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Postcards: We Ran Into a Gang of Key West Toughs

Enjoy the Christmas Lights

I was not sure how Samwise and Emily would handle Key West’s free-roaming roosters and hens—a throwback to the disgusting days of cock fighting, but you are about to see in the above video. 

Two weeks have gone by in a flash! That’s the problem with the opening chapters of a grand adventure. All the dreaming and plotting and planning and it zips by too quickly. I find myself comparing these first two weeks to what it feels like when first falling in love. You look back fondly at the intoxicating newness, those first throes, how your heart takes over, and the innocence of new beginnings. In travel, the road takes over, and if you are lucky, it’s akin to catching lightning in a bottle. Zip! Bang! Boom!

That’s how I feel at 4 am as I write to you. We have been swept away! I’m both giddy and at peace. 

Key West did a number on me—the very best kind. We stepped back in time and relished the tropical feel and the freedom, and there were moments when, in my mind, we were walking with Hemingway, Tennessee Williams, Audubon, and Harry Truman. As an empath, it can feel so real. In the shadows of our night and predawn walks, anything felt possible. I’ve been fascinated by the story of the friendship between Hemingway and John Dos Passos, which came to life for me during our Key West visit. Knowing how it began, thrived, and then crashed in a tumble—as most of Ernest’s marriages and friendships did. I could feel it all, and it made my heart ache. What a terrific gift.

Many of you know the magic of Key West. I was fortunate enough to tap into a singular branch of it. And when we crossed the Everglades and drove up the Gulf Coast yesterday (480 miles), I revisited the Dos Passos and Hemingway dance by listening to the audio version of a book I read a few months back, The Ambulance Drivers by James McGrath Morris

I’m fascinated by Dos Passos because of something I learned about him in Provincetown last winter. It continues to haunt me, and as I write more about two days on the Keys that could have been two decades, I’ll confess all.

By the end of a long travel day, we are exhausted, and we tumble into bed as early as school children. Being an old man, I wake up in the middle of the night, usually wondering, “Where are we?” But I wake up long before dawn with the excitement of a boy thinking, “Where will the road take us today?”

Where we stayed, a five-minute walk from Hemingway’s House.
Our private deck.

Two weeks: the Berkshires, all those dead author and artist visits, Shenandoah National Park, reuniting with Rachael and family, Isle of Palms, Savannah, Saint Simons Island, Everglades National Park, Key West—and here we are. 

Here’s a bit about where we are going. There are only six days until Christmas, and we expect a white one. Since we are still in Florida, east of Tallahassee, we have some driving ahead of us. Along the way, we’re undertaking another deep emotional dive while making new stops. Christmas Eve will be a roll of the dice. It has incredible possibilities, but it could easily get dark pretty quickly. You’ll know soon enough. The pace will continue to be a blur until December 27, when we will take our first extended stop. 

So buckle up and strap in. We’re only two weeks in and have more than four months left.

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Breakfast in paradise: mixed greens and fresh pineapple.