The Cool Key West Blog — Discover The Southernmost City in the USA

It is always cooler out on the water than it is on land. That is a wonderful thing in Key West because summer on the island brings excellent opportunities to beat the heat while experiencing some legendary Key West fishing. June and July mean great Offshore Fishing as light steady winds set in from the […]

What most people know as the Florida Keys is the chain of inhabited islands that are connected to each other and the Florida mainland by the overseas highway. However, these islands are actually only one small element of a 100-mile-long strip of shallow water flats, tangled channels, and wild mangrove islands that separate the Atlantic […]

The far west end of Key West beyond Whitehead Street holds several easily accessible points of interest that are well worth exploring. Fort Zachary Taylor and the local favorite Fort Zach Beach are both wonderful places to spend a day. Maritime history buffs will surely want to take in the Key West cruise ship docks […]

Key West is such a busy, vibrant little city that you are going to have your hands full with places to go and things to do from morning to night. You will be on the go, and, like many visitors, may find yourself wondering about the best way to get around town. Fortunately, Key West […]

Throughout its history, Key West and the Keys in general have held a bit of the frontier, outlaw mystique. Adventurers, castaways, smugglers, runaways, and renegade souls of various stripes have always been and still are attracted to the area. And a significant part of Keys’ regional lore is the many tales of the exploits of […]

The blue Caribbean waters, coral atolls, mangrove-shrouded inlets, and remote anchorages that make up the marinescape surrounding Key West have always attracted explorers, escape artists, and pirates of various stripes. From the notorious Edward Teach, also known as Blackbeard, to Captain William Kidd, Black Caesar, and Jean La Fitte, on to the rum runners of […]

The waters of the Florida Straits, the Gulf of Mexico, and the Gulf Stream-washed Atlantic seaboard of Florida are exceptionally rich in terms of maritime history. From the earliest Spanish and Portuguese explorers, through the golden sagas of over 200 years of Spanish treasure convoys, to the days of the slave trade and the pirates […]

Key West has gone to the dogs these days. You see them everywhere – capering in costumes, strolling the streets, reclining in doorways, resting in restaurants, tucked under bar stools, and of course splashing in (selected) surf. All days are dog days in dog-friendly Key West, because most everybody is chilling on the tropical vibe, […]

Being a resort island that is renowned for its nightlife and multitude of bars, clubs, and other types of party venues, it will come as no surprise that Key West has a very rich live music scene. Many local artists, as well as world-class acts, can be found performing on any day of the year, […]

The Gulf and Atlantic waters around Key West were already well-known for incredible sport fishing by the time writer Ernest Hemingway’s angling exploits thrust Key West fishing firmly into the national spotlight. Hemingway first arrived in Key West from Cuba in April of 1928, and it was not long before he struck up a friendship […]

Many visitors arrive in Key West with one question uppermost in their minds: Which way to the Key West beaches? Key West is a semi-tropical island surrounded by crystal blue waters and bathed in sunshine. Palm trees sway in the breeze and tropical flowers bloom exuberantly. First-time visitors and others who are unfamiliar with the […]

Are you considering driving to Key West but are not sure if you are ready to commit the time, energy, and expense required for the trip? How would you like to experience the wonder of a road trip down to Key West by bus? You can enjoy the scenic Overseas Highway, and cross the amazing […]

The southern Florida Keys, Marquesas Islands, and Dry Tortugas were known historically as bird-rich places where Native Americans, seafarers, and explorers would harvest birds, eggs, and plumage for food and trade purposes. Naturalist John James Audubon was possibly the first to enjoy Key West birdwatching, and he noted the amazing abundance and diversity of both […]

It’s a well-known stereotype that many literary authors are also raging boozers. Which, forgive us, doesn’t make us want to emulate them any less. In fact, at we can’t think of anything better than to sip a cool drink while typing away at our — er, laptops — out on the porch in the sweet […]

No matter which type of fishing you prefer, Cool Key West is sure to meet and exceed your expectations when it comes to the best fishing charters. Whether you prefer fishing with a small group or going solo we have the perfect package for you. Our goal at Cool Key West is to make your […]

See the entire island of Key West and the surrounding sapphire blue waters from the air as most visitors have never imagined. You’ll soar 300 ft. above the water (that’s 200 ft. higher than the tallest building in Key West). Panoramic vistas of Mallory Square, the marine sanctuary and Key West harbor are among the […]

Kayaking the shallow water flats around Key West’s backcountry is an exciting, and at the same time, a very relaxing adventure. It may be the perfect method of exploring the spectacular coastal scenery that is abundant in the waterways around Key West since much of it is only accessible by kayak. Kayaking is a uniquely […]

Are you up for a real adventure in Key West? Do you love the water and want to know more about the amazing coral reef environment unique to the Florida Keys? Have you ever dreamed of exploring the mysteries of a shipwreck? You can do it now with Cool Key West as your connection to […]

From Key West, to Maui, to Tahiti and beyond, the sunset cocktail cruise is a tropical vacation resort staple. Some may even claim that it has been overdone… maybe they want to brush the experience off as “too touristy” or “just for old folks” or “boring”. The way I see it, after years of living […]

Most everyone would agree that Key West is a scenic tropical paradise, with blue skies, turquoise water, exotic foliage, and an interesting urban and human landscape that catches the eye every way you turn. But what is often overlooked is the fact that, because Key West is a tiny island surrounded by a lot of […]

One of the great things about visiting Key West is the fact that it is a small island with a multitude of interesting things packed close together, making it easy to take in the sights. Most everyone knows about strolling along Duval Street, walking to the Southernmost Point, riding the Old Town Trolley and Conch […]