Key West Holidays 2025 & 2026

Get a taste of the Caribbean on American soil with a holiday to Key West. At the bottom of the Florida Keys, a string of islands descending from Florida, you’ll be at the southernmost point of the entire country, a mere 90 miles from Cuba. On this intimate isle recorded at just over a tiny four square miles, you can experience the tropical heat of the West Indies with the perks of flavoursome US cuisine and culture.  

Here the fun is just bursting, as you can take part in water sports, a lively nightlife, relax on golden beaches, and even visit museums and haunts of the famed author Ernest Hemmingway. You’ll also have the glamorous Duval Street for your fill of high-end boutiques, bars and cafés for your enjoyment. Of course, you better take a snap by the Southernmost Point Buoy too while you’re here, an obligatory addition to Instagram to tell the world you’ve been as south as you can get in the USA. Here you have all you need for a Florida getaway in one small tropical space; with plenty of activities to quench your leisure, cultural, and culinary thirsts, you will be in for a holiday extravaganza with a stay at Key West. 

Located on the waterfront of Key West’s Old Town next to a cruise ship port, Mallory Square is a plaza of restaurants, bars and cafés facing out onto the Gulf of Mexico. One of Key West’s main attractions happens here every day, the daily Sunset Celebration which features crafts, street performers and food carts. The festivities last two hours either side of sunset, so you’ll get a great evening mingling with the locals and be enjoying the party vibes every single day. 

Smathers Beach 

Smathers Beach is the largest in Key West, full of vast plains of white sands. Pull up a lounger and soak in the rays as you relax to the scenic vistas of the Gulf. According to the locals, this is the place to experience a phenomenal view of the sunset, a must-do if you’ve already enjoyed Mallory Square’s Sunset Celebration. Also on site are picnic areas, volleyball courts and jet ski rental outlets, so you can assure that an exciting day is afoot with a trip to this beautiful beach. 

Dry Tortugas National Park 

Dedicate a day to sailing 70 miles west of Key West to the Dry Tortugas National Park, a collection of small islands remote from any other main bodies of land. Around this area, the coral reefs are preserved to perfection and are recognised as the least disturbed reefs in the entirety of the Keys. With sea life in abundance and the corals clean from any pollution, you’ll be enchanted by the experiences you’ll have swimming, snorkelling and scuba diving amongst this gorgeous National Park.  

Fort Jefferson 

Within the Dry Tortugas is the valiant Fort Jefferson, a 19th-century fort built to protect the harbours of America. Though it was never complete nor armed, this makes for an excellent day out for anyone interested in a great piece of Floridian history. Accessible only by ferry or seaplane, you’ll fly or cruise over the beautiful ocean in true style, giving you the chance to catch lavish vistas of the Gulf of Mexico while exploring this archaic military fort.