A three day trip to Key West in can involve a turtle hospital, the Mallory Square sunset, President Truman’s Florida hideaway and the enormous Fort Jefferson.
Day One: Glass-bottomed boat, kayaking and sunset
With Key West, much of the fun is in getting there. The Overseas Highway across the Florida Keys is one of the country’s most staggering drives – taking around four hours from Miami, but worth making a day of. The mood gets more relaxed as you head down the Keys and over the bridges that link them, and a couple of stops are worth making.
The first is Key Largo, where a glass-bottomed catamaran heads out over the aquatic wonderland of the John Pennekamp State Park. The offshore reef makes for massive shoals of fish, graceful sea turtles and patches of multi-coloured coral.
The colourful Midway Café in Islamorada is a superb place to stop for lunch, especially if you’re a bakery-loving sweet tooth, while the hourly tours of the Turtle Hospital on Marathon Key are heart-melters.
Further along, the Bahia Honda State Park is arguably the best beach in the area, while a walk along the old rail bridge there is a great choice for those overwater bridge photos that are tricky to get from the car. Alternatively, explore the backwaters and mangroves in a kayak – Big Pine Kayak Adventures offers leisurely, nature-focused paddling trips.
By the time you roll into Key West, it should be time to watch the sun set at Mallory Square. Grab a beer, stroll around, check out the herds of street entertainers and see the sky turn pink and orange – it’s the perfect Key West introduction.
El Siboney – a no frills Cuban joint that’s popular with locals and serves up hefty portions of ultra-tasty ropa vieja – is a good bet for dinner.
5 great Key West experiences to book
- 🛶 Look for wildlife in the mangroves on a guided kayaking tour.
- 👻 Go on a ghosts and mysteries tour and discover Key West’s dark side at night.
- 🐬 Combine dolphin-watching and snorkelling on a half day adventure.
- 🍴 Take a cultural food tour and learn about Keys heritage as you eat and drink.
- 🍹 Explore lesser-known bars on a craft cocktail crawl.
Day Two: Little White House, Mel Fisher Museum and rum tasting
For its size, Key West has an absurd number of attractions – some tackier than others. Most are within walking distance of each other, although advance booking is usually a good idea for the Hemingway Home and Little White House.
The former is where Ernest Hemingway lived for the bulk of the 1930s, and is charmingly overrun by the descendants of the six-toed cats he kept as pets. The tour round is heavy on atmospherics, but if insight is what you’re after, the Little White House the better of the two. This is where President Truman spent his working holidays. The tours delve into his relatively simple tastes, his habits, and the logistical operations required to move the government down to Florida – but also provide a fascinating snapshot of the man and the era.
To find out more about the natural wonders of the Keys, the Florida Keys Eco-Discovery Center does a fantastic job of showing how the eco-systems work, and how man’s influence affects them. And, if you’re more interested in the social history of Key West, the Mel Fisher Museum concentrates on the shipwreck salvagers and smugglers that have given the place its somewhat law-ambivalent reputation. There’s some excellent salvaged booty on display, but it’s all about the stories.
In the past, the rum was smuggled in, but now Key West makes its own rum. Key West Legal Rum offers tours of the distillery and mojito-making classes. And taking one of them on in the late afternoon would be a perfect segue into what Key West does best – drinking. Duval Street is one of the world’s great party strips, but it’s a remarkably egalitarian affair. It doesn’t matter how old or how rich you are, everyone gets talking over margaritas on bar stools. It’s very much a case of following your nose – shamble down the street and you’ll end up finding the right bar for your mood.
Day Three: Dry Tortugas and upscale dining
Key West may be the last of the Keys, but there are more tiny specks of land further into the Gulf of Mexico. The Dry Tortugas are two hours, fifteen minutes away on the Yankee Freedom III fast ferry, and have a real desert island feel to them. A trip out there essentially becomes a day tour, and while beaches and snorkelling are the initial attractions, the Tortugas are also home to one of the most remarkable buildings in the country. Fort Jefferson on Garden Key is an astonishing 19th century fortress, built to protect the US in the event of attacks from the Gulf of Mexico.
It’s the largest masonry structure in the Americas, and cavernous once you start walking around it. Little museum style exhibits – including boats used by migrants from Cuba – can be found inside.
Once back in Key West, it’s probably time for a slightly classier evening – and Duval Street does get less rowdy as you head south down it. There are several galleries and specialist shops to check out, many of which stay open late, and a selection of the city’s better restaurants.
Nine One Five, for example, is about as buttoned up and upscale as Key West gets, with a menu that combines local seafood with internationalist recipes. They’ll still let you in wearing a Hawaiian shirt, though…
More Florida travel
Other Florida travel stories on Planet Whitley include:
- Key West mangrove kayaking guide.
- Visitor guide to the Key West Shipwreck Treasure Museum.
- Visitor guide to the Frost Science Museum in Miami.
- How to get the most out of the Graffiti Museum in Miami, Florida.
- What to expect at the Flagler Museum in Palm Beach.
