The Dream List: Cuba

(Last Updated On: January 11, 2023)

I had a chance to travel to Cuba in 2002. I didn’t go for a whole variety of reasons, including a (ridiculously optimistic) belief that travel restrictions would soon be lifted.I’ve continued to regret that decision, but — now that travel restrictions have been eased a bit – more tours are available. Is it finally time for me to visit Cuba?

Despite my belief that US policy toward Cuba is absurd, I’m not willing to travel there illegally. That leaves me with four options. I can travel to Cuba as:

  • Part of an academic program
  • The holder of a general license which allows visits by
    • Educational and other professionals in order to conduct research related to their job
    • Individual and religious groups visiting for religious purposes
  • Part of a pre-arranged and licensed “people-to-people” tour
  • The holder of a specific license for individual travel, which is allowed for freelance journalism and other professional and technical work not covered by a general permit

Note that NONE of these options allow visitors to travel truly independently. It is illegal to spend money or even accept anything for free in Cuba (doing so is classified as trading with the enemy) and all legal travel has to be arranged through an approved service provider. Under current laws, travel to Cuba is strictly regulated.

My “must-see” list
Cuba’s cities house a wealth of architectural and other cultural treasures, as well as art, music, and dance.

The top cities on my list include:

  • Havana is known as a photographer’s dream and is included on every itinerary. Old Havana and its fortifications are a UNESCO World Heritage site, but other parts of the city – not usually included in tours — seem well-worth exploring as well. In addition, Hemingway’s La Finca Vigía, lies a few miles beyond the city. And, of course, there has to be time for music.
  • The Viñales Valley is regularly cited as having Cuba’s best scenery. Tobacco is grown in the valley, which is also the home to unusual (and scenic) limestone mounds known as mogotes. The area is a UNESCO World Heritage site due to its traditional agricultural practices and the landscape with its mogotes.
  • Trinidad and the Valley de los Ingenios is also a UNESCO World Heritage site. The city is known for its treasure trove of colonial architecture.
  • Remedios is one of Cuba’s oldest settlements, a town that few people visit and guidebooks describe as “untouched by modernity.” The historic core is comprised of buildings that span three hundred years of history. It seems like the ideal place to simply wander.
  • Camagüey, the center of which is a UNESCO World Heritage site, is a city of architecture and arts. It sounds attractive, although maybe a bit touristy.
  • Cienfuegos is a lively colonial city, the historic center of which is yet another UNESCO World Heritage site.
  • Santiago de Cuba not only features a wealth of historic architecture, but is also awash in music and dance. San Juan Hill, where Theodore Roosevelt’s Rough Riders made history during the Spanish-American War, is located here, as is the Moncada barracks, where the Cuban revolution began.
  • Baracoa is Cuba’s oldest settlement. It also the island’s easternmost town and may enjoy the most stunning setting of any city in Cuba, tucked between the mountains and ocean. It is also quite remote, a place lost in time and a world apart even from the rest of Cuba.

Cuba has amazing natural areas, including wild, remote mountains that have barely been explored and some of the finest coral reefs in the world. The enticing options include:

  • The Sierra del Rosario, a UNESCO World Heritage Biosphere Reserve, includes a wonderfully reforested area and an orchid garden.
  • The Penísula de Ancón is a world of white sand beaches and blue-green tropical waters. It appears to be a bit of tropical paradise.
  • The Sierra del Escambray is an area of high, cool mountains. It is threaded with rushing rivers, home to many birds, and provides wonderful views of the landscape below.
  • The Jardines del Rey is described as a “wilderness of sandy coral islands.” While two of the islands are (over-) developed, the rest are uninhabited and perfect for exploring Cuba’s underwater world. There is a Hemingway connection as well, which makes it all the better.
  • The mountains of the Sierra del Cristal are a remote wilderness inhabited by rare endemic plants and birds, including orchids.
  • Santa Lucía sounds ideal for wandering the beach, snorkeling, and bird watching along the mangrove-lined lagoon.
  • The Guardalavaca area features beautiful beaches, great diving, mangroves, petroglyphs, forests, limestone mogotes, and archeological sites along with a few tacky tourist areas.
  • The Archipiélago de los Canarreos consists of one large island (with a colonial city and tourist facilities) and scores of uninhabited coral cays. The islands offer beaches, parrots, and nesting sea turtles alongside an underwater world of coral and shipwrecks.

I have a weakness for scenic drives and these also require getting off the tourist routes:

  • The North Coast Road between Mariel and Viñales is reputed to be a stunning drive, one that tours tend to skip in favor of the much faster (but far less scenic) autopista.
  • The Trinidad to Cumanayagua Loop connects Tinidad and Cumanayagua via some of Cuba’s most pristine scenery.
  • The coastal drive between Santiago de Cuba and Marea del Portillo features towering mountains, stark desert, blue-green water, and a few small villages. Of course, it could be impassible at any given time.

A tobacco field in Pinar del Rio, Cuba. Photograph by Henryk Kotowski via Creative Commons

Visiting Cuba on a People-to-People Tour
By far the easiest way for non-academics to visit the country is on a “people-to-people” tour. This is generally what is promoted in US travel ads and, because all of these tours must respond to the same peculiarities of US law, they all have a few things in common:
  • Every moment is accounted for on the itinerary and skipping a programmed activity in order to do something independently is strongly discouraged, if not actually prohibited.
  • All meals are provided.
  • The “people to people” focus means most of your time in Cuba is spent meeting artists, teachers, school kids, seniors, nurses, farmers, etc. (rather than out exploring and seeing things for yourself).
  • Pure “vacation” activities are prohibited. (Leisure travel to Cuba is illegal, making a morning of bird watching or an afternoon of snorkeling for the pure joy of it a violation of US law.)
  • Since there don’t seem to be any tours with a strong environmental focus, Cuba’s spectacular natural areas generally are not included on these itineraries.
  • There are no inexpensive tours.

Right now there actually aren’t very many companies listing fully licensed trips. Apparently the license needed has become harder to get recently and the number and variety of trips on offer has decreased accordingly.

Here is a sampling of what I found on offer for 2013:

  • Insight Cuba offers tours running from a long weekend in Havana ($2000) to their twelve-day Undiscovered Cuba tour ($4300). The latter spans much of the country, taking visitors to Havana, Santa Clara, Remedios, Camagüey, Bayamo, Santiago de Cuba, and Baracoa. This should be a good itinerary, as it includes some of the most beautiful and interesting areas in Cuba – but it appears that all of the time is spent in meetings and touring facilities, including a lot of things that just don’t interest me that much. It doesn’t include time to enjoy the country’s man-made or natural history. (Even the Scenic Cuba — which references the Sierra del Rosario, a UNESCO World Heritage Biosphere Reserve — doesn’t seem to actually stop there.)  Also missing is Cuban history, which doesn’t seem to be addressed in any meaningful way on any of the Insight tours.
  • Road Scholar’s Inside Cuba tour ($5600) allots fifteen days to explore the island, including stops in Havana, Santiago de Cuba, Camaguey, Santa Clara, Bayamo, Sancti Spiritus, Trinidad, and Cienfuegos. This tour includes a lot of history, architecture, art and culture. It also has the some of most interesting people-to-people meetings (for me) of any of the tours I looked at. While it covers much of the country, it seems a shame to be so close, and yet miss Baracoa in the far east and the lovely tobacco growing region of Viňales.
  • National Geographic Expeditions offers a nine-day Havana/Cienfuegos tour ($5800) that includes a day in Trinidad. It includes activities related to Cuban history, including the site of the Bay of Pigs invasion. The rest of the itinerary is similar to other Havana tours.
  • Smithsonian Journey’s Discover Cuba tour ($5900) is another nine-day trip with an itinerary similar to that of National Geographic, but without the Bay of Pigs activities and with more emphasis on historic architecture.
  • Overseas Adventure travel has three Cuba itineraries that run from nine to thirteen days ($3000 to $4300). Although each is focused on a particular region of the country, between them they spread across the island, including Havana, Baracoa, Santiago de Cuba, Cienfuegos, Trinidad, and the Viñales Valley. With a month or more to travel and adequate finances, these tours would cover the country.
  • Photo Workshop Tours offers six and nine-day tours ($4100-5000) with a lot of interesting activities, including photo walks with Cuban photographers, one-on-one critiques of work, and the chance to visit public and private photo collections. The nine-day tour takes visitors to Havana, Cienfuegos, Trinidad, Pinar del Rio, and Cojimar.
  • Friendly Planet’s nine-day Colors of Cuba tour ($3000) is at the “budget” end of the list. The tour is based in Havana, with day trips to Cienfuegos, Trinidad, Santa Clara, and Cojimar. It actually seems to include a little time to take in the scenery between meetings, but it also sounds exhausting. A six-day Discover Havana tour ($2100) is also available.

In addition to these fully-licensed people-to-people trips, Authentic Cuba Travel has a photo tour that advertises itself as an educational tour eligible for licensure for professional photographers as well as for “photographers seeking to improve their technique.” Their seven-day tour ($1800) includes photo tours of urban and natural areas AND free time to relax or take photos on your own. Along with Havana, the itinerary includes stops in Viñales, Cienfuegos, Trinidad, and Topes de Collantes National Park. (They also offer an architectural tour that looks good and would be appropriate for an urban planner.) Unfortunately, I am a bit skeptical of their claims of eligibility for licensure for Americans not affiliated with an educational institution.

Many of the cities I want to visit are included in at least a few people-to-people tours (although tours that include Baracoa are rare), so the challenge would be in finding a tour with the right mix of cities for me. However, that isn’t true of most of the natural and scenic areas, which not only aren’t included in standard people-to-people tours, but generally seem to be studiously avoided — as if the mere sight of a beach might invalidate the legality of the entire trip. The inability to spend time in natural areas, along with the busy ridged schedule and enforced togetherness, make most of the people-to-people tours rather unappealing.

Final thoughts
Right now options to visit Cuba are limited. That’s the reality at this point in time. So the question becomes whether I really have to see Cuba now or whether I can (should) wait?

And what will I miss if I decide to wait?

There is a chance that “normal” travel to Cuba will not be possible in in my lifetime. American access to Cuba has been restricted almost as long as I’ve been alive, so it is conceivable that this situation will continue indefinitely.

But I don’t think that will be the case.

The Cuban embargo is largely a grudge match and we are rapidly reaching a point where the principal players will not be with us for much longer. Castro is an ill old man. Once he is gone, it seems unlikely that the US will continue to feel such antipathy toward a ghost. Similarly, it seems unlikely that new generations of Cuban Americans — Americans who have never seen Cuba — will maintain the passion of their parents toward the loss of their ancestral homeland. Many of us don’t remember or understand why all of this was so important in the first place. Eventually we will all forget. At that point, the level of effort required to continue this strained relationship with a neighbor will seem foolish. Relations between the US and our tiny neighbor will be normalized and open and free travel will be allowed.

But a question remains: If I wait until that happens, will it be too late? Will the beautiful, decaying, lost-in-time Cuba I seek be gone forever?

The answer seems to be “it depends.”

While my crystal ball is as misty as the mountains of the Sierra del Escambray, I’ll venture a guess. Not only is there time, but that time might allow for the development of a form of tourism that is more authentic and less voyeuristic than the tourism of today.

Like the Americans before them, Canadians and Europeans come to Cuba largely to play in the sun. The resorts that have developed in response will continue to expand, with the future bringing more and better resorts. That expansion will likely destroy areas that are currently relatively unvisited and pristine (the diving paradise of the Parque Nacional Jardines de la Reina among them), but much of it will be confined to the areas where fungible tropical resorts exist today; for the foreseeable future their expansion will impact a relatively small piece of Cuba’s natural heritage. And along with them will come environmentally conscious eco-resorts that will provide less intrusive options for experiencing Cuba’s amazing natural areas.

The real threat to the Cuba of today lies in the loss of its cultural resources: the simple lives of its people, the crumbling historic architecture, lively arts, and traditional agriculture. But much of this exists as it is today simply because the Cuban people have few other choices. An end to the poverty that has turned Cuba into a time capsule would benefit the people of Cuba. It could also provide the resources needed to halt the slow disintegration of the island’s treasures. . . or it could be used to destroy them once and for all.

Money is (slowly) trickling in to save the country’s cultural and architectural treasures. It won’t be enough and it won’t come fast enough (especially without the help of the US), however, a wholesale makeover seems unlikely in the near future. Cuba’s urban treasures seem more likely to disappear through neglect and poverty over time than through the excesses of new development. Demise by neglect is the order of the day and is (sadly) likely to remain so long into the future.

Cuba’s agricultural tradition seems more likely to change rapidly as the country sees increased tourism, economic opportunity, and connection to the world at large. But what makes agriculture photogenic for tourists is a hard life for those living it. If tourism brings jobs and economic growth, traditional agriculture will begin to vanish as its practitioners seek better opportunities. While that may be disappointing for visiting photographers, it should make life better for the people of Cuba.

There will still be plenty to photograph when Cuba has a thriving economy and a normal relationship with the US.

I can wait.


The beach in Varadero, Cuba Photograph by Henryk Kotowski via Creative Commons

Sanctions information
Eased travel to Cuba not without hurdles (CNN)
Cuba Travel for Americans
Common Ground Education and Travel Services (Provides one-week people-to-people tours and will arrange independent travel for individuals holding their own licenses)
Authentic Cuba (Cuba Tourism Ministry)
Mark Moxon’s Travel Writing: Cuba

Cruising guide to Cuba (PDF) by Amaia Agirre and Frank Virgintino

Cuba Diving

More Dream Trips

1 thought on “The Dream List: Cuba”

  1. Excellent Dream List on Cuba! Thank you. Lots of informative factual data,
    both pros and cons. Your sentiments mirror mine almost exactly, and yes,
    it has been on my Bucket List for a long time. Perhaps one day we'll
    both get to visit and cross it off our lists.

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