just in time for the last tour before it closed at 5:00 pm. I didn’t get that much time to explore the house and garden because of this, so the staff allowed us to come back again the next day for free.

If you are interested in learning about other Key West Historic Sites, visit this website.

Sunset Celebration

The sunset celebration happens every night on Mallory Square. While the sun sets, a group of performers and different acts come out to entertain you.

Sunsets in Key West are stunning because the unobstructed view stretches for miles.

Dry Tortugas Island

Even though you may only have a weekend in Key West, if you are considering any day trips in Key West, I recommend visiting Fort Jefferson in Dry Tortugas.

This excursion was at the top of my to-do list, but I didn’t realise that it was the same for everyone else visiting the Keys. I nearly missed out on the opportunity to do it because I didn’t book early enough.

Dry Tortugas snorkelling near Key West
Snorkelling at Dry Tortugas

To get to Dry Tortugas National Park, there is only one company that arranges day trips. You can get to the island by ferry or seaplane. I opted to visit Dry Tortugas on the ferry. The day includes breakfast and lunch, as well as your snorkelling equipment.

You can spend an hour or two exploring Fort Jefferson. Then you have the rest of your time to snorkel or enjoy the breath-taking scenery. It had probably the most beautiful colour water I had ever seen. Even though the trip is brief, it was well worth it.

Best Key West Beaches

Smathers Beach

Key West is not known for its beaches, although Smathers beach is my favourite there. The sand is soft and white and has tropical palm trees; however, the sea is a little murky and slimy on the floor. So this is a good beach for relaxing on the sand and reading a book.

Fort Zachary Taylor Historic State Park

Another option for a beach in Key West is at Fort Zachary Taylor. You must pay a small entrance fee given that it is a historic state park.

The water is deeper and clearer than Smathers Beach, and it is a spectacular shade of blue. There is also good snorkelling at Fort Zachary Taylor.

Bahia Honda State Park

Although not in Key West, this is a beach that you must visit during your weekend in Key West. Bahia Honda was one of the most physically gratifying places I went to in the Keys. It is a state park located about 45 minutes from Key West.

You will have to pay for entrance to the whole park, which is about $8 per car.

The beaches there were fantastic, and it was not busy at all when we visited. You could spend the day there or just a few hours as we did on our way out of the Florida Keys.

Where to Eat and Drink During a Weekend in Key West?

Here are some suggestions of places to eat and drink in Key West. These are all places I visited and would recommend.

Onlywood Pizzeria Trattoria

I stumbled across Onlywood by accident while wandering Duval Street (the main street) for dinner one night and then went back two more times. The pizza, pasta and salad dishes were tasty, and they had an extensive wine list.

Conch Republic Seafood

For dinner one evening, my mum asked if we could eat with a view of the water. I chose Conch Republic.

The restaurant is on the waterfront amongst the boats, so you get a great view of the harbour and sunset. The specials were delicious, even if a little expensive, and the rest of the menu was great too.

Sunset Pier

Sunset Pier, Key West Florida
Sunset Pier

My favourite place to have evening drinks was at the Sunset Pier in Key West. If you want to have your drinks while the sun goes down, make sure you grab a table an hour or so before sunset because it will get busy.

Listen to the live music while sipping on cocktails on the lovely waterfront bar.

Key Lime Pie

Kermit's Kitchen - Key lime pie shop in Key West
Kermit’s Kitchen

If you want to learn about Key West food, you must try a Key Lime pie.

The Florida Keys is famous for key lime pie, a yummy lime-flavoured dessert with a consistency similar to cheesecake. Many places in Key West sell a slice of the famous pie.

Kermit’s Key Lime Shoppe is a classic; its two shops are filled with all things green. Or you can try the Key Lime Pie Company.

In my eyes, after trying three pies from three different shops/restaurants, there were slight differences in flavours, but they all tasted great. So, my advice is to try them all!

Tips for Your Weekend in Key West

Here is some advice for making the most of your Key West weekend.

Saving Money

There’s nothing more irritating than paying full price for something that is so readily available at a lower price. So as a tip, make sure you pick up coupon books on the streets in Key West.

These coupon books are on almost every street in the keys and contain loads of coupons and vouchers for restaurants, shops and activities. You could save yourself some money, something my family didn’t realise until the end of the holiday.

Walking around Key West

Key West town

One of the best things about Key West is how walkable the town is. It’s nice to be able to park up your car and explore this town in the Keys on foot.

As a result, you will need some good shoes. I recommended buying sandals that are comfortable to walk in, such as Tevas (also available on Nordstrom).

Alternatively, you should bring some trainers that you have worn in well.

I love Adidas or New Balance shoes because they are padded on the bottom and give good support. My recent favourites are Adidas U Path Run trainers.

Where to Stay During a Weekend in Key West?

I recommend that you book accommodation within walking distance to the main attractions and downtown areas. Most places will be around a 20-minute walk, so bring some suitable walking shoes, as I mentioned above.

Here are some ideas on where to stay for 2 nights in Key West or longer.

Hotel Recommendations for a Weekend in Key West

Orchid Key Inn$$$Click here
Almond Tree Inn$$$Click here
H2O Suites (Adults Only)$$$$Click here
Barbary Beach House Key West$$$$Click here

If you don’t mind being a little further out from the main town and not within walking distance to the main attractions, you could stay near Smather’s Beach at Barbary Beach House.

For more deals on hotels, visit Expedia or Hotels.com

Places to Visit on the Drive to Key West

The Everglades

Everglades in Florida

Taking an airboat tour around the Everglades to see alligators and other wildlife is a must-do. Sit on a precarious-looking boat with headphones on to hear your captain narrate and navigate the trip.

Your captain will slowly search for alligators and give you a chance to see the gators. Then he will whiz through the mangroves at a speed that feels very fast. Don’t take off your headphones when you are going fast because the airboat is extremely loud.

The Everglades is a large national park, so depending on which company you book your tour with will depend on where it is and how long it takes to get there from Key West (roughly 3 to 4 hours).

Here is an option for an Everglades wildlife tour.

Hollywood, Florida

Miami is the classic Florida location to visit. While you are in Miami, I recommend driving 30 minutes further to Hollywood, as well. It has a gorgeous beach and a strip of bars and restaurants that are lively.


The Sarasota area has some worthwhile things to see and do, which would complement your trip to The Keys. For example, Siesta Key is one of the best beaches in the United States.

There are also some excellent places to eat and drink in Sarasota, such as Shore and Whitney’s, both on Longboat Key.

Sarasota is around an hour and 40 minutes from Fort Myers, where the Key West Express ferry departs.

Clearwater Beach

Clearwater Beach
Clearwater Beach

Clearwater was my favourite beach in Florida, with stunning white sand that stretched for miles. I stayed in the Hyatt Regency Clearwater Beach Resort & Spa hotel, where the view from the outdoor pool was impressive and had an incredible spot to watch the sunset.

Note, Clearwater Beach is over 7 hours to get to from Key West, so it would be worth doing at the beginning or end of a road trip around Florida. You can fly home from Tampa airport, which is only 30 minutes away.

Further reading to a Weekend in Key West

If you are looking for more articles to read on travel in the United States, check out my post on Kauai, Hawaii travel blog.

For more ideas about weekend getaways in North America, consider my article on Things to do in Ontario, Canada.

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