One of the top questions I see online and get asked all of the time is what not to miss in Key West. What are the best things to do? Where are the best places to go? The quick answer… that’s a very long list! And, depends on what you like to do and why you are visiting. Want to simply relax? Or enjoy the nightlight? Or spend time on the water? The list is endless, but, let me break it down so you can plan your next trip a bit more easily. No matter if your trip is for one day or one week, here is what you should not miss.
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Of course, you will need to stroll down this world-famous street. This 1.25 mile stretch runs north and south and connects the Gulf of Mexico to the Atlantic Ocean. For those of us who sometimes lose our directional way while in Key West, north is the Gulf Side (think Mallory Square) and south is the Atlantic Side (think Southernmost Resort) Fun fact, it’s named after William Pope Duval, the first territorial governor of Florida.
Duval Street offers so much for visitors to see and do. From live entertainment, in just about every bar, to amazing food, to funky shops, this is the heart of Old Town. I love to walk down Duval in the morning. It’s quiet and peaceful. I window shop and then make a list of what I want to come back to buy. As much as I encourage all of you to explore off of Duval Street, there is a lot to see here, so if you only have a limited time to explore the island, then stick to Duval Street.
Mallory Square Sunset Celebration
Plan to spend at least one night at Sunset Celebration. Honestly, this is why I wanted to visit Key West for the first time. Any place that celebrates sunsets with a party and drinks… well I’m there. Here’s the thing, even after all of these years, it’s still one of my must do things each and every time I visit. I grab a cocktail, find my spot (I have a few favorites) and then … take it all in. The sights, the sounds, the music, the vibe. This is truly what makes Key West, unique. And, I think Sunset Celebration captures the true essence of the island.
About an hour before sunset (but usually earlier) the performers and vendors begin to set up. Come out and support the street performers, psychics, exhibits, and food carts. My favorites? Well, I love the fresh popcorn, and somehow a tarot card reading while watching the sunset seems to bring my life into perspective. Everyone begins to head home about an hour after sunset. Stay a while after sunset, my photographer husband always says the best sunset colors come out about 30 minutes after sunset, and usually, he is right (don’t tell him I said so).
There are so many museums in town. Check out all 18 on the museum trail here. But here are a few of my favorites:
Ernest Hemingway Home – Come see where Hemingway wrote and lived while in Key West. Meet the six-toed cats and stroll the gardens. Every time I take the guided tour I learn something new. I love the story about the pool. Do you know the story?
Key West Lighthouse – Climb the 88 steps to the top for a breathtaking view. Wander the grounds and see how the lighthouse keepers lived. Located across from the Hemingway House, plan to do them both in an afternoon.
Key West Aquarium – this place is so much fun. Want to see what is in the waters around Key West and learn more about the ecosystem? This is a great place to start.
Little White House – Come explore the place Harry S. Truman called home. This is Florida’s only Presidential Museum. If you are a history buff, this is a must-see. Want to learn more about President Truman’s trips to Key West? Check out the official logs about his visits.
Audubon House – a true hidden gem in Old Town Key West. This place looks small from the street, but plan to spend time wandering the gardens and exploring the home. So many beautiful things can be found in the gift shop as well. We spent a morning wandering the grounds and exploring the home. I have visited Key West many times, but never had visited the Audubon House, and have to say, I should have visited sooner.
You would think, due to its location, it would be a noisy spot, but actually, it’s very quiet. We took time to sit on the porch and take in the view and… even for a few minutes thought.. how cool would it be to live here.
Shipwreck Museum – come learn the history of the Key West wreckers. Climb to the top of the tower for an amazing view of Key West. Fun fact, the museum is a re-creation of a 19th-century warehouse built by wrecker tycoon Asa Tift.
Tennessee Williams Home – I learned so much about the man after visiting this place. Great place to duck out of the heat for a while and learn all about his writing and life. Tennessee Williams visited and lived in Key West from 1941 until his death in 1983. It is thought he finished a Street Car Named Desire while staying at the La Concha Hotel in 1947.
Key West Butterfly and Nature Conservatory – Come in and see up to 60 different species of live butterflies from all around the world. Meet Rhett and Scarlett, the resident flamingos. Or, shop the amazing gift shop. I love to take time and simply sit on a bench and watch the butterflies. Word of caution, in the middle of summer, when it’s hot outside, this will be hot too. No air conditioning inside with the butterflies. But the gift shop is nice and cool.
Who doesn’t want to spend time on the water while visiting Key West? Want to hop on jet skis and zoom around the island? Or head out to snorkel, or go dolphin watching or, go on a mangrove kayak tour, or relax on a floating Tiki Bar. Or… do them all??
Sunset Cruises – this is the very best way to see a Key West sunset. On the water. But, I get it, there are so many to choose from, how do you pick THE best? First, decide what kind of experience do you want? Party boat or more intimate. That really helps to narrow down your choices. Check out our article all about the options in Key West (with links to book!)
Glass Bottom Boat Tours – don’t want to go into the water? I get it. How about a glass-bottom boat tour. Check out the best ones here.
Jet Skiing and Parasailing – These are great ways to explore and see the waters around Key West. Check out the options and book with our link.
Want to head out for an eco-experience? See dolphins? Or simply spend time on a sandbar? Check out these options.
Did you know Key West is one of the most haunted places in the United States? And… you can go on ghost hunts, haunted pub crawls, and even meet Robert the Doll. I love to go on these walking tours because each time it’s totally different and I never tire of the stories.
On the Haunted Key West adventure, plan to spend 90 minutes walking through Old Town and hunting ghosts. This isn’t a typical ghost tour, it’s a ghost hunt. You can use ghost hunting equipment to detect supernatural activities.
Ghost’s and Gravestones trolly tour takes you through Old Town and has a more theatrical feel. A lot of fun.
Robert the Doll experience is definitely one to do if you love haunted stories and want to meet this legend. You will visit Robert in his home at the East Martello and learn all about his antics.
Or maybe you want to head out on a haunted pub crawl. Visit the haunted locations, get a t-shirt, and head home with amazing stories.
I get it… Key West isn’t known for its beaches, but hear me out. You are on an island. Sand and water, well to me that’s a perfect way to spend an afternoon. Especially if you have a cocktail in hand.
The waters around Key West are very calm, due to the coral reef that surrounds the Florida Keys. So, don’t expect too much wave action. But, sitting on sand and watching the blue waters is still a lot of fun in Key West.
Some places to check out include, Fort Zachary Taylor State Park, Smathers Beach, and Simonton Beach. Want to know the best beaches in Key West, then check out this list.
Who doesn’t love to shop… especially while on vacation? Well, Key West offers a lot of really cool shops and local events to satisfy any shopper’s needs.
First, let’s start with art. I collect art, and I not the really expensive stuff. I love pieces made by local artists that remind me of my favorite place. I especially love prints. Small scale pictures of Sloppy Joe’s or Irish Kevins. Or of the beautiful homes in Key West. Be sure to check out the many art galleries found in Key West. Some of my favorites include:
- 7 Artists & Friends Gallery – 213 Simonton Street
- Gallery on Greene – 606 Greene Street
- Funky Chicken Store – 814 Duval Street
- Guild Hall Gallery – 614 Duval Street
Kino Sandals – Made right in Key West, these are a favorite of anyone who buys a pair. They become your go to shoe. Ask anyone who has bought a pair… you can’t stop at just one.
Next to Kino Sandals is the Rodriguez Cigar Factory. This is the oldest cigar manufacturer in the Florida Keys. Not being a cigar smoker, I can’t truly appreciate the varieties they offer, but I love the smell of the shop and seeing the hand rolled cigars on display. There are other cigar sellers in town, but this place is tucked away and I simply am drawn to the history of the family and what they do to continue the art of cigar making.
Of course, you can’t come to a literary town, like Key West, and no go book shopping. Don’t worry, there are no box store options on this island. Rather amazing, locally owned and run places that offer books you will find nowhere else, plus a few current best sellers. No need to pack your beach and pool reads, come down and buy something that takes you on an island adventure. A few of my favorites are:
- Key West Island Bookstore – 513 Fleming Street. Used books as well as an amazing variety of local authors. I can spend hours here.
- Books & Books – 533 Eaton Street. This is a locally owned, nonprofit neighborhood bookstore. The bookstore was started by George Cooper and his wife, Judy Blume. Yep, that author all of us loved as kids.
Also, be sure to stop by the wonderful little carts outside of the Sponge Market next to Mallory Square. Lots of options for something special to remember your trip or to bring home to someone that didn’t come along.
Sometimes you don’t want to go out on the water, or maybe the weather has changed your water plans. No matter the reason, there are many other things to do in Key West on land. Like I mentioned before, you can visit museums, or shop, or explore.
I always suggest that first-timers orientate themselves with the island via the Conch Train or the Old Town Trolley. Each is a lot of fun and gives you and a good overview of what you can see and do. Plus, they offer hop-on and hop-off options so you can spend a day seeing the island without wearing out your walking shoes. Now, I did say, I recommend for first timers, but, truth be told… I think these are a long of fun no matter how many times you have been to Key West. But, what’s the difference?
Conch Tour Train is what I call the Jungle Cruise of Key West. For those Disney lovers out there you will appreciate this tour. Campy humor and a fun train-like ride. This ride stays in Old Town so you will see the highlights. There are four stops: Front Street Depot, Truman and Duval Depot (near the Lighthouse, Southernmost Point buoy), Conch Train Station, and Historic Seaport.
Old Town Trolley takes you outside of Old Town. There are 13 stops in all on this tour. If you don’t hop on or hop off, this tour is about 1 1/2 hours long.
Consider a bike tour. No better way to see the off the beaten path side of Key West than with Lloyd’s Bike Tours. Lloyd brings his perspective of the island on this tour and trust me… you will love his perspective.
Want to stroll through the streets of Old Town and see the beautiful historic homes? Then go on a self-guided Historic Marker Walking tour. Check out the stops here.
How about something totally different? Enjoy a movie at the Tropic Cinema. Order a glass of wine or a beer and then head to your seat to watch a great movie. Be sure to grab a photo with Marilyn Monroe outside.
Make sure you head down the Mile Marker 0, you will want to show yourself are at the end (or is it the beginning) of the road?
Eat Key Lime… anything
After all, you are in the town that invented Key Lime Pie, so you have to try everything Key Lime. The first place to start? Kermit’s Key West Key Lime Shoppe. Everything here is key lime, even wine. Stay for lunch or a slice of pie to enjoy in the garden. Or, grab a frozen slice of key lime pie dipped in chocolate. That’s my favorite!
Want to learn how to make a Key Lime pie? Then head over to Key Lime Pie Company. Take the class and then enjoy.
How about iconic Key West? Then head over to Blue Heaven restaurant. The food is amazing, the setting is iconic Key West, but they are famous for their Key Lime pie. Piled high with meringue it is a show stopper for sure. Which begs the question… whipped cream, meringue, or plain? How do you like your pie?
Of course, most bars in town offer Key Lime themed drinks… just ask!
Here’s where, if you love food, you will find your groove. Learn the history of Key West food or the history of the seafood industry. Or, skip the food and go out on a pub crawl or cocktail tour. What I love about these tours are the places you go. Probably they are places you wouldn’t normally stop in to try, but the tour gives you a quick stop and taste. Then you can head back to enjoy yourself at your leisure.
Eat and Drink
Well, you are on vacation and you will need and want to do both, right? Here are a few of my favorite places.
- Sloppy Joe’s Bar – yeah I know touristy, but I love the vibe, the food is good and the drinks are always on point.
- Irish Kevin’s – live music and raunchy humor, but who doesn’t love to drink and laugh the afternoon away?
- Conch Republic Seafood Company – fresh fish and awesome view
- Better Than Sex – best desserts in town
- Garbo’s Grill – food truck with outside seating and a bar, yep that good. I always order the White Sangria
- Harpoon Harry’s – great breakfast. Only accepts cash
- Moondog Cafe – breakfast, lunch and dinner all are great
- Banana Cafe – love their crepes and breakfast
- Bagatelle – lobster mac and cheese, need I say more?
- Onlywood Pizza – yummy pizza
- Caroline’s Cafe – big portions located on Duval
- Green Parrot Bar – free popcorn and the best dive bar in town and a good time will be had by all
- The Rum Bar – too many choices, but all are amazing
- The Bull – love the street view
- Schooner Wharf – the upper deck is my favorite
- Amigos’ – who can pass up great square tacos and great margaritas?
- Mary Ellen’s – frozen Irish Coffee and grilled cheese
- Vino’s – an evening glass of wine on the porch – heaven!
Head up the Keys
If you have a car, plan a day road trip up the Keys. Explore Bahia Honda, the Key Deer Refuge, and even the Blue Hole. Don’t want to drive? Then check out Up the Keys. They will do the driving for you.
Of course, you can plan to spend more time exploring the Keys. Be sure to check out our suggestions for an epic Keys road trip here. We explore all of the stops from Key Largo all the way to Key West.
Or… head even farther out? Then you must not miss the Dry Tortugas National Park. This adventure takes you to the Gulf of Mexico and is home to Fort Jefferson. Access to this National Park is via ferry or by seaplane. Plan to take the tour, and then spend time snorkeling the crystal clear waters surrounding the island. Truly a once in a lifetime event. But, be sure to book your trip early. This adventure fills up months in advance.
As you can see, there are many many things in Key West not to miss. So many, you will need multiple trips to see them all. That’s ok, Key West is the best place to visit and spend time enjoying its island vibe.
Want to see more of our suggestions on what to do? Check out these ideas.