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Our January Armchair Trip: Miami South Beach & Down the Keys to Key West

By Carolee Duckworth, NABBW’s Independent Travel Associate

Oh baby, it’s cold outside! Clearly winter is upon us. The world has turned drab and neutral, a dull pallet of brown and gray. Not a dot of color in sight looking out our windows. Oh, how we miss fuchsia and yellow and purple. And how can we possibly live for the next few months without green!?

And another thing… We’ve been cut off from travel for two years now by this pandemic. That’s long enough! We come up with trip ideas, and even make reservations. Then we hear the latest bad news and cancel everything yet again. The cruise to the Caribbean. No, maybe not. The trip to New Orleans? Well, maybe not that either since we would want to be able to go inside to listen to the music. New York City? No, not a good idea—yet. And we had been hoping that this year we might finally get to take that bucket list trip to Florence and Cinque Terre. Well, maybe next year.

Some of us have waited our entire working lives to reach the “someday” when we would have the latitude (and the money) to travel. And we thought that “someday” would have come by now.

Maybe we have someone we would greatly enjoy traveling with… a friend, a partner, a spouse. Or perhaps our book club has been talking about making a “women’s only” trip someplace interesting. We may want to arrange a trip with our grown children, one or two at time, or possibly with our grandchildren, to create shared memories of experiences and discoveries, camaraderie, and laughter.

One way or another, we are beyond ready to GET GOING. But where, if anywhere, can we go?

Plan B: The Virtual Alternative

Well, I have “a propose,” to quote the Murano glass salesman who sold us our unbelievable glass sculpture some years ago during our trip to Venice and the Greek isles. My “propose” is that we shift to “Plan B”— Armchair Travel.

Even if we still need to wait a while before we make our bucket list trips to France or Italy… And even if traveling in the US still makes us hesitate when we think about hopping aboard a jam-packed plane… The USA, and even the world, can be completely open and available to us even now if we just find a comfy chair and take our trip in our minds!

Traveling virtually means we can go wherever and whenever we’d like. It means that cost is no longer an object. And we can invite as many people as we want to come along!

Where Shall We Head First?

Well, that’s an easy one. Since this is the dead of Winter, let’s choose somewhere warm and wonderful! And PLEASE, let’s go someplace that’s colorful! So, where better than the Florida Coast and Keys? Close your eyes, open your “imaginings” and join me on our January trip to Miami South Beach and down the Keys to Key West.

We’ll begin our journey in the eclectic art deco mecca of Miami South Beach, where we’ll head from the airport straight towards the ocean, then turn right just before we hit the sand. No shortage of “colorful” here!

After three days immersed in the energy and creative variety of South Beach, we’ll take a leisurely drive down the Florida Keys towards Key West, stopping for two nights in Marathon. In Marathon we’ll visit exuberant dolphins and shift our internal clocks and personal attitudes to island time. Then we’ll continue on to Key West, where the road heading south runs out.

So, here goes. Let’s leave all this gray and brown behind us and venture into the land of vivid colors and sunshine as we take our imaginary trip to the paradise of the Florida coast and Keys.

So, Starting in Miami South Beach

Art Deco Hotel

We will board a plane to Miami on a Tuesday, in the dead of winter. When we land, we’ll step out into blazing sunshine. Don’t wear wool or fur-lined boots today, or you’ll soon be sorry!!

Here we’ll Uber out to South Beach, where we will be staying for the next three nights. We already will have booked a room at one of the creamsicle-colored art deco hotels on Ocean Drive, selecting one that’s between 5th and 14th streets so we’ll be across the street from the park and the ocean. The Beacon. The Majestic. The Bentley. The Cavalier. The Penguin. Even the names conjure up images of the “out there” ‘20s and ‘30s, and the wild days (and nights) during prohibition. Not to mention all that eye-popping color and style, ornamentation and neon.

Since this is a virtual trip, cost is no object. So, we may even stretch our imaginations and book a suite at Versace’s former mansion, the Villa Casa Casuarina. You remember Versace. He was the one who was murdered on his own front steps after coming from breakfast at the News Café where we will be lunching tomorrow.

Villa Casa Suite

Staying at Villa Casa would probably never happen in “real” life, since rooms in the winter season start at $1000 a night and quickly climb upwards. But since we’re not constrained by reality now, we can afford to take this as our opportunity to imagine ourselves in one of the over-the-top Master Suites, with access to a pool beyond our wildest dreams. From this bed we will feel like we easily could rule a small country.

Turning right on Ocean Drive will take us into the thick of the craziness. Progress will be slow, a feature of the lifestyle of locals and visitors alike. A vast diversity of humanity flocks here to see and be seen, cruising the boulevard in statement cars, rollerblading in bikinis, strolling along on the ocean side, dining at the hundreds of sidewalk tables, while sipping oversized drinks and ogling the perpetual parade.

Villa Casa Pool

During our days in South Beach, we will lunch at News Café, then follow Versace’s fateful path walking home from the Café on the day he was murdered on his front steps. Our second day in South Beach will be Art Deco Day, beginning with a visit to the Art Deco Museum and its treasure trove of a museum shop.

We will have set up a guided Art Deco Walking Tour, with an engaging guide who knows all the stories, lurid and otherwise, and who can teach us to spot the secret entrances to the prohibition-era speakeasies. Of course, we’ll want to spend some time on the beach and in the park. And there will be an afternoon visit to the Wolfsonian Museum, with all its fascinating displays and memorabilia.

To Marathon, Midway Down the Keys

On Friday, we will pick up our rental car, preferably a convertible in keeping with our now exuberant spirits, to escape the Miami bustle into the relative peacefulness of the necklace of islands that make up the Florida Keys. Our destination for the next two nights will be Marathon (Mile Marker 59), at the midpoint between Key Largo (Mile Marker 100) and Key West (Mile Marker 0). Since our whole drive today will be only about 2½ hours, we’ll take it slow, ease up, and breathe deeply to get ourselves into the Conch Republic spirit.

We’ll follow US1 past the last mainland town in Florida, Florida City, and then to the Overseas Highway, with its Belize-blue concrete medians and its underpasses to allow crocodiles, panthers, and other animals to cross safely underneath. Great idea!!

As we cross the stunning bridge over Barnes Sound, leaving the mainland behind, we’ll look out at the aerial view over Key Largo and the road beyond. Our first stop today will be in Key Largo, for lunch overlooking the water at Sundowners.

Conch fritters to start? Or maybe Hot Crab & Artichoke Dip? Then let’s go wild with the Key Lime Seafood—lobster, shrimp, and blue crab, with key lime tabasco sauce, tomatoes, scallions and rice. And it would be almost sacrilege not to follow up our feast with our first venture into Key Lime Pie.

After lunch, we’ll continue along one of the most stunning and unforgettable drives we’ve ever experienced, with the Atlantic Ocean on our left and the Gulf of Mexico on our right. We’ll want to stop at intervals along the way to soak in the sun sparkling on the aqua-turquoise water and marvel at the ghostly remains of Henry Flagler’s impossible and doomed railroad, constructed across 153 miles of open ocean.

Flagler’s train made its first historic trip to Key West in 1912, with the 82-year-old Flagler himself onboard, arriving in triumph to welcoming crowds. For the next 23 years, Flagler’s engineering marvel formed a needed connection between remote Key West, with its steamboat service to Cuba, and mainland US. And then his dream became a mirage, destroyed during the Category 5 storm of 1935.

In Marathon, set on 13 islands, we will be stay in a condo haven, with views of the Gulf and a gorgeous, shaded swimming pool. To get a picture in mind, check out Tranquility Bay Beachfront Hotel & Resort.

After stopping to stock up on nibbles, sandwich makings, and drinks at a local grocery store (since we’ll have a kitchen here), we’ll check in, kick off our shoes and make a beeline to the most comfortable chair on our deck or balcony for a little relaxation time with crackers, cheese, and wine.

Marathon Haven

Our second day in Marathon, we’ll start our day at the Stuffed Pig (MM 49), sitting outside in the Tiki hut with the fans going, enjoying one of their phenomenal breakfast specials. Crab Benedict? Shrimp and Grits? Or maybe pancakes with fresh blueberries? We’ll probably be coming back here tomorrow morning, so we’ll get a chance to pick another of our top choices then.

flirting Dolphins at the Dolphin Research Center

This afternoon we’ll spend several hours at the fascinating Dolphin Research Center (MM 59), situated directly on a bay off the Gulf of Mexico. Here we’ll look out over lagoons where various social groups of dolphins live their lives. We’ll see “up close and personal” how dolphins interact. How dolphin moms raise and teach their babies. And how those babies play and learn.

In some spots, the dolphins will be able to swim up close to us. And they love to “people-watch,” flirt, and otherwise make a play to capture attention!

If we opt to add a “Dolphin Encounter” to our General Admission ticket, we’ll have time in the water with the dolphins, including a dolphin kiss and handshake, and an exhilarating dolphin dorsal pull. Guided by one of the trainers, we will learn to use hand signals to ask for a specific interaction with “our” new dolphin buddy.

Sunday morning, after checking out and possibly going back for another awesome breakfast at the Stuffed Pig, we’ll make a visit to the Turtle Hospital (MM 48.5) for a 90-minute guided educational tour of the hospital facilities and the sea turtle rehabilitation area. At the end of the program, we will get to feed the permanent residents— April, Bender, Bubble Butt, Montel and Rebel. We even may end up “adopting” one of them (for $35/year). And later we’ll certainly check out the online catalog for a turtle carryall or other turtle-themed art and books, where our purchases will go towards rescuing, rehabilitating, and releasing more sea turtles.

Next Stop, Key West

As we leave Marathon behind, we’ll cross the 7-mile bridge and continue hopping island to island, all the way down to Key West (Mile Marker 0) at the southernmost tip of the Florida Keys. From here, our nearest large city will be Havana, Cuba, 90 miles across the ocean.

In Key West, we’ll join the “fun-dependence” of the Conch Republic, the self-declared “micronation” that “seceded” from the US on April 23, 1982. The impetus for secession was a torturous roadblock, where the stop-and-search backed up traffic for miles. Since these roadblocks essentially functioned as “boarder patrols,” the Mayor reasoned that “If we’re being treated like a foreign country, we might as well act like one.” So, the Keys seceded from the US and become the Conch Republic. And the Mayor became its Prime Minister. All in good fun, of course, but the road block was, in fact, removed.

Back garden at the Cypress House

In Key West we’ll stay in the heart of it all, within an easy walk to Duval Street, where all the action is. Imagine us at a charming Bed & Breakfast like the Cypress House, pictured here, with its warm welcome, refreshing backyard pool, and home-baked breakfast goodies… not to forget its complementary happy hour, with hor d’oeuvres that are so substantial, dinner will be optional.

The Cypress House’s location will put us close to Mallory Square, where we’ll join the nightly sunset celebration this evening. This sunset party has been taking place every evening since the late 1960s. Beginning 2 hours before sunset, visitors and locals alike gather in a salute to the majesty of one of nature’s wonders —the glorious descent of the sun. These happy festivities are frequented by magicians and jugglers, clowns and musicians, artists and food vendors (www.malloysquare.com).

For this first evening, we’ll join the sunset party in Mallory Square, where Duval Street ends. Tomorrow night, when we return, as we probably will, we’ll head to the square early and snag a table at the Sunset Tiki Bar & Grill, with live music nightly. This will be a calmer atmosphere for enjoying another magnificent sunset.

Jolly Rover at Sunset

Continuing with the sunset theme, we’ll book a sunset cruise on the 80’ red-sailed, square-rigged, topsail schooner, the Jolly Rover. And possibly, on our final night, we’ll make reservations (well in advance!) for a splurge sunset dinner at Hot Tin Roof, on the outdoor deck overlooking the harbor.

We’ll check out some museums, each with fascinating stories to tell. On Monday, at the Flagler Museum, we’ll learn more about Flagler’s wild dream of connecting New York City with Havana, culminating in what was to become both a remarkable accomplishment and a tragic disaster.

And, in keeping with the vivid stories from this remote outpost of the US, where “wrecking” was one of the few paying “careers” during the Depression, we’ll check out the Mel Fisher Maritime Museum to learn about the treasures Fisher uncovered from Spanish Galleons that sank offshore.

Tuesday, we’ll visit Hemingway’s home, with its dozens of 6-toed cats and its lasting imprint of a larger-than-life genius writer—mornings for writing, afternoons for boxing, swimming and drinking. We’ll take some selfies at the “southernmost spot” of the US, posing in front of the marker telling us we’re 90 miles from Cuba.

Shopping excursions will take us to the Duval Street gallery displaying the dazzling work of Alan Maltz, a photographic artist who “follows the light” and has made Florida his “life work.” And we’ll certainly want to make a stop at the Keywest Toy Factory in Clinton Square Market, with its “imagineering workshop” and its “picture puzzle machine.” Then we’ll visit the Blue-Turtle Gallery and Diva Designs Jewelry, with its one-of-a-kind creations.

Now to Travel Home…

Now it will be time to travel home, back to all that grey and brown. And we’ll have two options:

  • We can fly home directly from Key West, but with the possibility of a pricey drop-off fee for that convertible we picked up in Miami.
  • OR we could retrace our steps back to Miami along the Overseas Highway, and fly home from there, with the considerable advantage of one last opportunity to memorize the otherworldly color of all that aqua-turquoise water.

We know we’ll be back!

So, What Do You Think? Did You Enjoy Our Trip?

This imaginary trip to the Florida Coast and Keys has been our first of the 12 armchair trips we will take together in 2022. Why not? The price is right! And there’s not one single thing to stop us from getting our fill of armchair travel, except maybe the need to locate our perfect, comfy chair.

And if, at some point in the future, we get the chance to turn these armchair trips into real ones, we already will have some great trips in mind as options. We might even have an idea about which trip we want to take first. Possibly we will want to share this and other of the Armchair Trips with select others so they too can start thinking ahead about where they may want to travel with us. Meanwhile, you can ignite your passion for travel, while preserving your independence, with a Great Trip Guide by your side.

So Where to Next Month?

Well, next month will be February. Where will we head then? Any guesses? See you next month and we’ll all find out…



Carolee Duckworth Independent Travel Associate

Carolee Duckworth is an avid traveler, an expert trip designer, and co-author (with Brian Lane) of the books Your Great Trip to France, Your Great 5-Day Trip to Paris, and Your Great 5-Day Trip to Loire Châteaux, available on amazon.com. Coming soon: Your Great 5-Day Trip to Normandy and Your Great 5-Day Trip to the Côte d’Azur.

Visit GreatTripGuide.com for a free copy of our definitive guide to packing: "How to Pack Like a Pro," and to receive periodic emails with new trip itineraries and travel tips. Ignite your passion for travel, while preserving your independence.

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