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What to Do on A Day Trip to Key West

24 hours in paradise, exploring Key West, Florida
September 28, 2007 By Doug in  | 7 Comments


Roughly three hours south of its flashy sister, Miami, folksy Key West dances to a different beat.  The drive down along Highway 1 prepares you for this change in tempo, as you coast past mangrove swamps and miniature islands, kitschy souvenir stands and billowing coconut palms, traversing endless two-lane bridges, while the glowing sea beckons to you with a myriad of changing hues.  The mile marker numbers slowly descend as you go, in direct proportion to your stress level, and once you’ve hit 1, you know you’ve arrived.  Once there, the scenery morphs from Wal-Mart sprawl to woodframe cottages in no time, and soon you can feel creativity oozing out of the sidewalks, in a town where writers and artists thrive, and free-roaming chickens outnumber the pedestrians 10:1.  This is New Orleans with palm trees, Mayberry on acid, a setting where you can momentarily set your watch on island time and forget your big city cares.

For South Florida vacationers, Key West is often envisioned as a side-trip rather than a primary destination, and the time allotted for a visit there is frequently rather brief.  It is with these travelers in mind that we’ve crafted this handy guide to experiencing the cream of the conch chowder!  The information here should prove useful for visits of anywhere from a few hours to several days.



If you happen to have your own wheels, getting to Key West from Miami Beach is as simple as taking the Turnpike south to route 1 (here’s the map).  While the road is often just a two-lane highway and the going rather slow, at least you aren’t likely to get lost.  You’ll find plenty along the way to pique your senses, as you journey through fishing villages, awe-inspiring panoramas, and wildlife refuges.  Here, perhaps moreso than anywhere, the philosophical refrain holds true: the journey is the destination.

“Wait a minute!” you sigh, remembering that you left your car back home, thinking taxis and buses would satisfy your only need for transportation here.  Fret not, dear traveler! arranges reasonably-priced single and multi-day trips to the Keys that can be booked here on the website!


Spanish for Deep Bay, Bahia Honda might have more appropriately been named Shallow Cove.  Located near mile marker 37, approximately 45 minutes before Key West, this park features what might possibly be the most beautiful beach in Florida.  Enjoy it here, because while Key West offers many delights, a plethora of sandy beaches isn’t one of them.  You can camp, kayak, and snorkel the day away, or simply content yourself with a swim in its shallow, crystal clear waters, which maintain their minimal depth outward for several yards from the shoreline.  In addition to its pristine beaches, Bahia Honda also retains fragments of the old highway, which, years before it succombed to the ravages of hurricanes past, served as the main route of transportation to and from Key West.  (See additional pictures.)



Only have a few hours to spare in Key West, and want to get the most bang for your buck? Though it might sound a little hokey, hop aboard the Key West Conch Tour Train! Just so you’ll know—it’s not a real locomotive—think of it as a tram with an ego.  The 90 minute tours, first begun in 1958, depart from Mallory Square and the Welcome Center (3840 N. Roosevelt Blvd.) every day from 9:00 am until 4:30 pm, passing such famous landmarks as the Key West Aquarium, Mallory Square, the Hemingway House, Sloppy Joe’s Bar, and much more.  You’ll be regaled with local legends and stories about Hemingway, John James Audubon, and Harry S. Truman as you learn about the Key’s history from its ominous beginnings as a (literal) pile of bones to the times of the cigar barons and sponge magnates.  Tickets retail at $27 for adults and $13 for children, but you can save money by buying them online through their website or by calling them at 305-294-5161.


If your time in Key West includes an overnight stay, lodging will be among your primary considerations.  In this resort area, prices for a night’s stay can easily sway upwards of $150.  However, if you’re willing to sacrifice a few amenities, such as a swimming pool, sundeck, and spacious digs, the Caribbean House (226 Petronia St., Key West, FL,  305-296-0999) will save you a bundle.  Now run by a wonderfully outgoing French couple, rooms here average only $85 a night in this clean and colorful pet-friendly hotel.  Situated on the edge of the Bahama Village, this makes a convenient base for exploring nearby attractions, such as Duval Street (two blocks away) and the Hemingway House.




For a deliciously unpretentious seafood feast, you can do no better than Bo’s Fish Wagon (801 Caroline St, Key West, 305-294-9272)—Cats sprawl lazily across the bar of this dilapidated seafood shack, located just steps away from the William Street Seaport, where you can book sunset sails, snorkeling expeditions, and fishing excursions galore.  Here at Bo’s you order at the counter and take your seat at one of the surrounding wooden picnic tables, eagerly waiting for them to bring your food out.  The cash-only menu items range from fish sandwiches to conch fritters, and there is many a baby chick around to pick up the crumbs.  Despite its slightly rundown boathouse feel, the food is surprisingly delicious, and successfully relieves your noontime munchies.  You can always splurge later, after all, at Blue Heaven.


Tucked away at the end of a side alley off Simonton St., between Southard and Fleming (One Free School Lane, Key West, 305-294-0015) Nancy Forrester’s Secret Garden is the remedy for all your ills.  This mini-rainforest, though only an acre in size, feels much larger.  It offers meandering pathways amid dense, tropical vegetation, exotic birds, and meditative nooks, well-hidden from the world outside.  Nancy has tended this lush assortment of ferns, orchids, bromeliads, cycads, heliconias and bamboo for over 35 years now, surviving the fiercest onslaughts by hurricanes and developers alike, and her dedication shows.  You’ll feel like you’ve returned to a vision from your childhood, as you explore this peaceful world.  Admission is $10 per person.  (Additional pics here.)


Perched on the roof over the Bull & Whistle bar (224 Duval St., Key West, 305-296-4565), The Garden of Eden is the perfect place to go if you want to take your clothes off to have a good time.  Called “the best kept secret in Key West” by Rolling Stone magazine, this bar-in-the-buff opens daily at 10 am for those wanting to get that all-over tan, and keeps hopping till the wee small hours of the morning.  There are live bands, body painters, drink specials, and exquisite views, both human and non, in addition to the simple pleasure of gettin’ nekkid.  If you get there early enough, be sure to participate in their signature event, the Naked Sunset.  If you’re feeling shy, you won’t be out of place if you choose to remain clothed, but be sure to put your camera away, or else you may be expelled from paradise.


The great WC Fields once said, “Never work with children or animals.”  Thankfully, eccentric French comedian Dominique LeFort wasn’t paying attention! Every evening, around 5:30, he and his feline friends, Oscar, Cossette and pals make their way to the western end of Mallory Square, joining scores of other street performers entertaining the crowds who gather there to watch the dramatic sunsets.  While the other acts are often impressive, none are quite as spellbinding as Dominique’s.  He has a rapport with these former strays that has to be seen to be believed.  He’s got them soaring through flaming hoops, playing leapfrog, and performing acrobatic feats your own cat would probably never even contemplate.  Of all the things to do in Key West, this had to have been the most unforgettable.  And seeing as how the admission fee is only what you choose to contribute in the passing hat, this is too good a deal to pass up!
(See related article.)


Back in 1889, wealthy Cuban cigar maker Francisco Marrero built this picturesque home to lure his future wife, Enriquetta, from Europe to Florida.  His efforts proved successful, and they enjoyed a long and happy life there, with 8 children to show for it.  Unfortunately, (perhaps out of sheer exhaustion from fathering eight children) Francisco died, and Enriquetta and her spawn, cheated out of their inheritance, were soon evicted.  However, before she left, she stood before a gathering crowd, proclaiming that even if they kicked her out, she would always be there in spirit.  And, if the local ghost tour guides are to be trusted, her spirit is still wandering the hallways of Marrero’s Guest Mansion (410 Fleming St, Key West, 305-294-6977) to this very day, keeping a “benevolent eye” on the guests.  The rooms are exquisitely decorated, with private balconies off the back.  Rates range from $100 in the low season to $220 for the choicest offerings in the high; check with management to confirm rates.


Key lime pie, hell, they’ve got the best food….period! Located on the corner of Thomas and Petronia Streets, Blue Heaven (729 Thomas St, Key West, 305-296-8666) has an illustrious past: once a bordello, Ernest Hemingway later refereed boxing matches here.  Today, the place continues to make history with some of the tastiest dishes around.  Enjoy your dinner on their back porch or their outdoor seating as roosters, hens and chicks cavort beside you, while live music drifts upon the balmy breezes.  The service is excellent, the dishes superb.  Just be sure to save room for that award-winning key lime pie for dessert! If breakfast is more your thing, this establishment also happens to have some pleasing conch fritters and pancakes. 


If you’ve only got a few hours to spare and you want to get a feel for the locale, saunter on down to the Hemingway Home and Museum (907 Whitehead St, Key West, 305-294-1136), home of the famed author from 1931-39.  In addition to the picturesque house and tropical gardens, the descendants of the writer’s 6-toed cat Snowball preside over the household and grounds, welcoming visitors with a certain reserved affection.  Admission $11 adults, $6 for children.  The Hemingway Home is open 365 days a year, from 9 am - 5 pm.


If the idea of seeing thousands of drunk people clothed in next to nothing appeals to you and New Orleans’ Mardi Gras feels a little too tame, Key West offers you a better pay-off for your plastic beads.  Every October, locals and tourists alike cast their inhibitions to the wind and party like there’s no tomorrow.  Since its inception in 1979, the yearly attendance has surpassed 100,000 people, more than three times the population of Key West.  Festivities include parades, costume balls, drag queen contests, body painting competitions, and the crowning of the Conch King and Queen, chosen annually during the celebration.  To get the scoop on this year’s festivities, check out the official website.



These have been but a few suggestions of what to see and do in the Conch Kingdom.  However, the sights here are as varied as the people who see them, and finding what’s most enjoyable to you is a highly personal—yet enormously fun—undertaking.  Few places on the planet combine the carefree feel of a small town with the openness of a large city, and Key West excels at both.  It’s no wonder people come down here and decide never to leave.  For a few hours or several weeks, a little change in latitude can do you a world of good!

Related Categories: Tours & Day Trips

Douglas Eames is a freelance writer, homespun philosopher and budget bon vivant who divides his time between Southern California and South Beach.

See more articles by Doug.

See more articles by Doug

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7 Comments on

"What to Do on A Day Trip to Key West"

Jeff Kittay says:

Many thanks for the information.  We can stay only one night in KW and appreciate the recommendations.

Posted on 03/25/2008 at 8:33 PM

Cal says:

Thanks, Doug. This is a very interesting article. I just had KW recommended to me as a vacation destination and was researching it on the web. Your info. is very helpful.

Posted on 02/26/2010 at 2:20 PM

eric says:

already booked the carribean house. I cannot wai

Posted on 02/25/2011 at 1:08 PM

Judy says:

Thanks Doug…been to KW many times and now I have a couple of more things to do…other than relax..great suggestions and pics.  PS already booked Caribbean House and from there will camp for 2 add’l nts closeby…just didn’t want to have to set up camp at 9PM the night we arrive

Posted on 04/08/2011 at 1:35 PM

Doug says:

Hi Judy, I’m glad I could come up with a few new things for a Key West veteran! The Caribbean House is a great little spot, and so is yummy Blue Heaven across the street…

Posted on 04/08/2011 at 2:00 PM

V says:

It’s 2013 and am currently staying at the Caribbean house, perfect for what we need, the neighborhood has shops, restaurants etc right on the same block, parking, and is a short walk to duval n the beach! And the staff are super nice.

Posted on 04/22/2013 at 3:21 PM

Elaine says:

I was surprised to see my husband and I in the Hemingway house photo! We love Key West, and plan a trip every January.

Posted on 08/25/2016 at 11:14 PM

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