Jul 01, 15 KEY WEST by LAND & WATER

WARREN RESEN – North American Travel Journalists

Photographs by JEANNE O’CONNOR –  NATJA

As they say, “the grass is always greener…”  We were staying at a 5-star hotel in Puerto Villarta, Mexico while attending a travel writer’s conference. The hotel, ocean views, holiday atmosphere and Mexican culture left little to be desired. Most of the other travel writers in our group were from the west coast, California not Florida.  When they learned we had just returned from a trip to Key West, many told me they would like to visit there someday.

Much of the world views Key West as an exotic, remote location.  Well, it’s pretty remote even for many Floridians.  Jacksonville is more than 500 miles north and Pensacola, in the Central Time Zone, is more than an 800 mile drive.  Yes, Florida is a long state which puts Key West way out there.  One has to make a concentrated effort to visit.  It is not a case where a visitor can just say, “I was in the neighborhood and just thought I’d drop in.” But for those who make the effort, the trip is definitely worthwhile.

Private pool & breakfast area at Chelsea House.

For general information, the Florida Keys do not end at the southern most point in Key West but further west (70+miles) in the Gulf of Mexico in the Dry Tortugas. Traveling south on US 1 to Key West, also known as the Overseas Highway,  the compass slowly begins turn to SW as you near Key West and then due west, something that confuses most first time visitors who, having looked at a map,  believe they are traveling south.

Choo-choo sightseeing in Key West.

A must for first timers in Key West is a ride on the Conch Tour Train or one of several other sightseeing lines. Key West is a different world.  An hour and one-half sightseeing excursion will help orient you to this magical, exotic isle.

Accommodations run the gamut from motel row from where you first enter Key West to 5-star hotels in Old Town and everything in-between. Our base of operations was the historic Chelsea House in Old Town.  It was a delightfully private compound of buildings with each room having its own privacy deck or balcony.

The Chelsea House provided a wonderful buffet breakfast in an area next to its very private, lushly landscaped pool. Best of all was the off-street parking on the property, something worth its weight in gold in Old Town Key West. The location, just off Duval Street, allowed us to wander the streets of Old Town during the day.

Selfie at Sloppy Joe’s.

Duval Street is the heart of Key West.  Some wags refer to it as the longest t-shirt shop street in the world.  But how can you return home without a Key West t-shirt or hat?

Walking on Duval Street takes the visitor past an amazing number of shops and restaurants and directly to Mallory Square where at sunset everyone heads to see this daily extravaganza but also to be entertained by street performances doing all sorts of “stuff. “

Mallory Square - where it’s at.

During a Duval Street stroll, visitors pass by the world famous Sloppy Joe’s, made famous by Ernest Hemingway, Hog’s Breath Saloon, and the original  Jimmy Buffets’ Margaretville to name only a few of the better known watering holes.

Surrounding   Mallory Square is Mel Fisher’s Museum, the Key West Aquarium, markets and of course stores selling more t-shirts. Visitor’s guides are available almost anyplace in Old Town to help direct tourists to places of interest, and there are many.

Visits to the Hemingway House, The Little White House (President Truman’s get away), the Audubon House, or just wandering the streets of Old Town on a self-guided tour to marvel at the diverse architecture is a delight. Almost everything of interest is located in the downtown historic Old Town district except the famous concrete Southernmost Point Buoy which is some distance away but easily reachable on your sightseeing train tour. This is the area where you will find the beautiful white sand beaches.

Fort Jefferson - Gulf of Mexico, moat, and fort.

During the day, Duval Street is the haunt for sightseers and families.  It’s after dark when the residents who give Key West its unique flavor make their appearance.

Having previously covered the land portion of Key West, we decided that this trip would have a different focus, so we took to the water from the downtown wharf areas. There is a bewildering choice of options visitors.

Many of the boats operate day and night offering a diverse selection of activities: Glass Bottom boat tour, fishing, diving, snorkeling, kayaking, wave runners, daytime cruises out into the Gulf of Mexico, nighttime sunset cruises and probably as many different things as you would like to do on the water.

Key West sunset.

For our first evening-on-the-water, we took a sunset sail on the schooner  SEBAGO.  Immediately on leaving the dock, the sails were hoisted with the help of passengers and crew. The wind did the rest as we glided past the festivities on Malory Square heading out into the Gulf of Mexico for the nightly sunset extravaganza.

The crew served complimentary refreshments and laid out a spread of fresh fruit and cheeses while we savored a glorious Key West sunset. Passengers relaxed on deck or took turns at the ships wheel.  The only sounds were that of the boat cutting through the water and the quiet conversations of the passengers.

We arrived back at the dock in the dark of night well rested and ready to face the tomorrow’s activities. The next evening was a completely different experience on what is known as the “Commotion on the ocean” catamaran CARIBBEAN FURY.

Pre sunset activity at Mallory Square

When the dock lines were freed and the craft started moving, so did the trio playing almost non-stop for the next couple of hours.  Food appeared and the crew began dispensing a variety of liquid refreshments which like the band went on non-stop for the duration of the cruise.  Did anyone see the sunset?  No one seemed to care.

Sail raising on the SEBAGO.

It was to be our last day in Key West and the crowning touch was a full day’s outing on the Yankee Freedom. Our destination was historic Fort Jefferson in the Dry Tortugas.  At 70 miles west of Key West, it is America’s most remote National Monument.  After an extended tour of  the largest masonry fort in the US, it was back on the boat for the long ride to Key West.

The trip to the Dry Tortugas is highly recommended but book your tour in advance since this popular trip can fill up days in advance of your visit. For a quick, but much pricier round trip, sea plane tours are available.

That’s all folks.

Key West is always changing but always retains its unique character. Restaurants and shops come and go but the familiar highlights always stay the same. There is so much to see and do at this outpost of civilization that it can’t be covered in depth in one trip.  Every time we return we find something new to see and do but the old standbys give Key West  a sense of permanence, familiarity, and history.

The Florida Keys & Key West Tourism website will provide all the information you need to help plan your trip to the Florida Keys. Go to

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