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Capturing the Caribbean in Key West

 By Jeff and Stephanie Sylva

You begin to feel it as soon as you drive the long causeway south of Miami and onto the Florida Keys. It’s that laid-back, care-free attitude inherent of the Keys.  This relaxed change of attitude, which seems to increase with each mile on the Overseas Highway, culminates in the southernmost city on the continental U.S. and is no more evident than in the adopted Key West tradition of liming – the art of doing nothing.

It is the unique blend of Key West’s history, vibrant arts and culture scene, lush tropical scenery, classic island architecture, and numerous watersports, together with the laid-back feel of the Keys and a whole lot of funkiness, that makes Key West feel more like a Caribbean island than a city in the Sunshine State. (Actually the residents of Key West proudly celebrate April 23 as Independence Day, when the city declared itself the Conch Republic in a tongue-in-cheek secession from the United States spurred by serious concerns with some federal policies.)

“Arrive – Relax – Be Local” 

These words are the motto of the Historic Key West Inns, and

Cypress House pool
The Cypress House pool provides the perfect spot for some “liming.”

they proved to be right on target for us. We stayed at the Cypress House, one of the six Historic Key West Inns, all of which are located in the historic district, close to all the best that Key West has to offer.

Like each of its sister properties, the Cypress House is quintessentially Key West. The inn is a charming tropical retreat within easy walking distance of Duval St. and Key West’s waterfront – a perfect way to be “local.” And the secluded pool was a perfect place to “relax” and cool off after a day of experiencing Key West. The inn offers a daily “liming hour” where a selected cocktail and appetizer are offered complimentary to guests, providing a perfect opportunity to engage in a “local” custom. 


The Cypress House front porch

Each of the Historic Key West Inns provides a complimentary continental breakfast, and the Cypress House also includes one hot item such as a breakfast burrito or egg and sausage scramble. All of the inns have a variety of rooms, all of which exhibit the lovely charm that is a trademark of the inns.

Get some bikes!

The first thing you need to know about Key West is that it’s easy to get around – just not with a car. Street parking in the historic district (referred to as Old Town) is nearly impossible. (Public parking lots charge $13 a day and allow overnight parking.) We were lucky enough to find a parking spot on the street just a few blocks from our inn but didn’t touch our car for five days.

A great way to get to know Key West, its history, architecture, and its hot

Photo by Bob Krist/Florida Keys News Bureau
Photo by Bob Krist/Florida Keys News Bureau

spots is to take a tour such as the Conch Tour Train. Our guide, Kenny, was a retired chef who has lived and worked in Key West for decades. His presentation was as much fun as it was informative. The 90-minute tour has three stops at special points of interest and allows passengers to disembark and then board another train.

The best way to get around Key West is just like the locals do – on a bike. We had arranged to have bikes delivered to the Cypress House by We Cycle of Key West. Offering great bikes (we rode Fuji cruisers), free delivery and pick-up, roadside assistance, and a full satisfaction guarantee, We Cycle is a great choice for bike rentals.

Even though the Cypress House was within easy walking distance of Duval St. and the waterfront, we wanted to get away from the crowds and experience more of Key West. One afternoon we booked a jet ski tour Southernmost Point in Continental USAwith Barefoot Billy’s which has a location on the beach at the Casa Marina, a Waldorf-Astoria Resort. We biked over to the Casa Marina, stopping at the famous Southernmost Point in the Continental U.S. marker for a picture, and then over to the beachside café, Sun Sun, at the Casa Marina for a delicious lunch with a great view of the beach.

After lunch we experienced Key West from another perspective – an adrenaline-pumping two-hour jet ski tour around the island. Our guide stopped at various places to point out interesting tidbits about Key West, like the location of Oprah Winfrey’s home.  Barefoot Billy’s also has tours and rentals for snorkeling, glass-bottom kayaks, stand up paddle boards, 11-foot zodiacs, as well as parasailing, schooner sunset sails, bike and scooter rentals, Hobie Cat sailboats, and free shuttle service to and from your hotel.  

Another day we experienced a great bike ride on the wide bike path offering great views of the ocean surf, safe from traffic, along Key West’s southern beaches including Higgs Beach, Rest Beach and Smathers Beach. We then enjoyed a delicious lunch at the Doubletree Hilton’s Grand Key Resort’s Tiki Bar and verandah restaurant, a perfect half-way spot to regenerate for the trip back to the Cypress House.

Crawling Duval Street

A very popular attraction in Key West is the scene on Duval St. This one and a half mile street has something for just about everyone. The street has a wide selection of places for shopping, dining, people-watching, and crawling – as in pub crawls. World renowned saloons such as Sloppy Joe’s, a favorite watering hole for Ernest Hemingway; the original Jimmy Buffet’s Margaritaville; Captain Tony’s Saloon, the oldest bar in Florida; and the Hog’s Breath Inn are very popular with the party crowd and the hordes of visitors from the cruise ships. Commercial tour companies even conduct organized pub crawls.  

Numerous cafes with outdoor seating offer great spots for people-watching, while a selection of restaurants offer some very good dining, and some upscale shops and galleries offer great shopping opportunities beyond the ubiquitous T-shirt and tchotchke shops.

Sensational Sunsets

A favorite activity in Key West is watching the sunset. Key West has glorious ones, and we experienced a couple of the many places to view them. One that we particularly enjoyed was aboard Danger Charter’s “Wind & Wine Tour.” Featuring an array of fine wines and upscale beers and a full complement of hors d’oeuvres, the sail 2 hour tour aboard the schooner Danger provided a magnificent setting for a stunning sunset.

Mallory Square at sunset
Mallory Square at sunset
Photo by Bob Krist/Florida Keys News Bureau


Another popular sunset spot is Mallory Square, where crowds gather an hour or so before sunset to enjoy the menagerie of street entertainers and food vendors and then view the sunset along the waterfront. We spent an hour or so here enjoying some of the street performers and the beautiful sunset, before walking to what proved to be our favorite dinner spot, Santiago’s Bodega – Tapas Restaurant on Petronia St.

The selection of small plates (tapas) is wide and intriguing, with such choices as yellowfin tuna ceviche, beef carpaccio, cherry-hoisin glazed beef short ribs, and dijon mustard, pecan and thyme encrusted half-rack lamb. Although the suggested order is 2-3 plates per person, we were more than satisfied with five plates and the avocado and pear salad for four of us. All of our choices at Santiago’s were extremely fresh and delicious.

Quiet and Funky

Kermit's Key Lime
Kermit displays his famous Key Lime pie.

While in the neighborhood, be sure to try a chocolate-dipped key lime pie bar on a stick from Kermit’s Key Lime Shoppe, located at the corner of Elizabeth and Greene Streets. A couple of other funky choices found in this area include some incredible fish tacos from Garbo’s Grill, a food cart on Greene St. across from Kermit’s; Key West Pretzels and their wide assortment of

BO's Fish Wagon
BO’s Fish Wagon

homemade mustards located in a small shop on Lazy Way; BO’s Fish Wagon, an open-air shack on Caroline St. that turns out some great seafood; and, finally, try some great café con leche at the Cuban Coffee Queen, a small (in size only) coffee stand on Margaret St.

History and Theater

One of the most well-known and oft-visited sites in Key West is the Hemingway Home and Museum, the 19th-century house where famed writer Ernest Hemingway lived with his wife Pauline and their two sons from 1931 to 1940.

Ernest Hemingway's writing studio
Ernest Hemingway’s writing studio


Thirty-minute guided tours of the gardens and house, where a number of photos of Papa are on display, are conducted daily. Dozens of six-toed cats lounge about the grounds. Hemingway purportedly loved having cats at the home, and it is believed that some of the current cats could be descendents of Hemingway’s pets. This was our favorite house/museum tour because visitors are able to spend time re-visiting the house and enjoying the grounds after the tour.

Just across Whitehead St. from the Hemingway Home is the Key West Lighthouse and Museum, where we climbed the 88 steps to the balcony for some great views of the island and surrounding waters.

Another cultural attraction of Key West that we enjoyed was the local theater. The Red Barn Theatre’s production of Time Stands Still was Broadway-worthy. The venue, located in a quiet backyard oasis on Duval St., is a wonderfully intimate theater, and the company has established itself as a cultural cornerstone for the Key West community. Arrive early and enjoy a glass of wine in the garden-like waiting area.

The Waterfront Playhouse, located on Wall St. in Mallory Square, is another cultural jewel that has been presenting outstanding theater for over 70 years.

The Key’s Disease 

Our visit to Key West was great, but we did begin to feel the disease during our visit. Actually we met a number of locals who had succumbed to the malaise of the Key’s Disease. It’s the irresistible desire to give up one’s life “up North,” move to Key West, and just… Relax and Be Local.




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