The Perfect Key West Vacation: What To Do, Where To Stay, & More

Famed for pastel conch-style houses, nightlife, beautiful water, and its “renegade attitudes and good times”, Key West is one of the iconic American long weekend trips.  So whether you fly in directly or roadtrip down from Miami along the Overseas Highway, I’m giving you a jam-packed list of the best things to do in Key West!

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A little bit about Key West, Florida

Located at the very southern tip of the Florida Keys, Key West is a 2-mile by 4-mile island (key) connected to the other Keys and the Florida mainland by the Overseas Highway.

It was discovered by Ponce de Leon and claimed by the Spanish in 1513.  The historical fact that kind of blew my mind is that Alabama man John W. Simonton bought (BOUGHT) the island for $2,000 in 1821 and it was then claimed for the United States as part of ceded territory from Spain.

It boasts quite a lot of great pirate and military history (somewhat related to each other), has enjoyed close relationships with both U.S. presidents and many famous writers, and attempted to secede from the United States in the 1980s.  For such a tiny place, it packs a big punch!

Today it makes for a great getaway, whether your interest is history, booze-fueled nightlife, or snorkeling along barrier reefs and enjoying its year-round sunshine.

Other Florida Keys adventures for your trip!

Where To Stay In Key West: Review Of H2O Suites

Two of the Best Sunset Spots in Key West (That Aren’t Mallory Square)

The Ultimate Florida Keys Road Trip Guide

Ranking the Best Key Lime Pies In The Florida Keys

A Spe-“Shell” Experience…Touring The Florida Keys Sea Turtle Hospital

Exploring Bahia Honda State Park: A Must On Any Keys Roadtrip

Florida Keys Brewing Company: A Must-Stop On A Keys Road Trip

John Pennekamp Coral Reef State Park: Is A Short Visit Worth It?

Where to Stay in Marathon:  Grassy Flats Resort Review

Exploring Historic Fort Jefferson In Dry Tortugas National Park

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Where to stay in Key West

My recommendation would be to stay somewhere central, where you can park your car.  Then you can walk, bike, or Uber wherever you need to go.  I stayed in two different hotels while I was there, so here are a couple good places to stay in Key West.

For a bit of a splurge stay, I recommend H2O Suites.  As you can see from the pics below (& check out TripAdvisor reviews), it’s beautiful and peaceful, and you get your own little private pool!  I booked the Premier Luxury Suite with Private Pool, and the room was large with a separate seating area.  The staff was very welcoming and the shared hotel areas were lovely as well.

The one downside was that since I was only staying one night, my pool never really got full sun during the hours I was there (check-in mid-afternoon to check-out late morning).  But for people who like to go for a dip whenever they feel like, and have it to themselves, this is perfect.

Read my deep-dive review of H2O Suites here!

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The other place I stayed was the Kimpton Ella’s Cottages (TripAdvisor reviews), and it was really cute and has strong Key West aesthetic vibes.  I’d wanted to stay at Kimpton’s Winslow’s Bungalows (Kimpton has five small properties spread throughout Key West), but they were sadly sold out while I was there.

The lady at the front desk was super helpful and welcoming, and the property is beautiful.  The room itself is quite small and simple and the walls were pretty thin.  I love this little porch, perfect for sitting with a cocktail in the heat of the afternoon, with the fan blowing on you.  They do have a small pool area and patio as well.

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Some general tips for your Key West vacation

First, let’s talk about logistics and getting around…

• Parking in the main parts of Key West can be a real challenge—both to find, and then it’s super expensive when you do find it (like $4-5 an hour, whether lot or street).  You’ll usually pay by an app on your phone.
• Because of this (and traffic being a pain in the ass), as I mention above I recommend finding a centrally-located hotel where you can park, then walk, bike, or Uber/Lyft.
• There’s also a free Duval bus that goes around every 15 minutes or so (10a to midnight usually), so you can stay a bit further away and take that as well.
• Key West is extremely pedestrian-friendly, but still just be careful when crossing the street.  I know that sounds like a “duh”, but after a few cocktails I’ve seen people do dumb things.

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And then here are some miscellaneous tips that may help:

• While parts of Florida are known for gorgeous white sand beaches, the Keys are different.  They’re formed atop coral reefs and so don’t have traditional sandy beaches.  I’ll share what I think are the best beaches in Key West below, but if you’re looking for an amazing beach experience then Key West may not be the best destination.
• There’s a ban on plastic straws here, so I recommend you bring your own reusable metal ones.
• One thing I appreciated was that a lot of of the live music and nightlife starts pretty early, so if you’re wanting to make a decent night of it but not be out til the week hours of the morning, it’s totally doable.  You can watch the sunset, have a great dinner, hit a couple bars or live music spots, and be in bed by 11:00 or midnight.
• In case you were wondering, you CAN drink on sidewalks and walking around.
• Like…literally everything is named “southernmost”.  Make sure you know which one you’re looking for before calling an Uber or booking.

This sounds kind of weird, but you need a midday strategy.  Like, that afternoon time from, say, 2pm to close to 5pm, when it is brutally hot and the lighting is terrible for pics.  Yes, you can lay out on the beach or at the pool but it is wicked hot.  You can siesta.  You can find a bar with decent AC for some day drinking.  But think ahead on this.

Related to that, you’re going to be doing a lot of walking and the heat, humidity, and sun here are no joke.

• Make sure you bring plenty of sunscreen (here are my faves for travel) and hydrate super well!
• Comfortable shoes are a must…these are my absolute favorite (cute) walking sandals for this type of trip, with loads of cushioning and never any blisters.  I also found thigh glide super helpful to prevent heat rash on my inner thighs.
• I have a detailed post on packing for this type of hot weather beach/pool trip, with everything from my favorite swimsuits to beach coverups to sandals, beach bag, sunglasses, and much more.

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Some of the best things to do in Key West

I’m giving you some of my favorite things to do here, including mentioning a few towards the end that were fine but skippable—I wouldn’t go out of my way.  At the end of this section I’ve also listed a number of different things that were on my “maybe” list but I didn’t get a chance to try.

Key West has something for everyone, from history and architecture, to rowdy nightlife or just basking in the sun at the beach.  It goes without saying that you should pick and choose what appeals most to you.

Explore the downtown area & Duval Street

Duval Street is the epicenter of Key West’s vibe, including its well-known nightlife.  Lined with tons of restaurants and shops (and, thankfully, trees for shade!), every visitor needs to spend some time walking up and down the street.

At night it is HOPPIN’, with tons of bars, loads of live music, and basically whatever nightlife you’re looking for.  Swing by Sloppy Joe’s Bar, opened in 1933 and designated a National Historic Landmark.

Walk down the street and listen for a musical style that fits what you’re looking for.  You’ll see plenty of bachelor and bachelorette parties swarming as well (that’s the scientific animal kingdom term, a “swarm of bachelorettes”…).

During the day it’s still busy, but definitely more chill.  My one complaint was that I wished there’d been places to sit and drink your coffee or eat a takeaway slice of key lime pie.  Give me a bench!

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A special shout-out goes to the bars and live music in Key West.  I intended to see more live music, but was honestly tuckered out after long days of heat and 20,000+ steps.  Whether it’s a solo acoustic guitar, a jazz quartet, or a full band, seeing some live music here is a must!

Some of the places you’ll see recommended the most are Sloppy Joe’s, Green Parrot Bar (blues), Smokin’ Tuna Saloon, Virgilio’s (jazz) and Captain Tony’s Saloon.  But also just walk up and down the main streets and listen…you’ll find a style of musician that will pull you in.

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Try all the key lime pies

I made it my mission on my Keys roadtrip to find the best key lime pie in the Florida Keys.  And 15+ different pies later, I feel pretty good about my success.

The origins of Florida’s state pie date back to the 1800s, and it’s one of America’s iconic desserts.  Traditionally it only has six main ingredients, but the execution and end result can vary widely.  I had a whole list of different places I wanted to try, and while I didn’t get to all of them, I put quite a dent in the list!

My ultimate #1 wasn’t in Key West, but there were three Key West spots in my “cream of the crop” grouping.  I definitely recommend Pepe’s Café, Banana Café, and Kermit’s Key West Key Lime Shoppe.  And while it looks impressive, Blue Heaven’s famous Mile High version (below) was middling at best, IMO.

See my detailed ranking of the best key lime pies in the Keys

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Take a sunset sail

I love boats and I love sunsets, and combining the two is one of the best things to do in Key West.  As I was planning my Key West itinerary, I knew that having a strategy for sunset each evening was a must…everyone talks about the sunsets here.  And while I didn’t get an epic sunset either night, my sunset SPOTS were primo.

As I was looking for sunset sail companies, I wanted to avoid a big crowded boat and a party atmosphere—we are all about CHILL here on this site.  I also wanted more of a traditional sailboat experience (there’s an intimacy and visceral “on the water” feel), rather than a giant yacht or catamaran.

After looking through a number of options I decided on the Danger Charters “Wind & Wine” tour (you can also see it on Viator).  They are the rare five-star tour company on TripAdvisor, and also offer a variety of eco tours and on-the-water nature-based adventures, including snorkel and kayak tours.  Their boats are 65-foot schooners designed to replicate the classic skipjacks used in the Keys in the 19th century.

I also loved the wine and hors d’oeuvres aspect of this particular tour…we tried 8 different wines throughout our sail, and they were actually good and interesting rather than just cheap alcohol.  There was a sparkling rosé, a Torrontes, a Pinot Grigio, Chardonnay, Pinot Noir, Merlot, Bordeaux, and a Cabernet Sauvignon.  I definitely recommend!

You can read more about my sunset sail (including some video) here!

A Florida Keys roadtrip was on my list of where to travel in 2022!

Or, watch the sunset from Fort Zachary Taylor’s beach

If you’re a landlubber and a boat’s not your style (or you’re just looking for a different experience), I strongly recommend heading to the beach at Fort Zachary Taylor State Park.  More on the park and the beach in a few minutes, but from a Key West sunset standpoint it’s a winner.

The rock wall here is considered by many to be the best place to watch the sunset in Key West (and I agree, it’s especially romantic), but there is a super long stretch of land that looks out toward the sunset so no one needs to fight for space and you never feel crowded.

As you can tell, I was actively staying away from the Mallory Square sunset celebrations just due to personal preferences, but I’ll speak to that a bit later.

Read more about this sunset experience (including some video) here!

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Go on a coffee walkabout

This is one of my favorite things to do in some cities where the coffee is a big draw (like Istanbul’s Beyoglu neighborhood).  And BOY, Key West qualifies!  Specifically, the area is famous for its plethora of delicious Cuban coffee, and I tried to sample as much as I could.

Both mornings in Key West I went around and uber-caffeinated in my pursuit of the best coffee spots.  First stop was the iconic Cuban Coffee Queen at their original Margaret Street location (with the beautiful mural).  I got the cortadito (which became my go-to on this trip).  In fact, I got two of them…because why not??

Another big winner that was more unique was Keys Coffee Company, right on Duval Street.  They have a frozen café con leche here that is DELICIOUS.  It’s not like fully thick slushy frozen, but is just the perfect amount of icy, sweet, strong…truly amazing.  I went back multiple times because I couldn’t get enough.

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Wander around and enjoy the unique charms of Key West

Key West is a great city to explore on foot (or bike), with a very up-close, residential feel…think shaded sidewalks, profusions of flowers, and charming balconied houses (called “Conch House style”).  If you only drove around, you’d miss the heavy doses of quirk and many unique, small beautiful details that pop up around every corner.

If you want a more official walking guide, check out this one from GPSMyCity or join a free walking tour, but I enjoyed just wandering.  I had a handful of sights I wanted to check out, but also just walked up and down little side streets that looked cute.

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Key West also boasts many interesting historical buildings, from the Custom House to the Ernest Hemingway House, Oldest House Museum to the Audubon House.  You’ll see historic markers scattered throughout town and can explore on your own or join a tour geared toward the historic side.

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Catch some rays on the best beaches in Key West

As I mentioned earlier, the Keys are not known for their beaches, at least not in the traditional gorgeous powdery white sand way.  But there are a few decent beaches in Key West and of course the water and sun are awesome.

I’ll show a couple of your best choices below, though I didn’t get a chance to visit Dogs Beach or South Beach so can’t speak to those.

Smathers Beach is a bit further from downtown Key West, but might be #1 or #2 for sunbathing and water sports, and has pretty nice sand (tied with Fort Zachary Taylor on all counts).

It has these lovely tiny boardwalk paths onto the beach that also make a great photo.  There are public bathrooms and showers, watersport rental options (and chair/umbrella rentals), and sometimes there are food trucks.

I swear by my (totally affordable) prescription snorkel mask…here’s where I got it!

Not a beach necessarily, but something to mention briefly (as I walked from Smathers to Higgs)…right near Higgs Beach is White Street Pier, also known as Edward B. Knight Pier.

During the day this isn’t really anything to see, but I heard that sunrise from White Street Pier is awesome.  I intended to check it out but was so tired I never got out for sunrise.

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Then you have Higgs Memorial Beach Park, also on the southern coast of Key West and a bit closer to downtown.  This beach is smaller, with White Street Pier on one side (so it’s also beautiful at sunrise) and a small pier or break wall on the other (where there’s supposed to be decent snorkeling).

There are quite a few amenities here, including a restaurant, children’s playgrounds, a dog park, tennis and volleyball courts, bathrooms, and showers.  One interesting aspect as well is that there’s both an AIDS memorial and an African refugee cemetery, both right around or just after White Street Pier.

Higgs Beach was okay, but for a beach experience I’d personally do Smathers or Fort Zachary Taylor State Park before this one.  And speaking of Fort Zachary Taylor…

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Combine beach & history at Fort Zachary Taylor State Park

Speaking of beaches, Fort Zachary Taylor State Park provides a two-fer…a cool historical fort plus one of the better beach options in Key West.  Add to that the great sunset views I showcased above, and you’ve got a perfect half-day in your Key West itinerary.

The park is located on the southern edge of Key West, and you can get there by car, bike, or on foot (I took an Lyft there and walked back).  Something to be aware of is that, while the park closes at/after sunset, the fort and all amenities, bathrooms, concessions, etc. close at 5:00pm.  You can learn more about hours and entrance fees here.

The water at the beach is crystal-clear and it has interesting marine life, making it great for beach snorkeling, paddling, and scuba diving.  You can rent snorkel equipment in the park, and they have bathrooms, showers, and a café.

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And then there’s the fort itself.  It predates the Civil War and is a National Historic Monument in its own right, boasting the largest cache of Civil War armament in the world.  It’s worth a little of your time, especially if you’re not getting out to Dry Tortugas.  But it doesn’t hold a candle to Tortugas’ Fort Jefferson…more on that in just a second!

The park also supposedly has great biking and hiking trails, but I didn’t get a chance to check these out.

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Take a day trip to Dry Tortugas National Park

This is one of the things I absolutely think you need to do if you’re visiting Key West.  Dry Tortugas National Park is one of the most remote U.S. national parks, about 70 miles west of Key West and 150 miles south of the U.S. mainland.  It’s also 100 square miles of water, with seven tiny islands in it.

The vast majority of people who visit Dry Tortugas do it as a day trip from Key West, either by sea plane or ferry, and so they get to explore Fort Jefferson.  When I visited, I did it on a private charter sailboat as part of a multi-day sailing trip, so got to see some other parts of the park (like stunning Loggerhead Key).

Fort Jefferson was built in the mid-1800s to protect the U.S.’s gateway to the Gulf of Mexico (as shipping was king), and it’s the largest all-masonry fort in the U.S.  It is SO much cooler than Fort Zachary Taylor.  Plus, it takes up basically the entirety of Garden Key, so it has gorgeous views out over the water.

Read more about visiting Dry Tortugas & Fort Jefferson!

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The logistics of building a massive fort out in the middle of the ocean in the 1800s is…mind-boggling.  And sadly, by the time the fort was completed, it was obsolete.  It was built over 20+ years with the height of technology, but right in the midst of the U.S. Civil War (1860s) military technology made some leaps (including the rifled cannon), and the fort no longer could compete.  It never saw action.

It’s really beautiful, with lots of decorative brickwork and over 2,000 arches.  Yes, you read that right!  I was kind of obsessed with the way the arches stacked infinitely.

You can see how to plan your visit to Dry Tortugas at the official national park website.  Both the ferry and seaplane sound cool, but to me the seaplane would be the clear winner.  One thing to note, there is no cell signal out here, so plan ahead for that.

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See the southernmost point in the continental U.S.

One little corner of Key West that’s nice to stop by is the buoy marker for the southernmost point in the continental United States.   Yes, it’s kind of cheesy and touristy, and no, I personally wouldn’t wait in line to take pics.  I managed to catch it uncrowded on an early Sunday morning run.

From here, you’re only about 90 miles away from Cuba…the joke you’ll hear is that you’re closer to Cuba than a Walmart.  And it’s 100% true, because Key West is more than 120 miles from the nearest Walmart 🙂

Just a few steps away is the gate to Southernmost Point Guest House, a beautiful and unique old house that’s a hotel now, and makes for a pretty photo shot on a blue sky day.  It was on my shortlist of possible hotels, and I chatted with a lady who was staying there who loved it.

You’ll find that seriously everything is called “Southernmost” (it’s a bit like Peachtree in Atlanta), so make sure you know exactly which one you want if you’re getting an Uber, looking on GPS, or booking a particular hotel.

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Play pirate at Key West First Legal Rum Distillery

One of the few *indoor* things I found to do in Key West was a rum tasting at Key West First Legal Rum Distillery.  You can taste different rums, buy all the different ones they offer, or get a cocktail instead (their piña colada was delicious!).

I spent a half hour trying a few different rums and grabbing a couple small bottles to take home.  Supposedly they offer free tours as well from 11am to 6pm, which take around 20 minutes.  No one offered when I walked in and I didn’t feel like asking.

You can also take a tour or cocktail class at Hemingway Rum Company’s Papa’s Pilar Distillery, named after his beloved boat from what I can tell.

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Sunset Pier & Mallory Square (fine but skippable)

After a loooong and hot day of walking, I ended up at Sunset Pier, so stopped for a cold drink and some shade.  It’s not anything special, but the drink was fine.  It would have a good sunset view as well.

Just around the corner (to the left if you’re facing the water) is Mallory Square.  This spot is famous for its nightly Sunset Celebration, a street festival that happens leading up to the sunset.  There are food vendors, local artists, street performers, and more.

Everyone says this is one of the best things to do in Key West, and I can’t necessarily argue as I haven’t done it.  Crowds aren’t really my thing, but if you do decide to do this, it’s recommended to get to Mallory Square an hour or two before sunset to secure a good spot by the water and enjoy the festival atmosphere.

See my reco for best sunset spots in Key West!

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Snap a pic at Mile Marker 0 (skippable)

US 1 stretches down the entire East Coast, from Maine to the tip of the Keys.  This is its termination point, and only takes a second to snap a fun pic and move on.  There’s typically not a long line here, either (which isn’t often true of the Southernmost Point marker.

See the famous Kapok Tree (skippable)

Native to Central American rainforests, this cool-looking tree is just down Whitehead Street from Mile Marker 0, so it’s easy to walk by for a glimpse.  You’ll probably see some of Key West’s ever-present roosters boppin’ around as well.

There were several items on my list of what to do in Key West that I didn’t get around to doing, either due to logistics or prioritization.  These include:

• A snorkeling trip (I’d hoped to do one closer to mid-Keys, but the weather didn’t cooperate)
• Take a walking food tour or craft cocktail crawl or cocktail class; I really wanted to do one of these, but the days and times just didn’t work out (or they were booked up)
• Kayaking eco tours of mangroves, or dolphin eco tours on a boat
• Hemingway Home and Museum – I’m not a museum person so wasn’t too sad to miss it, except for the polydactyl (six-toed!) cats.  My coworker told me this is “a must for cat ladies” which cracked me up.
• Butterfly Conservatory – The highlight is apparently the flamingos, not the butterflies…and the great gift shop, which has local art and souvenirs for a good price.
• Key West Lighthouse
• Key West Cemetery
• West Martello Tower

Where to eat in Key West

Oh man, where to start…I already mentioned the great Cuban coffee spots above, so won’t go into that as much here.

One great spot for breakfast or lunch (not sure on dinner) was Banana Café.  I had a delicious veggie crepe with beets, asparagus, caramelized onions, goat cheese, and avocado, and as I mentioned above their key lime pie was in my top-five for the entire Florida Keys.  My breakfast and key lime pie at Pepe’s Café was also great.

And a shout-out to Key West Cuban Coffee, which had a fabulous menu.  I’d already eaten a bunch and so didn’t get to try their arepas or the other delicious things on their menu.  I got an iced espresso/cortadito and guava and cheese empanada, but the coffee had WAY too much granulated sugar in it to be drinkable.

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I tried to go to Blue Heaven but the wait was too long…however, the hostess told me I could go around the corner to their indoor bar area and get a seat right away.  I did so, and had a decent fresh fish meal along with a mojito and their famous “mile high meringue” key lime pie (which I wasn’t a fan of).

Dinner was a bit uneven for me both nights, mostly because I didn’t plan ahead and make reservations and I’m not willing to wait more than like 15 minutes for a seat.

My first night I ended up at Moondog Café, where I devoured the Frenchman burger, truffle fries, and sweet potato fries with lime curry sauce while sipping their peach basil sangria.  Generally speaking everything was great.

My second night I ended up at Tiger Bar.  It’s definitely unique.  They have an interesting wine menu (I got the Lambrusco) and no real cocktails.  It’s a limited small plates menu, with some fascinating dishes (but a number that I couldn’t eat).  I tried their tea-deviled eggs (delicious and interesting), beef tartare (good but hot, my favorite), Korean fried chicken (delicious but spicy), and lamb ribs (great flavor but fatty and hard to eat).

One other thing to mention is that a stop for ice cream at Flamingo Crossing is a must!  I tried the strawberries & cream and Cuban coffee flavors and both were great…I wish I could have tried more.  One note, it’s cash-only.

Wowza, that was a lot!  But as you can see, there are so many things to do in Key West and it makes a great short vacation.  I recommend pairing it with a bigger Florida Keys roadtrip, which is what I did…I spent two days in Key West and then another 3-4 days exploring the rest of the Keys, and absolutely loved it.

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