15 Fun Things to do in Key West On Your Next Trip

View of sunset behind sailboat near key west - fun things to do in key west

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Headed to Key West soon in search of tropical vibes without having to leave the United States? This island city is flanked by the Atlantic Ocean and Gulf of Mexico, and is famously connected to the mainland U.S. via the Overseas Highway. However, unlike your typical tropical vacation destinations, Key West is lively, quirky, and energetic with loads of fun things to do.

There is truly something in Key West for everyone, whether you like history, beach time, partying, and even literature. That’s why I keep returning – as I evolve I find something new in this eclectic city to enjoy. Though only 2×4 miles in size, it’s impossible to get bored here.

If you are in the process of planning a Key West trip, look no further. This list will give you plenty of ideas for fun things to do in Key West for an unforgettable time in The Conch Republic.


15 Super Fun Things to Do in Key West

Fun Outdoor Things to do in Key West

1. Visit Fort Zachary Taylor State Park

Turquoise water at Fort Zachary Taylor State Park - fun things to do in Key West

Fort Zachary Taylor State Park has the best beach in Key West and is a welcome respite from the craziness of Duval Street.  The park is within five minutes of downtown Key West if traveling by car or bike.

Entry to Fort Zachary Taylor State Park is $6 per vehicle or $2.50 for pedestrians and bikers. There is plenty of parking available once you enter the park.

You could spend a full day at this park wandering down hiking trails, exploring Fort Taylor, and enjoying the gorgeous beach.  Beach chairs are available for rent and there is a concession stand for refreshments.  The park also has a western facing section that allows for beautiful sunset views.

2. Take a Photo at the Southernmost Point

Couple posing for picture next to Southernmost point in Key West

One completely touristy, but fun thing to do in Key West is taking a photo by the Southernmost Point concrete bouy.  This supposedly marks the Southernmost Point of the Continental United States. It’s a bit cheesy, but easy to fit into your day, as the marker is just a block away from Duval Street.

Besides the photo op and bragging rights about how far south you ventured, there isn’t a whole lot to it. There is almost always a line here of people waiting for their photos, so your best bet is to go first thing in the morning when it’s shortest. 

Some people might sniff at the thought of waiting in line for a photo. However, it does help if at least one person is over there with you, so they can take your photo!

3. Bar Hop on Duval Street

View of Duval Street facing south

By far one of the most fun and popular things to do in Key West is bar hop on Duval Street. This energetic street is where you can find all of the action (and crowds), as you pass bar after bar. Many of them have live music and open onto the street, which allows for great people watching.

Of course my favorite spot, The Rum Bar, happens to be on the quieter end of Duval, closer to the Southernmost Point.  Their drinks are super high quality, and some of the best you’ll find in the city.  My husband and I personally love their painkillers, and came here every day on our last trip.

Still, the more action-packed opposite end of Duval may be calling you, as there is much more bar hopping to be done over there. That is where you’ll find Sloppy Joe’s, where Ernest Hemingway famously used to frequent. However, I found that many of those bars get sort of repetitive and run together after a while.

4. Join the Sunset Celebration at Mallory Square

Sunset celebration at Mallory Square - fun things to do in Key West

The number one sunset viewing spot in Key West is Mallory Square.  Get there early, as every night two hours before sunset there is a Sunset Celebration. 

You will see local vendors and street performers drawing crowds in various parts of the square.  This livens up the mood and heightens the anticipation as onlookers await the main event.

About a half hour before sunset, head towards the edge of the water to get a spot if you want to sit.  Seats on the concrete ledge fill up very fast, and it’s nice to be comfortable while watching the glowing yellow orb ease its way behind Sunset Key in the distance.

5. Go to the Beach

View walking down Smathers Beach in Key West

While Key West is not exactly known for being the greatest beach destination, they do have a few worth visiting:

  • Southernmost Beach: Located right at the end of Duval Street heading south. There is also the Southernmost Beach Cafe right behind the beach, where you can order drinks and grab lunch.
  • Smathers Beach: This beach is lengthy with fluffy white sand, but has the disadvantage of being located along a busy road near the airport. That said, the water is beautiful and there are chairs, umbrellas, kayaks, and stand-up paddle boards available to rent on site.
  • Fort Zachary Taylor State Park: Already mentioned, but worth bringing up again because I consider this to be the best beach in Key West.  The water at this park is simply stunning, and it’s nice to be more secluded in a natural park setting. Chairs and umbrellas are available for rent here as well.

6. Watch the Sunrise at Higgs Beach

Girl standing on pier at Higgs Beach during sunrise - fun things to do in Key West

Much attention is given to sunsets in Key West, but we cannot forget about sunrises!  After all, Key West is surrounded by water for miles both to the east and west.  That means you have a perfectly unobstructed view of the sunrise to appreciate as well, with a fraction of the crowds.

One of the best sunrise viewing spots is Higgs Beach, which is about a mile from Duval Street.  This is easily reachable with a five minute bike ride, though you will have to rise quite early.  However, it’s totally worth it once you reach the Edward B. Knight Pier at Higgs Beach. 

The colors over the water are truly remarkable, and it’s nice to see Key West at such a peaceful hour. You know – before everyone wakes up and another fun-filled day of festivities begins.

Awesome Tours

7. Climb the Key West Lighthouse

Key West Lighthouse from Whitehead Street during dusk

A climb up the Key West Lighthouse is easy to fit into your day.  The lighthouse is located downtown on Whitehead Street and is only 88 steps to the top. After a short climb, you can walk around the top and view Key West from above, along with the surrounding waters.

The metal steps have gaps in between each one with thin railings, so take note if you’re uncomfortable with heights. I have a heights problem myself, but have learned to force my way up after bailing at the Currituck Beach Lighthouse a few years back.

Your ticket gets you access to the Key West Lighthouse and Keeper’s Quarters Museum.  You can purchase them right on site for $17 or online for $15.40.

Fun Fact: This lighthouse opened in 1848 with a female Keeper, Barbara Mabrity – a rarity at the time.

8. Visit the 6-toed cats at the Hemingway Home & Museum

White exterior walls and yellow shutters of Hemingway House - fun things to do in Key West

The Ernest Hemingway House is one of the most iconic places to tour in Key West.  Not only is it historical and inspiring, but also beautiful. In fact, the grounds often serve as a wedding venue in the evening.

Ernest Hemingway lived here with his second wife, Pauline, from 1931 until their divorce in 1940.  During that time, Hemingway wrote several novels in his studio above the carriage house, when he wasn’t away on trips or lengthy fishing excursions.

During your visit, you’ll likely encounter the current residents of the property: approximately 60 six-toed cats.  Many of them are descendants of a white six-toed cat that Hemingway received from a ship’s captain. You can even find a little cat cemetery on the property.

The Hemingway House is open for touring from 9am to 5pm, 365 days a year for walk-ins. Tickets cost $16 and must be paid in cash. A 20-30 minute guided tour is included with your ticket.

9. Do a Sunset Sail

Girl aboard sunset sail during sunset in Key West

Sunsets in Key West are legendary, and the best way to watch them is on the water. Boats are able to maneuver to isolated spots where your view is completely unobstructed, save for the occasional sailboat on the horizon.

There are numerous tours available, from party boats to more family friendly options. I personally was partial to our relaxed sunset sail, which served us various wines and hors d’oeuvres.

Over two hours, the staff and crew kept things fun and helped take everyone’s photo in front of the sunset.  On the night of our tour, the conditions were so unbelievably calm with no wind, the water was like glass with barely any waves.

10. Join a Walking Tour

The best way to explore Key West is on foot, and a local guide will make sure you don’t miss any of the highlights. There are many different types of walking tours you could do in Key West, from learning the city’s history to doing a pub crawl.

Key West also happens to be a great foodie city, and a food tour will give you the chance to taste a variety of local fare in a short amount of time.

Unique Dining Experiences

11. Indulge in Dessert at Better Than Sex

For the ultimate indulgent experience during your Key West trip, get a little naughty with sinfully good desserts at Better Than Sex.  This nighttime establishment doesn’t open until 6pm, and keeps their lights low. They play up the evening ambiance with small tables that can fit four at the most, as well as details like candles and privacy curtains.

The menu is full of seductive options like Peanut Butter Perversion and Blueberry Birthday Suit.  If you’d prefer something a little less sweet without sacrificing the mood, Better Than Sex also features chocolate-rimmed wine glasses and other cocktails.

12. Eat Key Lime Pie at Blue Heaven

Cross section of a Key Lime Pie slice from Blue Heaven

We cannot talk about dessert in Key West without mentioning its signature dessert: Key lime pie.  What better place to enjoy it than at Blue Heaven, an old Key West standby famous for its gravity defying layer of merengue?

The merengue is not just a gimmick – the Key lime curd is amazingly tart and the graham cracker crust has just the right amount of crunch. The fact that you’ll be enjoying it in their beautiful garden-like outdoor space among the chickens is an extra bonus.  If you visit in the evening, you might even get to hear some live music.

13. Ferry over to Latitudes on Sunset Key

Waterfront dining at Latitudes on Sunset Key
Ignore the fact that my eyes are closed – the scenery is otherwise magical!

One of the most romantic and fun experiences to have in Key West is ferrying over to Latitudes for dinner on Sunset Key.  The ferry leaves from Opal Key Resort & Marina and is complementary with your reservation. Just be sure to make your dinner reservation far in advance, or you risk being left with super late times or missing out altogether.

I returned recently to see if Latitudes was still as good as I remembered, and it was just as mind blowing the second time. Everything we ate and drank was sophisticated and amazing, and I don’t think there is a wrong choice on the menu. Even the key lime pie was one of the best we’ve eaten in Key West. 

The service was also excellent and attentive without being overbearing.  Frankly, Latitudes is not kind on the wallet, but it definitely delivers in elegance and beachy atmosphere as you dine right along the water.

Fun Excursions from Key West

14. Seaplane or Ferry to Dry Tortugas National Park

View of Fort Jefferson at Dry Tortugas National Park from above

One of the most unforgettable experiences you can give yourself during a trip to Key West is a day trip to Dry Tortugas National Park. As this remote park is only accessible by boat or seaplane, you are guaranteed to witness some incredible views along the way.

As Dry Tortugas is seventy miles west of Key West in the Gulf of Mexico, it is one of America’s most remote National Parks. The biggest feature of this park is Fort Jefferson, which is a large masonry structure located on Garden Key.  Hands down, the best way to appreciate its hexagonal shape is by viewing it from above on the seaplane (pictured).

Once either the ferry or seaplane drops you off on Garden Key, the entire island is yours to explore.  Whether you choose a full day or half day tour, you can spend the day lounging on a perfect white sand beach, taking a self-guided tour of the fort, or snorkeling the coral reefs in the surrounding waters.

15. Road Trip Down the Overseas Highway

View out the windshield of the Overseas Highway

A road trip down the bridges of the Overseas Highway is so worth it. In fact, Aaron and I have done the 3.5 hour road trip from Miami to Key West twice now. I mean, how many other places give you the chance to drive over this much water? 

With the Atlantic Ocean on one side and Gulf of Mexico on the other, this is one of the most scenic road trips you could ever do.  While the drive starts out a little commercial and hectic in Key Largo, things mellow out the further south you go as you pass through sleepier, lesser known Keys.  Get an awesome tropical playlist ready (here’s mine), sit back, and enjoy the views. 

If you flew into Key West, but have a rental car, you could also simply do a smaller version of this road trip heading north. Consider driving up to Bahia Honda State Park and grabbing dinner at Hogfish Bar & Grille on Stock Island on the way back down.

• • •

Key West is an exciting place with so many fun things to do for an awesome vacation. This list will help get you started and ensure you don’t miss out on the best experiences that Key West has to offer. You are guaranteed to have an amazing time in this tiny island city in The Conch Republic.

15 totally awesome things to do on your next Key West vacation.  From bar hopping on Duval Street to taking a sunset sail, you are guaranteed to have the best Florida Keys getaway.  Includes the Ernest Hemingway House, breakfast at Blue Heaven, key lime pie, and so much more!
15 totally awesome things to do on your next Key West vacation.  From bar hopping on Duval Street to taking a sunset sail, you are guaranteed to have the best Florida Keys getaway.  Includes the Ernest Hemingway House, breakfast at Blue Heaven, key lime pie, and so much more!
15 totally awesome things to do on your next Key West vacation.  From bar hopping on Duval Street to taking a sunset sail, you are guaranteed to have the best Florida Keys getaway.  Includes the Ernest Hemingway House, breakfast at Blue Heaven, key lime pie, and so much more!

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