Best things to do in Key West – the perfect guide for a first time visitor

Last Updated on April 1, 2024

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If you are looking for a sunny getaway, that is also full of history, has great night life and a whole lot of personality, look no further than Key West. It’s the Southernmost city in the US, the most popular destination in Florida Keys and a place like no other in the country. It’s colorful, quirky and laid back with a very distinct Caribbean vibe. So if you crave a tropical getaway, but don’t want to leave the country, Key West is the place to go. Its vibrant night life is legendary, but there are plenty of other things to do in Key West than never ending happy hours and bar hopping.

Key West is surrounded by blue waters and beautiful reef, that rival those found in the Caribbean islands. Getting out on the water is a must and there are plenty of opportunities to do so.

There is also a lot of history in Key West. The beauty and laid back vibe of this island city attracted many writers like Ernest Hemingway and Tennessee Williams, as well as President Truman, who all at some point resided in the Conch Republic. Their houses are now museums open to visitors.

If you are planning to visit Key West for the first time, you are in for a treat and this guide is for you. I included some practical info, that will hopefully come in handy when planning your trip and of course a list of top things to do in Key West.

How many days to spend in Key West

To see the main sites and get into the vibe of Key West, I’d say 2-3 days is a minimum. But there are also so many things to do in Key West and the nearby Keys, that you could easily spend a week and stay busy. If you have a car, you can visit the lesser known, but absolutely beautiful places like Big Pine Key. Marathon is just 1 hour away, which makes for a great day trip and will give you a whole different taste of Florida Keys. So it all depends. If Key West is your only point of interest, then 3 days will be sufficient. If you want to do more exploring, then you can easily spend a week.

How to get to Key West

Key West is the Southernmost point in Florida, located about 160 miles from Miami. Getting there is an adventure in itself, and there are several ways to choose from.

Getting to Key West by car

Most people fly into Miami or Fort Lauderdale Airport, then rent a car and drive down to Key West. Driving down the Overseas Highway, a stretch of Rt 1, that extends from Miami through Florida Keys, is spectacular and something everyone should experience at least once in their lifetime. It’s considered one of the most beautiful drives in the country, and having done it twice, I can vouch for it. If you have time to make stops along the way, definitely do it. There are many great ones between Miami and Key West. If you want to head straight to Key West, plan at least 4 hours to get there. ( Search for a car rental here ).

Getting to Key West by plane

Key West has its own small airport ( EYW ), so if you want to fly right into it, it is possible. American Airlines, United, Delta and Silver Airways are the airlines that operate out of EYW. If you are flying out of one of the major airports like Hartsfield Jackson Airport in Atlanta, Reagan Airport in Washington DC or La Guardia in NY, you can take advantage of the direct flights in season ( February through April ). Jet Blue just announced it will also add direct flights from New York’s JFK and Boston starting February 11, 2020 (through April). If you are flying from any other airports, you will most likely connect through Miami or Fort Lauderdale.

Getting to Key West by ferry

If you are coming from Southwest Florida, you also have an option of getting to Key West by ferry. Key West Express runs daily from Fort Myers ( year round ) and Marco Island ( seasonally ), leaving around 8.30 am and arriving in Key West around noon. It’s a very comfortable 3.5 hour boat ride, with TVs and a full bar. It’s recommended that you book your tickets at least a week ahead of your departure date. You can check the most up to date schedule and book your tickets on the Key West Express website.

How to get around Key West

Key West being small, just two miles wide by four miles long, is best explored by foot. If you stay anywhere in or near the Old Town, you can walk to most attractions. Biking is another great option, as well as a fun activity. There are plenty of bike rentals all over Key West, and many hotels have them for their guests.

Even if you arrive by car, plan on leaving it parked for the duration of your stay. Don’t even attempt on driving through downtown, as finding parking is extremely difficult. Honestly, there’s no reason for it. And if you do want to give your feet a rest or need a quick lift after a late night out, there’s always Uber or Lyft.

READ: Miami to Key West road trip – best stops along the way

Things to do in Key West, Florida

Take a Trolley Tour

There are a couple of reasons I start the list of best things to do in Key West with a trolley tour. First, I think they are a great way to not only see the main sites in a short time, but also learn about the history of Key West. They are narrated, so you will get a detailed tour, as you pass by the most popular spots, as well as those you might not have necessarily visited on your own. Second, it will give you an idea of the layout of Key West.

There are two trolley tours that operate in Key West: Conch Tour Train or Old Town Trolley. You can’t go wrong with either one, but which one you choose will depend on how much of Key West you want to cover.

Conch Tour Train is on open air train, that originated in 1958. It takes you on a 90 minute tour around the Old Town. There are 4 stops during the tour when you can get off and explore a different area.

Old Town Trolley is more of a hop on hop off tour, that goes around the whole island, not just the downtown area, so you will get to see places, that are a bit further away. You can either complete the whole loop, or hop on and off at any off the 12 stops and explore at your own pace. Your ticket is valid all day, and you can use the trolley as an alternative to taxis or driving your own car.

Get a picture at the Southernmost Point

Getting a picture next to the Southernmost Point is one of the must things to do in Key West, especially if it’s your first time in the Conch Republic. The giant, colorful buoy sits at the corner of Whitehead Street and South Street and marks the lowest latitude land and the southernmost point of the continental USA. Even though this is not a 100% accurate, as the actual point is on a private island 10 miles away, it’s still one of the biggest landmarks in Key West.

As it’s always the case with popular photo spots, there’s usually a long line of people waiting for their turn to get their picture. If you want to avoid it, come really early in the morning.

Stroll Duval Street

The 1.25 mile Duval Street is the most famous street in Key West and the one with the most action. With over 40 bars, it’s the prime destination for bar hopping. From Hemingway’s favorite Sloppy Joe’s, to Bull and Whistle, World’s Smallest Bar with literally two stools to clothing optional Garden Eden, your choices are endless. Just walk up and down the street and pick a place, that looks fun. You can also join this 2.5 hour Key West Pub Crawl, that takes you to 5 different bars. You’ll enjoy a drink at each place while learning about the history of Key West.

Even is bar hopping is not your thing, Duval Street is not to be missed. Besides bars, there are plenty of restaurants, interesting stores, galleries and some of the best people watching.

Visit Ernest Hemingway’s Home

Even though Ernest Hemingway wasn’t born in Key West, he was very fond of it, lived there for over a decade and become was one the most beloved residents. His house is now a museum dedicated to the life and work of the writer and one of the top Key West attractions. You can explore the house and the grounds on your own, or take advantage of the 30 minute guided tour, which is included in the $18 admission price.

While exploring the house, you won’t be able to miss its current residents, about 50 cats. What sets them apart from cats you might usually come across, is that they are all polydactyle cats. In less fancy terms, that means they have six toes. Some of them are descendants of Hemingway’s own cat, Snow White, that was gifted to him by a ship’s captain.

The Ernest Hemingway Home and Museum is located at 907 Whitehead St and it’s open daily 9 am – 5pm. General admission is $18 and tickets can be purchased at the main gate. No credit cards, cash only!

Climb to the top of Key West Lighthouse

Once you are done exploring the Hemingway Home, go across the street to the Key West Lighthouse. If you up for a climb, head up the 88 steps for some great views. You can also visit the Keeper’s Quarters and the small museum on site to learn more about the history of the lighthouse.

The admission cost is $17, but you get a bit cheaper if you book online ( $15.50 )

Admire Key West’s architecture

One of my absolute favorite things to do in Key West was just walking around and checking out all the beautiful houses. The architecture is quite unique and definitely eye catching. Old Town is dominated by Victorian inspired houses, colorful cottages and pastel conch houses. Many of them have beautiful, lush gardens and quite interesting decorations.

Architecture is not the only unique thing you will notice while strolling the streets of Key West. Chicken and roosters will be a common sight, and you won’t have to work hard to find them. They famously roam around town, cross the streets and visit outdoor cafes. It’s one of those things, that makes Key West the unusual place that it is.

Take a Sunset sail

Sunset cruises are one of the most popular things to do in Key West, and that is for a good reason. There is no better way to end a long day of exploring than to relax on a boat with a cold drink in your hand, as the sun sets and live music plays.

This 2 hour catamaran cruise with Fury Adventures was a lot fun and one of the highlights of our 3 days in Key West.

If you are looking for any other type of water fun, they have you covered as well. Some of the other activities offered are Snorkeling, parasailing, jet ski rentals or a 3 hour Dolphin Watch Eco Tour , where you can see dolphins in their natural habitat, then make a stop for some snorkeling. Whatever you choose, make sure to include some type of water activity during your Key West visit. It’d be a shame not to.

Try Key Lime pie

Key Lime pie is the official dessert of Key West, and you simply can’t leave until you have at least one slice. It’s made with a special kind of limes, that give the pie that signature tart flavor. Finding it won’t be a problem, as it’s virtually served everywhere, with most places claiming to have THE best one. Some of the favorite places include Kermit’s Key Lime Pie Shoppe, Blue Heaven and Key Lime Pie Bakery.

You can also go on a quest trying to find your personal favorite, which would definitely be one of the fun things to do in Key West and the perfect excuse to indulge in the iconic dessert.

Catch a sunset at Mallory Square

One of the things Florida Keys are famous for are their spectacular sunsets. They are truly some of the best I’ve seen and in Key West they become quite a celebration. If you are looking for the perfect spot to catch a sunset, Mallory Square is the place to be. Each night, the square fills with street performers, food and craft vendors. It does get quite crowded, so get there a couple of hours earlier, not just to get a good spot, but also to enjoy all the commotion.

Take a day trip to Dry Tortugas National Park

Dry Tortugas is a cluster of seven islands, located 67 miles from Key West. It’s one of the most remote US National Parks and therefore one of the least visited ones. Visiting Dry Tortugas is definitely one of those travel bucket items and makes for an excellent day trip from Key West.

There are three ways you can get to Dry Tortugas from Key West, either by a ferry, a seaplane or a private charter. Taking a ferry is the cheapest option, although it’s not cheap by any means. A seaplane is definitely a splurge, but if you don’t mind spending a little extra, it’s without a doubt an amazing experience.

• Ferry – Yankee Freedom III ferry is a 2.5 hour boat ride each way, leaving you with about 6 hours on the island. The round trip costs $200, but includes breakfast and lunch, as well as the $15 park entrance fee. It’s the cheapest and most popular option, so be sure to plan ahead. You can book your Dry Tortugas Day Trip here.

• Seaplane – Key West Seaplane Charters is the only company with flights to Dry Tortugas and offers either a Half Day Excursion ( $397/ 2.5 hours on the island ) or a Full Day Excursion ( $697/ 6.5 hours on the island ). Add the $15 National Park entrance fee ( paid in cash only ).

• Private charter – you can also get to Dry Tortugas via a private charter, as long as the boat is authorized by National Park Service. There are many boat operators, that hold those permits and offer all kinds of trips for sailing, snorkeling, fishing etc.

No matter which option you choose, getting there will be a fun adventure. Also, keep in mind, that visiting Dry Tortugas will take up the entire day, but if you have that extra day in Key West, it’s absolutely worth it.

And there are many ways to spend your time there. Dry Tortugas is home to the massive Fort Jefferson, which you can explore either on a guided tour ( included in your ferry ticket ) or by yourself. However, the main draw are the crystal blue waters and amazing marine life. Florida Keys is home to the last living reef in the United States, and there are several great snorkeling spots in Dry Tortugas. Make sure to bring your snorkel gear, towel and reef safe sunscreen.

Where to stay in Key West

Before I suggest some places, you need to know, that Key West is not a cheap place, and that is especially the case when it comes to accommodations. If you want to stay downtown, near all the action and a walking distance to most attractions, be prepared to pay for it. You’ll get a better deal if you stay a bit further away, in New Town or near the airport, but then you will also have to pay to get around. So if your budget allows, staying in the Old Town is ideal, especially if you only have 2 or 3 days in Key West.

• Southernmost House Hotel – beautiful, adults only, beach front hotel located on the lower end of Duval Street. Close enough to many attractions, but removed enough to ensure some quiet and relaxation.

• The Gardens Hotel – steps away from Duval Street, but you will feel like you’re worlds away staying in one of the rooms, surrounded by lush gardens. You can choose from either a beautiful guest room or one of the 5 private cottages. 4 of them have their own pool, and there is a main pool on the property as well.

• Marquesa Hotel – a small, boutique hotel, with 2 pools and beautiful grounds, just a block away from Duval Street. It’s one of the highest rated hotels in Key West and it’s easy to see why. Even though you will not need a car, as everything is within a walking distance, there is a complimentary parking on site, if you arrive in Key West by car.

• Duval Gardens – beautiful and cozy Bed and Breakfast, perfectly located on the quiet end of Duval Street. This is an adult only property, so it’s perfect for those looking for a grown up get away.

If you do decide to stay further away from the downtown area, these are a couple of great, highly rated places:

• The Perry Hotel – this is a perfect choice, if you are looking for more of a bigger resort type of place. The Perry Hotel is located next to a marina and most of their 100 rooms come with water views. The hotel is located about 5 miles from all the action on Duval Street, but they offer a scheduled shuttle to Old Town.

• Havana Cabana – beautiful, waterfront resort with strong Cuban influence. Besides more than a 100 Cuban themed rooms, there is a big pool and a permanent food truck on site. Havana Cabana is about a 10 minute ride to downtown, but there is a complimentary shuttle service, that stops in the historic seaport area. From there you are just steps away from all the main Key West attractions.

Where to eat in Key West

• Blue Heaven – hands down my favorite restaurant in Key West. We had dinner, which was amazing, but it’s also a popular for breakfast and one of the best places to get Key Lime pie. Even though it’s considered one of the best restaurants in Key West, it’s unpretentious and has a very casual vibe. It’s very popular, but they take limited reservations. Bonus points for being very dog friendly as well.

• Andy’s Cabana – a simple place, right across the street from Blue Heaven. We ended up there while waiting for our table at Blue Heaven, but came back a couple more times during our stay in Key West.

• Sarabeth’s – if you are looking for a great breakfast or brunch place, Sarabeth’s is one of the best places. It’s located a bit off the beaten path, a couple a blocks away from Duval Street, so the atmosphere is more laid back.

• Caroline’s Cafe – this open air cafe right on Duval Street was a pleasant surprise. Because of its location, I expected it to be an overpriced tourist trap, but it was anything but. The food was great and reasonably priced, service very friendly, and the already mentioned location perfect for people watching.

• Better than Sex – this place not only has the most catchy name, but is also one of the best dessert restaurants in Key West with the menu consisting only of cocktails and decadent desserts.

READ MORE:

• Fun things to do in Islamorada, Florida besides fishing
• The Ultimate Guide to Marathon, Florida
• Miami to Key West road trip – best stops along the way

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