You booked the trip. Now the list starts.
Sunset cruises. Key lime pie. Beaches. Live music. Happy hours. Seafood. Duval Street. Twenty browser tabs and a mild panic about how to fit it all in.
Welcome to Key West trip planning.
Here’s the thing: Key West rewards people who show up with a loose plan and good instincts more than those trying to optimize every hour. There’s always something happening, something worth eating, and somewhere worth wandering into.
Whether this is your first visit or your fifteenth, this is the guide to things to do in Key West I wish someone had handed me: the things worth doing, the things worth skipping the line for, and a few that might end up being the reason you come back.
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Jump To What Sounds Fun
If This Is Your First Trip To Key West…
Feeling slightly overwhelmed?
Totally understandable.
There are a lot of options.
If I only had a few days in Key West and wanted the classic experience, here is roughly how I would spend my time:
Day 1: Welcome To Key West
✔️ Cuban coffee and breakfast
✔️ Southernmost Point Buoy photo
✔️ Explore Duval Street
✔️ Happy hour with food
✔️ Sunset Celebration at Mallory Square
✔️ Live music at night
Day 2: Get On The Water
✔️ Beach or brunch
✔️ Snorkeling, jet ski, or sandbar trip
✔️ Seafood dinner
✔️ Sunset cruise
Day 3: Slow Down & Explore
✔️ Hemingway House
✔️ Historic Seaport wandering
✔️ Butterfly Conservatory
✔️ Rum tasting
✔️ One last slice of Key Lime Pie (strictly for research purposes)
David’s Take
You do not need to cram everything into one visit.
One of the reasons people keep returning to Key West is that they leave saying:
“Well… guess we’ll have to come back.”
And somehow, they always do.
🍋 Eat Key Lime Pie
If this is your first trip to Key West, trying authentic Key Lime Pie is practically a requirement.
You will find everything from towering meringue slices like this one from Blue Heaven to frozen bars on a stick, and strong opinions about which version is best. Consider it research.
No visit to Key West feels complete without at least one slice of our iconic Key Lime Pie.
And yes, people here absolutely have opinions about where to get the best one.
You will find Key Lime Pie on nearly every menu in town, but not all slices are created equal.
Want a towering, mile-high slice? Head to Blue Heaven or sister restaurant Salute! On The Beach.
Want something fun and portable? Try the famous chocolate-dipped Key Lime Pie on a stick from Kermit’s.
David’s Take
If you ask ten locals where to find the best Key Lime Pie, you are probably getting ten different answers, and maybe starting a friendly argument in the process. My advice? Vacation calories do not count. Try more than one.
Good To Know
- Expect meringue or whipped cream debates
- Frozen Key Lime Pie bars are underrated
- Some restaurants make theirs more tart than others
🦞 Try Our Delicious Seafood
If seafood is your thing, you are in very good hands here.
Start with an order of Conch Fritters because it feels almost mandatory. Then move on to Key West Pink Shrimp, local fish like Yellowtail Snapper or Grouper, Oysters, Stone Crab (season permitting), and if you are lucky enough to find them, Royal Reds.
And please do not skip out on trying Hogfish.
Locals love it for a reason.
Whether blackened, grilled, fried, or piled into a sandwich, fresh seafood is everywhere in Key West.
If It Were Me
Sometimes the best seafood meal is a pound of peel-and-eat shrimp, a cold drink, flip-flops, and watching boats drift by.
Good To Know
- Ask what fish is local and fresh that day
- Happy hours with seafood items are worth seeking out
- Hogfish, Grouper, Yellowtail Snapper, and our Shrimp are local favorites
➡️ Related: Looking for a Seafood Restaurant? Check out my guide to Alonzo’s Oyster Bar.
🌅 Take A Sunset Cruise
If there is one thing that feels undeniably “Key West,” it is being out on the water at sunset.
The breeze, the music, the drinks, the sky changing colors, and it is hard not to understand why sunset cruises are one of the island’s most popular activities.
You will find everything from party boats to romantic sailing charters and classic schooners.
Personally, I tend to enjoy the cruises that include food, drinks, and maybe even a live band to set the mood while the sun slowly melts into the Gulf.
There are plenty of beautiful sunsets in the world, but watching one from the water in Key West with a drink in hand feels unfairly good.
If You Only Do One Thing
If you only splurge on one paid activity in Key West, this would be near the top of my list. Sunset hits differently when you are out on the water.
Good To Know
- Book early during busy seasons
- Bring sunglasses (yes, even in the evening)
- Some cruises are adults-only
- Food and drink inclusions vary
My Favorite Options
- Live music sunset sail
- Romantic classic schooner sunset trip
- Wind, wine & cheese cruise (and beer)
🌅 David’s Take: Picking A Sunset Cruise
If it were me?
First time visiting Key West?
You really cannot go wrong with Commotion On The Ocean. Fun atmosphere, easygoing crowd, drinks, and a good “classic Key West vacation” vibe.
Want something more romantic or relaxed?
Go with a classic schooner sail. It feels a little more old-school Key West and a little less party boat.
Want drinks, music, and more of a social vibe?
Look for a catamaran with an open bar and live music. No judgment here.
To be fair, there is not really a bad choice here; it mostly comes down to what kind of evening you want.
🌅 Want to skip the research?
I rounded up a few sunset cruise options below that are worth looking at.
🌴 Take Part In The Sunset Celebration
There are sunsets… and then there are Key West sunsets.
Every evening, crowds gather at Mallory Square to watch the sun slowly disappear into the Gulf while street performers, musicians, artists, and vendors create a festive atmosphere around them.
And the best part?
It is completely free.
You will see everything from talented performers balancing impossible things to musicians playing island tunes while people wander around with drinks in hand, trying to decide which food stand smells best.
Even if you plan to do a sunset cruise during your trip, I still think everyone should experience the Sunset Celebration at least once.
Quick Local Tip
Don’t make the mistake of showing up five minutes before sunset and expecting a prime viewing spot. Key West sunsets are serious business.
Good To Know
- Arrive 30–45 minutes before sunset
- Bring cash for local artists and vendors
- Great place for photos
- Parking nearby can be limited
➡️ Nearby: Dinner and drinks around the square or at Front Street locations
🎶 Catch Some Live Music On The Island
If your idea of a good vacation includes live music and a cold drink, Key West has you covered.
We are known for our bars, and many of them feature live music every single day.
Seriously.
Walk down Duval Street, wander through the Historic Seaport, or simply follow whatever sounds good drifting through the air.
You will find everything from acoustic island tunes and classic rock to blues, country, reggae, and talented musicians playing requests deep into the night.
The best part?
Most venues do not charge a cover fee.
You can simply wander in, grab a drink, and enjoy yourself. You’ll soon discover that hearing music from somewhere random and deciding, “Well… I guess we’re going in,” is how it’s done.
My Take
Let your ears guide you. Some of my favorite Key West nights happened because I randomly heard music coming from a bar and wandered inside. Also, and I cannot stress this enough, tip your musicians and bartenders. Especially if they humor your song requests.
Good To Know
- Most bars offer free live music
- Happy hour + live music = ideal combo
- Music starts earlier than you might expect
- Duval Street and the Seaport are great starting points
Popular Music Spots
- Schooner Wharf Bar
- Hog’s Breath Saloon
- Willy T’s
- Green Parrot Bar
- Halo at The Saint
- Two Friends
🍹 Duval Street
Love it or hate it, you are probably spending time on Duval Street.
This famous stretch runs from the Atlantic Ocean to the Gulf and acts as the unofficial heartbeat of Key West.
Restaurants, bars, live music, quirky shops, drag shows, people-watching, art galleries, and occasional chaos. You will find all of it here.
Some people spend all day hopping between bars.
Others stroll with an iced coffee and window shop.
Personally?
I think the best approach is somewhere in the middle.
A Quick Thought
Duval is fun, but pace yourself. It has a sneaky way of turning “one quick drink” into accidentally wondering why it is suddenly midnight.
Also, watch out for the gravity vortex. You do not want to end up featured on certain local Facebook pages.
Good To Know
- Most lively at night
- Great for bar hopping
- Easy to walk end-to-end
- Prime people-watching territory
➡️ Perfect Combo: Duval crawl + live music + late-night food stop
📍Have Your Picture Taken At The Southernmost Point
You really cannot leave Key West without at least considering the obligatory Southernmost Point Buoy photo.
Located at the corner of Whitehead Street and South Street (currently in the pocket park at the end of Duval, 1 block from the original location), this colorful buoy marks one of the island’s most famous landmarks and proudly reminds visitors they are only 90 miles from Cuba.
Fair warning:
There will probably be a line.
But everyone is usually pretty friendly and patient while waiting for their turn to snap a picture.
And yes, it is touristy.
But some traditions are worth doing anyway.
Family Tradition
My father always says that if you take your picture with the buoy, you will be lucky enough to return to Key West someday. Personally, I’m not willing to risk skipping the photo and testing the theory.
Good To Know
- Early morning = shortest lines
- Sunset hours can get crowded
- It is free to visit
- Nearby spots make a great breakfast or coffee stop afterward
Nearby Favorites
Grab breakfast at the nearby cafes or reward yourself afterward with a drink by the water.
🏖 Make It A Beach Day
Key West is not like most of the rest of Florida. You are not getting Miami Beach here, and that is perfectly fine; most people are not coming for that anyway.
What you do get is a handful of genuinely good beach options, each with a different personality. Knowing which one fits your trip makes all the difference.
Smathers Beach is your classic stretch, long, palm-lined, shallow water, and the kind of place that actually looks like a postcard. Food trucks occasionally set up nearby. Good for a full lazy beach day.
Higgs Beach has a local feel and a lot going on around it. Free parking, showers, bathrooms, bocce ball, pickleball, volleyball, a playground for the kids, and Salute on the Beach right there for lunch or a drink. If the shoreline is shallow or the sargassum is hanging around, use the pier and climb down the ladder into better water.
South Beach at the Southernmost Beach Resort is small and tucked at the end of Duval. They work to keep the sargassum managed, but it can still appear, especially in summer.
Dog Beach is small but has “that view”, palms, water, Louie’s bar sign, the works. Good for laying out, swimming, or bringing your furry travel companion. Louie’s Backyard as mentioned, is right there, and on the other side, The Reach Resort with Four Marlins restaurant and bar, happy hour, brunch, all the things.
The Best Beach In Key West
Fort Zachary Taylor is the best overall pick. Its position on the island means sargassum is rarely an issue. Beautiful water, a concession stand, BBQ pits, shade, history, and some of the best sunsets on the island. There is an entry fee, as it is a state park. The rocks are sharp; water shoes are not a suggestion here.
Simonton Street Beach at Lagerheads is small, casual, and easy. Rent a chair, walk into the water, and have Lagerheads right there for food and drinks. Simple afternoon sorted.
Good To Know
- Summer sargassum is real; it can affect most beaches, and right now it is significant. Check conditions before committing to a beach day
- Water shoes are strongly recommended, especially at Fort Zach
- Higgs has the best amenities package of any beach on the island
- Fort Zach charges an entry fee
- Free parking at Higgs Beach
When beach conditions are not cooperating, a sandbar trip fixes everything.
🚂 Take A Scenic Ride On The Conch Train
If this is your first time in Key West, the Conch Train is one of the easiest ways to get your bearings.
Hop aboard, relax, and let someone else do the driving while you learn about the island’s quirky history, famous residents, architecture, and landmarks.
You will roll past many of Key West’s most recognizable sights while hearing stories you probably would not stumble upon walking around on your own.
And yes, some of the jokes are delightfully cheesy.
That is part of the charm.
🚂 Thinking About The Conch Train?
If this sounds like your kind of activity, it is worth booking earlier during busy seasons.
→ Check Conch Train Tickets Here
Worth Knowing
I think the Conch Train gets underrated by first-time visitors because it sounds touristy. But if you do it early in your trip, it helps you figure out where you want to spend more time later.
Good To Know
- Great activity for first-time visitors
- Best done early in your trip
- Bring water (the Key West sun does not mess around)
➡️ Bonus Tip: Use the train ride to make mental notes of places you want to revisit later. There is also a Trolley tour that you could look into.
🐓 Meet The Locals
No, not just the humans.
One of the first things visitors notice in Key West is that we have a lot of free-range roosters and chickens wandering around.
And when I say wandering around, I mean everywhere.
Sidewalks. Parking lots. Restaurant patios. Random intersections where they somehow look like they have somewhere important to be.
These unofficial island mascots and ambassadors are protected, so admire them, photograph them, but please leave them alone.
You will also spot iguanas sunning themselves, geckos darting around, and giant tarpon waiting patiently near the docks for someone to toss them a snack.
And then there are the mosquitoes and no-see-ums…
They are excited for your arrival too.
David’s Take
The baby chicks, which I affectionately call “nuggets”, are somehow adorable and chaotic at the same time. Personally, I find it impossible not to smile when I spot them running around.
Also, if a rooster wakes you up at sunrise, congratulations: you are getting the authentic Key West alarm clock experience. Take note: Sometimes the rooster is drunk and will wake you at 3 am.
Good To Know
- Please do not feed, chase, or harass the chickens
- Tarpon feeding can be fun to watch at the waterfront
- Bring bug spray, especially after rain
- Iguanas mostly mind their own business; many are at the cemetery
➡️ Best Spot To See Tarpon: Around the Historic Seaport and marina areas.
🥃 Experience Key West Rum Culture
We like rum here.
Considering Key West’s maritime history, proximity to Cuba, and salty island spirit, it makes sense.
You will find no shortage of mojitos, rum runners, piña coladas, and tropical cocktails around town.
In fact, the Rum Runner is one of Key West’s signature drinks, sweet, tropical, and probably stronger than it tastes.
For a slower pace, grab a seat on the porch at the Rum Bar at the Speakeasy Inn and watch life unfold along Duval Street while sipping something delicious.
Want to dive deeper?
Take a free rum tasting tour at the local distilleries and learn a little island history while you are at it.
Worth It?
Sitting on a porch in Key West with a rum drink while nothing productive happens for a while feels oddly perfect. I highly recommend it!
Good To Know
- The Rum Runner is a Key West classic
- Free tours are available at some distilleries
- Rum flights are a fun way to sample different styles
- Pace yourself, vacation memories are nice to keep
Popular Rum Stops
- Key West First Legal Rum Distillery
- Papa’s Pilar Rum Distillery
- Rum Bar at the Speakeasy Inn
🌊 Have Fun On The Water
This is where Key West really delivers.
The beaches are good. The water activities are the reason people come back.
Key West is surrounded by two distinct bodies of water, the Atlantic on one side, the Gulf on the other, and the options for getting out on both of them are excellent.
Sandbars are the move if you want the quintessential Keys water experience. Crystal clear, shallow, warm water with nothing around you but sky and sea. No sargassum, no crowds, no agenda. Most trips include snorkeling stops, wildlife sightings, and a cooler. If you only book one water activity, make it this.
Snorkeling is spectacular here. The Florida Reef is the third-largest coral reef system in the world, and it is right in our backyard. Half-day trips are easy to find, and the underwater visibility can be jaw-dropping.
Fishing is a big deal in Key West. Offshore, backcountry, reef fishing, snapper, mahi. The options are serious. Many charters will clean your catch, and several local restaurants will cook it for you. That is a pretty good deal.
Kayaking and Paddleboarding through the mangroves is one of those quietly great experiences that does not get enough attention. Calm water, wildlife, and a completely different side of the island.
Eco Tours are worth considering if you want something more guided and educational. Dolphin watches, bird tours, backcountry adventures, good for families or anyone who wants more than just splashing around.
Jet Ski Tours around the island are exactly as fun as they sound. Fast, scenic, and a good way to see Key West from the water in a short amount of time.
Parasailing if you want the bird’s eye view and a story to tell.
More Ways To Get On The Water
Sunset Cruises deserve their own section, and they have one, but they belong in this conversation too. Getting on the water at golden hour in Key West is one of those experiences that is hard to oversell.
If It Were Me
One of the biggest mistakes visitors make is spending their entire trip on Duval Street. Key West is an island. The water is the point. Even a half day out on it changes the whole feel of your trip.
Good To Know
- Morning water is generally calmer
- Book ahead during busy seasons — trips fill up fast
- Many fishing charters clean your catch
- Several restaurants will cook what you catch
- Reef-safe sunscreen is your friend out there
- Snorkeling gear is typically included on reef trips
Ready to book something? Here are a few water activity options worth looking at.
📚 Follow In Hemingway’s Footsteps
You really cannot talk about Key West history without mentioning Ernest Hemingway.
Visit the Hemingway Home and Museum to see where he lived and wrote some of his most famous works while surrounded by lush gardens and famous six-toed cats.
Yes, those cats are descendants of Hemingway’s originals.
And yes, you will probably take way too many photos of them.
You can also continue your Hemingway-themed day around town.
Grab a drink at Captain Tony’s, one of his former favorite watering holes, or stop by Blue Heaven, where it is said he once refereed boxing matches.
Because apparently Key West has always been delightfully askew.
You might hear a saying about Key West, “This is where the weird go pro.”
Worth Knowing
Even if you are not a huge literature person, the Hemingway House is worth doing. Between the cats, history, architecture, stories, and gift shop, it ends up being way more interesting than people expect.
Good To Know
- Arrive earlier in the day to avoid the heat
- The cats are minor celebrities
- Great spot for history lovers
- Easy walk from Duval Street
➡️ Nearby Stop: Pair it with breakfast or lunch at Moondog Cafe and make a morning out of it.
🍳 Enjoy A Memorable Breakfast Or Brunch
There are two schools of thought in Key West:
People who sleep in on vacation…
…and people who wake up hungry and immediately start planning breakfast.
I firmly support the second group.
Key West has no shortage of memorable breakfast spots, whether you want something hearty after a late night or a leisurely brunch with mimosas and island vibes.
Start early at Harpoon Harry’s if you are an early riser. They open before many places even turn the lights on, and the portions do not mess around.
The “oldest restaurant in Key West” serves up a fresh and hearty breakfast. Check out the offerings at Pepe’s Cafe.
Want something more “Key West”?
Grab breakfast at Blue Heaven, where chickens casually wander around while you eat under the trees. Their BLT (L = Lobster) Benedict and giant banana pancakes have a loyal following for a reason.
Don’t sleep on Banana Cafe or Moondog Cafe either. There is usually a line for a reason.
Moondog Cafe & Blue Heaven just made the Michelin Guide. They are the first Key West restaurants to do so and to hold this distinction.
Craving waterfront views?
Places like Four Marlins at The Reach, Salute on the Beach, and Southernmost Beach Cafe make breakfast feel a little extra special.
David’s Take
Key West does Benedicts unusually well. I did not expect that the first time I visited, but now I almost feel obligated to order one every couple of outings like this one from La Te Da.
Good To Know
- Breakfast spots can get busy quickly
- Outdoor seating is common
- Early morning is cooler and quieter
- Coffee lovers: Cuban coffee is a must
- Bloodys and Mimosas are hangover gold
🍻 Explore The Island Happy Hours
If there is one thing Key West does as well as sunsets, it is happy hour.
Actually. Happy hours. Plural.
You will find daily drink specials, discounted appetizers, waterfront views, and enough options to turn “just one drink” into a legitimate afternoon plan. Some spots lean mostly on drinks. Others have great food deals worth building your afternoon or evening around. Done right, happy hour in Key West saves you real money while letting you sample multiple places in a single day.
I have spent more time than I care to admit researching this particular topic. Vacation math works differently here. Appetizers become dinner. One happy hour becomes three. Nobody is mad about it.
If waterfront views, food specials, and knowing exactly which spots are worth your time sounds useful, that is precisely what my Key West Happy Hour Food Guide is for. It has been the most-read thing on this site for years, which says something about Key West or about the people who visit it. Probably both.
Sports Bars
Key West is not a city you typically associate with sports bars, but they exist, they are good, and when there is a big game on, they deliver. Whether it is football season, playoff time, or a major international tournament like the World Cup, there are solid spots to catch the action with cold beer and good food.
➡️ Best Sports Bars In Key West
🚶Stroll Down The Historic Seaport
One of my favorite ways to slow down in Key West is simply wandering through the Historic Seaport.
There is always something happening.
Fishing boats unloading their catch.
Mega yachts parked beside tiny dinghies.
Sailboats heading out for sunset.
People lingering over drinks while live music drifts through the air.
It somehow feels busy and laid back at the same time.
And when hunger strikes?
You are surrounded by solid options.
Grab seafood, oysters, cocktails, or just sit somewhere with a view and watch island life unfold.
David’s Take
This area feels especially magical that hour before sunset when the boats start glowing in the sunlight, and everyone collectively decides productivity can wait until tomorrow.
Good To Know
- Great area for sunset wandering
- Plenty of seafood restaurants nearby
- Live music is common
- Excellent people-watching
Popular Spots
- Half Shell Raw Bar
- Alonzo’s Oyster Bar
- White Tarpon
- Schooner Wharf Bar
- Boat House
- Conch Republic Seafood Company
🦋 Spend Time With Our Winged Friends
Need a little break from bars, beaches, and sunshine?
The Key West Butterfly & Nature Conservatory feels like stepping into a completely different world.
Inside, hundreds of butterflies float through a lush tropical habitat filled with flowers, waterfalls, and quiet corners to slow down for a bit.
You will also meet the resident flamingos, Rhett and Scarlett, who somehow manage to completely steal the show.
Even people who think:
“I do not know if butterflies are my thing…”
usually end up loving it.
David’s Take
This is without a doubt, one of my favorite peaceful spots on the island. There is something oddly calming about slowing down and watching butterflies casually ignore your personal space.
Good To Know
- Nice break from midday heat
- Great rainy-day activity
- Family friendly
- The gift shop is dangerous if you like souvenirs
➡️ Perfect Pairing: Combine with breakfast or lunch nearby on the southern end of the island.
🎨 Explore The Artsy Side Of Key West
Key West has always attracted creative people.
Writers, musicians, painters, photographers, performers, and wonderfully eccentric personalities somehow all seem to find their way here.
The island feels better and thrives because of it.
Take some time to wander through galleries, peek into studios, and admire the colorful architecture sprinkled throughout Old Town.
One of my favorite low-key activities is simply walking around in the morning before things get busy. You notice details, colorful cottages, hidden courtyards, funky art, and tiny surprises you somehow missed the day before.
Keep an eye out for sculptures near the waterfront, local art displays, and even the sidewalk poems tucked throughout town if you remember to occasionally look down.
Quick Local Tip
I think some of the best Key West moments happen when you are not rushing anywhere. Grab a coffee, wander around, and let the island show you weird little details.
Good To Know
- Mornings are perfect for wandering
- Many galleries are free to browse
- Local art makes a fun souvenir
- Architecture lovers will have a field day
➡️ Perfect Pairing: Cuban coffee + morning walk through Old Town
☕ Go Cuban
We are closer to Havana than the nearest Walmart.
Seriously.
So it should not surprise anyone that Cuban influence runs deep throughout Key West.
And one of the best ways to experience that?
Food and coffee.
Start your morning with a strong Cuban coffee. Cuban coffee in Key West has a funny way of convincing you that suddenly you can accomplish absolutely anything.
Then work your way toward Cuban sandwiches, café con leche, croquetas, ropa vieja, or other delicious island staples.
Fortunately, you will not struggle to find good options.
Places like Cuban Coffee Queen, Ana’s Cuban Cafe, Frita’s, 5 Brothers Grocery & Sandwich Shop, and Sandy’s Cafe tend to have loyal fans.
And if you are hunting for a sit-down Cuban meal, check out El Siboney Restaurant or El Meson de Pepe.
David’s Take
Trying to decide where to get the best Cuban sandwich in Key West feels suspiciously similar to the Key Lime Pie debate. Everyone has strong opinions, and in fairness, your best move is to try several.
Good To Know
- Cuban coffee is stronger than regular drip coffee
- Great breakfast and lunch option
- Many local favorites are casual and affordable
- Perfect fuel before a long day exploring
💃 See A Risqué Show
Only in Key West can someone casually say:
“Want to go watch drag races?”
…and nobody expects cars.
During Conch Republic Days in April, drag queens race down Duval Street in heels, tackle obstacle courses, and stop for shots along the way. It is exactly as entertaining as it sounds and should not be missed!
For something completely unexpected, keep an eye out for the famous Vibrator Races at Mary Ellen’s Bar. Equal parts hilarious and wonderfully weird, these charity races perfectly capture that “only in Key West” energy.
Key West nightlife has personality, and one of the most entertaining nights out can be catching a drag show, cabaret, or performance.
Expect big personalities, incredible makeup, impressive costumes, and plenty of laughs.
Venues like 801 Bourbon Bar, Aqua Nightclub, and La Te Da know how to put on a show.
Even if this is not normally “your thing,” many first-time visitors end up saying:
“Okay… that was way more fun than I expected.”
What To Expect
Do not be surprised if their makeup looks better than yours. Also, audience participation sometimes finds you, whether you volunteered or not.
Good To Know
- Shows can sell out during busy seasons
- Arrive early for better seats
- Drinks beforehand are strongly encouraged
- Bring cash to tip performers
➡️ Perfect Pre-Game Spot: 22&Co for a fun cocktail beforehand (yes, the glitter espresso martini deserves consideration)
🎉 Come For A Festival Or Event
One thing Key West does exceptionally well?
Finding reasons to celebrate.
There is always something happening here.
Seriously, there is almost always something happening.
Music festivals, quirky local traditions, food events, boating races, costume parties, island celebrations, you could visit multiple times and have a completely different experience depending on the season.
A few favorites include:
- Fantasy Fest
- Key West Songwriters Festival
- Mile 0 Fest
- Just A Few Friends
- Goombay
Then you have Mini Lobster Season, Rum Fest, Key Lime Pie Festival, Boat Races, Pride, Conch Republic Independence celebrations, weddings, random themed parties, and enough live entertainment to accidentally lose track of time.
David’s Take
If you are visiting during Fantasy Fest and somehow did not realize it beforehand… surprise. You are about to have a very memorable trip.
Good To Know
- Hotels book early during festivals
- Prices rise around major events
- Check event calendars before booking
- Some weekends feel dramatically busier
➡️ Planning Tip: If traveling during major festivals, book accommodations early.
🏝 Visit Dry Tortugas National Park
If there is one Key West activity people regret not planning far enough in advance, this is probably the one.
Located about 70 miles west of Key West, Dry Tortugas National Park feels like stepping into another world.
Crystal-clear water.
Massive historic fort.
Excellent snorkeling.
And a level of quiet you do not always find with the roosters, leafblowers, and crowds in Key West.
Most visitors arrive either by ferry aboard the Yankee Freedom or by seaplane if they are feeling especially adventurous.
I’ve done both.
Worth Knowing
This is one of those “future-you will thank present-you” experiences if you plan well ahead.
The same goes for dining at Latitudes on Sunset Key; if it is on your wish list, book as early as possible. It is one of the toughest reservations to get in Key West and can fill up months ahead.
Every time someone comes back from Dry Tortugas, they usually say some version of:
“Okay… that was incredible.”
Good To Know
- Book far in advance
- Ferry and seaplane spots can sell out
- Bring sunscreen, water, a sarong, or a hat for shade
- Snorkeling gear is included
🏝 Planning A Dry Tortugas Trip?
If Dry Tortugas is on your list, book it early. Reservations often fill up well in advance.
Most visitors take the ferry:
→ Yankee Freedom Ferry
Want the splurge option?
→ Dry Tortugas Seaplane Adventure
One Last Thought
However you decide to spend your time, Key West has a funny way of turning “just one trip” into “when are we coming back?”
Full stomachs, sunsets, chickens, and stories tend to have that effect.
And to tell the truth, that’s part of the magic.
🧳 Still Planning Your Trip?
Still planning your visit?
If happy hour sounds like your kind of vacation activity, you are definitely in the right place and on the right page!
🍹 Key West Happy Hours With Food
One of my favorite ways to enjoy Key West, and apparently many of yours too.
Waterfront views, food specials, drinks, and plenty of places worth making time for.
→ Key West Happy Hour Food Guide
Planning Where to Stay in Key West
If you are still figuring out where to stay, I recommend booking earlier rather than later, especially during busy seasons and events.
Old Town is usually best if you want to walk to restaurants, bars, sunsets, and most of the fun. If beaches are more your thing, you may prefer staying closer to Smathers or Higgs Beaches.
Find places to stay in Key West below:
More Key West food, drinks, happy hours, travel ideas, and adventures are coming soon. 🌴☀️🐓