Ernest Hemingway — Theodore Roosevelt and the Rough Riders — Bay of Pigs
Improved U.S. relations with Cuba means new tourism opportunities, and there are already many ways you can experience the island nation, but few opportunities to dive deep into the most momentous times and places in U.S.-Cuba history. Our Cuban-American History Tour covers more than 500 miles and 500 years of history. With historian Clay Jenkinson and a select group of English-speaking Cuban guides, you will experience first-hand the history and culture of this incredible island.
We’ll begin in the region of Cuba’s “Second City,” Santiago de Cuba. We will visit the site of the Battle of Las Guasimas, where Theodore Roosevelt and the Rough Riders saw their first action of the Spanish-American War, then travel to San Juan Hill, where Roosevelt famously overrode orders and led a successful charge that led to U.S. victory. We’ll see the Caribbean bay outside of Santiago where the U.S. Navy pummeled the vaunted Spanish fleet, leading to Spain’s ultimate surrender.
Then we’ll take a day to travel through the heart of the island towards Havana, Cuba’s capital city, with a stop at Bay of Pigs to explore the site of perhaps the biggest near-disaster in American history—and to take advantage of the world-class swimming and snorkeling opportunities there.
Once in Havana, we will visit Finca Vigia, where Ernest Hemingway lived and wrote some of his most memorable works. We’ll also direct you to some of Papa Hemingway’s favorite watering holes, such as La Floridita and La Bodeguita del Medio. And we’ll visit the Hotel Nacional de Cuba, the site of the infamous Havana Conference, a meeting of mafia bosses memorably dramatized by Francis Ford Coppola in The Godfather Part II.
Trips includes all ground transportation, and we’ve selected excellent casa particulars (the Cuban version of B&B’s) and other 4-star accommodations. For all of our in-country logistics we have teamed up with Experience Cuba, owned by Joslin Fritz. A long-time traveler and international guide, Joslin began leading people-to-people exchange programs to Cuba in 2012. Travel with us and experience an unparalleled, hassle-free dive into the rich history and culture of Cuba!
My interest in Cuba is fourfold. First, and most important, Cuba has been a problem for the United States since 1959. The Bay of Pigs and the Cuban Missile Crisis were key moments in the Cold War. Virtually every President from Eisenhower to Bush 41 had to worry about Cuba and Castro. You cannot make sense of the Cold War without factoring in Cuba, almost as much as Berlin.
Second, Theodore Roosevelt and the Rough Riders. TR had to jump over half a dozen hurdles, a few of them remarkably challenging, to get himself to San Juan Hill in 1898. He called his heroics there "my crowded hour." San Juan Hill propelled TR into the Governorship of New York and, soon enough, into the presidency. Cuba is one of the handful of most important places in Roosevelt's biography. I want to scale those heights.
Third, Ernest Hemingway. Hemingway was one of the handful of greatest American writers of the 20th century. We associate him with Key West, the Caribbean, and Cuba. His footprint in that region is considerable, and it helps to illuminate his art and his life. I hope everyone will read the Nick Adams stories, A Farewell to Arms, and The Sun Also Rises before we gather. We will spend some time in Cuba talking about Hemingway's writing.
Finally, now’s the time to visit Cuba before the gates burst open and Costco rushes in. Because of Castro, the communist movement, the Cold War, and America's implacable refusal to come to terms with Cuba's independent way of being a Western Hemisphere country, Cuba has been in many respects frozen in time. Now is the moment to see it in that state before it begins to be transformed by corporate capitalism.
I've got my TR scarf and my copy of the short stories of Hemingway. Let us go and see what was the principal taboo nation of the Americas, before it's too late.