Find out more: Antonia’s Restaurant Website.
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Find out more: Kermits Website.
If you want an insight into how unique Key West is, visit the Sails to Rails museum. There are two themes – 500 years of maritime history including big sail boats but also Henry Flagler’s epic building of the overseas highway which connected Florida with Key West by train. At one point, it was possible to book a ticket all the way from New York to Cuba via a combo of the train and ferry. Sadly, a hurricane hit the rail bridge and it was never rebuilt – you will drive past it on the way down to the Keys so keep an eye out.
Etched on Zimbabwe granite, the Key West AIDS memorial is a tribute to the people who have died of AIDS who lived in and loved the Florida Keys. Each year there is a commemorative ceremony and candlelit march.
75 Best Things To Do in Key West
How to do it: I have a whole post dedicated to the 21 Best Things To Do in The Florida Keys.
Getting around Key West
You won’t be short of beautiful choices for where to stay in Key West but don’t expect those beautiful choices to come cheap. I lean towards budget accommodation and even a dorm room will set you back around – a night. For a basic apartment rental, I paid 0 a night with a friend. The best hotels in Key West are going to cost a pretty penny. The upside is that even though you pay a bit more, the quality is very good. Here are the places I have stayed and some alternatives that look good/are quirky:
1. Drive down Highway 1 with the wind in your hair
Interesting fact: The Key West lighthouse is a bit unique as it’s not on the coast. The original lighthouse was wiped out in a hurricane so the replacement was built further inland.
How to do it: I don’t have any recommendations for you except that if you’re curious but don’t want to waste a whole meal, try the Cuban sandwich (shared with a friend?) at Cuban Coffee Queen.
How to do it: You can check prices and reviews of the Southernmost hotel here.
Find out more: Hemingway Rum Distillery Website.
2. Take the Key West Old Town Trolley
Key West Florida Reef Half-Day Snorkeling Excursion
While there is a fee if you want to go inside, for many people, a picture of the front of Key West’s oldest house is enough.
Find out more: Garden of Eden Website.
2. Take the Conch Train Tour
How to do it: You can book tickets here on Get Your Guide or here on Viator.
Find out more: Pinchers Website.
4. Take the free Duval Loop
If there’s 10 of you, you’ll pack the place out and only 3 of you will get a seat. It’s slap-bang on Duval and worth a stop though do move on after a drink to let others give it a try.
Travel Life tip: don’t do anything that will make you see the inside of the courthouse. Reference above: don’t steal ‘mile 0 sign’.
5. Get around Key West by golf buggy
There is also a haunted pub-craw which you can book on Viator or Get Your Guide.
How to do it: You can find a list of the top Key West art galleries here.
Southernmost Key West
6. Rise early for a picture at the Southernmost Point Key West
Find out more: Pepe’s Cafe Website.
Find out more: Green Parrot Website.
How to do it: You can find out more on the Custom House website here.
7. Stay at the Southernmost House
I visited this place about 10 years ago when it was newly opened and I’m pleased to see it is still going. It’s no longer serving the famous square tacos, but the round ones are still pretty good. And this from the girl who has eaten her way from coast to coast in Mexico.
A Mallory Square institution for drinks at sunset. There’s Cuban food and therefore accompanying mojitos. Not to be confused with Pepe’s Cafe, recommended above.
8. Check out (but don’t steal) the Mile 0 Sign
Want a bite without the frenetic noise of Duval Street? Pop into Sloppy Joe’s Tap Room. Same great beer and service but in a slightly more sophisticated surrounding just off Duval Street.
Serving some of the best coffee in the world (IMO), Cuban Coffee Queen is a must stop in Key West. Don’t be a gringo – order the cafe con leche or don’t order at all.
9. Go Cuban at Cuban Coffee Queen
Alternative rum tasting: Key West First Legal Rum Distillery for more rum tasting. You might visit here if this distillery is included in your sightseeing ticket instead of the Hemingway or distillery. Or, if you really like rum.
The Key West Old Town trolley is my favourite thing to recommend for first timers in Key West and is the closest thing you’re going to get to a hop-on hop-off in Key West. In under two hours you’ll be given a complete tour of the island together with plenty of hop-on-hop-off opportunities. It’s the ideal way to get oriented and decide what you want to see during your time on the island. You’ll get a bunch of history as well as plenty of bar and restaurant recommendations.
10. Try Cuban cuisine (but don’t blame me)
Dine at the bar. Chat with the locals. Eat the specials (they know what sells and they sell it cheap). Pepe’s is an authentic Key West eatery. They’ve been serving since 1909; the year, not the time. However, turn up at 9 a.m. and the liquor bar is doing business like it’s 5 minutes from closing.
I’ve been in the Clink myself before, but that was for a different reason.
Free Cultural Things To Do In Key West
It wasn’t until my 4th visit to Key West that I organised myself to climb up the lighthouse. Honestly, the view from the top rubbed a bit of shine off my notion that Key West is a cutesy town. From the top, you see the island sprawl and it isn’t that pretty. However, it’s still worth a visit. Key West and the surrounding islands are so low lying, they were hazardous for ships so the lighthouse was vital to the island for many years. Stop into the keepers house for more information on what lighthouse life was like.
11. Visit the Oldest House in Key West
Serving brunch seven days a week and with prime people-watching on Duval, Bagatelle is so popular it won the open table Diner’s Choice Award. If you can’t get a spot for brunch, they have a good range of fish and meat options for dinner.
Find out more: Willie T’s Website.
12. Take the Key West Historic Seaport Walk
Find out more: Blackfin Bistro Website.
Find out more: Fausto’s Website.
Find out more: Smallest Bar Website.
13. Explore the Key West Cemetery
Whether it’s the famous Cuban sandwich or a take on the chicken, rice and beans dish that’s endemic in Cuba, it’s worth giving Cuban food a go. Personally, having spent over a month in Cuba across two trips, I can firmly say I’m not a fan of Cuban cuisine but don’t let me sway you.
Find out more: Hard Rock Cafe Website.
14. Check out the Kapok tree at the Monroe County Courthouse
One thing that surprises a lot of visitors to Key West is the absence of beautiful beaches. Most of them are man-made but that’s not to say you can’t enjoy Key West’s Caribbean vibes. You just need to go offshore on a day trip. Here’s some of the best options.
Find out more: Alonzo’s Oyster Bar Website.
How to do it: You can find out more on the official website here.
15. See the Birthplace of PanAm
Fun fact: this was a popular spot for old Hemingway (though I suspect most of the bars in Key West were).
You can get to Key West by plane, boat or shuttle but by far the best way is to drive down Highway 1. Ideally in a cabriolet/convertible. I highly recommend a Mustang. Yes, your car choice screams ‘tourist’ but so what – you’re are on vacation, right? If you are making a list of what to do in Key West, start the list right with a stylish arrival.
16. Wander the art galleries
One of the things I love about Key West is the cultural buildings littered about the island. Without spending a cent, it’s easy to spend a day wandering around old town Key West, taking pictures of one historic building, famous location or Key West sight after another. Here are my favourites.
Find out more: Dirty Pig Website.
17. Pay Your Respects at the Key West AIDS memorial
Find out more: Sloppy Joe’s Website.
18. Count the Key West roosters
Southernmost House – this one wins for location and claim to fame. If you stay here, let me know what it’s like. It’s always been out of my price range.
I was museum-ed out by the time I got to the Truman Little White House and the scheduled tour had just left so I ended up skipping this. However, it looked impressive. It’s still in active use and has seen lots of presidents (USA and overseas) visit. Make sure you check the schedule before you go to see the tour times.
19. See the sunset from Mallory Square
A real insider tip for Key West is to dine near the historic waterfront during happy hour (usually around 4 p.m. to 6 p.m.) when you’ll get 50% off a good range of small plates. I had a 1/2 lb of peel and eat shrimp plus lobster bisque for . It’s a great, cheap way to get a seafood or oyster fix. I chose Commodore because it was a large place and could seat me (happy hour is popular) but all the waterfront eateries have an offer on.
The best time to visit is between March and May. October and November are also decent enough shoulder season months.
20. People Watch on Duval Street
How to do it: Check out the official website here. If you visit here and Custom House museum, you get a discount.
Want to do something fun? Try this scavenger hunt that will take you through the cemetery.
Museums And Cultural Things to Do in Key West
Fly – Key West has an airport (Key West International airport, to be precise) if you’re flying from within the USA. Key West airport is 3 miles from Duval Street. You can search for flights here.
21. Hit up Hemingway House
How to do it: You can find out more about the Sails to Rails Museum here. This museum is included with your Trolley ticket.
Right on Duval Street with an outdoor patio, Fogarty’s is a great spot for people watching while you eat. Unlike many of the bar-eateries on Duval, you get a proper seat and won’t feel jostled or rushed. You’re supposed to eat the tacos. I went rogue and ordered the fish plate, which was lovely.
22. Climb the Key West Lighthouse
Key West Travel Tip: You don’t really need a car in Key West if you’re staying in the old town but if you do have one, there is plenty of free parking – just stick to the marked bays and avoid the ones with ‘residents’ written on them.
How to do it: You can book tickets here.
How to do it: You can book a haunted pub-craw on Viator or Get Your Guide.
23. Visit Custom House for an overview of Key West
How to do it: unless you have a car with you, the museum is a bit tough to get to but is included on the Ghost and Gravestones Tour.
24. See 50o Years of History at the Sails to Rails Museum
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‘We’re going on a tiki hut sunset cruise,’ the couple explained to me and it took a minute (and further questions) for me to connect the dots. Sure, I knew what a tiki hut was. And I’d been on many sunset cruises. But a tiki hut that floats and does a sunset cruise? That was definitely new to me. And, it’s possible in Key West. I have yet to try it but it looks amazing and surely has to be one of the most fun things to do in Key West?
25. Learn about treasure hunting at the Mel Fisher maritime museum
I tried to eat at Turtle Krawl but they didn’t like that I was a solo diner and would only give me a spot in the back despite having lots of sea view seats available. Boo. Hiss. I took my business elsewhere.
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26. Visit the Truman Little White House
I was so caught up in my own self-guided food tour that it wasn’t until another tourist recommended this to me that I thought ‘oh yeah, that would be a good idea’. Anyway, here are a few Key West tours focusing on food. Let me know if you try them.
Heading to Miami? Here’s my list of 40 Cheap Things To Do in Miami
27. Tennessee Williams Museum
Southernmost Sanctuary – I had a very enjoyable stay here (probably given I was sleeping in the double bed not on the sofa bed, which my friend graciously took). For the price, it was one of the cheaper apartment stays in Key West. Very close to Southernmost…everything.
How to do it: Take a picture of the sign out front or stop in for a beer. More details here.
28. Take a ghost tour
I’ve just completed my 4th visit to Key West and, although I’ve spent my fair share of time in the bars on famous Duval Street, I’ve dug deeper and uncovered many of the small but otherwise-fascinatingly-formed sights. What follows is my guide to the 75 best things to do in Key West. It’s unlikely you’ll fit them all into one trip so mix and match according to the kind of trip you want. Or just slate in several return visits. Key West deserves it.
How to do it: You’ll find the kapok tree on Fleming Street, a short walk from popular Mallory Square (more on that below). I recommend taking a picture of yourself in front of the tree to give some perspective.
How to do it: you’ll find the marker on street.
I wouldn’t have found this place if I wasn’t pretending to my dad that I totally knew where I was going. Anyway, we ended up here and dined on very authentic Mexican food at surprisingly good prices. A real find, tucked off Duval Street with very nice staff (that served us even though it was closing time).
We may as well start with Key West’s oldest bar. If you want to sip a beer in an historic institution, get to Captain Tony’s Saloon.
29. See Robert the Doll at East Martello museum
So, that’s my guide to 75 Things To Do In Key West. Got any questions or anything to add? Let me know in the comments below.
By car – I always rent from Miami airport with Sixt. Great prices. No hassle. Easy pick-up and return.
Find out more: Cuban Coffee Queen Website.
30. Shipwreck museum
How to do it: You can find out more here.
NYAH Key West – short for Not Your Average Hotel, NYAH Key West has 4 pools with different temperatures, a mix of dorm and private rooms and is a very short walk to Duval. This is my go-to in Key West and as cheap hotels in Key West go, I don’t think you are going to find much better.
Find out more: 801 Bourbon Bar Website.
Water Based Things to Do in Key West
Find out more: Harpoon Harry’s Website.
31. Day trip to the Dry Tortugas
Key West’s Roosters are so famous they’ve made it onto t-shirts. The locals have a love-hate relationship with them but either way, being federally protected (it’ll cost you 0 if you kill one) they’re here to stay.
Key West Ghosts and Mysteries Tour– this is a walking tour and quite a bit more serious. Probably too serious for me but if you’re a believer and want to visit purportedly haunted spots and maybe get a picture of a ghost in action, this is the tour for you. You can book here.
32. Go on a snorkelling trip
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Not your average cemetery, the Key West Cemetery is unusual in a few respects. First, it’s above ground (lesson learned after a hurricane washed all of the bodies out of their graves). Second, it’s full of gravestones that feature cracking one-liners and creative shapes (conch shell, anyone?). My favourite is the gravestone that says: ‘I told you I was sick’. Oh, and there are some locally famous people buried there, too, like Sloppy Joe. There’s even tales of grave robbing (bodies, not just things).
This place was recommended to me but I was so busy working my way through the fish and seafood menus in Key West that I didn’t have time to try it. I’m including it in case you want a meat fix. Let me know if it’s good.
Key West is full of crazy shit and this is just another activity to add to the list. You won’t find me doing a shot of booze that contains a scorpion chaser but people do. I’d recommend watching some other fools do it rather than trying it yourself.
How to do it: You’ll find Key West’s Oldest House on 322 Duval Street. You can find out more, including tours of the house here.
33. Take a Tiki Hut sunset cruise
Not a bar as such but included with your Key West Trolley ticket or Conch Train ticket. You’ll get a quick intro to rum making followed by a few tastings of the Hemingway rum brand (named in his honour not by him).
After missing the Little White House tour, I trotted over to the Tennessee Williams Museum and was delighted with this one-room whirlwind introduction to the life of the man who wrote so many famous screenplays (A Streetcar Named Desire is probably the work you’re most familiar with). It’s probably not the most famous of the things to do in Key West but it ended up being one of my favourites.
34. Explore the Key West beaches
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You’ll find live music (which you’re probably coming to expect in Key West, right?) but what I like most is the ability to spill out onto the front yard area when the risk of getting someone else’s elbow in your beer becomes too high.
35. Go fishing in Key West
Can’t be arsed to plan your own night? Take a Key West pub crawl and let an experienced guide show you a good time. The theme seems to be a side of (other-worldly) spirits, which will add to the fun.
Not much for walking? Take the free Duval loop. It does a small but useful loop around the streets that parallel Duval Street and is a good, free way of orienting yourself.
What and Where to Eat in Key West
Death, disease and hurricanes litter the history books of this tiny island so it’s no surprise that ghost hunters abound in Key West and taking a shot tour is one of the top Key West attractions. Looking to save my liver from another night on Duval Street, I decided to book a ghost tour. In fact, I’ve tried two ghost tours on the island (two visits with two people) and here are the tours I tried and would recommend:
36. La Grignotte for breakfast
I’m not going to recommend a Hard Rock Cafe very often (ever?) but you do get the chance to dine in the beautiful surrounding of the historic Curry Mansion (which is also reputed to be haunted). It’s also one of the few eateries open late on Duval, without having to eat something from a street vendor.
December to February can be a bit chilly – I was most recently there in January and there were grey skies, smatterings of rain and a breeze strong enough to need a jumper.
37. Kermits for key lime pies
I love the ladies at this bar and if you’ve never seen a drag show before (or have and want to go again), this is one of the most popular places to do it, right on Duval. The show happens twice a night. Get there early to enjoy happy hour and get a good seat.
It may look like a year-round destination thanks to the location edging the Caribbean but Key West weather is more tricky than that. Not only does it get hit by hurricanes, it isn’t all that warm in winter. If you can, avoid June to October (with the September being the most risky for hurricane).
38. Mallory Square for street food snacks
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39. Pepe’s Cafe for the specials and dining with locals
How to do it: You can find out more about what’s there and what’s on here.
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40. Harpoon Harry’s for diner dining
If you want a quick bite, head to Fisherman’s Cafe, a small hole in the wall eatery that serves up large lunch portions at good prices. I had the lobster tacos (not bad considering I don’t think you should batter lobster). The food was fresh, quick and tasty.
If there’s one thing I’ve done a lot of in Key West, it’s eat. From conch fritters to Key Lime pie to an abundance of fresh seafood and fish, here’s a list of some of my favourite places to eat as well as a few recommendations from other people. In no particular order…
41. Half Shell Raw Bar for catch of the day
Find out more: Date & Thyme Website.
Find out more: Amigos website.
42. Commodore Waterfront for happy hour bites
How to do it: The best beach in Key West depends what you’re after. Siminton beach is the closest beach to old town Key West and is walkable. Otherwise check out Higgs Beach or Smathers Beach. Fort Zachery beach is great for a combination of history, walking trails and a great sunset beach spot. Find out more here.
I’m not a fan of Cuban food (spent too much time in Cuba) but if you forced me to eat the stuff, I’d be going to Cuban Coffee Queen for a Cuban sandwich. Beyond that, I’d be heading to Calle Ocho in Miami but that’s too far to drive.
As well as being a book nerd, I’m also a reformed lawyer, so courthouses hold particular interest for me. For most visitors to Key West, it’s not the courthouse building (pretty as it is) that is photo worthy, but the gigantic kapok tree that sits outside.
Bull & Whistle has a choice of drinking floors – stay downstairs for quick access to Duval Street or head upstairs for a sports bar feel with darts and a pool table. Just don’t go too many floors up unless you intend to go al fresco…
43. Sloppy Joe’s tap room for a chilled bite with beer
Not so much an eatery but with scores of different chilli sauces at various intensities on the scorville scale, it’s a fun way to spend 15 minutes to challenge your chilli tolerance. The staff will temper the chilli to your tastebuds so don’t be too scared.
Find out more: El Meson De Pepe’s Website.
44. Alonzo’s Oyster Bar for oysters (and lobster roll)
Find out more: El Meson De Pepe’s Website.
The best thing I can compare Duval Street to is Bourbon Street in New Orleans. You can check out my post about New Orleans here.
63. Green Parrot for a local vibe
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If you’re loving the southernmost groove and are looking for places to stay in Key West, go all in and stay at the Southernmost House. I’ve not stayed here but it looks very cute. If you don’t fancy staying here, it’s a good alternative photo spot if the buoy is overrun with people.
Find out more: Lucy’s Retired Surfers Bar Website.
64. El Maison de Pepe for sundowners
Whenever someone French recommends a restaurant, I take it seriously. I didn’t get around to eating here but it looked like a good spot for some fine(r) dining on Duval with a good wine list.
Find out more: Jimmy Buffet’s Website.
65. Hog’s Breathe Saloon for outdoor drinking
How to do it: You can find out more about the Duval Loop here.
Key West Travel Tip: Includes free entry to the Sails and Rails Museum and the Hemingway Rum Distillery.
66. Bull & Whistle for a sports bar vibe
Small-Group Key West Food Tasting and Cultural Walking Tour
The bones are long buried but I’m sharing this piece of history so you can realise that Key West is much more than a party island. Key West’s history is filled with pirates, shipwrecks, and rum runners. It’s no wonder it has attracted so many creative people over the years (most famously, Earnest Hemingway).
67. The Garden of Eden for naked drinking
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68. Hemingway Rum Distillery for rum tasting
I’ve tried and failed to do this many times because I’m not good at booking ahead and the ferry that goes out to the Dry Tortugas is popular. However, if you are planning ahead and booking some Key West excursions, put this at the top of your list. You get a full day of adventuring with a visit to Fort Zachary as well as time to snorkel.
You can find out more here.
I had to Google who Jimmy Buffet was (thought it was a brand of buffet-style dining) so it’s no surprise that I haven’t actually visited this place. However, for Buffet fans, I believe this place is a big deal.
69. The Smallest Bar for a cosy drink
How to do it: You can book Key West snorkelling tours here:
How to do it: I don’t think this one needs instruction?
70. Jimmy Buffet’s Original Margaritaville for Buffet fans
For car hire, I usually rent from Sixt from Miami airport. Good prices, nice staff and they’ve never tried to tag on any unnecessary insurance extras or found scratches that didn’t exist (or did exist, eek) when I returned the car.
Abundant booze and bedlam can really slam your body so if you want to feed yourself some nutrients, visit Date & Thyme. They will let you off-menu order juices and smoothies (I know, I’m picky) and their sandwiches are divine (Asian tuna: recommended).
71. Waterfront Brewery for craft brew flights
How to do it: You can find out more here.
How to do it: Cuban Coffee Queen is by far the best Cuban coffee you’ll get in Key West. And I’m not prepared to get into a fight about it 🙂 Order a cafe con leche to get the authentic taste. You can check the locations here.
72. Lucy’s Retired Surfer’s Bar for scorpion shots
Find out more: Mallory Square website.
Find out more: Fogarty’s Website.
73. Willy T’s for a dollar bar experience
Find out more: Commodore Waterfront Website.
When in Rome….or Key West, and craving Italian food, go to Antonio’s. I’m seriously picky about Italian cuisine (what with me running my own tour business in the Prosecco region of Italy) and this was the best Italian food I found in Key West.
74. 801 Bourbon Bar for a drag show
How to do it: You could park yourself in one of the many sunset bars (but get there early). Otherwise, pull up a pew on the conveniently located wall and watch the sun set over the most southern island in the USA.
How to do it: You can find out more and book tickets here – Get Your Guide (my favourite tour booking site) or Viator.
Find out more: Sloppy Joe’s Website.
75. Take a Key West pub crawl
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It’s barely 5 square miles (20 square km) and most of the sights are conveniently located around Key West’s old town but there are still several ways to explore the island. Start with a…
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Key West Travel Tip: Don’t miss the Western Union Schooner – the official flagship of Florida, which is berthed right here at the seaport.
Related posts: You can check out the posts I wrote about my trips to Cuba here.
How to do it: You can find out details here. The climb is up 88 stairs and gives you a 6 mile view. And no, you can’t see Cuba from the top.
It’s hard to tell whether there are more ‘Hemingway was here’ or ‘Southernmost bakery/hotel/gift shop’ signs in Key West but either way you’ll quickly come to know that Key West is the southernmost point of the USA. And there’s a big buoy to prove it. This will no doubt be on every list of what to do in Key West.
If you want tips for eating out as a solo diner, see my guide here.
Key West Travel Information
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You’re unlikely to want to do the Trolley and the train in the same trip and by all objective measures the trolley is better (more stops, more information, more discounts) but I LOVE the train. It’s cute and playful and ideal if you don’t have much time. My friend told me trains were for kids so I waited until I visited the Keys with my dad when technically (at 43 years old) I was a kid.
Tip: Visit the one at the end of Margaret Street and you can grab a picture in front of the Key West sign while you wait for your brew.
How to do it: You can find out more here.
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The bones on the beach are relevant because that’s how Key West got its name – Cayo Oueso is Spanish for ‘bone island’ and over time the pronunciation has been bludgeoned into its present day Key West. (Still fixed on the scattered bones thing? Don’t worry – it was the native burial ritual, leaving the dead on the beach and in the hands of nature; there wasn’t some Netflix-worthy massacre).
Hyatt Centric – you can’t beat this spot for a blend of location and well-know brand. If you’re not a boutique hotel fan (they can be hit and miss), check in here.
All I need to say is that Mel Hunter, after a lifetime of searching, struck gold (literally) when he and his treasure hunting team recovered nearly half a billion (yes, billion) dollar’s worth of sunken treasure when they finally found the Spanish Galleon Atocha. Laden with gold, silver and emeralds, it’s an amazing story that’s well captured in this museum. Got some gold burning a hole in your pocket? There’s a store where you can buy some of the recovered treasure.
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Find out more: Peppers Website.
Find out more: La Grignotte website.
Is there anything better than being face down in aqua coloured waters? What Key West lacks in golden sands, it makes up for with beautiful waters so go ahead and book some water-based Key West activities.
Key West Travel Tip: while we’re on the subject of things not to do in Key West, don’t go collecting conch on the beach. It’s illegal to take a live Queen conch shell and this woman, who collected 40, ended up in the clink.
Shuttle service from Miami to Key West – if you don’t plan on exploring the rest of the Keys, you don’t really need a car. There are several shuttle options. I’ve tried a couple and, to be honest, they all come with various (service-based) complaints. Also, prices bounce around a bit. For that reason, I’d recommend you read the reviews and see what’s coming out top when you book.
I’ve got more on Duval Street below but if the nightlife or bar hopping isn’t your thing, at least take a stroll down this crazy street – it really is a must do in Key West. The first time I stepped onto Duval, I saw a woman in drunk tears accusing her husband that he didn’t love her because he wouldn’t buy her a slice of pizza. The guy shrugged and handed her a rapidly purchased slice. It was 11 a.m.
Not only is Key West the southernmost point of the USA, it’s only 90 miles away from Cuba. In fact, stood at the southernmost point, you’re closer to Cuba than mainland USA. And don’t you know it. Cuban cigars, Cuban sandwiches, Cuban rum and Cuban music, it’s sometimes hard to imagine you’re not in Cuba – and that’s not something to complain about. My favourite Cuban activity is sucking down as many Cuban coffees as I can lay my mitts on.
I don’t know about you, but if I stumbled upon an island where the beach was scattered with bones, I’d be doing an about turn, pronto. But it was 16th not the 21st century and Ponce de Leon was more brave (or foolish?) than I am. And thus Key West was discovered*.
Ghost and Gravestones – if you’re not in the slightest bit a believer, this is the tour for you. It’s a fun history of the macabre side of Key West that involves stories of stolen corpses and haunted dolls. A visit to the Shipwreck Museum and East Martello Museum to visit Robert the Doll are included. You get driven round in a open sided vehicle which allows drunk people to heckle you. Heckle back. You can book here (Get Your Guide) or here (Viator).
Look inland and you have street performers and musicians plucking out a tune, but the real highlight of Mallory Square is the sunset.
Round the corner from Pepe’s is Harpoon Harry’s, another local haunt. You might not get the best quality food but it’s ultra cheap and offers a proper 1950s diner experience with booths and bar dining to boot. Very friendly staff.
Find out more: Bull & Whistle Website.
I’ve swerved oysters since I got food poisoning that time in Loch Fyne in Scotland but they looked good and if my lobster roll was anything to go by, Alonzos is a good oyster choice.
Blog posts to help you plan your trip
How to do it: if you want a picture next to the buoy or a picture without anyone else next to the buoy, you either have to get up hellishly early (like I did), or stand in a photo line for 20 minutes (I refused to), or visit back in 2010 when the photo line wasn’t a thing. I do accept that this last option might be a touch difficult.
How to do it: You can book a fishing excursion here (this is a brilliant price if you ask me) or just wander down by the docks and negotiate a price.
If you visit just one museum after Hemingway House, make it Custom House. For me, a museum nerd, this was one of the best things to do in Key West. With exhibitions covering the ship wrecks, pirates, the Civil War, treasure hunting and the art and literary scene, you’ll get the best overview of the threads of Key West life over the ages.
How to do it: You can find out more and book tickets here. Want to read some Hemingway to get you in the mood, click here.
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