Key West Holidays 2024/2025 from £1624pp

Why go to Key West

Closer to Cuba than Miami, Key West sits off the coast of Florida in the Gulf of Mexico’s crystal-clear waters. The tiny island city – just four miles long and one mile wide – doesn’t do things by the book, offering travellers an inimitable mix of the absurd and the familiar. Party hard or take it easy – it really is up to you.

Flip-flops are welcome almost anywhere in Key West – but leave your watch at home. Known for being progressively liberal, a quality that has lured everyone from hippies to literary titans to its shores, Key West is innately easy-going. With the tropical climate bringing sun-soaked days and balmy nights cooled by ocean breezes, you’re only a cocktail away from a true tropical paradise.

The azure waters surrounding Key West are a crowd-puller due to their reputation as fishing hotspots. Depending on the time of year, you can expect bites from different types of snapper, grouper and shark. If you’d rather just observe, strap on your scuba gear and hit dive sites to spot colourful coral, giant grey angelfish and submerged ships.

Lazy days often give way to lively evenings - the city’s nightlife is the stuff of legends. As the sun sets, the party starts at Mallory Square where you can expect incredible performances, from fire eaters and sword swallowers to cats jumping through flaming hoops (yes, this is a real thing). Afterwards, the numerous bars and clubs lining Duval Street keep the party going all night.

In a place filled with watering holes and celebrated for its fishing, you can see why Ernest Hemmingway found Key West appealing. The celebrated American writer lived on the island for ten years and you can visit the impressive house and grounds where he wrote, as well as his favourite drinking hangouts.

When to go to Key West

As the southernmost city of the continental United States, Key West enjoys a tropical climate with consistently warm weather year-round. Even in winter, the temperature rarely dips below 20C and the waters surrounding the island are always warm enough for swimming.

Winter is a popular time for holidaymakers, who flock to Key West to experience warm and dry weather. If you want to beat the crowds, head out between March and May – the weather stays pleasant and hotel rates are more affordable.

While hurricane season extends from June to November, short, sharp rainstorms is as bad as it usually gets. For a cheap deal, the humid summer months are your best bet.

While Key West is always ready for a party, things crank up a notch for Fantasy Fest in October. Ten days of pre-Halloween partying draw tens of thousands of revellers for a wild festival featuring fancy dress and plenty of skin.

What to do in Key West

Trying to reel in one giant fish after another is a fine way to spend your time in Key West. But discovering the history of the island – and of its most famous former resident – is another way to get the most out of your stay in the city. Evenings, of course, are defined by its iconic sunset parties, good food and fine wine.

Hemingway House

Ernest Hemingway lived in this Spanish Colonial-style house in the early 1930s. Set in the heart of the old town, the lodging dates back to 1851 with wraparound verandas and the first in-ground pool in Key West.

A guided tour of the home reveals the studio where the author produced some of his most notable works in between fishing trips. Some forty, six-toed cats (that’s one more than most) roam the gardens, descendants of Hemingway’s own cat, Snow White.

Mallory Square

Mallory Square is the social and cultural hub of Key West, partly thanks to its famous ‘Sunset Celebrations’. Starting two hours before the sun goes down, the nightly festival is filled with entertainers such as acrobats, magicians and musicians, as well as food vendors and local artists.

The square also hosts shops and restaurants but the real highlight is the view of the radiant pink and yellow skyline as the sun disappears into the ocean.

Museum of Art & History at the Custom House

Built in 1891, this imposing building once represented Key West’s flourishing industries and increasing wealth. It originally housed the island’s customs office, postal service and district courts, before becoming a museum in 1991.

Recounting the history of Key West, “Old 91” has a permanent collection of historical photographs, paintings and other artefacts. Discover the engineering excellence behind the Overseas Highway connecting Key West with the Florida Keys and see rare paintings by celebrated playwright and former resident Tennessee Williams.

Fishing and diving

Deep-sea fishing off Key West can reel in various big catches including sailfish, wahoo and tuna. You can hire a boat or head out with a guide to find the best spots for a bite.

Within Florida Keys National Marine Sanctuary, the USS Vandenburg artificial reef is a popular spot for snorkelling and scuba diving. Around 7 miles off-shore from Key West, the site has a 525-foot-long ship and nearly 200 species of fish around the wreckage.

Dry Tortugas National Park

Dry Tortugas National Park covers an archipelago of seven islands in the Gulf of Mexico. Day trips from Key West dock at Fort Jefferson, where you can tour the 19th-century building used as a remote prison during the Civil War.

The stunning natural surrounds include pristine white beaches leading to aquamarine waters. Below the water are coral reefs and seagrass beds teeming with tropical fish. During summer, sea turtles bury their eggs on the national park’s beaches.

Where to stay in Key West

For families

Key West isn’t in short supply of resort-style hotels featuring pools and other on-site activities like kids clubs and sports courts. Stay near the Southernmost Point of the Continental United States (marked by a colourful buoy) and you’ll have easy access to other attractions including the Key West Butterfly and Nature Conservatory. Duval Street, which puts a family-friendly face on during the day, will also be on your doorstep.

Further along the coastline to the east, Higgs Beach has a picturesque pier and calm waters ideal for swimming. There’s also a playground and an arts and crafts market. Accommodation ranges from high-end resorts to homely guesthouses.

For travellers on a budget

Finding budget lodgings on Key West can be a challenge. There are a couple of cheap hostels, but most accommodation is quaint B&B-style guesthouses or fully equipped resorts.

The old town – essentially the western side of the island – offers the most variety in terms of B&Bs, including some with shared bathrooms to keep costs down. Staying on another of the Florida Keys and visiting Key West on day trips is usually a cheaper choice.

Once in Key West, there are enough restaurants to find tasty meals at decent prices and many bars offer happy hour drinks and snacks.

For food and drink

Bahama Village in the old town has some of the best restaurants on the island, featuring Caribbean-influenced ingredients like plantains, coconut, and jerk-seasoned meats. Meanwhile, on the Historic Seaport, you’ll find oyster bars overlooking the dock, perfectly positioned for sunset. Cottage-style B&Bs line the streets a few blocks back from the waterfront.

The island has two rum distilleries, both on Simonton Street. Head to either for a tour followed by a smooth taste of the Caribbean. If you want to follow in Hemingway’s steps, visit Duval Street for a daiquiri in one of the watering holes he frequented.

For nightlife

Home to shops and art galleries during the day, Duval Street transforms into a raucous night-time hotspot. You’ll find everything from dive bars to live music venues open until the early hours and, you’ll be pleased to hear, you’ll be able to stumble home to inns and B&Bs on the famous street – if you don’t mind the inevitable ambient noise, that is.

Mallory Square is the place to be in the hours leading up to sunset, and has a good selection of upmarket guesthouses nearby. Some are set in tropical mansions and breezy Caribbean-style ‘conch’ houses – named for Key West’s early settlers.

For culture

Bahama Village is a colourful 16-block neighbourhood within the old town. Once considered an area to avoid, these days it’s filled with popular brunch spots and cafés. With Bahamian migrant roots, the area is also known for its outdoor Village Market selling artisan products. Wander the streets to take in pastel-coloured homes, tropical plants and calypso music wafting from windows.

The broader old town is home to the city’s historic monuments and a whopping 187 historic buildings. You can stay in some of the buildings that help give the area its character. Choose from Victorian-era guesthouses or 19th-century conch houses – all equipped with modern touches like swimming pools and bars.