Culturally, architecturally, meteorologically and culinary speaking, Key West feels different to the rest of Florida and indeed the USA. To understand Key West's difference, it helps to understand a little of it's geography and history.
Closer to Cuba (90 miles) than to Miami (165 miles) it is no surprise therefore that Key West feels nearer to the Carribean in terms of culture, cuisine, and architecture. Key West also has a different climate to the rest of Florida too: tropical savannah, which is the driest of all the tropical climates. Of all the cities in Florida, Key West has the least rainfall. The thunderstorms that they do get down there are early in the morning rather than mid-late afternoon in the rest of the State. Indeed, Key West gets so dry during the dry winter season that the Old Firehouse was key (if you'll pardon the pun) to keeping Key West safe as all the old wooden houses get tinderbox dry in the winter. As one Conch so succinctly put it to me: "Key West has the climate that the rest of Florida thinks it has." This was certainly true with my 5 day-stay there over New Year's 2022, where I was greeted with wall to wall sunshine and not a cloud in the sky; and a consistent temperature profile each day of 27C/ 21C. It was absolutely perfect for me for sightseeing; and on only one day did it get too humid, requiring a little siesta in the height of the afternoon in the wonderful air conditioning of my hotel room. Key West boasts the largest variety of palm trees anywhere in the United States: fig palms, coconut palms, Spanish palms, Californian palms as well as native species, as they positively thrive in this tropical, frost-free environment all over the island.
Key West is the Southernmost point in the Continental United States, connected via the 113m Overseas Highway which connects the Florida Keys to mainland Florida. It is not the most westerly Key though (that distinction goes to the Dry Tortgugas islands, which lie 68 miles west of Key West). Key West gets its name via an Anglicised corruption of the original Spanish name for the Island : 'Cayo Hueso' (meaning 'bone island', so called because the island is derived from Coral reefs and the remains of animals and plants).
In its early days, Cuban and Bahamian fisherman fished around the Keys, including Key West, but it remained uninhabited during both the Spanish and British periods of ownership of Florida. When the United States acquired the Keys in 1822, two events settled the future of Key West: the US Navy recognising the strategic importance of its location and creating a naval base in Key West; and the US 1825 Federal Wrecking Act, which prescribed all property wrecked in US waters be taken to a US port of entry. Salvaging ship wrecks, to Key West's deep water port (which to this day remains vital to the economy of Key West via cruise ships) suddenly became big business. By the 1890s Key West became the wealthiest city in Florida. Its legacy is Key West Old Town, where most of the buildings date from the 1840s to the peak of its boom in the 1890s.
After World War 2, Key West was running out of land so the US Navy tripled the size of the island via dredged fill. New Town today contains the International airport and shopping malls and is obviously very different in character to the Old Town. Key West always had a reputation for being a little wild and different; and things came to a head in the early 1980s when US Border Patrol set up roadblocks to search for illegal narcotics for visitors entering Key West. Key West council were not happy about the impact on tourism and so the Mayor (Dennis Wardlow) declared independence on 23rd April 1982 and immediately declared war on the United States! As the inhabitants of Key West are known as Conchs, it became the Conch Republic. He then quickly surrended and applied for $1bn in foreign aid! This symbolic succession from the United States is re-enacted in a typically humorous Conch manner every April in the Battle of the Conch Republic. Previous years have included a huge Key Lime Pie and the hilarious re-enactment of the Great Sea battle of the Conch Republic, where tomotoes are thrown at the US Navy . What is it with food always being involved in American revolutions? Tea in Boston; tomatoes in Key West :)
So as you may have guessed from the above you have several choices of getting to Key West: road, air or cruise ship. If you are electing to drive, it is a 3-4 hour drive from Miami and an 8-10 hour drive from Orlando. Be warned though - it can be, as one British friend described it, "like driving down to Cornwall in England". Just like driving to Cornwall, it does have periods of single-lane highway and also very high traffic volume and occassional accidents. Another issue is that the Victorian town of Old Town Key West is not suited to traffic and consequently there are few places to park (as an example, my hotel charged $50 a night to park at the hotel). I elected to fly with Silver Airways from Orlando, and the direct flight took just under an hour and a half. Key West International airport is a short taxi ride to the Old Town. Given that Key West is only one mile wide by 4 miles long, it is one of those cities in America which is perfectly walkable. I personally felt that a car is a hindrance, rather than a help in Key West. I also felt coming into the Keys by air offered more spectacular views of the interconnected islands via bridges than would be the case via road, since the landscape is flat and as the driver you would be concentrating on the road and not the views!
I stayed at the Southernmost House (renamed in 2023 as the Mansion on the Sea) which is convieniently located at the end of Duval Street, overlooking the Atlantic Ocean. This adult-only hotel is perfect for honeymooners or couples or singles who want a calm oasis tucked away from the party street that is the main city's thouroughfare. It was built in 1897 at the height of Key West's boom for Florida's first multi-millionaire. His standards were so exacting that Thomas Edison himself installed electricity into the home. Frequent visitors have included King Juan Carlos of Spain and several US Presidents including John F. Kennedy.
I have nothing but praise for the hotel itself - it is full of character and Victorian charm and although I wasn't staying in the main mansion (but the house opposite as above) my room was beautifully appointed with antique Cuban tile flooring. The air conditioning was superb (so much so that it created confusion one morning for me after a night partying as to why I couldn't remove the condensation off the window - in Key West condensation forms on the glass outside due to the temperature gradient and humidity; in the UK it forms inside where the windows are single glazed). I had a beautiful veranda (as shown above) to people watch and view the amazing Key West sunsets. The pool is spotlesssly clean and private and overlooks the Atlantic Ocean. Was there room for improvement? Well the food aspect was disappointing - just a buffet for breakfast and a street truck which was quite a shock given the price of this hotel. I would have expected an on-site chef and restaurant ; but then prices for hotels in Key West are expensive generally, especially around New Year.
Key West is one of those places that has so many activities on offer and things to see that it can be quite overwhelming, and also remarkable given its small size (in that aspect it reminds me of the Orkney Islands in Scotland, which are also interconnected islands and where cruise ships stop too - of more another time!). So I'm going to call out all the things I did over the course of my 5 day stay in Key West:
A really good way to get your bearings in Key West is to take a trip on the Conch Train Tour.. A recommendation from an American friend, I usually baulk at such touristy activities but in this case I think it's a really good idea if your time on the island is limited. This way, you can get your bearings quickly; work out what you do and don't want to see and not waste time looking for places of interest. You can board and vacate the train at various locations , but the 75 minute tour starts at Front Street. Done with typically Conch humour (Key West natives have a wonderful sense of humour and for Brits decrying Americans don't do irony: they haven't got this message down in Key West:) it covers all the tourist attractions in Key West.
The Ernest Hemingway House on Whitehead Street was constructed between 1848 and 1851 for a wealthy shipping merchant, which the Hemingways acquired and restored in the 1930s. It is a now a private museum. Be sure to see the polydactyl cats, who have 6 toes to their paws and lounge about in the sun around a suitable minatured size Hemmingway House which serves as a catery. Aspects of the mansion's past can be seen in the architecture, especially at the entrance, with a ship-shaped ornamental pool which is now a raised garden.
Another famous resident of Key West was Harry S. Truman, 33rd President of the United States. Originally part of the US Navy complex built in 1890, the building was converted to a private residence in 1911. Harry Truman made it his base for 175 days of his Presidency during his time in office, taking advantages of technological developments which allowed him to hold meetings away from the traditional office of the White House in Washington DC. You could say he was a pioneer of working from home!
Of particlar interest is Harry S. Truman's poker table, which has sunken World War One shells as chip retainers, and was hidden from view during the day with a wooden cover. At a time when gambling was illegal, journalists were often resting on the biggest news story of the day in the Little White House without realising! The home was also the venue for a 1961 summit between John F. Kennedy & UK Prime Minister Harold Macmillan.
A trip up Key West's lighthouse (the current structure, dating from 1848 is the third such structure as previous ones have been destroyed by hurricanes) offers stunning views across the island. It probably goes without saying it's not an activity for those without a head for heights, but I think more so than usual on this occassion. You climb a very narrow spiral staircase and once outisde the walkway is very narrow and the guardrail quite low. A museum at the bottom covers the history of the lighthouse and lamps which have been rebuilt and replaced respectively throughout its history.
Mallory Square is the place to watch the spectacular Key West sunsets, which are celebrated each evening with a free open-air festival of street art, performers, acrobats, musicians and conjurers. If you spot a cruise ship in port - don't worry! It will soon be vacating the port as a local bylaw prohibits cruise ships staying in the port and blocking the view, so they must be vacated before the sun sets over the Gulf of Mexico. The sunsets are so spectular due to a combination of the lattitude and the fact that there is no air pollution in Key West. If you are very lucky you may also catch a gimpse of Key West's numerous famous inhabitants, such as the Scottish comedian Billy Connolly who has made Key West his home.
Many boat operators will try to entice you on a boat trip to go out to sea to see the sunsets but you don't really need to do this to see the sun setting - you can easily do this for free on Mallory Square. Other good reasons though are to take advantage of seeing the offshore coral reef, the third largest in the world. Options are snorkeling or you can do as I did and take a glass bottomed boat tour:
There are several tour operators and tickets can either be bought online or via the numerous ticket booths on Duval Street. I chose Fury and its glass bottomed boat; but as you can see from their website they also offer numerous watersports options too such as parasailing, snorkeling, and sunset party cruises. Tours depart from the top of Duval street . If you choose the last glass-bottomed tour of the day they also stop to admire the sunset when returning to port whilst serving champagne. The glass bottomed boat really does offer good views of the coral reef as it has a large viewing area:
St. Mary, Star of the Sea Catholic Church is the oldest Catholic Church in the State of Florida. The current structure dates from 1905, replacing an earlier church which burnt down in 1901:
The church is remarkable for two other reasons as well. It features in the pre-titles sequence of the 1989 James Bond movie License to Kill where the groom and best man parachute in for the wedding ceremony. Apparently Key West's overhead power lines had to be turned off for filming ! The first half of the movie is set entirely in Key West and features many of its well-known attractions including the Ernest Hemingway House, the lighthouse and Mallory Square. The church's other remarkable feature is its amazing Nativity Scene which takes centre stage across the whole altar across Christmastime. Given I was commemorating someone special for whom the Nativity held a special place in her heart; this turned out to be the perfect venue:
Key West butterfly and nature consevatory, located at the southern end of Duval Street is a great way to see all kinds of tropical butterflies, not just native to Key West, but spanning the world's main continents. The large conservatory allows you to walk amongst them and see them feeding on fruit and nectar. Also there you will see flamingos and birds in an environment which is a mini-tropical paradise.
As was the case with my write-up of long weekends in Bath earlier this year, I could easily spend an entire blog on the restaurants of Key West as it is such a culinary paradise. I want therefore to call out a few-standouts during my 5 day stay:
Louie's Backyard is one of those rare restaurants in life which combines a spectacular venue with a spectacular menu. Located at the southern side of the island overlooking the Atlantic Ocean, it takes alfresco dining to new heights:
This fine dining restaurant offers modern Carribean-American cuisine. I opted for some local choices for all three courses for lunch on New Years' Eve: Conch Friters, which are something of a speciality on the island; Carribean rice with the local catch of the day (both utterly delicious) followed by Key Lime Pie. Whilst the flavours of Key Lime Pie were very sharp it seems there is no consensus on the island as to how to make it - which is odd given it originated in Key West!
Next was one of those amazing discoveries you find entirely by chance on holiday and then just keep going back to over and over it's so good! Moondog Café, sandwiched between the major tourist attractions on Whitehead Street. This became a favourite which I revisited on several occassions. They make the most amazing gourmet burgers there. Their patisseries - whilst often being an American take on European classics, such as adding additional flavours to chocolate éclairs are nevertheless stunning; they also have a wide selection of craft beers; and it's a very friendly place with both bar, alfresco and indoor seating available.
Another reason I call out Moondog Café is they are the winner of the best Key Lime Pie of those I tasted! It seems there is no consensus on how this should be made in Key West, despite the fact it originated on the island. To my mind, the interpretation of it we have in the UK is: meringue, a curd-like lime filling and a biscuit base. Their interpretation hit the sweet spot for me:
Another great shout out for Viv's Wine Bistro on Petronia Street. I've struggled to find any authentic French bistro in previous visits to the State of Florida further north, but this one is just like stepping into one in France. The selection of wines is outstanding, and the French owners are wonderfully enthusiastic about food in the way that typifies the French lifestyle. I really enjoyed both the food (I opted for their French onion soup followed by beef bourguignon) ; the ambience and chatting to the owners in French for my special New Year's Day dinner.
Next on my list of shout-outs is Fogarty's and the Flying Monkeys Saloon Bar at the northern end of Duval Street. Their frozen cocktails are legendary and worked just a treat in the tropical heat. Most of the bar is open air and it reminded me of many bars over in Los Angeles where you can appreciate the warmth and breeze of the evening whilst drinking outside. They also have a great food menu as well, serving amonst other things: Conch fritters, tacos, Tex Mex rolls, salads and a variety of sandwiches and seafood. Great friendly service as well so it became my go-to bar in the evening!
If all this wasn't enough, next we come onto Duval Street itself which is both the city's main thoroughfare and Key West's "party street". In many ways it reminded me of Bourbon Street in New Orleans, except here you have much more diversity. To illustrate, some of the things you can find on Duval Street (in no particular order) are: a Cuban restaurant; several nightclubs; an upscale Jazz/piano bar (which would not look out of place in Upper Manhattan); the aforementioned Fogarty's Bar; several art galleries; several LGBTQIA+ bars; an Irish Bar; Sloppy Joe's bar (frequented by Ernest Hemmingway) ; Key West Women's Club; a photographic studio; an ice-cream parlour; many boutique shops selling arts and crafts; and several Southern-style bars.
Come New Year's Eve, Duval Street is closed to vehicular traffic from around 7pm onwards, where the street just becomes one big festival. There are also three variants of New York's "ball-drop" each done in a typically Conch humourous style: a giant red shoe (reminiscent of Judy Garland's red slipper from The Wizard of Oz) descends from the Bourbon Street Bar; at Sloppy Joe's a giant Conch shell (the symbol of the Florida Keys) descends to signal the New Year; whilst over in the Historic Seaport a Jolly Roger descends on a pirate ship. Another variant in previous years has also included a a massive Key Lime Pie descending into the water! My tip is to get there early as come later it does feel as though half of North America has descended on Key West to celebrate New Year's Eve!
Every morning I had the habit in Key West of getting up for an early morning stroll to see what I could capture with the camera. Come New Year's Day, after the shock of condensation outside of my hotel window :) due to the super cool air conditioning, I noticed how already, all traces of New Year's Eve revelry had been removed: not a trace of litter or confetti from all the cannons, and the streets had already been hosed down. This is typical American efficiency and Civic pride and is to be commended!
Key West has all the magic ingredients I look for in a holiday: a fantastic climate; an interesting culture; beautiful architecture; a wonderful and thriving independent food scene; a vibrant arts scene; some local history and most of all very friendly people with a great sense of humour. I'm sure this will be the first of many visits to the Conch Republic!
You can see more of this wonderful New Year's visit over on Instagram