1. Adj.: Describing a person born between 1 Jan. 1946 and 31 Dec. 1964
2. Adj.: Description of a person, place or thing possessing Baby Boomer je ne sais quoi
3. See also, Boomer, Esq.: A Baby Boomer who is also a licensed attorney (See, e.g., About).

Key West, Florida – The Literal End of the Road (Or Maybe the Beginning)

by Suzanne Fluhr on January 11, 2013 · 33 comments

Key West, Florida Sunset from Mallory Square

Some years ago, on our first visit to Key West, Florida, the southernmost city in the United States, my husband, Steve, and I arrived by cruise ship. Unlike a good many of our fellow passengers (811,458 in 2011), we didn’t head for Duval Street to start drinking at 10:00 a.m. No Sir. Mister and Mrs. Excitement went on a wholesome bicycle tour.

On our most recent visit to Key West in early December, we drove down from Miami for a two night stay, enjoying the ride along the picturesque Overseas Highway. The Overseas Highway, a portion of U.S. Route 1, ends (or begins) at mile marker zero in Key West. Keep going and you’ll get wet.

Conch Republic flag key west, florida

Flag of the Conch Republic (Photo credit: Wikimedia by Jmckean)

Key West, like Austin, Texas,  has a reputation for keeping it “weird”; and, like Texas, Key West has shown its displeasure with policies of the United States government by threatening to secede from the Union as the Conch Republic, mostly recently in 1982 in response to a U.S. Border Patrol blockade of U.S. Route 1 that interfered with Key West’s vital tourism industry.

Key West reminded us of an admixture of:

  • the French Quarter and the Garden District in New Orleans;
  • the quaint Victorian seaside town of Cape May, New Jersey;
  • the gay friendly, Delaware River artist town of New Hope, Pennsylvania; and,
  • a sprinkling of aging hippies displaying varying degrees of attention to personal hygiene; with,
  • occasional flyovers by fighter jets from the Key West Naval Air Station.

Singer Jimmy Buffet’s association with Key West has also given it the appellation “Margaritaville”. Indeed, the opportunity to consume margaritas and probably every other alcoholic beverage is available pretty much 24/7, especially along bar heavy Duval Street, Key West’s version of New Orleans’ Bourbon Street. Personally, I enjoyed an outdoor mojito on Mallory Square where locals and tourists convene to enjoy Key West’s celebrated sunsets.

Chicken and cat at Mallory Square, Key West, Florida

A Feral Chicken and Cat Co-existing at Mallory Square, Key West, Florida

Key West’s “live and let live” vibe even extends to the feral cats and chickens wandering around who seem to  ignore each other benignly.

Using TripAdvisor, I picked a Bed and Breakfast some seven blocks off the main shopping/drinking area of Duval Street, in a mostly residential area. The Artist House on Fleming is a restored 1896 house. Our second floor room required us to use an outdoor staircase (slippery when wet) and opened onto a shared porch, overlooking the rear garden and a whirlpool. While the setting appeared charming and tranquil, some of our fellow guests — not so much. Their nocturnal comings and goings were readily audible. Breakfast was self-serve continental with tables on the outdoor back deck. With a rear-facing bedroom, breakfast chatter was not conducive to staying asleep. (OMG, I realize that this paragraph makes me sound like a curmudgeonly Baby Boomer traveler. Please don’t roll your eyes while I admit that we are addicted to our white noise smart phone app when we travel.)

Key West is a popular year round vacation destination. In order to have your choice of accommodation reserve something as far ahead as possible.

Restored Key West Home Surrounded by Lush Tropical and Subtropical Vegetation

Restored Key West Home Surrounded by Lush Tropical and Subtropical Vegetation

We used the afternoon of our arrival for a walk around town. Indeed, “walking around”, looking at the restored houses surrounded by lush tropical vegetation is a bona fide visitor activity. Fortunately, Steve convinced me that tired feet notwithstanding (lawyer word?), we needed to head to Mallory Square to check out the iconic Key West sunset.

Key West, Florida Sunset from Mallory Square

Key West, Florida Sunset from Mallory Square

Thanks to the Christmas lights, we also enjoyed walking around after dark. Key West Home with Christmas Lights

Home at Night Decorated for Christmas, Key West, Florida

On your first visit to Key West, I would recommend taking a bicycle tour or the popular 90 minute Conch Tour Train so you can learn some history and identify places to which you want to return for a more in depth visit.

I returned to TripAdvisor to find somewhere for dinner. We chose Zulma’s Colombian Grace restaurant. It was an excellent choice. We ate outside on the front patio where I very much enjoyed my coconut encrusted red snapper entree. The restaurant’s website has color photos of the food, so except for the specials, you can get a very helpful preview of the menu. I had a chat with Zulma’s sister from Bogotá who complimented me on my Spanish. I’m always more fluent after some sangria:) (Add a mojito and you could be “treated” to some impromptu flamenco.) Olé, Baby!

The restaurant is located in a somewhat transitional neighborhood that is not completely gentrified. While we were eating, an elderly gentleman rode up to the house next door on a bicycle completely decked out in illuminated Christmas decorations with a loud musical accompaniment. Our waiter pointed out a somewhat dilapidated house across the street and explained that the man had been born in that house and had turned down an offer of a million dollars to sell it because he wanted to keep the neighborhood affordable for his tenants.

Shut Gun Style House in Key West, Florida with December Bougainvillea

Typical Shot Gun Style House in Key West, Florida with December Bougainvillea

Ernest Hemingway's House - Key West, Florida

Ernest Hemingway’s House – Key West, Florida

The next day we devoted to museums. We tried to visit Harry Truman’s Little White House, but were thwarted by a power failure. Instead, we made our way to the home of raconteur author, Ernest Hemingway. There is an admission cost of $13 for adults which includes a half hour guided tour although you are also free to wander the house and grounds independently. The home was decorated by Hemingway’s second of four wives and the house retains much of the Hemingways’ furnishings. “Papa” lived there from 1931 until 1940 when he decamped to Cuba. The house and grounds are also controversially home to over 40 descendants of Hemingway’s six toed cat. Some feel the cats are exploited by being “on show”, but they wander at will and seemed well fed and very content to me — especially the three napping on Hemingway’s bed.

Victorian Home with Wrap-Around Porches on Two Stories, Key West Florida

Victorian Home with Wrap-Around Porches on Two Stories, Key West Florida

Our next stop in the Old Town section of Key West was the Mel Fisher Maritime Museum. Mel Fisher was the underwater salvager who after many expensive years of searching, discovered the 1622 wreck of the Spanish treasure galleon Atocha. (He prevailed in a protracted litigation with the State of Florida over to whom the treasure belonged). I feared that this museum had the potential to be cheesy, but we paid the $12.50 admission fee and an extra $2.00 for the audio-guide and were pleasantly surprised. If you are interested in underwater archaeology and colonial Spanish history, you will find this to be a well curated, interesting museum. In a disconcerting juxtaposition, the upstairs had a Harry Potter exhibit next to an exhibit explaining the horrific slave trade.

1891 U.S. Custom House Museum, Key West, Florida

1891 U.S. Custom House Museum, Key West, Florida

We were next drawn to a building just off Mallory Square that resembled the 1897 administration building at our New England college built in the style of architect H.H. Richardson. We were told that the building, unlike any other in Key West, was indeed designed by Mr. Richardson in 1891 as the United States Custom House and government office building. (I knew my Art History 101 course would come in handy some day!) Today, it houses a museum that showcases local artists downstairs and is dedicated to the history of Key West in artifacts upstairs, including a first rate video about the Overseas Railroad to Key West that was destroyed by a hurricane in 1935. Admission is a modest $7.00. Actually, we only paid $6.00 because we were “carded” —  that is, we were asked if we qualified for the AARP discount. We did. Ouch!

After home-made ice cream and a rest, it was time to head back to Mallory Square for another Key West sunset.

Key West Florida Sunset at Mallory Square

A Final Key West, Florida Sunset from Mallory Square

Our final night’s dinner was at Paseo Restaurant. This restaurant is rated #1 of 278 restaurants in Key West on TripAdvisor, so reservations are highly recommended. We had a stone crab special — an easier crab eating experience than the New Jersey shore blue crabs to which we are accustomed. We were a little disappointed with Key West’s signature key lime pie. We didn’t even finish the piece we ordered to share — trust me, a highly unusual occurrence.

Two nights and a full day are not enough time to do Key West justice. Other than doing a lot of walking, we did not even begin to explore the outdoor activity possibilities on both land and sea. I guess we’ll just have to go back some day. Yay!

(All photos by Suzanne Fluhr unless otherwise indicated).

This post is now part of a blog parade on the theme of “Travel in Winter” on Monika Fuchs’ bilingual (English/German) blog, Travel World Online and also part of Noel Morata’s beautiful photo essay on the southernmost tip (as opposed to city) of the United States at

Please comment below to share any Key West stories or recommendations? What’s your favorite beach town destination?

{ 32 comments… read them below or add one }

Debbie January 11, 2013 at 5:52 am

Really enjoyed this article; thanks. Key West is the only place in Florida that I’ve always wanted to visit. One of these days!


Just One Boomer January 11, 2013 at 10:28 am

It’s a dog friendly town too — dog parks and dog beaches. Unfortunately, our dog had to stay home.


Debbie January 11, 2013 at 7:27 pm

I love dog-friendly towns! 🙂 If your dog can’t go, that’s where people like me come in. I have a doggie hotel in my home. It’s just like a commune. Lots of fun! Thanks for stopping by my blog earlier.


Josie January 11, 2013 at 12:30 pm

Hi Suzanne,
Great pics!
Feral chicken? That’s too funny. And that you caught the cat together with the bird in one photo is precious. That in itself makes me want to go there. Key West has been on our wish list for a long time.
Since we’re house sitting in Baltimore, Ocean City has been our beach destination here. A bit kitschy but fun. Has the boardwalk with lots of restaurants and good people-watching. One of my faves has to be Provincetown on Cape Cod.


Just One Boomer January 11, 2013 at 5:38 pm

Thanks for the comment. We were in Provincetown over the summer. P-town is a little like Key West, but in a New Englandy kind of way.


santafetraveler January 11, 2013 at 4:54 pm

Love Key West. There used to be a bar (and may still- haven’t been there in years) named Billie’s right next to Mallory Square and we used to adjourn there after the sunset show. I LOVED their strawberry daqueries back then. The post brings back memories.


Just One Boomer January 11, 2013 at 5:41 pm

Well, there are still plenty of places around Mallory Square to have a post sunset strawberry daqueri. I’m afraid I didn’t notice if Billies is still there —— but, I bet Mr. Google knows.


Leigh January 11, 2013 at 8:01 pm

I’ve yet to visit Key West. The furthest south I’ve made it is Everglades NP but one winter in the next few years when I can’t take the snow a minute longer I’d love to go down and explore/relax for a week. It looks like there is plenty to do.


Just One Boomer January 11, 2013 at 8:15 pm

I don’t think you’ll find any challenging hiking opportunities on the Florida Keys although there are some State parks on the Overseas Highway with nice places to walk (Bahia Honda State Park). However, Key West is very bike friendly and if you like to ride on water ;-), there are sections of the old Overseas Railway that have bike-able portions out over the water.

Here in Philadelphia we have had a quite mild winter so far with no accumulating snow actually in the city. However, around February, winter gets to me and I need to walk outside without a coat and to see turquoise water (the mid-Atlantic is never that color). Next month I get to be a trailing spouse to Hawaii, so that should take care of it.


Roz Warren January 12, 2013 at 12:06 am

I’m right with you when it comes to noise and chatter when I’m trying to snooze and I hope for the sake of the travelers who come after you that you mentioned the lack of quiet in your Trip Advisor review of that B&B. Don’t think there’s anything wrong with wanting peace and quiet when I’m trying to relax, and if that makes me a grouse then so be it. Loved the photos, particularly the rooster & the cat.


Just One Boomer (Suzanne) January 12, 2013 at 4:02 am

Roz, does this make us curmudgeons of a feather?


Lissie January 13, 2013 at 9:03 am

Wow – it looks far more old-worlde than I associate with Fl – my brother has just moved to Pennsylvania – so I may add this to my rather long list of road-trip ideas!


Just One Boomer (Suzanne) January 13, 2013 at 10:31 pm

Thanks for checking out Boomeresque — all the way from NZ. Key West is actually quite Victorian looking – in a Southern U.S. and Caribbean sort of way.


Madaline Fluhr January 13, 2013 at 9:09 pm

Great pics – looks like a wonderful, quirky place! I’m reminded of the locale because at some point I read a biography of Tennessee Williams, famous American playwright, (The Glass Menagerie, Streetcar Named Desire, Cat on a Hot Tin Roof, etc.) who spent quite a bit of time in Key West. Your text is always entertaining and informative and the photos take it one step further to bring it all to life for us armchair travelers! Keep it up!!


Just One Boomer (Suzanne) January 13, 2013 at 10:32 pm

Hey, Mads. It is “wonderful and quirky” — two adjectives I might actually use to describe you!


David January 16, 2013 at 9:41 pm

Hi there,

So glad you enjoyed yourself and really threw yourself into the Conch life. Its interesting that you feel that the place reminds you of the French Quarter in New Orleans. Having spent much time in both places, I hadn’t really linked the similarities.but I suppose Bourbon Street does have that Key Westy, out for a good time vibe.

Lovely photos and a nice bit of writing too.

Thanks for spreading the Key West appeal



Just One Boomer January 25, 2013 at 2:51 am

Thanks, David. Your Florida Keys website looks useful. If anyone wants to check it out, just click on David’s name.


Pamela | Something Wagging This Way Comes January 17, 2013 at 8:33 pm

I loved your description of all the cultural/place mishmashes of Key West. Except for the fighter jets, it sounds like a blend of some of my favorite places.

I’ve been looking for dog friendly sailing charters in the area so we can check it out for ourselves.


Just One Boomer January 17, 2013 at 10:15 pm

I hope you find something. I think it would be a nice place to visit with a dog, especially if the dog likes to swim.


Franca January 18, 2013 at 2:48 am

I have never been to Florida, in fact never been to America, not yet!
I’d go to Key West for the sunsets alone, they have got something magic! 🙂


Just One Boomer January 18, 2013 at 3:00 am

Grazie, Franca. I know that you and Dale have been to some amazing places in your travels, but North America (comprised of Canada, the U.S. and Mexico) really is worth a trip also. I know you enjoyed the deer in Nara, Japan. The lower Keys in Florida also have an endangered species of deer call Key Deer. There is a refuge for them about 30 miles north of Key West. So, when you come, Dale can get his deer fix while you enjoy the sunset.


The Vegan Gypsies January 21, 2013 at 10:28 pm

Beautiful pictures. Key West has been a place I have wanted to go for a while now. My sister used to live there and enjoyed her time there very much. Thanks for sharing.


Just One Boomer January 22, 2013 at 12:02 am

It’s certainly an interesting place. I hope you have the chance to visit there one day.


Debbie Beardsley @ European Travelista January 23, 2013 at 6:15 pm

I have wanted to visit Key West since I was a child and had a mad crush on Sandy Ricks of Flipper fame! I could see myself enjoying the bike ride and train. Plus I wouldn’t miss those sunsets. . . they are beautiful!


Just One Boomer January 25, 2013 at 3:07 am

Thanks for your comment.

I don’t remember any of the people who were on the TV show Flipper. I just remember Flipper him or herself. There are lots of biking opportunities around Key West and along the Overseas Highway on the way to Key West, but there is no more train. That was wiped out in a Hurricane in 1935. Some of the interesting biking is along the old abandoned railroad right-of-way.


Sam @ My Carolina Kitchen May 10, 2013 at 6:27 pm

I believe we did get a photo of the same chicken! How cool. Love your tour of Key West and a fabulous shot of the sunset. We drove down from Fort Myers, but next time will take the boat from Fort Myers Beach. so much easier to party on a boat than drive.

Thanks for stopping by my blog.


Marcia July 25, 2013 at 12:07 pm

Love this post, Suzanne. I can feel Key West from your descriptions.
Any place that’s a cross between Cape May and New Hope (I’ve not been to New Orleans) sounds like someplace I’d love. Come to think of it, a fortune teller told me once that if I go to Key West, I’d stay there. I’d have a problem with the flyovers and personal hygiene though.


Suzanne Fluhr August 6, 2013 at 2:48 pm

Marcia, there are actually quite a few people from the Islands who have settled in Key West. It’s a pretty diverse, live and let live place. Hence, the flyovers and personal hygiene issues 😉 Given your interest in food, I think you’d fine plenty to like there — starting with some good key lime pie.


Cathy Sweeney July 28, 2013 at 4:32 pm

Eating coconut encrusted red snapper outside on a patio in Key West sounds awesome to me. I’ve never quite made it to the Keys, but have always wanted to visit. Too bad about the key lime pie — that would be a huge disappointment.


Suzanne Fluhr August 6, 2013 at 2:49 pm

Cathy, as a world traveler, I think you would enjoy Key West (not to mention the red snapper and key lime pie). It feels like you’re someplace “else” when there.


David Ralph September 18, 2018 at 3:44 pm

This is a great site for sure. I love Key West and being down on Mallory Square watching the sunset with the crowds. I havent seen the green flash yet…heres hoping….


Suzanne Fluhr September 19, 2018 at 1:46 pm

I actually once saw the green flash. I was pretty sure it was apocryphal until then. However, I saw it from Magic Island in Honoulu, Hawaii, not in Key West.


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