CUBA – the People, the Food, the Culture

DATES: 03/15/2024 - 03/23/2024
PRICE: $5,995.00

This will be an independent program without instruction.

This will be an independent program without instruction.

 An exploration of the exotic, enchanting island of Cuba!

This March Il Chiostro-Upside Down takes us to the “Pearl of the Antilles”:

Cuba is a fascinating and mysterious island country, closed to many Americans for decades. In this specially-curated Il Chiostro program, we’ll get up close and personal with its culture & history, getting to know this amazing country through various vantage points  around the island.

Of course we’ll explore the stunning city of Havana, but, we will also travel out to several colonial towns like Cienfuegos and Trinidad, and into the rural farmlands on the coast and in the Viñales area rainforest. In this expansive program we’ll engage with locals, experiencing their food, music, art, and architecture firsthand. Our Cuban guides will lead the program, explaining their diverse history and checkered politics of their unique island nation. Peeling away years of inaccurate news reporting, together we will uncover the true beating heart within the authentic Cuba!

Proposed itinerary (subject to change):

  • March 15 – meet in Miami for our first dinner together and an all-important orientation introducing our trip manager, distribution of visas, flight tickets and meeting one another.  You are free to arrange your own accommodation that night or we can make arrangements for you if you prefer.
  • March 16 – morning flight together Miami-Havana.  Check into hotel then intro to Cuba discussion over lunch with university professor.  Afternoon guided walking tour of Old Havana.   Dinner at a “paladar” – private family-run restaurant
  • March 17 – explore more of Havana, including waterfront, the infamous Hotel Nacional, dinner and an evening of jazz at the Buena Vista Social Club
  • March 18 – board our van for the rural western area of Viñales, lunch at an agroecological farm, explore the town, country dinner together followed by local music
  • Old Havana

    March 19 – tobacco/coffee plantation, local cooking lesson with lunch.  Optional: visit to local artist’s gallery, hiking with a resident naturalist,

  • March 20 – transfer to Cienfuegos with stops along the way, including lunch with a seafood chef; introductory walking tour of town center; dinner on the harbor, musical evening; overnight at hotel in Cienfuegos
  • March 21 – day trip to Trinidad, est. 1514, including walkabout with guide and local lunch; return to Cienfuegos for paella dinner and another optional musical evening
  • March 22 – return to Havana, experience Santeria, Cuba’s primary Afro-Cuban spiritual faith with a leisurely neighborhood walk, late afternoon visit to the amazing and provocative Fabrica de Arte Cubano; farewell dinner nearby the 9pm Canon Ceremony for the closing of the gates.
  • March 23 – morning return flight to Miami; make independent connections to transport home anytime after 2pm.

Daily excursions will allow abundant time for seeing visually and intellectually stimulating venues. Bring your cameras, bring your sketchbooks, bring your appetite.  We’ll combine the sights, music and stimulation of Cuba with an opportunity to meet and interact with plenty of local artisans, farmers, chefs and average Cubans.  For the entire trip we will have our own, independent van and be escorted by local guides who can help us understand customs, history and daily life in Cuba.

Join us for a true Il Chiostro-Upside Down experience!


Price: $5,995 p/p

  • single supplement $995 (limited number available)


  • Round-trip airfare Miami-Havana
  • All visas, permits and required paperwork
  • Room (double or single) in modern hotels with private bathroom (3 nights hotel in Havana, 1 night in Viñales, 1 night at inn in rainforest, 2 nights at hotel in Cienfuegos)
  • 3 meals per day
  • Local and Il Chiostro guides throughout program
  • Transportation for all excursions

Price does not include:

  • Transportation to/from Miami
  • 1 night hotel in Miami (although we can book a room for you)
  • Personal shopping
  • Tipping, which is encouraged and welcomed by the local Cubans

To Register:  just click on the Sign Up Now button.  A non-refundable* deposit of $1,000 is required to secure your spot in the workshop.  Payment can be made on line with a credit card, or you can follow the instructions to send in your registration and payment by mail.  Once we receive your deposit we will send you a formal Registration Confirmation with further information about the program.  You will receive 2-3 other correspondences by email prior to the workshop with information about Cuba, a supplies list and an electronic invoice for the balance.  Final Balance is due by December 30.  Any time prior to your arrival, if you have questions about anything regarding the trip or the program, you can contact us by email or phone and we’ll be happy to assist you.

*If we need to cancel or postpone this workshop for any reason, we will either return your deposit or allow you to apply it to any future workshop.  You will not lose your investment.

Contact us for more information: or speak to us live at 800-990-3506.

Viñales Valley


In Cuba, hotel options vary greatly.  Tourists are only allowed to stay in government-approved hotels set aside for foreigners.  To provide our participants an authentic flavor of the Cuban culture, from urban to rural and places in between, we’ve chosen a nice variety of cool places to stay.

Here is our plan for accommodations:

  • Miami – Hotel is not included in this package as we assume many people might arrange to extend their stay here independently or have access to their own accommodations.  If you would prefer us to organize a room for this night, we can make arrangements in the hotel where we’ll have our first dinner and orientation.  Just click that option on the registration page.
  • Havana – For 2 nights at the start of the trip and another night at the end of the program, we’ll be staying at the luxury-boutique Miramar Hotel with pool, jacuzzi and ocean views directly on the Caribbean.
  • Viñales –the picturesque town is the gateway to one of the more beautiful valleys in all of Cuba.  Here we’ll stay in a large tourist villa.
    Locals will tell you that only outside of Havana, in the farms and countryside and small towns, is where you’ll really find the heart of Cuban culture.  
    Viñales is just the place — a picturesque town in Western Cuba where you’ll find more authentic, serene, slower-paced Cuban culture and lifestyle. Lined with colorful colonial-era wooden houses, and featuring the sprawling Casa de Caridad Botanical Gardens, the town is known as the gateway to the fertile Viñales Valley, encircled by dramatic mountains and rolling limestone hills. Their traditional methods of agriculture (notably tobacco growing) have survived unchanged for several centuries, one of the reasons it was declared a UNESCO world heritage site in 1991.
  • Rain forest in the mountains outside of Viñales – we’ll be staying at a hilltop inn, Las Terrazas, for 1 night
  • Cienfuegos City – this small, quiet port city lies in the Cienfuegos Bay, on the south-central Cuban coast.  Here we’ll stay at the Hotel Jagua, for two nights, overlooking the bay and the Caribbean. The hotel also has a large pool and a spacious pool-deck overhanging the bay. The Jagua lobby bar is a popular gathering spot.

    The town is elegant and colonial, unique in that that it was originally settled by French immigrants, not by Spaniards! Its French charm creates a unique overlay to the Caribbean vibe and the Spanish influences. Cienfuegos is famous for its stunning sunset views from the malecon when the locals emerge and the boardwalk comes to vivid life – yet another unique glimpse of Cuba. In 2005, Cienfuegos was declared a UNESCO World Heritage site thanks to its well-preserved historic center.



The first time the group will meet is in Miami.  Participants should make plans to arrive there independently.  Our orientation is planned for 6pm on March 15th.

The next morning, we’ll travel to Havana as a group.  The round trip flight between Miami and Havana is included in the program fee.  Tickets and visas will be organized for everyone.

On Saturday, March 23rd we will return to Miami by mid-afternoon.  You can make connecting plans from there for your final destination.  We can assist you in making your connecting flight, if you would like.  But we ask that you don’t plan to depart before 2:30pm.

It is perfectly legal for Americans to travel to Cuba.  However, the United States and Cuba still have a strained relationship, so there are a few restrictions that apply to Americans.  For a primer on the history of US-Cuba relations, this article from the Council on Foreign Relations paints a thorough picture.

Here are a few things to keep in mind when traveling there:

Money – What’s the best way to pay for things in Cuba? How much money should travelers bring?  The Cuban Convertible Peso is what tourists use.  (You cannot use the American dollar.)  Exchanging money in Cuba can be unreliable and can take an inordinate amount of time, so our agency will exchange in advance whatever cash you think you will need.  If you have cash left over, they will exchange it back into American dollars at the end of the trip.  Note that American visitors can’t spend money at businesses linked to the Cuban military.  You are also required (by the American government) to keep your receipts from Cuba for 5 years.

A Cuban bar

Credit and ATM cards – leave them at home.  You cannot use these anywhere in Cuba.

Internet – is not readily available in many places.  You should plan to reduce your dependence on the internet during this trip.

Guides – throughout our trip we will have local guides who can answer our questions, direct us to the best places to see and to help us with any problems that may arise.

Transportation – we will have our private vans and drivers throughout our program.  They will take us between primary locations and on short excursions. We will not be taking any internal flights between locations.

Visas – also known as the Cuban Tourist Cards are required for all visitors.  All tourists also need a type of travel license stating what the category of your tourism falls under. These will be arranged for us by our tour managers and distributed to us at the first night orientation in Miami.

Travel Insurance – is required for all visitors to Cuba. Your insurance needs to cover any unexpected medical expenses you may incur during your time on the island

Safety – Cuba is an extremely safe country to visit.  But we still recommend taking the same precautions you would in any foreign country or big city.