The Best Things to Do in Key West, Florida for an Unforgettable Vacation
- Amy Harris
- Apr 9
- 8 min read
Key West, the southernmost point of the United States, offers a unique blend of sun, sea, and culture. With its stunning beaches, rich history, and a lively atmosphere, this island attracts visitors from all over the world. Are you ready to explore what makes Key West unforgettable? Let’s jump into the top activities that will make your vacation truly memorable.
Best time to Visit Key West?
If you are looking for perfect weather, especially when it's likely cold where you live elsewhere in the country, then look no further than Key West during the months of January to May! The temperature is perfect, it's not unbearably cold and if you go between March and May it's less crowded and hotel rates become a little more reasonable.
If warm temperatures and extreme humidity don't bother you, then visit in the Summer months of June-August, and plan to spend most of your time in or on the water, because it's sweaty out there during those months.
September - November is Hurricane season so it's considered the off season, making it more affordable. However, I've been in both September and October and it was still perfect! Just pay attention to the weather and maybe purchase travel insurance. If you are looking for something a bit wild and crazy, then go during Fantasy Fest in October (more on that later).
Getting To Key West
You can fly directly into Key West, which is really convenient if you are going for a quick weekend getaway!
However, I absolutely love the drive from Miami. All of the Florida Keys are beautiful, and if you are willing to sit in traffic or make a day of exploring a few places along the way, the drive can be a lot of fun! Also, there are quite a few more flight options if you fly into Miami or Fort Lauderdale vs directly to Key West.
If you choose to make the drive South on Hwy 1, plan to stop at few dive bars or beautiful beaches along the way. Enjoy
cool vibes, great food and drinks (unless you're the driver). One of my favorite places to stop is Snappers Oceanfront Restaurant and Bar in Key Largo!
Where to stay in Key West
Where you choose to stay largely depends on your plans during your visit. I prefer to stay in Old Town Key West which is the historic district and the area around the famous Duval Street, known for it's bars, shopping, restaurants and many attractions. I've enjoyed staying at ocean-view resorts that are within walking distance of Mallory Square, and I've also had a great experience at a Bed and Breakfast on Duval Street. One time, we stayed in New Town Key West which is farther from the main attractions, we didn't like that area as much, but it was quieter and more budget-friendly if that's what you're seeking.
Explore some excellent accommodations....
Hotels in Key West
Location, Location, Location:
These upscale Oceanfront hotels are located within walking distance to Duval Street and are near or overlook Mallory Square.
Duval Street Bed and Breakfast
We loved the Tropical Inn Bed and Breakfast! We are not typically B&B kind of people, but this place is unique and the Key West style rooms are fun. Plus, it overlooks Duval Street!
It is an adult only property and features a beautiful lush garden with a heated pool. Also you don't want to miss the Love Lock birdcage!
Oceanfront Beach Front plus great location!
This is a popular resort for its waterfront location on the beach and it's steps away from the Southernmost point at the end of Duval Street. If you like a big resort style vacation, this is the place for you. They have four bars, three heated pools, two beaches, and an oceanfront restaurant.
Best Things to do in Key West
Take a Sunset Cruise
Key West is renowned for its breathtaking sunsets, and there’s no better way to enjoy them than on a sunset cruise.
There are several local companies offering options that cater to every budget—ranging from relaxed boat rides to upscale experiences that include dinner and drinks. On average, these cruises are about two hours long, giving you plenty of time to take in the view. Whether you are looking for a party on the water with a large group and open bar or a private romantic excursion, you will find the perfect trip for you.
Explore Duval Street
Duval Street is the lively heart of Key West, offering a diverse array of shops, bars, and restaurants.
Stroll along the street and visit quirky souvenir shops or indulge in high-end boutiques. Make sure to stop by famous bars like Sloppy Joe’s, known for its vibrant live music scene and signature cocktails, Willie T's which is covered in dollar bills, also, don't miss the Margaritaville Restaurant, where you once might have spotted Jimmy Buffett but always find strong delicious margaritas. There are seemingly endless bars and restaurants and all of them are usually lively and serving strong drinks and delicious food.
Whether you want to dance the night away or enjoy a quiet drink, Duval Street has something for everyone. In fact, this iconic stretch is often bustling with both locals and tourists, especially during the busy winter months when visitor numbers can exceed 400,000.
Take a Snorkeling or Scuba Excursion
It is hard to go to Key West without wanting to dive into the beautiful turquoise waters, and because this area is home to the only living coral reef in North America, it is the perfect spot to go snorkel or scuba diving! This is one of my favorite places I have ever been snorkeling and I have also been on some amazing dive trips!
Dry Tortugas National Park
If you are up for a full day on the water, a day trip to Dry Tortugas National Park is essential. Located approximately 70 miles west of Key West, this pristine park features crystal-clear waters perfect for snorkeling you will encounter vibrant tropical fish, majestic sea turtles, and intriguing shipwrecks. According to recent statistics, the park hosts around 200,000 visitors each year, all drawn by its natural beauty and underwater wonders.
Explore the Key West Butterfly and Nature Conservatory
For a tranquil escape, visit the Key West Butterfly and Nature Conservatory.
As you explore the lush greenhouse, you will encounter hundreds of butterflies and colorful birds among tropical plants and cascading waterfalls. An informative guide provides insights into the butterfly life cycle and the crucial role these creatures play in our ecosystem.
Visit the Southernmost Point Buoy
A visit to Key West isn’t complete without snapping a photo at the Southernmost Point Buoy.
This iconic landmark marks the southernmost point of the continental U.S. and boasts vibrant colors that make it a favorite photo spot. Be prepared for some crowding, as this spot attracts thousands of tourists every year who want to check it off their travel bucket list!
Take a Historic or Literary Tour of Old Town
Uncover Key West's rich history by taking a guided tour of Old Town.
You'll see architectural gems and landmarks that tell the story of the island’s past. Key stops include the Harry S. Truman Little White House, the Oldest House Museum, and charming conch-style homes. You can also take a literary walking tour where a knowledgeable guide will show you the former homes and favorite hangouts of writers that have called the island home. You've likely heard of Ernest Hemingway living in Key West, but there have been many other famous writers such as Shel Silverstein, Tennessee Williams, and Robert Frost to name just a few. Judy Blume, still lives on the island and you can sometimes find her working at Books & Books which she co-founded. Furthermore, if you have a passion for literature or writing, you should check out the Key West Literary Seminar that takes place every January with a new theme.
These guided experiences give you a deeper understanding of how different cultures and histories have shaped Key West into the vibrant community it is today.
Visit the Historic Key West Cemetery
Right in the heart of Old Town, this 19-acre cemetery is full of history and is also a must visit for many, is is reported that it attracts some 50,000 visitors annually. You might even get a chuckle as you stroll by the gravestones and read some of the messages. One says, "I told you I was sick," another reads, "I always dreamed of owning a small place in Key West."
Because of the hard coral rock beneath the cemetery and the high water level which would cause the bodies to rot quickly, the tombs are above-ground. It is a very fascinating place to walk through and worth a visit. You can take a guided tour or just explore on your own.
Go on a Fishing Excursion!
Whether you want to go deep sea or inshore fishing, you will not be disappointed! Or try your hand at flats fishing where you get to "hunt" for the catch! There are so many different fishing charters available to choose from, plan a large group excursion or charter your own private trip with a knowledgeable captain and crew. The fishing in the Keys is always fantastic!
Another really fun thing to do is book a lobster charter, during lobster season from August to March, it is so much fun to harvest the spiny lobsters, and they are delicious too! And to kick off the lobster season, don't miss the Key West Lobsterfest that that has taken place on Duval Street for the last 28 season!
Fantasy Fest
To experience one of the largest celebrations in Key West, be sure to attend Fantasy Fest which takes place every October. It might get a bit wild and extremely lively, but if you're ready for it, you'll enjoy a party unlike any other! This ten day, very adult only party, started in 1979 and has increased in size and craziness ever since. Fantasy fest is a Halloween festival of nonstop parties, day and night. At night Duval street basically becomes one big night club!
We had the best time and are always talking about when we can make it back for this celebration! **my husband was a huge hit as Tiger King in 2020.
Sunset Celebration at Mallory Square
As the sun sets, Key West bursts to life with a variety of nightlife options. You do no want to miss the nightly sunset celebrations at Mallory Square, where local performers and artisans showcase their talents. Two hours before sunset, visitors and locals alike enjoy everything from live music, jugglers, magicians, clowns and psychics to local artists, musicians and food vendors. And when the celebration is over, the party doesn't stop, with live music echoing through the streets, you’ll find plenty of places to unwind after a day of exploration, no matter your style.
Brunch!!
If you are anything like me, after a fun night of partying, you are searching for the best brunch the next morning! Because, why not keep the party going?! Key West is always alive and with so many great restaurants and fun dive bars, you are sure to find a lively brunch. One of my absolute favorite places to brunch is Blue Heaven, it is located just 2 blocks from Duval Street on the corner of Petronia and Thomas Streets. There history is so fascinating, the food is delicious and the atmosphere is fun! Another popular brunch spot that serves brunch daily, is Bagatelle, located right on Duval Street, they offer both indoor and al fresco dining and unique and indulgent menu! Try the famous lobster mac 'n' cheese, you won't regret it! We also, really like Rams Head for brunch or lunch.
Indulge in Delicious Key Lime Pie
Lastly, don't forget to treat yourself to the famous Key Lime Pie. This tangy dessert represents the essence of the Florida Keys and is a must-try while visiting. You can find it at several cafes and restaurants throughout the island, often with options ranging from traditional graham cracker crust to more elaborate versions topped with fresh whipped cream. Statistics show that this iconic dessert sells thousands of slices each week, highlighting its popularity among visitors and locals alike.
One last note, if you really want to explore as much as the island as possible, it is fun to rent a golf cart or moped to zip around in!
Key West is like no other place!
With its rich history, vibrant culture, and stunning natural beauty, Key West, Florida, offers a range of unforgettable experiences for every traveler. I have barely touched on all of the many activities and endless fun that you will, but whether you’re relaxing on the beach, exploring historic sites, or diving into the underwater wonders, you will create lasting memories on this beautiful island. So, grab your suitcase, and get ready for an adventure in paradise—Key West is waiting for you!
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