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USA: Florida – Florida Keys – Key West

🌴 No Rest for the Wicked — Key West

As they say, there’s no peace for the wicked. So we completely ignored Karen’s desperate need for sleep and pointed the car south towards Key West — the furthest point you can drive to in the entire Florida Keys, sitting at a frankly improbable 26 degrees north latitude, barely 90 miles from Cuba. Key West has been many things over the centuries: a Spanish colonial outpost, a base for wreckers who grew fabulously wealthy salvaging cargo from ships that came to grief on the surrounding reefs, and later a hub for the sponge-fishing industry. Ernest Hemingway lived there in the 1930s, which gives the place a slightly literary air that it wears rather self-consciously, if you ask me.

The morning didn’t look particularly promising weather-wise — the sort of grey, flat sky that makes you wonder whether you’ve made a terrible mistake — but by the time we rolled into Key West the sun had done the decent thing and shown up. We were basking. Result.

We parked down near the main marina area, which turned out to be a genuinely enjoyable place to wander around. The waterfront was lined with gift shops selling the usual array of things you absolutely don’t need — novelty rum bottles, T-shirts with questionable slogans, that sort of thing — alongside a decent selection of bars and eating places. We walked out along the jetties, where various companies were offering trips aboard tall ships out into the Gulf of Mexico. These are working replicas of the kind of wooden-masted schooners that once dominated these waters in the 18th and 19th centuries, when Key West was one of the wealthiest cities per capita in the entire United States, largely off the back of wrecking and salvage. The sunset dinner cruises caught our eye. They were, as you might expect from anything involving the words “sunset,” “dinner,” and “Key West,” eye-wateringly expensive. We admired them from a safe distance.

For the more adventurously inclined, there was the option of hiring a boat and heading out into the Gulf for some serious deep-sea fishing — tarpon, marlin, wahoo, the full set of things that are enormous and very cross about being caught. Key West has been a sport-fishing destination since the early 20th century, when wealthy Americans started making the journey down the Overseas Highway — itself a remarkable feat of engineering, completed in 1938 after a series of hurricanes had done for the original railway. We were not, it has to be said, the adventurously inclined portion of the group that day.

Instead, we settled into a bar. This seemed entirely reasonable. It offered alcohol, perfectly decent food, and live music — the holy trinity of an agreeable afternoon — and we were very happy indeed. Jack and Emily amused themselves hunting for fish in the harbour, which was not as futile as it sounds. Lurking among the moored boats were some quite extraordinary tarpon — great silver prehistoric-looking brutes, some of them getting on for four feet long, drifting about with the languid confidence of animals that know perfectly well nobody is going to do anything about them. They were magnificent, in a slightly alarming way.

The grown-up Hoblets, meanwhile, occupied ourselves with people-watching — one of our most reliable hobbies and completely free of charge. Key West attracts a wonderfully eclectic crowd: retired couples, day-trippers down from Miami, serious sailors, people who look as though they’ve been sitting on that particular bar stool since 1987. We also watched the large charter boats and motor yachts manoeuvring around in the tight confines of the marina, which is the nautical equivalent of watching someone try to parallel park a bus. Quietly satisfying.

After this brief moment of civilised repose, we continued our wander and stumbled upon a small museum tucked into a dockside building — the Turtle Museum, as it turned out, which tells the rather sobering story of Key West’s turtle fishing industry. The building itself was once an actual working turtle cannery, which gives the whole visit a certain grim authenticity. From the mid-19th century right through to 1971, when sea turtles in the United States finally received legal protection, Key West was one of the main centres of commercial turtle fishing in North America. Turtles — green turtles in particular — were caught in their tens of thousands, processed here, and shipped out primarily as the key ingredient in turtle soup, which was considered a fashionable delicacy in Britain and America for well over a century. Queen Victoria was reportedly fond of it, which perhaps tells you something.

By 1971, the green sea turtle population in the region had been reduced to a tiny fraction of its former numbers. Thankfully, the species has since made a cautious recovery under protection, though it remains vulnerable. The museum does a good job of presenting all of this without being too preachy about it, which we appreciated. There is only so much ecological guilt one can absorb on holiday.

🗺️ Mile Zero, Mayhem, and a Bit of a Scene on the Beach

We decided, after wandering back from the port, to have a proper look around the old town and hunt down a beach. It being a Sunday afternoon, Key West was absolutely heaving — as it tends to be when the tourist machine is running at full tilt, which, let’s be honest, it pretty much always is down here. The place thrives on visitors, has done since the late 19th century when it was briefly the most populous city in Florida, and it has absolutely no shame about it whatsoever. Good for them, I suppose.

The traffic was something else. The narrow streets of Old Town — which follow a layout that hasn’t changed much since the town was properly settled in the 1820s — were clogged with the usual chaos, made considerably worse by a procession of open-sided tourist trolleys and those lumbering double-decker buses ferrying passengers on narrated loop tours. The Conch Tour Train, as the locals call it, has been doing this since 1958, so it’s practically a heritage attraction in its own right at this point. We shuffled along with everyone else, not going anywhere particularly fast, which is apparently the Key West way.

Then, to our considerable delight, we stumbled upon Marker 0. For those unfamiliar — and I was vaguely aware of it but hadn’t really thought it through — this is the official southern terminus of US Route 1, marked by a rather modest but photogenic buoy-shaped sign on the corner of Whitehead and Fleming Streets. Route 1 stretches some 2,369 miles from right here, at the very bottom of Florida, all the way up to Fort Kent in northern Maine, making it one of the longest and most storied roads in the entire United States. It was designated back in 1926, when the American highway system was being properly organised for the first time, and the Key West end has been drawing pilgrims with cameras ever since. We duly joined that long and undistinguished tradition and stepped out for a photo. Tick.

Then it was on to find a beach, which — and here’s where our complete lack of forward planning becomes relevant — we did entirely without any of the necessary equipment. No swimming costumes. No towels. No sun cream, no bags, no nothing. Impeccably prepared, as ever.

Jack and Emily were not remotely bothered by any of this and promptly decided to go in anyway, stripping down to their underwear with the breezy confidence of people who hadn’t thought about it for more than four seconds. It was, as beach plans go, perfectly reasonable. For about ninety seconds.

Emily, who is at that age where the world is suddenly full of things to feel self-conscious about, decided she absolutely could not be seen in a state that she described — with some drama — as “topless,” despite being in a perfectly acceptable amount of coverage. There followed what I can only describe as a full theatrical production, complete with everything short of a lighting rig. And then, as if to bring the whole enterprise to a conclusive end, she scratched Jack’s back — hard enough that he was not best pleased — and that, as they say, was that. Beach trip over. We retrieved what dignity remained, which wasn’t much, and headed back to the air conditioning like sensible people.

📍 The Southernmost Everything, and a Sunset We Nearly Missed

From the beach debacle, we made our way down to the Southernmost Point of the contiguous United States — which is, as the name rather unambiguously suggests, the southernmost bit of America you can stand on without actually being in Cuba, which is only 90 miles away across the water. The Cubans, incidentally, have been aware of this proximity rather longer than most Americans have, but that’s a whole other story.

The spot is marked by a large concrete buoy, painted in red, black and yellow, which was installed in 1983 and has been one of the most photographed objects in Florida ever since. It’s not especially beautiful. It’s a big painted lump on a street corner. And yet there we were, queuing up with approximately four hundred other people to have our picture taken next to it, because that is simply what you do and there’s no point pretending otherwise.

What struck us, beyond the monument itself, was the sheer concentration of superlatives in the immediate vicinity. The southernmost hotel. The southernmost café. The southernmost house — which is a rather handsome Victorian-era place that has been trading on its geographical distinction since at least the 1990s. There was, if memory serves, also a southernmost this and a southernmost that, to the point where you began to wonder whether anyone in Key West had ever named anything without first checking its coordinates. It’s impressive dedication to a theme, you have to give them that.

From there we had a wander into town, through the dense and cheerfully mercantile streets of Duval and its surrounding area, which exist almost entirely to separate tourists from their money in exchange for things they absolutely do not need. Conch shells. Novelty T-shirts. Fridge magnets. Key West hot sauce. We did the whole circuit with the practised air of people who know perfectly well they’re going to buy something pointless and have made their peace with it. Several mementoes were duly acquired. I’m not saying what.

We were just about ready to call it a day when we got chatting to a couple of genuinely wonderful ladies who asked, with some incredulity, whether we were planning to watch the sunset at Mallory Square. We were not, because we hadn’t known it was a thing. They put us right on that fairly sharpish.

Mallory Square, it turns out, has been hosting its famous Sunset Celebration every single evening since the 1960s, when a loose gathering of hippies and locals began congregating at the waterfront to watch the sun go down over the Gulf of Mexico. It has since evolved into something considerably more organised — jugglers, acrobats, living statues, musicians, food stalls, craft sellers and several hundred visitors all crammed onto the old dockside as the sky turns orange. It’s been called one of the great free shows in America, and on that particular evening, we went to find out if that was true.

So off we went.

🌅 Applauding the Almighty at Mallory Square

Mallory Square sits right at the northwestern tip of the island, hard up against the waterfront, and it has been the social heart of Key West for rather a long time. The square itself dates back to the mid-1800s, when it served as a commercial hub for the wrecking industry — Key West made an extraordinary amount of money salvaging cargo from ships that came to grief on the surrounding reef, and for a time in the 1800s it was the wealthiest city per capita in the United States. These days the wrecking trade is somewhat less active, and the square has reinvented itself as the place you go to watch the sun go down. Which is, it must be said, a considerably more relaxing business.

The famous Sunset Celebration has been a nightly ritual here since the 1960s, when it apparently started as a rather more informal gathering of hippies and free spirits who simply turned up to watch the sky do its thing. It has since become a fully organised, ticketed-adjacent affair with a proper roster of street performers working the crowd, but it retains just enough of its original laid-back spirit that it doesn’t feel entirely like a corporate event. Just mostly.

We arrived with a bit of time to spare and fell in with the crowd drifting between the various acts. There were the usual suspects — a fire performer, someone doing something improbable on a unicycle — but we ended up stopping for a juggling act, which turned out to be a very good decision. Not so much for the juggling itself, competent as it was, but because the performer had two dogs who participated in the act with an enthusiasm and a sense of timing that frankly put the human involved to shame. Emily was absolutely beside herself. After the earlier beach debacle, this was clearly the highlight of the day, possibly the trip.

Then it was time for the main event. We found ourselves a spot, the crowd thickened considerably around us, and we settled in to watch the sun make its exit. And it did not let us down. The sky went through the full range — orange, deep red, something approaching violet — and the sun itself, enormous and very orange indeed, dropped towards the horizon with a stateliness that made you feel the world was doing it on purpose. Which, depending on your theology, perhaps it was.

When it finally slipped below the water, the entire crowd burst into applause and cheering. A proper round, enthusiastic and genuine, as if someone had just landed a particularly tricky gymnastics routine. I’m still not entirely sure of the protocol here — whether one is applauding the sun, the sky, Key West in general, or simply the fact that the day is over. Perhaps all of the above. But if God is keeping score, He got a very solid reception down at Mallory Square on a Sunday evening in Florida, and I imagine He’s had worse.

Planning your visit to Key West

📍 Location

Key West sits at the southernmost point of the continental United States, roughly 90 miles from Cuba and approximately 130 miles south-west of Miami. It is the last in the chain of islands that make up the Florida Keys and sits at mile marker zero on US Highway 1, the road that connects the entire archipelago to the mainland. The island is small — just about four miles long and two miles wide — giving it an intimate, walkable character quite unlike larger American cities.


✈️ Getting There

By Air

Key West International Airport (IATA code: EYW) sits directly on the island, just a few miles from the historic centre, and is served by several major American airlines including American, Delta, United, JetBlue, and others. Direct flights are available from a number of US cities, though the range is more limited than at larger hubs. Many visitors find it more economical to fly into Miami International Airport (MIA) or Fort Lauderdale-Hollywood International Airport (FLL) and either drive or take a shuttle south.

By Road

Driving to Key West is an experience in itself and one that many regard as a highlight of the trip. From Miami, the journey covers approximately 160 miles and takes around three to four hours, depending on traffic. From Fort Lauderdale, allow four hours or more. The route takes you along the famous Overseas Highway, part of US Route 1, which traverses 42 bridges and hops between the islands of the Keys. The Seven Mile Bridge — spanning Knights Key to Little Duck Key — is a particularly dramatic stretch, with open ocean stretching out on both sides.

Speed limits are strictly enforced throughout the Keys, dropping significantly in certain areas. Around Big Pine Key, limits fall to 45 mph during the day and 35 mph at night to protect the endangered Key Deer. Be aware that this stretch is actively monitored.

Petrol stations become less frequent as you head further south, so it is wise to fill up in Florida City before joining the Overseas Highway proper.

If you are not driving yourself, coach services such as Greyhound and FlixBus operate routes connecting Miami and Fort Lauderdale to Key West, with stops along the way. Private shuttle companies also offer door-to-door services from the mainland airports.

By Ferry

The Key West Express ferry service connects Key West with Fort Myers and Marco Island on Florida’s Gulf Coast, sailing on jet-powered catamarans. The journey takes a few hours and includes onboard amenities such as a bar, air conditioning, and sun decks. It is a popular option for those wishing to avoid the drive entirely and adds a nautical dimension to the arrival experience.

By Cruise Ship

Large numbers of visitors arrive by cruise ship, docking near Old Town. Several major cruise lines include Key West as a port of call.


🚲 Getting Around

Once on the island, a car quickly becomes more of a hindrance than a help. Parking is limited and expensive, and the historic Old Town district, where most of the attractions, restaurants, and bars are concentrated, is compact and best explored on foot.

Walking is by far the most enjoyable and practical way to navigate Old Town. Most key sights, eateries, and Duval Street are within comfortable walking distance of one another.

Cycling is extremely popular and very much woven into the local culture. Bicycles can be hired from numerous outlets across the island. If cycling at night, the law requires a white light at the front and a red light at the rear — this is enforced. Ride with care, as streets can be narrow and busy, and pedestrians are everywhere.

Scooters and mopeds are widely available for hire and are a classic Key West mode of transport. They can be great fun, but exercise caution — traffic rules still apply, and accidents among tourists on hired scooters are not uncommon. Locals can be understandably irritated by riders who ignore the rules of the road or honk unnecessarily.

Public buses serve the island and beyond. The city operates a free service known as the Duval Loop, which connects the main car park area with the length of Duval Street and nearby attractions. This is a useful option if you wish to avoid the parking headache altogether. Bus services also run up to Marathon and Stock Island.

Taxis, Uber, and Lyft are readily available, particularly around the airport, Mallory Square, and busy bar areas in the evenings.

For those staying outside the Old Town area, renting a bicycle or using rideshare apps tends to be the most practical combination.


🍋 Food and Drink

Key West has a vibrant dining scene rooted in fresh seafood, with strong Cuban and Caribbean influences reflecting the island’s history and geography. Conch fritters, grilled fish, lobster, and stone crab are staples. Look out for local favourites such as Cuban sandwiches and black bean dishes, which reflect the island’s close cultural ties to Cuba.

Key lime pie is essentially the unofficial dessert of the Florida Keys. Made from the small, tart Key limes that grow in the region, it was declared Florida’s official state pie in 2006. You will find it on virtually every menu, and opinions among locals about who makes the best version are fiercely held.

Dining is overwhelmingly casual. Outdoor seating is the norm, and it is not uncommon to have a rooster stroll past your table — more on those below.

Duval Street is the main hub for bars and nightlife, and it is energetic, colourful, and very much unapologetically itself. That said, some of the best dining and drinking spots are tucked away on the quieter side streets just off Duval, and exploring those is well worth doing.


🎨 Culture and Atmosphere

Key West has a long tradition of attracting writers, artists, and free thinkers. Ernest Hemingway lived here for much of the 1930s, and his former home — complete with descendants of his famously polydactyl cats — is one of the most-visited attractions on the island. Tennessee Williams also made Key West his home for many years.

The town is known for its distinctive architecture, particularly in Old Town, where you will find Victorian-era “conch houses,” gingerbread-style mansions, and former cigar-makers’ cottages painted in tropical hues. The area is a designated National Historic Landmark.

Key West has a long and proud history as one of the most welcoming destinations in the world for LGBTQ+ visitors and residents. The Key West Business Guild, formed in 1978, was the first LGBTQ+ destination marketing organisation in the United States. The island attracts around 250,000 LGBTQ+ visitors annually and the community is an integral and celebrated part of island life and identity.

The famous daily Sunset Celebration at Mallory Square is a beloved Key West ritual. As the sun approaches the horizon each evening, performers, artists, and craft sellers gather at the waterfront, and crowds applaud as the sun finally dips below the sea. It is joyfully eccentric and well worth attending at least once.


⚠️ Things to Be Aware Of

The chickens are protected by law. This is not a joke. Wild chickens roam freely across Key West — on pavements, in gardens, outside restaurants, and seemingly everywhere else. They are a deeply embedded part of island life and are protected under local ordinance. It is illegal to harm or kill them. If you accidentally strike one while driving, there is a real possibility of receiving a fine. Do not attempt to shoo them away aggressively or disturb them.

Iguanas are everywhere too. Green iguanas have become a significant presence across the island. They are not native and are considered something of a nuisance by many locals, but they are still protected by anti-cruelty laws. Do not feed them, as this encourages large numbers to congregate.

Open container laws apply. Despite its reputation as a party town, drinking alcohol in public — including on the streets of Duval Street and on most beaches and in parks — is technically prohibited under Florida’s open container laws. You will see people carrying drinks in plastic cups, but be aware that the law is on the books and can be enforced. Beaches and parks that are state-managed are strictly no-alcohol zones.

The legal drinking age in the United States is 21. This is universally enforced. Photo ID will be required at bars and off-licences, regardless of how old you appear.

Environmental laws are taken seriously. The waters around Key West are part of the Florida Keys National Marine Sanctuary. There are strict regulations protecting coral reefs, seagrass beds, mangroves, marine wildlife, and protected species. Anchoring on coral, removing shells, touching or disturbing marine life, and damaging seagrass with a boat propeller are all illegal and subject to penalties. If you are snorkelling or diving, use reef-safe sunscreen — legislation to ban sunscreens containing chemicals harmful to coral reefs has been actively debated and some restrictions are in place.

Protected wildlife on land and sea. The Queen Conch (the large, beautiful shell that is the symbol of Key West) cannot be taken from the wild. The American Crocodile, various shark species, and sea turtles are all protected by state and federal law. Feeding, harassing, or interfering with any of these animals is illegal. Sea turtle nesting areas on beaches have strict rules around disturbance, lighting, and access.

Cycling lighting is legally required at night. A white front light and red rear light are mandatory when cycling after dark. This is actively enforced.

Sunburn is a genuine concern. Key West sits at latitude 24°, meaning the subtropical sun is considerably stronger than most visitors are accustomed to. Unprotected skin can burn within minutes. Apply sunscreen frequently, stay hydrated, wear a wide-brimmed hat, and seek shade during the hottest part of the day. The heat and humidity can be intense, particularly in summer.

Hurricane season runs from June to November. Key West has been directly impacted by hurricanes in the past and takes the threat seriously. If visiting during this period, monitor weather forecasts and be aware of evacuation procedures should a storm threaten the area. The island has a well-organised emergency communication network.

Island Time is a real thing. The pace of life in Key West is deliberately, cheerfully unhurried. Service may be slower than you expect, plans may shift, and an easygoing flexibility goes a long way. Arriving with a rigid itinerary and an impatient attitude will make the experience harder than it needs to be. Lean into the rhythm of the island and you will find it deeply enjoyable.

Residential parking. Key West is a small community of around 25,000 permanent residents, and residential parking in the Old Town area is protected and limited. Parking in spaces reserved for residents will result in a ticket or tow. Use the designated public car parks, which are well-signposted.

Crime is generally low. The Florida Keys have a low crime rate, and Key West is considered a safe destination. As with anywhere, use common sense at night, particularly around the busier stretches of Duval Street and Mallory Square. Keep an eye on your belongings and be aware of your surroundings, especially if you have had a few drinks.

Mosquitoes. The tropical climate means mosquitoes are a fact of life. Use insect repellent containing DEET or picaridin, particularly at dawn and dusk. Eliminating standing water from around your accommodation helps reduce their presence.

Best time to visit Southern Florida

Southern Florida is one of the most climate-diverse destinations in the United States, offering warm sunshine virtually year-round. However, the experience varies enormously depending on when you arrive. From the balmy perfection of winter to the steamy, storm-lashed days of summer, each season brings its own character — and its own trade-offs.


🌸 Spring (March to May)

Spring is widely regarded as one of the finest times to visit Southern Florida. Temperatures are warm and pleasant, typically sitting between 22°C and 28°C, with lower humidity than the summer months and very little rainfall. The beaches are inviting, the wildlife is active, and the Everglades are teeming with birdlife as wading birds congregate around shrinking water pools.

March brings Spring Break crowds — particularly around Miami Beach, Fort Lauderdale, and the Florida Keys — but by April things quieten considerably. May is something of a sweet spot: the humidity begins to climb slightly, but visitor numbers drop, prices ease, and the weather remains gorgeous. Outdoor activities such as snorkelling, kayaking in the mangroves, and cycling through national parks are all excellent at this time of year.

What to pack: Lightweight trousers and shorts, short-sleeved shirts, a light cardigan for evenings, swimwear, reef-safe sunscreen (SPF 50+), polarised sunglasses, comfortable walking sandals or trainers, a small day rucksack, and a reusable water bottle.


☀️ Summer (June to August)

Summer in Southern Florida is not for the faint-hearted. Temperatures regularly exceed 32°C, the humidity is oppressive, and the region enters its wet season, bringing near-daily afternoon thunderstorms that can be sudden and intense. June through August also falls within the Atlantic hurricane season, which runs officially from 1 June to 30 November, though the peak risk period is August through October.

That said, summer has its merits. Hotel rates and flight prices drop significantly, making it the most budget-friendly season. Many families from Latin America and Europe travel at this time, giving the region a lively, cosmopolitan atmosphere. Early mornings are the best time for outdoor activities before the heat peaks, and the rain typically arrives in dramatic afternoon bursts that clear quickly. Theme parks near Orlando attract crowds, but the beaches themselves are often quieter than in winter.

What to pack: Lightweight, moisture-wicking clothing, a packable waterproof jacket or poncho, quick-dry shorts, breathable footwear, very high-factor sunscreen, insect repellent (mosquitoes thrive in the wet season), a wide-brimmed hat, and electrolyte tablets or a sports drink for staying hydrated in the heat.


🍂 Autumn (September to November)

Autumn is Southern Florida’s most underrated season. September and October carry the highest hurricane risk and the tail end of oppressive humidity, but by November the weather begins to transform dramatically. Temperatures ease to around 25°C–28°C, rainfall diminishes, and the landscape — particularly the Everglades — begins to dry out, concentrating wildlife in spectacular fashion.

November is arguably the finest month of the entire year in Southern Florida. The tourist crowds have not yet returned in earnest, hotel prices are still reasonable, and the weather is close to perfect. The Florida Keys are particularly lovely in November, as are the coastal areas around Naples and Marco Island on the Gulf Coast. Birding is excellent from October onwards as migratory species arrive for the winter.

What to pack: A mix of short-sleeved and light long-sleeved tops, a compact umbrella for September and October, breathable trousers, swimwear, comfortable walking shoes, sunscreen, and a light jacket for November evenings, especially on the water.


❄️ Winter (December to February)

Winter is peak season in Southern Florida, and with good reason. While much of North America shivers under frost and snow, Southern Florida basks in reliably warm, dry, and brilliantly sunny conditions. Daytime temperatures sit comfortably between 20°C and 26°C, humidity is low, and rainfall is minimal. This is the season that the region was built for.

Miami, Palm Beach, the Florida Keys, and Naples are at their absolute finest from December through February. The “snowbird” population — retirees and seasonal residents from the northern United States and Canada — swells the population considerably, and with them come vibrant social scenes, excellent restaurant experiences, and a lively cultural calendar. Art Basel Miami Beach takes place in early December and is one of the world’s premier art events. The downside is cost: winter is when prices are at their highest, rooms must be booked well in advance, and popular spots can feel very busy.

What to pack: Mostly summer clothing, but include a medium-weight jacket or fleece for evenings and air-conditioned interiors (restaurants and shops are frequently very cold), light layers, smart-casual evening wear if dining out in Miami or Palm Beach, comfortable walking shoes, sunscreen, and swimwear.

🏆 Overall Best Time to Visit

If you can visit only once and want the most reliable combination of superb weather, manageable crowds, and reasonable value, November stands out as the single finest month. It sits in the sweet spot between the wet summer season and the expensive winter peak — the humidity has dropped, the skies are clear, the sea is warm, and the Everglades are beginning to teem with wildlife. That said, for those who prioritise balmy dry weather and do not mind paying a premium, the December to April window represents Southern Florida at its most inviting. Budget travellers willing to brave the heat and occasional storm will find June and July offer the best value of the year. Whatever your preference, Southern Florida rewards every visitor who comes prepared — the key is simply knowing what to expect from the season you choose.

Where to stay near Key West

1. Andrews Inn and Garden Cottages

Andrews Inn & Garden Cottages is a small bed and breakfast tucked down a quiet lane just off Duval Street in Key West’s historic Old Town, next door to the Ernest Hemingway Home and Museum. The property dates to around 1900 and comprises six rooms in the main inn along with garden cottages, each furnished with four-poster beds, flat-screen televisions, refrigerators, and free Wi-Fi. Guests staying in the main inn receive a complimentary hot breakfast served poolside each morning, and a daily happy hour by the heated outdoor pool is included for all guests. Complimentary bicycles are available, which makes sense given the location — most of Key West’s main sights are within easy walking or cycling distance. The inn holds a TripAdvisor Certificate of Excellence and a Two-Palm designation under Florida’s Green Lodging Programme. It does not accept children or pets.

2. The Artist House

The Artist House is a Victorian-era bed and breakfast located in the heart of Old Town Key West, Florida. Built in the 1890s, the property is one of the island’s most recognisable historic buildings, with a gingerbread-trimmed exterior that reflects the architectural style typical of the period. The house offers a small number of individually decorated guest rooms, each with its own character, blending period furnishings with modern comforts. It is perhaps best known for its association with Robert the Doll, a supposedly haunted toy now housed at the Fort East Martello Museum, which once belonged to a former resident of the property. The surrounding neighbourhood is walkable, with easy access to Duval Street, local restaurants, and galleries. For travellers looking for a stay with genuine historical context rather than a generic hotel experience, the Artist House is a solid and distinctive choice.

3. Seashell Motel

The Seashell Motel in Key West, Florida, is a small, no-frills property that suits travellers who want a straightforward place to stay without paying resort prices. Located on South Street, it sits within walking distance of Duval Street and the main attractions of Old Town, making it a practical base for exploring the area. Rooms are basic but functional, and the motel has a small pool which is welcome given the Florida heat. It caters largely to budget-conscious visitors and backpackers, and has a relaxed, unpretentious atmosphere that regulars tend to appreciate. Parking is available on site, which is a genuine convenience in a town where space is tight. It is not the place to go if you want spa treatments or a cocktail bar, but for travellers who plan to spend their time out exploring rather than sitting in a hotel room, it does the job well.

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