Ernest Hemingway — Theodore Roosevelt — The Bay of Pigs
February 23 – March 6, 2025
Miami’s Little Havana, Santiago de Cuba, Camaguey, Trinidad, Playa Giron (Bay of Pigs), Playa Larga, Havana
12 days / 11 nights
$6,695 per person, double occupancy
$1,200 single room supplement

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 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.

When Clay began planning trips to Cuba with Wayne Fairchild, he insisted on three things. He wanted to see where the Castro revolution began and where Castro is buried. He wanted to see Ernest Hemingway’s villa Finca Vigia, preserved untouched since he left on June 25, 1960. And he wanted to go the Bay of Pigs. Then Wayne discovered a Bay of Pigs Museum in Miami that gives voice to the expats who wish the revolution had succeeded and still have fading dreams of going back someday. So before leaving Miami for Santiago de Cuba, we visit the Bay of Pigs Museum in Little Havana. The old men of the museum are gentle and charming and proud and a little dreamy. It’s so important to see that perspective (which, by the way, is the dominant American view) before we arrive in Cuba and experience the Bay of Pigs from a Cuban viewpoint as an imperial episode in their history. 

From Miami we fly to Holguin, Cuba. From there we’ll head for Santiago de Cuba, the nation’s “Second City,” stopping along the way to visit the Castro family ranch. 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 pouch-shaped 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 few days 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 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. We’ll visit the Hotel Nacional de Cuba, site of the infamous Havana Conference, a meeting of mafia bosses memorably dramatized by Francis Ford Coppola in The Godfather Part II.

Tour includes ground transportation, and some excellent casa particulars (the Cuban version of B&B’s) as well as 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!

Please note that this is an active tour requiring a spirit of adventure and flexibility. While comfortable motorized transportation is provided where possible, all guests should expect to walk 1-2 miles per day on varied surfaces including cobblestone streets, uneven sidewalks, gravel, and stairs. Our accommodations are very comfortable, but some amenities typical in the United States such as in-room WIFI or king size beds may not be available at every casa particular. Cell service is limited and costly. No United States bank credit cards work. While we make every effort to accommodate dietary restrictions, food variety is limited in Cuba and dietary alternatives may not always be available. Much of the food is grown or raised on the island so you see a lot of what is in season, but it will always be prepared with love and generosity.

As we travel under the Support for Cuban People visa, we will have many opportunities to engage with (and spend our travel dollar with) local business owners and artisans. Cultural visits to artisans, business owners, markets, and more will be included in our itinerary. We expect all guests to engage with our lodging hosts, restaurant proprietors, and guides with appreciation and respect.

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 20^th 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’s transformed by corporate capitalism. 

I’ve got my TR scarf and my copy of the short stories of Hemingway. Let us go, before it’s too late, and see the nation that was once a principal taboo to Americans.

February 23–March 6, 2025
Itinerary is subject to change. Travel in Cuba is an adventure, and we have learned to expect the unexpected. 
Locations: Little Havana in Miami, Santiago de Cuba, Camaguey, Trinidad, Playa Giron (Bay of Pigs), Playa Larga, Havana
Length: 12 days, 11 nights, including 10 days, 9 nights, in Cuba.
Meals: B, L, D signify meals included on the daily itinerary.
Note: Travelers are encouraged to bring donations for local organizations and individuals we are scheduled to meet.

Itinerary

February 23 — Day 1: Arrive in Miami

• Arrive at Miami International Airport and check into nearby Sheraton.
• Dinner on your own (the Rickenbacker is in the hotel and we will provide a list of nearby restaurants).
• Introductory get-together at 7 pm at the hotel.

February 24 — Day 2: Little Havana and the U.S. Bay of Pigs Museum (B, L, D)

• Breakfast at hotel.
• Mid-morning orientation meeting in hotel.
• Bus to Bay of Pigs Museum for exhibits, conversations, and lunch.
• Dinner at Cafe La Trova in Little Havana.

February 25 — Day 3: Arrive Santiago de Cuba (B, L, D)

• Shuttle to Miami International Airport for early morning flight to Cuba.
• Arrive in Holguin Airport in Cuba.
• Pick up luggage and clear customs, meet your local guide and driver outside of the airport.
• Bus to Santiago de Cuba, stopping along the way at Castro family homestead.
• Check into your accommodations (private bed and breakfasts — La Hiedra and surrounding homes).
• Enjoy dinner with your group at a local paladar. Review the trip itinerary with your guide and ask any questions you may have.

February 26 — Day 4: Santiago de Cuba (B, L, D) 

• Explore Cuban/Spanish-American War sites including Siboney, Las Guasimuas, El Caney, San Juan Hill, the Surrender Tree Monument. A local expert will lead the tour and share a Cuban perspective of the battles. 
• Lunch at a private paladar with a spectacular view of Morro Fort. 
• Visit Morro Fort to discuss the naval portion of the battle with a local expert and get the Cuban interpretation.
• Afternoon visit with a lively private dance troupe. Enjoy a presentation of traditional Cuban dances. Afterwards, chat with the dancers and learn about their work and inspiration.
• Dinner in a private paladar.

February 27 — Day 5: Santiago de Cuba (B, L)

• After breakfast head to Gran Piedra National Park. Tour the park with a local guide. Stop at a coffee farmer’s house and learn more about coffee cultivation. Learn about local flora and fauna from an expert guide. 
• Lunch in the Gran Piedra Park at a local paladar.
• Walking tour of Santiago de Cuba with a local expert guide. Here we will stop at various private enterprises to talk with entrepreneurs and small business owners.
• Dinner on your own, with a list of recommended private paladars.

February 28 — Day 6: Santiago to Camaguey (B, L, D)

• Drive to Camaguey (6 hours). On the bus you’ll have time to chat with your guide about culture, history and politics of Cuba.
• Lunch in Camaguey at a local paladar.
• Enjoy a fun bici-taxi ride through Camaguey to visit all four town plazas. Due to its narrow streets, a bici-taxi is the best way to explore this town.
• Visit Martha Jiminez Artist Studio and talk one-on-one with the artist about her work.
• Dinner in Camaguey at a private paladar. You’ll have an opportunity to talk with the restaurateur about his business and the challenges of operating a restaurant in Central Cuba. 
• Overnight stay in private bed and breakfasts in Camaguey.

March 1 — Day 7: Camaguey to Trinidad (B, L, D)

• After breakfast travel to Trinidad from Camaguey (4 hours).
• Visit former sugar plantation Iznaga Manaca and learn about the importance sugar production played in this region. Learn how sugar cane juice is made from a local private enterprise worker, and try some of this delicious juice yourself.
• On arrival to Trinidad, enjoy lunch at a local paladar.
• Visit Plaza Mayor and tour the UNESCO World Heritage site.
• Visit a women’s crochet cooperative that employs nearly 30 women from around the island.
• Check into your private bed and breakfasts for the night.
• Dinner in a local paladar.

March 2 — Day 8: Trinidad to Playa Larga (B, L, D)

• Travel to Playa Larga (1.5 hours).
• Tour the Bay of Pigs Museum with a local guide who will share his unique Cuban perspective.
• Lunch at a local paladar.
• Go snorkeling and swim in a cenote and learn about coral restoration from a local expert guide.
• Check into private bed and breakfasts.
• Dinner as a Group.

March 3 — Day 9: Havana (B, L, D) 

• After breakfast depart for Havana (2 hours).
• Enjoy lunch at a private paladar with a community center dedicated to providing activities to neighborhood seniors. Interact with members and employees to learn more about their services.
• Visit Hemingway’s home Finca Vigia. Tour with a local expert guide.
• Continue onto Havana.
• Check into accommodations in Havana (private bed and breakfasts).
• Dinner as a group in a private paladar.

March 4 — Day 10: Havana (B, L)

• After breakfast visit a car restoration workshop and talk with the entrepreneurial couple of the private business. Afterwards enjoy riding in a few of their classic cars to areas of Havana less frequented by travelers.
• Lunch in a private paladar.
• Visit Cabana Fortress on the way back to town and learn the history of the fortress from your local guide.
• Dinner on your own.

March 5 — Day 11: Havana (B, L, D)

• Enjoy a morning walking tour of Old Havana with an expert guide. Visit various private enterprises and talk with entrepreneurs partaking in independent businesses. 
• Enjoy lunch in a charming Old Havana paladar with a chance to chat with the owner afterwards. 
• Visit the Museum of Revolution and tour with a local guide. Take an opportunity to visit the Fidel Museum, newly opened in 2021.
• Farewell dinner at a paladar.

March 6 — Day 12: Travel Day (B)

• After breakfast depart for your flight back to the States.

Cost: $6,695 per person
Deposit: $1,500 per person deposit secures your spot.
Final payment due by December 3, 2024.
Single supplement: $1,200 (for those traveling alone who prefer not to have a roommate.)

Not Included:

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SPECIAL NOTICE CONCERNING THE RECENT COUNTRY-WIDE POWER OUTAGES IN CUBA:

There have been several country-wide power outages in Cuba in recent days and we understand this may raise concerns if you are considering this trip. We are in year-round contact with our associates and guides in Cuba and some of our staff will visit Cuba in early November to assess the situation.

In the meantime, we have received the following assurances from our partners in Cuba: 

We wanted to take a moment to address the recent country-wide power outages in Cuba. We understand that this news may raise concerns for your upcoming trip.

Cuba has faced ongoing energy challenges for the past decade, even longer in fact than a decade. While the current situation is certainly concerning, it is important to note that many properties, including government hotels, private properties, and restaurants, are successfully operating with generators. This allows travelers to continue enjoying their experience on the island, even amidst the power challenges.

We have operated successful trips to Cuba during the past nine years, and we have received much positive feedback from travelers who appreciate the resilience and hospitality of the Cuban people. We are optimistic that with fuel deliveries expected soon and ongoing repairs at the main thermoelectric plant, we can look forward to the stabilization of the energy situation as we approach the upcoming travel season. This is an evolving situation that we are monitoring closely on the ground, and we will continue to be in touch with any updates or changes that should affect your trip.

We remain committed to ensuring that our travelers have a memorable and enjoyable experience in Cuba.

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Terms and Conditions

Deposits and Payments
A nonrefundable deposit of $1,500 per person will reserve your spot on the tour. Full payment is due in our office at least 75 days prior to departure.

Refunds and Cancellation Policy
We recommend you purchase travel insurance to protect you if for some reason you must cancel your reservation.

You will receive your full refund less your deposit and credit card transaction fees up to 75 days prior to the tour; a 50% refund if you cancel within 75 days prior to the event, minus any additional hotel or supplier expenses, which cannot be recovered. No refunds in the last 30 days prior to tour departure. Full refund is always available if you can find a replacement traveler.

Travel Insurance
We are not an insurance provider. If you are interested in purchasing travel insurance, please notify your travel insurance company at the time of your initial payment. Travel insurance information can be obtained from your local travel agency.

Tour Cancellation
We do not like to cancel tours. In the event a tour must be canceled, we will refund all monies paid to us.

Participation Courtesy
We ask there be no audio or video taping of presentations without the prior consent of the individual presenters. Participants are requested to refrain from smoking inside all modes of transportation, during group meals, and lectures or events.

Itinerary or Program Modifications
The itinerary is subject to modifications and change. Every effort will be made to carry out the program as planned, but alterations may still occur after the final itinerary is sent.

Responsibility
Our company acts only as the agent in making arrangements for the owner or operators of such transportation, accommodations, services or facilities engaged in our tours. Our responsibility is limited to that of an agent. We accept no responsibility for accidents, injuries, property damage or personal loss to you or to those traveling with you in connection with any accommodations, transportation or other travel or guide services, or resulting directly or indirectly from any occurrences or conditions beyond our control, including but not limited to acts of terrorism, defects in vehicles, breakdown in equipment, strikes or theft.