Thanksgiving in Cuba

For Grandparents, Parents and Children (ages 9-16)

OLLI has been traveling to Cuba for eight years now, with each new journey building on the last. Frequently, OLLI members will bring their adult children with them but we have never offered an intergenerational trip for the whole family, including grandchildren. That changes this Thanksgiving, as we invite OLLI members to ThinkOutside the traditional holiday and take your family on a journey that will stretch the mind as well as give everyone much to reflect on the privilege of living in the United States. The trip will be led by Eckerd College Vice President and Dean Kelly Kirschner who has been visiting the island since 2002.

A four-night, five day journey, we will spend our first two days in the Playa Girón area, also known as the Bay of Pigs, learning about the history of Cuba and getting to explore some of the island’s most pristine natural habitat, including the opportunity to snorkel the shallow but vibrant coral reef just off the beaches of Girón.  Our final three days, including Thanksgiving, will be spent in Havana, discovering one of the world’s most fascinating cities, currently celebrating its 500th Anniversary. Throughout the trip, we will have opportunities to interact with Cuban academics, artists, and musicians who will educate and entertain all generations of our delegation. Thanksgiving dinner will be a lo Cubano in Havana (i.e. no turkey!) and we will invite a number of our Cuban friends and hosts to join us for a Thanksgiving celebration with their families as we all enjoy a Cuban feast.

Direct flight from Tampa, Cuban visa, bus, guides, entrance fees, lodging, and all meals except one dinner are included. Lodging will be in private homes. Activity level is high and includes significant amounts of walking, including stairs. Trip is limited to the first 35 travelers to register. We expect the trip to fill quickly.

Update on U.S. Travel Guidelines to Cuba

November 26–30, 2019

This trip is full.

Cuban street art

OLLI participant enjoys “interactive Cuban street art”

The Oshers smiling

In Their Own Words

“We have been to Cuba twice with OLLI. The activities and side trips were unique from ice cream parlors to the U. S. Embassy to a visit with the Cuban National Water Polo team at their training facility. We definitely recommend the trip to others.”
– Susan and Gary Osher

Program Inclusions

Round trip flights from Tampa to Havana, and transportation within Cuba.

One night in a private home in Playa Giron and three nights in the beautiful neighborhood of Vedado, known as “the Mediterranean of Havana,” including homemade breakfasts. 

Excursions and Guided Tours
All excursions, guided tours, and visits with artists, intellectuals, musicians, etc.

Curated dining experience in exclusive, privately-owned paladares (all breakfast, lunches and three dinners).

Unparalleled Experience
A program that offers meaningful people-to-people exchange and supports Cuba’s nascent entrepreneurial sector.


How are we able to travel to Cuba in light of the new administrations announcement??

You are able to travel to Cuba with OLLI at Eckerd because it is considered group people-to-people travel. From the Department of Treasury:  “Group people-to-people travel is education travel not involving academic study pursuant to a degree program that takes place under the auspices of an organization that is subject to U.S. jurisdiction that sponsors such exchanges to promote people-to-people contact. Travelers utilizing this travel authorization must maintain a full-time schedule of educational exchange activities that are intended to enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people’s independence from Cuban authorities, and that will result in meaningful interaction between the traveler and individuals of Cuba. An employee, consultant, or agent of the group must accompany each group to ensure that each traveler maintains a full-time schedule of educational exchange activities.”

What can you tell us about the homes where we will be staying?

The owners/managers of the homes in which we will be staying are all run by former professionals who have since decided to participate in the new private sector in Cuba. It is life changing for them to be able to provide private services as opposed to working in the State sector. They go above and beyond to provide a welcoming and clean home with a traditional Cuban breakfast of eggs, ham, toast and exquisite Cuban coffee. We will be in the neighborhood of Vedado, known as the Mediterranean of Havana, which is just one mile from the U.S. Embassy.

Nearby is one of the ten best independent restaurants in all of Havana and a former mansion turned government building, which includes a tree-lined outdoor cafe serving authentic, inexpensive Cuban food until late in the evening, as well as rum and cervezas.

I have researched private homes in Cuba online and the reviews are mixed. Some people were placed in a home with wonderful accommodations and others were placed in an unkempt home. Have you used these homes, previously? Also, how many people share the same bathroom?

Hotels as well as private homes will often have mixed reviews. As a result we have pre-vetted the homes to ensure that they are well-managed, very clean, and centrally located in the upscale Havana neighborhood of Vedado. Eckerd College staff have stayed in several of the homes. Given that Cuba is still a communist country, our hosts go out of their way with the limited resources that are available to them to make sure that guests are comfortable and enjoy a truly unique experience.

Eckerd believes that comfort and convenience is paramount for our Lifelong Learners, no matter the destination. You will likely share a bathroom with another room. We find though, that given the history between our two countries, the experience of staying in a private home with a Cuban host living there or nearby is a much more gratifying and memorable experience than staying in a hotel for the duration. It provides the opportunity for our Lifelong Learners to engage with Cubans more directly, develop lasting friendships, support them in their entrepreneurial pursuits, and experience the country on a new level.

We believe it’s important for our participants to feel that their experience was of great value from start to finish, and we go to great lengths to ensure that your accommodations meet your expectations.

Is all of the lodging in private homes? Is the group split up and lodged in different homes, how many in each home?

Yes, all of the lodgings are in private homes. The trip participants can easily visit each other among the venues in Havana and there will be plenty of opportunity for storytelling and sharing a glass of rum on one of the open terrace balconies. The homes are also just six blocks from the Malecon, the famous waterfront in Havana. You will have the freedom and flexibility to come and go as you please. Given that even the most high-end hotels in Cuba still needing a significant amount of updating, participants often realize why it is such a unique and enjoyable experience to stay in a private home.

Can you give me some idea of the level of physical ability needed for the various activities?

You will need to go up two-three flights of stairs periodically. Visits to the center of Habana Vieja (Old Havana) require walking since the cobblestone streets are closed off to vehicles. The tour of Old Havana involves probably the most amount of walking, but otherwise, we have designed the trip to make all other destinations convenient and accessible for our participants. We will be traveling in air-conditioned vans and, for the majority of the trip, we will arrive close to the front entrance of our destination. For participants who opt out of the walking tour, we will have an alternative site visit to a museum. The average temperature in Havana in January is around 70 Fahrenheit, which also helps to mitigate any heat exposure.

Do you have to be a member of Eckerd's Osher Lifelong Learning Institute (OLLI) to go on the trip?

At least one member in your travel group must be an OLLI member to participate.

How much will I need to bring in additional cash for the trip?

We design the trip so that it is all inclusive with the exception of alcoholic beverages at restaurants and one of the dinners. While participants enjoy having the trip excursion planned from start to finish, we have also found that they value the opportunity to explore and dine on their own on at least one occasion. We like to think we’ve achieved the right mix of inclusivity and exploration, and always welcome your input. Apart from the one dinner, you will just need funds for any gifts, meriendas (snacks), souvenirs, cigars, rum, and artwork you choose to purchase. Handcrafts are very inexpensive, ranging from $5 to $50. We will also be seeing the artwork of some of the most renowned, independent artists on the island. Americans are allowed to bring back up to $400 in merchandise as accompanied baggage. However, for purchases from independent Cuban entrepreneurs, the $400 limit does not apply.

Does this trip meet the U.S. requirements for travel to Cuba?

The trip meets the requirements for people-to-people engagement and humanitarian projects, as set forth under the general license for travel to Cuba under the Office of Foreign Assets Control (OFAC) at the U.S. Treasury Department.

Visitors enjoying a cafe in Cuba

Our programs immerse you in study/travel experiences designed especially for you and features expert speakers, behind-the-scenes tours, delicious meals in specially selected restaurants, live performances, and a great balance of planned and free time.