See Cuba through the lens of Cuban-American history!

  Travel changes you. As you move through this life and this world you change things slightly, you leave marks behind, however small. And in return, life – and travel – leaves marks on you. – Anthony Bourdain

November 3-12, 2025

U.S. relations with Cuba allows travel between the two countries. We travel to Cuba under the designation “Support of the Cuban People” This category of travel allows you to directly support our Caribbean neighbors, individuals and families by participating in guided tours of their homeland, eating in their privately owned & operated restaurants (Paladars) staying in a combination of hotels & homes and so much more…

Our tour that caters exclusively to history buffs, that gets you up close and personal with the most momentous times and places in U.S-Cuba history!

The Cuban-American History Tour from Lewis & Clark Trail Adventures is an immersion into one of the most colorful places on Earth, covering more than 500 miles and 500 years of history. Between Lewis & Clark Adventures’ history buffs 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. You 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. You’ll travel to San Juan Hill, where Roosevelt famously overrode orders and led a successful charge that led to U.S. victory. And you’ll see the Caribbean bay outside of Santiago where the U.S. Navy pummeled the vaunted Spanish fleet, leading to Spain’s ultimate surrender.

You’ll also have plenty of time to soak in the culture of Santiago de Cuba, a city known for its music and dancing, as well as its rich heritage of Afro-Cuban religions.

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.

Lewis & Clark Trail Adventures has a long and successful track record of combining history, adventure and culture in our tours of the American West, and we bring that same level of detail and excellence to our Cuban-American

History Tours. Trips include all transportation, and we’ve selected excellent casa particulars (the Cuban version of B & B’s) and other uniquely cuban accommodations. Travel with us and experience an unparalleled, hassle-free dive into the rich history and culture of Cuba!

For all of our in-country logistics we have teamed up with Custom Latin Travel, owned by Joslin Fritz – Long-time traveler and international guide, Joslin began leading programs to Cuba in 2012.

 Some Important Dates in Cuban and US History relating to this tour

• 1492 – October 28 – Christopher Columbus lands in NE Cuba near the town of Baracoa
• 1492-1898 – Spanish colonization and rule of Cuba
• 1808 – President Jefferson sends General James Wilkinson (later to be known as a Spanish spy) to Cuba to find out if the Spanish would consider ceding Cuba to the United States. Spain was not interested.
• 1808-1897 – US Government was very much in favor of the annexation of Cuba
• 1897 – November – Spain’s Queen offers Cuba autonomy. Cuban loyalists and rebels reject the offer. Meanwhile in Washington, D.C., Navy Assistant Secretary Teddy Roosevelt is urging President McKinley to intervene.
• 1898 – April – The battleship Maine blows up in Havana harbor. “Remember the Main” becomes a battle war cry. Responding to a perceived Act of War, U.S. enters the war with Spain. A later investigation named an internal fire as the likely cause of the explosion.
• 1939-1960 Ernest Hemingway lives part-time in Havana.
• 1959 – January 1 – Rebel Forces led by Fidel Castro overthrows the Batista dictatorship.
• 1961 – April 17 – U.S. Finances and organizes military invasion of Cuba at Bay of Pigs.
• 2018 – February – Lewis and Clark Trail Adventures travels to Cuba to explore the island and put together a hassle-free tour covering major historical sites and culture.

Dates: November 3-12, 2025

Itinerary & Provisions

Places Visited: Havana, Trinidad, Playa Giron, Playa Larga, Sancti Spiritus, Santiago de Cuba

Length: 9 nights, 10 days (B,L,D signify meals included)

*Itinerary is subject to change

*travelers are encouraged to bring donations for local organizations and individuals that we are scheduled to meet*

 

Day 1: Arrival to Santiago de Cuba (L,D)

• Arrive in Santiago de Cuba International airport
• Pick up luggage and clear customs, meet your local guide and driver outside of the airport
• Lunch at a local restaurant
• Check into your accommodations (private bed and breakfasts-La Hiedra and surrounding homes)
• Tonight enjoy dinner with your group at a local paladar. Review the trip itinerary with your guide and have a chance to ask any questions you may have.

 

Day 2: Santiago de Cuba (B,L,D)

• Explore Cuban/Spanish-American War battlefield sites including Siboney, Las Guasimuas, El Caney, San Juan Hill, the Surrender Tree Monument. During this time you will be led by a local expert guide who will share a Cuban perspective of these battles.
• Lunch at a nearby private paladar to the Morro Fort with a spectacular view.
• Visit to Morro Fort and discussion of the naval portion of the battle, again learning from a local expert to guide their interpretation of the battle.
• This afternoon visit with a lively private dance troupe. Here you’ll enjoy a dance presentation of the traditional dances of Cuba. Afterwards, you will have time to chat with the dancers to learn about their work and inspiration.
• Dinner tonight in a private paladar

Day 3: Santiago de Cuba (B,L)

• This morning after breakfast head to Gran Piedra National Park. Here take a tour of the park with a local guide. Stop at a coffee farmers house and learn more about coffee cultivation. Also learn about local flora and fauna from a local 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 also include stops to various private enterprises to talk with entrepreneurs and small business owners
• Dinner on your own, with a list of recommended private paladares

  

Day 4: 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 Hostal San Rafael-light sandwiches at hotel
• Enjoy a fun bici-taxi ride through Camaguey to visit all 4 plazas of the town. With its narrow streets, a bici-taxi is the best way to explore this town
• Visit to Martha Jimenez Artist Studio and have a chance to talk one-on-one with the artist about her work
• Overnight in private bed and breakfasts in Camaguey
• Dinner in Camaguey at a private paladar, where you’ll look to talk with the restaurateur about his business and the challenges of operating a restaurant in Central Cuba.

Day 5: Camaguey to Trinidad (B,L,D)

• This morning after breakfast continue onto Trinidad from Camaguey (4 hours)
• Visit to Iznaga Manaca former sugar plantation to learn about the important role 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 to Plaza Mayor, touring the UNESCO World Heritage site
• Visit to 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 tonight in a local paladar

Day 6: Trinidad to Playa Larga(B,L,D)

• Continue to Playa Larga (1.5 hours drive)
• Visit the Bay of Pigs Museum and tour this museum with a local guide, who will share his unique Cuban perspective
• Lunch at Playa Giron-sandwich shop Marlon has contact
• Have an opportunity to 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
• Fireside chat on the beach

Day 7: Havana (B,L, D)

• After breakfast depart for Havana (2 hour drive)
• Lunch at El Cafe
• Visit to Finca Vigia Hemingway home, here 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

Day 8: Havana (B,L)

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

Day 9: Havana (B, L, D)

• This morning enjoy a walking excursion of Old Havana led by an expert guide. Along your tour you’ll stop and visit various private enterprises and talk with entrepreneurs partaking in independent businesses.
• Enjoy lunch in a pizza paladar in Havana
• Visit to the Museum of Revolution and tour with a local guide. Also, an option to visit the Fidel Museum newly opened in 2021
• Farewell dinner at a paladar

  

Day 10 : (B)

• After breakfast depart for your flight back to the States

You are welcome to stay additional days in Havana / Cuba if you choose.

 

Price per person $4850 (based on double occupancy) Book Now

$630 Single Supplement applied after booking

Includes:

• Experienced Cuban tour guide
• Bottled water during trip
• Legal, licensed OFAC requirements completed as best described by the Office of Foreign Assets Control
• Meals outlined in the itinerary
• Accommodations outlined in the itinerary (Standard bed and breakfasts)
• All entrance fees for activities in itinerary
• Air-conditioned transportation while in Cuba
• 1 Airport transfer to/from each Havana and Santiago de Cuba 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,

 Expectations: We recommend all participants are in good health and fit enough to walk unassisted at least 1 mile, keep a brisk pace while walking on cobblestone, uneven sidewalks, up & down stairs and hills. Please feel free to email or call to chat more about what to expect.

For all our in-country logistics we have teamed up with Custom Latin Travel, LLC, owned by Joslin Fritz – Long-time traveler and international guide, Joslin began leading people-to-people exchange programs to Cuba in 2012.

If you have your own group, other areas of interest, dates, we can customize a tour with that in mind. Just let us know!

Questions about this trip or booking this tour, please Contact Us and type Cuba in the comments.

Travel, Trip and Cancellation Insurance

Why is travel insurance so important?

Your trip fees are non-refundable. In today’s changing travel environment, it’s important to protect your travel investment so you can relax and enjoy your trip. Unforeseen events such as flight delays, baggage loss or even a sudden sickness or injury could impact your travel plans. LCTA recommends that you purchase a travel protection plan to help protect you and your travel investment against the unexpected. For your convenience, we offer travel protection through Travelex Insurance Services.

For Cuba Trips you MUST CALL vs apply online Travelex Insurance Services at 800-228-9792 and reference location number 26-0048.

Travelex Insurance Services, Inc. CA Agency License #0D10209. Insurance coverages underwritten by Zurich American Insurance Company (NAIC #16535, state of domicile: New York), 1299 Zurich Way, Schaumburg, IL 60196. Certain coverages not available in all states.