Meals Included: 7 Breakfast, 5 Lunches, 5 Dinners Group Transfers: To/from Airport Accommodations: 3*Star Hotel,Standard Room

We love Cuba so much that we visit annually. To understand Cuba and the people, you must experience Cuba.

Participate in discussions about Cuba’s history, agriculture, music, religion, and art; engage with musicians discuss private enterprise in Cuba with local restaurant owners and staff; and meet Cuban baseball players to discuss this favorite pastime in both Cuba and the U.S.

On this Cuba tour program, you’ll also have a chance to explore some of Cuba’s colonial cities with their cobblestone streets and historic architecture. In fact, the city centers of Cienfuegos, Trinidad, and Havana have all been named UNESCO World Heritage Sites. Fascinating, informative, and insightful discoveries await you on this rare opportunity to visit the “Pearl of the Antilles.” It’s an experience like no other!

Book 2021 at 2020 Rates Today!!

  • Trip Outline
  • Trip Includes
  • Trip Excludes
  • Reviews
  • Booking
  • FAQ

This tour is ideal for anyone interested in Cuba and truly want to Unplug. No matter what you're into: food, wine, history, art, music, etc. you will find it in Cuba.

Please note, the itinerary may change slightly and you will be notified if it does. Cuba requires advanced planning however even still scheduled activities become unavailable. Rest assured, we won't disappoint with the alternative activity.


Day 1


Arrive in Havana, Cuba’s capital city, and transfer to your hotel. In the evening, meet your Cuban National Tour Director for a welcome dinner. This is a good time to get your questions answered, and prepare for your time in fascinating Cuba.

Day 2


Your day begins with a walk through the streets of OLD HAVANA, a UNESCO World Heritage Site. Discuss with your Cuban Tour Director Havana’s unique architecture, the challenges of renovating the city’s exquisite historic buildings, and the future of these restorations. Enjoy lunch at a local paladar (a special, privately owned restaurant) where you will be treated to a special interactive cooking DEMONSTRATION and discussion. This afternoon, our attention turns to Nobel Prize-winning novelist Ernest Hemingway, who lived in Cuba for more than 30 years and left behind an enduring legacy. From his beloved home, FINCA VIGIA, he wrote several books, participated in fishing contests, and enjoyed the laid-back ambiance and warmth of the Cuban people. Next, visit a COMMUNITY PROJECT and interact with the children and volunteers who run the program. This evening is free to explore Havana on your own. Your Cuban Tour Director will have suggestions for dining and additional activities.

Day 3


Today, travel through the countryside passing sugar cane and banana plantations. Arrive in Cienfuegos often referred to as the “Pearl of the South” because of its impressive beauty and colorful history. After time for lunch, take a walking tour around the historic center of the city, a UNESCO World Heritage Site, and learn more about the immigrants from France and Louisiana that settled here more than 150 years ago. Later, enjoy a performance and interaction with the Cienfuegos ORCHESTRA. Dinner toperson is at a local paladar.

Day 4


Travel to Trinidad, the crown jewel of Cuba’s colonial cities, founded in 1514 and today a UNESCO World Heritage Site. Upon arrival, enjoy lunch at a paladar and discuss private enterprise in Cuba with the owners and staff. This afternoon, stroll the streets of Trinidad, a cobblestone showcase of colonial architecture and pastel-colored houses decorated with wooden shutters and wrought-iron grilles. Spend time at CASA CHICHI POTTERY STUDIO to learn more about the unique wares made here, the family that runs the studio, and the connection to Spanish colonialists. After dinner toperson, enjoy a rum and cigar pairing.

Day 5


Today’s travels bring us to PLAYA GIRON, site of the Bay of Pigs Invasion. Discuss with your Cuban Tour Director the history of this event and the role it played in the Cold War. Over lunch, meet a Naturalist from the local Zapata National Park and join in a DISCUSSION about the concerns we all have for our environment. Continue to the white sand beaches of Varadero.

Day 6


Music and dance is an important part of Cuba’s culture so start the day with an interactive DANCE LESSON. Enjoy lunch at historic Mansion Xanadu, which sits overlooking the blue waters of the Caribbean. Later, visit Matanzas, known as the “Athens of Cuba” for the many renowned artist and intellectuals it has produced. Join in a discussion with workers at EDICIONES VIGIA, a print and binding shop, and learn about the traditional craft that is still done by hand. Return to Havana where this evening is free to explore the city on your own. You may wish to see the exciting show at the famous Tropicana Nightclub, visit some of Hemingway’s old haunts, or explore the charming cobblestone streets of Old Havana.

Day 7


This morning, enjoy a workshop at HAVANA COMPASS DANCE COMPANY. Watch one of their rehearsals, then take some time to speak to the dancers and teachers about their training, daily lives, and future careers. Next, visit JOSE FUSTER’S STUDIO; cleverly nicknamed the “Picasso of the Caribbean.” Here, you will discover a surreal world-like nothing you have seen before. Interact with members of the neighborhood to discuss the project’s impact on the surrounding area. Over lunch, meet a former Cuban baseball player for a DISCUSSION about the history and the love of this favorite pastime in Cuba and the United States. Then it’s on to the SAN JOSE MARKET where you can interact with local artists and perhaps find a favorite souvenir. Before your farewell dinner this evening, enjoy a ride in a classic 1950’s OLD STYLER car – the perfect ending to your time in Cuba.

Day 8


After breakfast we begin departing on individual schedules. Airport transfers are provided.

Itinerary Highlights (Included in pricing):

  • Hotel accommodations
  • Meals as specified in itinerary (7 breakfast, 5 Lunches,  dinners)
  • Sightseeing and activities with entrance fees as specified in itinerary
  • Private transportation with an experienced tour guide (gratuity included)

Excluded (Not Included in pricing):

  • Airfare
  • Entry visa
  • Travel Protection
  • Any meals other than the ones stated in this itinerary
  • Beverages at meals or any other meals not specified in this itinerary
  • Optional tours/excursions
  • Personal expenses such as telephone bills, laundry, room service, etc.
  • Tips/Porterage (gratuity is only included for tour guide and driver).

There are no reviews yet.

Be the first to review “CUBA: The Cuban Life”

Passport: A valid U.S. passport is required to travel to Cuba and it must be valid for a minimum of six months after date of arrival.

A visa is also needed for Cuba however, this can often be obtained via your Airline (i.e. JetBlue).

To secure your booking, a non-refundable deposit of $200.00 is required. Your deposit amount will be deducted from your remaining balance and final payment has to be made by August 1, 2021You can submit full payment at the time of booking or you can be provided a monthly payment plan for the remaining balance. Roommates must submit their deposit on the same day.

Yes. Following the submission of your deposit, you will receive the option to build your own installment payment plan.


Due to the nature of this trip, bring only soft sided bags (i.e. duffel bags, hiking and book bags). Suitcases and checked baggage are unsuitable. Retractable luggage carts are permissible. Baggage should not exceeding 15kgs and 65x46 cm.

We take your security very seriously. We utilize a third party for the following reasons.

1. We use the same booking system for our groups that we offer to our Clients.
2. To safeguard all parties against fraudulent bookings and request for refunds.
3. To keep your personal information protected. Only under certain circumstances do we request credit card information directly.

Under certain circumstances UpLift Financing is available. Please email us at

For the acceptance of your booking for this trip, we will require that you acknowledge all of our terms and conditions.

1. Health and Other Hazards: You agree that it is your personal decision to travel, and you are doing so with full knowledge of current travel recommendations and travel restrictions with regards to the risks of COVID-19. We assume no responsibility for and shall not be liable for unsafe conditions or health hazards including pandemics or other illnesses. We have no special knowledge of dangers during travel or at destinations. For information related to such dangers, we recommend going to the State Department travel website at, click on "Find International travel Information” then click on "Country Information", and fill in the name of the destination country. For medical and health information, we recommend going to the Centers for Disease Control website at, then click on “Destinations” and scroll to the name of the destination country.

2. Rules of Travel Suppliers and Governments: We have no responsibility for COVID-19-related requirements that travel suppliers and governments may impose from time to time, such as health affidavit forms, health screenings prior to departure or upon arrival, face coverings, or quarantines. For the latest COVID-19 government travel regulations, we recommend going to IATA’s website at For the latest travel supplier requirements, check the supplier’s home page.

3. Financial Condition of Travel Suppliers: We are not responsible for the acts or omissions of travel suppliers or their failure to adhere to their own schedules, provide services or refunds, financial default, or failure to honor future trip credits. We have no special knowledge regarding the financial condition of the suppliers, and we have no liability for recommending a trip credit in lieu of a refund.

4. Rebooking: If requested, we will assist with obtaining any refunds due or rebooking trips using future credits, but we will charge a nonrefundable fee for such services.

5. Insurance: For your protection, we strongly recommend that you purchase trip cancellation and travel accident insurance. Please note that, unless you buy a cancel-for-any-reason policy, most policies have a specific clause stating they do not cover epidemics and pandemics, especially when travel warnings are in place. No representation or description of the insurance made by our staff constitutes a binding assurance or promise about the insurance. You agree to hold us harmless for your election not to purchase travel insurance or for any denial of claim by travel insurer as it relates to COVID-19 or any other claim under the policy.


7. Claims Deadline and Exclusive Jurisdiction: You agree to present any claims against us within 30 days after your trip ends and to file suit within one year of the incident, and you acknowledge that this expressly limits the applicable statute of limitations to one year. You agree that the courts in
Allegheny County, Pennsylvania will be the exclusive jurisdiction for all claims brought by you or us, and you hereby submit to the personal jurisdiction of those courts.

Yes. A cancellation fee of $200.00 will be assessed per traveler for the cancellation of a trip. The fee will be collected at the effective time of cancellation.

Your trip is a significant investment, and we recommend the purchase of travel insurance. If you choose to decline this valuable protection, you are assuming any financial loss associated with your travel arrangements. By declining to purchase travel insurance you fully understand that your travel agent is not liable or responsible for any expenses incurred as a result of cancellation or interruption, emergency medical and transportation, baggage and personal effects, flight and travel accident, and/ or rental car physical damage.

All group excursions are quoted with travel protection included. Declining coverage won't change the cost of your trip.