David Kelly Consulting

There is no place on earth like Key West.

What was once Florida’s biggest and wealthiest city has transformed itself into a quirky paradise, replete with funky open-air bars, wild roosters roaming the streets, cool shopping and architectural districts, amazing history and upscale resorts, all of it under a radiant blue sky and warm tropical sunshine.

Some 5 million people will visit Key West this year, where live music drifts from the open windows on Duval Street and sleek catamarans traverse the local waters, delivering snorkelers to pristine coral reefs for colorful underwater adventures.

But many of the folks that have visited Key West for decades speak of changes to what they often refer to as the Conch Republic – the title given to the city in 1982 when then-mayor Dennis Wardlow led a tongue-in-cheek protest of the roadblocks and inspections points set up by the United States Border Patrol on the only road into the islands.

Colorful and historic Key West cottages now share their shade-covered streets with glitzy storefronts. Cruise ships dock for the day at Mallory Square. Souvenir shops abound on Duval Street, the city’s busy main drag.

So we asked ourselves: Does the classic Key West that we had loved for so many years still exist?

With that question in mind, we headed south on U.S. Route 1, the picturesque Overseas Highway that traverses 42 scenic bridges in the Florida Keys before dropping you at Mile Marker 0 — the country’s southernmost point — in the heart of Old Town Key West.

AUTHENTIC VIBE

The Key West Historic District that runs from White Street to the Atlantic Ocean, known as Old Town, has been the island’s epicenter of business, living and visitor activity for almost 200 years. There is a romantic and quirky ambiance here of conch-style, pastel homes, fun shops and watering holes that attract people of every kind. It has survived Caribbean pirates, the Civil War, and countless hurricanes and makeovers. It is the centerpiece of Key West, a city that is by itself about 4 miles long by a mile wide.

Arriving in town we are thrilled to discover that many of the old haunts we love in Old Town still hop, looking and feeling the same - welcoming and exciting.

We visit such iconic bars as Sloppy Joe’s, Capt. Tony’s, Rick’s and Irish Kevin’s, all with live music playing to enthusiastic guests.

Up one side and down the other on Duval and Front streets, smiling people wander in and out of these classic bars and shops, finding that authentic Key West vibe they were longing for. (Continue reading below photos).

We knew that we wanted to base our visit in the center of this activity, so we booked our accommodations at the Pier House Resort & Spa, a deluxe destination tucked into a magnificent space between the Gulf of Mexico and Front Street. The Pier House is the doorway to Old Town’s action, merely steps from all our week’s planned activities.

And because we were in such a central location, we parked our car at the resort … and never needed it again.

The Pier House Resort & Spa embodies authentic Key West, opening in 1967 as a 50-room motel. And while it has increased in size to over 140 rooms and suites, its verdant grounds are still overgrown and lush. The resort even contains an exclusive private sandy beach – almost unheard of due to Key West’s often rocky shoreline. It also houses two restaurants, a world-class spa, and the cozy Chart Room bar.

For our accommodations, we chose the Spa Junior Suite – one of a dozen or so spacious rooms located in a quiet building that houses The Spa. The room itself was huge and included a luxury bathroom, fridge, and large seating area.

But the best feature of all was its full-length balcony that directly overlooked Old Town. We relaxed there every evening and watched the magic below us unfold.

Although the Pier House is truly in the middle of it all, its vibe is laid back and chill, and we found that there was no better place to appreciate this atmosphere than The Spa, which offers a full array of services designed to rejuvenate guests after their various Key West adventures. We chose a couples’ massage and enjoyed an hour of stress relief and relaxation. The site also includes a fitness gym, whirlpool, and an outdoor hot tub, perfect for unwinding after exploring.

The Pier House’s premiere restaurant, One Duval, fit our needs perfectly. You can choose from indoor or outdoor meals in a fine dining or casual atmosphere. These options let us customize our dining experience each day.

One morning, we had a delicious homemade-style breakfast outside on the water. On another occasion, we took advantage of the high-end dining room and opted for Chef Maria’s filet mignon, served that evening with crispy onions, fresh asparagus, and a wild mushroom burgundy sauce. It was simply amazing.

The resort’s other dining option, Beach Bar, plays to that old Florida feel. Bar or tableside, this open-air, swimsuit-friendly location is quintessential Key West and features tropical cocktails, fresh seafood, and street tacos to enjoy while the waves crash on the beach beside you.

The Pier House’s historic bar, Chart Room, embodies everything Key West. Over the years, such local luminaries as the musician and business titan Jimmy Buffet and the treasure hunter Mel Fisher have spent time in this bar, sharing countless colorful stories. Entering, we noticed dozens of neckties on the ceiling – collected over the years from guests who unknowingly entered this true dive bar overdressed.

We kicked back and absorbed the casual atmosphere, taking in the true Key West feel.

We wandered off Duval Street and were called to a true Key West treasure – the Half Shell Raw Bar. Located on Key West Bight just a short stroll from our resort, the Half Shell opened in 1972 and for over 50 years has featured the freshest seafood on the island. Local shrimp boats supply the best product around, and if you order fresh oysters, you may just see Half Shell staff shuck them while you wait.

Options on the menu were plentiful, so we ordered the Raw Bar Sampler, giving us a variety of oysters on the half shell. They also feature seafood towers and baskets, with a table full of Florida goodness served up hot and fresh. We topped that off with a mile-high Key Lime Pie.

And what is Key West without adventure?

We were excited to discover Sebago Watersports, a local company that features parasailing, snorkeling trips, sunset cruises, and more. We chose options that allowed us to see Key West from two new perspectives –air and water.

First up was parasailing, so we met a captain and crew at the marina off Elizabeth Street and headed out onto the water … and were ready to begin within minutes. The crew explained that our takeoff and landing from the boat would be dry, but we could opt to be dipped in the water on the way back in, so why not? We eased off the boat platform in tandem as the cable unspooled, and in no time we were 300 feet in the air.

The sky was bright blue, the wispy clouds scuttled by, and the views were breathtaking. We could see much of the island and its surrounding waters, pointing out places that we had visited and recounting stories from the week. Finally, as we were reeled back in, the captain took the opportunity to dip us in the crystal clear waters as we had requested. We arrived back on the boat platform safe and sound, thrilled to have taken part in such an invigorating adventure.

On our final night, we set out for our Schooner Champagne Sunset Sail on the Appledore Star, Sebago Watersports’ 65-foot wooden two-masted schooner. We launched 30 minutes before sunset, which gave us time to learn about the ship’s history, to view many of Key West’s landmarks from the sea …and even to sip a tropical cocktail or two from the onboard bar.

The ship carries a maximum of 22 guests, allowing for an intimate experience. Hors d’oeuvres and cocktail shrimp were served as we headed out, and we were even encouraged to help the crew raise the sails.

As the captain maneuvered to get us the optimum view when the sun went down, we all shared a toast – yes, classic Key West still does exist, and we will be back soon.

ROUND UP

Pier House Resort and Spa

One Duval Street Key West Florida

www.PierHouse.com

Half Shell Raw Bar

www.HalfShellRawBar.com

Sebago Watersports

KEY WEST FLORIDA

QUIRKY AND AUTHENTIC, IT'S STILL PARADISE

WATCHING THE MAGIC UNFOLD

SUBSCRIBE TO FLORIDA COUNTRY MAGAZINE!

SIP A TROPICAL COCKTAIL AND MORE AT THE PIER HOUSE