End Of The Road: Destination Key West

    Few places have the mystique and allure as those towns at “the end of the road”. There’s just something special about having nowhere else to go but back from whence you came that attracts interesting and adventuresome characters to ‘come see’ yet engenders a “live and let” live attitude among those who stay.

    Not only does Key West fit this description very well but it is perhaps the quintessential end of the road town. It has quirky local characters, a 24-7-365 party atmosphere replete with whacky parades and festivals, and also a daily carnival celebration of the sunset on Mallory Square with jugglers and escape artists and tight rope walkers.

    Key West’s colorful history revolves around the sea and includes pirates who hid out on Bone Island before it was settled. And later by barely-above-the-law wreckers who made a rich living by salvaging the ships that fell afoul of the barrier reef in the days before lighthouses warned of natural treachery along the Florida Straits. These wrecks came ashore at least once a week before the lighthouses were built and many of them are still accessible even today for divers and treasure hunters.

    The Pirates Well, Key West
    The Pirates Well, Key West

    Today this rich and colorful history is on exhibit in the many museums, and in walking, biking or other guided tours along old streets lined with quaint architecture, standing witness to many interesting and romantic stories. As the island became more ‘civilized’ and law-abiding, deep sea and big game sport fishing has become the biggest attraction to the area and more than a few colorful characters have been drawn by the lure of sportfishing to make their home in Key West.

    In the late 1920s, the legendary sportsman and author Ernest Hemingway discovered the attractions of Key West – its warm water fishing and its watering holes for relaxing after a day at sea. Several of his literary works reflected his friendships and adventures in the Key West environment which he came to love so much.

    Today that tradition continues; sport fishing is one of the island’s largest “industries” and sources of tourism. Not only do deep sea charters line marinas such as Charter Boat Row, but anglers avidly pursue other types of fishing – flats and fly fishing is very popular along the shallow waters and channels of the backcountry (Gulf of Mexico) waters.

    Fishing Catch of the Day!
    Fishing Catch of the Day!

    Key West and the Florida Keys are blessed by both the shallow and warm waters of the Gulf of Mexico on one side and the deep blue and green waters of the Atlantic and it’s deeper water fishing along the reefs and on the Gulfstream. The “Stream” runs north and moves along at a fair clip of a few knots per hour – where it meets the waters of the Florida Straits is an area rich in bait fish, which attracts the larger pelagic fish – the big game prized by anglers.

    Will Soto juggles against the sunset backdrop
    Will Soto juggles against the sunset backdrop

    History buffs – especially those interested in the US Civil War — are fascinated by Key West. The island city had a quirky role in the Civil War as the only city held by the Union south of the Mason-Dixon line even though city residents were pro-South. When the war broke out, an Army captain ‘captured’ the unfinished Fort Zachary and held it for the entire conflict. The securing of the fort allowed the Union to interferre with shipping into the Gulf of Mexico, and many experts agree, shortened the duration of the war. For Civil War buffs, the massive Union fort built at the southwest end of Key West is still an impressive sight and contains the largest collection of Civil War era cannon in the US.

    To fully savor the off-beat attributes and characters at this end-of-the road destination, put these attractions on your Key West bucket list:

    Mallory Square: Mallory Square reminds us of a time when people didn’t care to work all the time but instead insisted on taking time to enjoy life in the companionship of their friends in the community. It’s a great place to relax, unwind and watch the sun go down. The nightly festival, known as Sunset Celebration, has a wide variety of street performes and local arts and crafts vendors. Even locals still check out Mallory once in a while – and you know they do their Christmas shopping here. (

    Hemingway House: This is the home of the man who arguably put Key West on the map. Key West’s most popular tourist attraction, Hemingway’s home is still beautiful and has many elements of his life still in it. (

    Oldest House: Considered by many to be the best attraction in town not only because it’s free but also because of its uniqueness as Key West’s oldest home…it’s called simply The Oldest House and Gardens. It’s a Classic Revival style home built around 1829 and is the oldest all-wood structure in Florida. It’s built entirely of cedar and pine and constructed entirely without nails. Of note is the detached Cook House, the only remaining one in Key West. And the stories told by the docents will give you a sense of how the early settlers lived and a glimpse into the life of the wreckers who settled Key West. (

    Cook House at the Oldest House
    Cook House at the Oldest House

    Fishing Charters: the marinas abound with fishing charters of all sorts. You can go out with a group of 4-6 on a sportfishing yacht, a large group on a party boat, or you can get smaller boats with just you and a guide – either way your captain will know exactly where the kind of fish you want to target are biting. (

    Watersports: If fishing isn’t your cup-of-tea, you can try other activities like wreck diving or snorkeling the reef. Just get out on the water – whether it’s kayaking, stand up paddle-boarding, or on a charter to meet some friendly dolphins.(

    Eye contact with dolphin
    Eye contact with dolphin

    Watering Holes: On the other hand, if you just like to ‘hang out’ and meet people there’s plenty of locally and nationally famous watering holes such as Sloppy Joe’s, Margaritaville and The Green Parrot where you’ll meet the friendly people of Key West who really appreciate you visiting their area and you might even encounter a fellow-tourist from someplace else you’re familiar with.

    All in all, Key West may be the end-of-the road but there’s an amazing amount of beauty, fun and friendliness there. The things mentioned here barely scratch the surface. However long you stay, it won’t be long enough.

    Featured images:
    •  License: Creative Commons image source
    •  License: Creative Commons image source
    •  License: Image author owned
    •  License: Image author owned
    •  License: Image author owned
    I have spent the past 15 years in the travel industry. Today focused on promoting different ways of traveling, I'm in the process of creating few travel websites, which will be launched shortly. I have a great passion for travel and the travel industry. My goal here atTtripOutlook is to connect to other proffessionals in the travel industry and to exchange experience.

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