The Historical Cuba tour is booked to capacity. No additional reservations are being accepted.

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!

Cuba February 2019 (16) - El Carney Spanish-American War-Santiago de Cuba.JPG

Clay's Notes:

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.


Havana – Trinidad - Playa Giron - Sancti Spiritus - Santiago de Cuba

8 nights, 9 days

(B,L,D signify meals included)

*Itinerary is subject to change

Day 1 - Saturday, Feb. 8th

Santiago de Cuba (D)

● Arrive at Holguin Airport

● Depart for Santiago de Cuba

● Stop in Biran to tour the homeplace of Fidel Castro

● Check in to accommodations (Hotel Imperial)

● Welcome dinner

Day 2 - Sunday, Feb. 9th

Santiago de Cuba - Spanish American War sites (B,L)

● Explore Cuban/Spanish American War battlefield sites including Siboney, Las Guasimuas,

El Caney, San Juan Hill, the Surrender Tree Monument

● Lunch at nearby restaurant to the the Morro Fort with a spectacular view

● Visit to Morro Fort and discussion of the naval portion of the battle

● Dinner on your own

Day 3 - Monday, Feb. 10th

Santiago de Cuba (B,L)

● Walking tour of Santiago de Cuba

● Visit the Santa Ifghenia Cemetary to visit Fidel Casto’s grave

● Visit to Moncada barracks, the site where Fidel first tried to overthrow Batista in 1953.

● Lunch at local paladar

● *Optional hike to La Gran Piedra and Cafetal Isabelica

● Explore the Emilio Barcardi Museum

● Dinner on your own

Day 4 - Tuesday, Feb. 11th

Sancti Spiritus (B,L,D)

● Drive to Sancti Spiritus (7-8 hours)

● Explore the town on Sancti Spiritus with a local guide

● Overnight in hotel Don Florencino

● Dinner in Sancti Spiritus

Day 5 - Wednesday, Feb. 12th

Trinidad (B,L,D)

● After breakfast, depart for Trinidad (1.5 hours)

● Visit to Plaza Mayor, touring the UNESCO World Heritage site

● Lunch in Trinidad

● Visit to Valley de los Ingenios and Iznaca Manaca Former Sugar Plantation

● Check into private bed and breakfasts

● Dinner as a group in a restaurant

Day 6 - Thursday, Feb. 13th

Trinidad, Playa Giron, Havana (B,L,D)

● After breakfast depart for Playa Giron

● Visit the Bay of Pigs Museum

● Lunch in Playa Larga

● Check into accommodations in Havana in Hotel Capri

● Dinner as a group

Day 7 - Friday, Feb. 14th

Ernest Hemingway’s Havana (B,L)

● Visit Monument of Maine

● Visit to Finca Vigia Hemingway home

● Lunch in Cojimar fishing village, checking out the spots where Hemingway used to stay

● Visit to the fishing base where Hemingway kept his boat

● Visit to Cabana Fortress on the way back into town

● Enjoy mojitos at the Hotel Nacional and learn about its famous history

● Dinner on your own

Day 8 - Saturday, Feb. 15th

Havana (B,L,D)

● This morning enjoy a walking tour of Old Havana led by an expert guide

● Enjoy lunch in a charming paladar in Old Havana

● Visit to the Museum of Revolution

● Free time in the afternoon to spend time in Old Havana. Wandering the streets of Old Havana with a map in hand is truly the best way to explore this UNESCO World Heritage Site

● Farewell dinner at a paladar

● Optional Tropicana show (to be paid on own)

Day 9 - Sunday, Feb. 16th


● After breakfast, depart for your flight back to the States


February 8-17, 2020

$5295 per person (based on double occupancy)
$650 single supplement

Capacity is limited. This is a small group tour with a maximum of 16 openings.


  • Experienced tour guide

  • Bottled water during trip

  • Legal, licensed people-to-people tour requirements completed

  • Meals outlined in the itinerary

  • Accommodations outlined in the itinerary

  • All entrance fees for activities in itinerary

  • Air-conditioned transportation while in Cuba

  • Airport transfers to/from Havana airport

Not Included:

  • Airfare to/from Cuba and tourist visa

  • Travel and medical insurance

  • Meals not specified in itinerary

  • Gratuities for guide and driver

  • Items of personal nature—laundry, internet, etc.

Your journey begins at the Holguin airport in Cuba, with departure from Havana. Your package includes pickup and transportation from and back to the airports in Cuba (airfare is not included). We recommend flying into Ft. Lauderdale/Miami the day prior and taking the early morning Jetblue flight from Miami to Holguin. Travel visas to Cuba can be completed at the Miami Jetblue terminal ($50) or online ($85). Our staff will be happy to help you make your travel arrangements.

A $1,000 non-refundable deposit will secure your reservation. Price is per-person based on double occupancy. Traveling single? No problem. We offer a single supplemental fee to arrange for single accommodations.

A note on visas: our Cuba tour is completely legal for US citizens to attend. In June 2019 President Trump announced the elimination of the People-to-People educational travel visa (515.565B). There are many other types of Cuba visitation visas, however, that are unaffected by this announcement. Our small group tour is designed under general license Support for the Cuban People (515.574). As of July 2019, there have been no changes to this category. We will continue to monitor any changes to Cuba visa law. If US federal law becomes more prohibitive and prevents our visit, you will be reimbursed your tour fee. Travel insurance is also recommended.

Please review our Terms & Conditions.