Discovering Key West


One of my funnier friends up north likes to joke about our various trips around Florida.  He says, “So glad you were able to get out of sunny Sarasota for a few days.” 

True, we live in paradise—but it is still fun to get out of Dodge and knock the cobwebs off…and where better than Key West?

Discovering Key West

Going to the Keys from Sarasota is tricky, because even though it is due south of us you drive across the state to Miami and then circle back west again.  That’s about 375 miles or six hours in the car.

The other option is to drive an hour-and-45 minutes to Ft. Myers Beach and board the Key West Express for the 4-hour trip. That’s exactly what we did.  

Tickets prices have a wide range pending time of week, time of year, age (discounts for seniors/juniors), but most of us would pay about $300 for a round-trip ticket.

The staff made sure passengers wore masks when they walked around the ship.  There’s a concession stand, a bar and plenty of places to ‘drop anchor’ and enjoy the cruise—both inside and outside the main cabin area  

Once you arrive in Key West, the ferry docks in a convenient spot.  You walk off the ship and you’re immediately in the middle of fun.  (

We made arrangements to be picked up and brought to our hotel across from Smathers Beach.  The Barbary Beach House Key West is in a perfect location across from the Atlantic Ocean and still a short bike-ride into town.

We knew we were checking in to the right place when the front desk clerk offered us a choice of tropical drinks, poured right there at the counter.  She also gave us stylish wrist bands that takes the place of room keys–and helps open a secure cabinet for pool-side towels.

The hotel was lush, full of beautiful palm trees with an outdoor restaurant and pool as the centerpiece.  Our room was ideal—high-top table, living room, large bedroom and bathroom, balcony with chairs — all overlooking the beach! 

We’ve stayed at many hotels in Key West, but this was the best.  It was classy and elegant but not stuffy.  The location is just off the beaten path, away from the touristy areas. (

We walked across the street to feel the sand on our feet and stroll the beach.  We stumbled upon Barefoot Billy’s Watersports and wound up renting a couple bikes for the next three days.  They also rent boats, kayaks, jet skis, scooters and sunset cruises.  They’re all over the island–and their upbeat customer service is a nice perk.  (

After riding our bikes in and out of all the interesting side streets with the eclectic homes we came back to the hotel and got ready for dinner. 

It was a short commute down to the pool area for a great meal at “Drifter’s Cove.”

We started with the Ahi Tuna Poke from the raw bar, and for dinner Erin had “The Duval Cure,” which was a hamburger with bacon, lettuce, tomato and a special sauce.  She loved it.  I had the Caesar Salad with New York Strip Steak.  Perfect.  We really felt like we were on vacation—winding down our first day with dinner by the pool of our hotel…across from the beach. 

We awakened to a view of the ocean with walkers and joggers already up going back and forth on the beach. We went back downstairs for breakfast by the pool.  Tasty omelet with potatoes, fruit and coffee.  The Food & Beverage Manager, Batu, made us feel special.  He’s a high-end hospitality expert who was recruited out of Chicago.

We rode our bikes down the famous Duval Street and enjoyed the people-watching. Key West is such an interesting place. To get a little extra inside knowledge we joined a bike tour that went beyond the usual spots.

Lloyd’s Tropical Bike Tour is an interactive experience led by a fun guy who moved down to Key West in the early 1970s from the northeast and never looked back.  He knows the key, and the key knows him.  We felt like celebrities as everyone knew Lloyd as we peddled through the nooks and crannies of the various neighborhoods.

We even stopped several places where Lloyd pointed out oddities that you will see when you take the tour! 

We stopped regularly, sampled local fruit off the vine and heard great trivia. I learned about this tour before the trip when Google sent me an article about Top Ten Things to Do in Key West. Lloyd’s tour was on there—and rightfully so. (

We ate dinner on Duval Street during our final night in Key West, and I re-affirmed why I think Irish Kevin’s is the most fun bar for a nightcap:

The singer, who was actually “Irish Kevin,” cast aside political correctness and had a field day—focusing much attention on a bridal party from Cincinnati.  They took it well, and the rest of us laughed non-stop.  (Though it was crowded, all patrons had to wear masks when walking around—and the singer also performed behind a plastic shield.)  Sloppy Joe’s seems to get more attention, but I much prefer Irish Kevin’s.  (

By the third day we were ready to catch up on our sleep and get back to sunny Sarasota.  I always say the second-best part about going away…is coming home.

It was nice to drop off our rental bikes and walk onto the waiting Key West Express shuttle boat and sleep our way back to Ft. Myers Beach.  A wonderful trip. Now I can’t wait to relax from that vacation!

(Since 2011, Ray Collins has written over a hundred articles for Family Beautiful and has reviewed dozens of destinations from Hawaii to Cape Cod.  He’s a former TV newscaster who now sells real estate.)