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Cuba: Why 2015 Is The Year To Go

by Wendy Perrin | January 5, 2015

When the White House announced last month that the U.S. was charting a new course on Cuba and easing certain travel restrictions, TripAdvisor’s U.S. site traffic to Cuba spiked nearly 300%, and more than half (55%) of respondents to a TripAdvisor site poll said they were interested in traveling to Cuba in 2015. And I thought to myself: Damn. I’ve waited too long.

As you know, my New Year’s Travel Resolution each year is to hightail it to whichever country is about to change forever. In 2015 that’s Cuba. Once the U.S. lifts the embargo and American hotel companies, cruise lines, and other travel businesses are able to start upgrading the country’s infrastructure for U.S. travelers, Cuba will inevitably start to look and feel less and less like Cuba and more and more like, well, America. U.S. travel brands are eager to pounce on Cuba because it’s got all the ingredients of a Caribbean playground—unspoiled white-sand beaches, sparkling blue sea, fabulous water sports—but with a robust culture, a flourishing arts scene, and renowned music and food to boot. On top of that, it’s got the allure of a place that’s been forbidden (to U.S. citizens, though not to Europeans, Canadians, or anybody else) for decades, yet it’s only 90 miles from Florida, so in future it could be just a quick nonstop flight from the U.S. Cuba’s hotels and restaurants have, until now, been forced to import their food, furniture, and all other supplies from Europe and elsewhere, but now they can start bringing in all that stuff from the U.S. Once hotel bedding and bath amenities change, once U.S. hotel and restaurant chains start to pop up, once cruise lines start to develop ports—and long before they start disgorging 20,000 cruise passengers a day into Havana—the experience of traveling in Cuba will change forever.

I have a number of well-traveled U.S. friends who’ve been to Cuba. Some have gone the authorized way—on an educational mission or group tour—and some have traveled on their own, the unlicensed way, flying there via Mexico or Canada and paying for their hotel and almost everything else in advance through a non-U.S.-based Cuba travel agency. For years I’ve heard their tales of strolling along the Malecon in Old Havana, being serenaded by street musicians who ask for only a few euros in exchange for hours of fabulous music, tooling around in vintage 1950s cars, biking across the country from beach to beach, and, as my intrepid-traveling friend Mary Munn Laronge recalls, “sitting on the porch of the wonderfully crumbling Hotel Nacional, sipping the world’s best mojitos—because Cuba is where they were invented—made by the same bartender who’s been making them the same way, with the same sugar cane and the same Havana Club rum, for the past 50 years.”

So when the news about Cuba broke, I spoke to assorted friends who’ve been there and came away with the following advice that I’m passing on to you:

* If you want to experience authentic—and relatively uncrowded—Cuba, go this year.
Once U.S. companies rush in to upgrade the tourism infrastructure and build the sorts of travel products that masses of Americans want and expect, Cuba will grow less…Cuban. With every year that goes by, the experience will grow more diluted and more geared to U.S. tourists, not to mention more crowded with them. So, if your goal is to see a place where time has stood still, get on the horn and book your trip now. Use a Cuba travel specialist (see below).

* If you want American five-star creature comforts, wait.
Right now Cuban hotels meet a certain European standard of comfort, but that is not the U.S. or international luxury standard. Sure, there are luxe beach resorts such as the Royalton Cayo Santa Maria, named the #1 all-inclusive resort in the world in the 2014 TripAdvisor Travelers’ Choice Awards, but that’s on a small island, north of mainland Cuba, that’s a planned resort development where employees are bussed in; you won’t find authentic Cuban culture there. If what you want is a true luxury hotel in the heart of old Cuba—one with round-the-clock ice-cold drinks, industrial-strength air conditioning, high-functioning Wi-Fi, and all those other niceties that Brits, Germans, and Spanish aren’t so picky about but that many Americans demand—wait till Cuba’s breaking-in period is over and the kinks in the infrastructure have been worked out.

Which Cuba travel specialist to use?  If you write to me here and provide as much detail as possible about the type of Cuba trip you’re envisioning, I can recommend the right travel planner for you, based on your trip goals, timing, and budget. 

UPDATE: If you’re seeking a Cuba trip, please read this updated Cuba advice.

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  1. Anyela D. O

    My partner and I have traveled to Cuba 2 times. Cuba is a beautiful country in the next days I travel to Havana and Varadero with . I recommend everyone to visit Varadero, it is an excellent spa. I also recommend rental houses they are cheaper than hotels.

  2. Mary Drobny

    I have been leading people to people tours for almost 15 years and over 100 groups with my license and also other licenses. I bring small groups on a variety of itineraries. This past Dec. 30 I had a New Year’s Eve group staying in Havana and then to Pinar del Rio with trips to Soroa orchid farm and the MOKA biosphere. The Jan. 7 photography group stayed in Havana with day trips out of Havana, a special off the beaten path day trip was to Angerona, an 1800s ruined sugar plantation. The Jan. 15 trip visited Havana, Cayo Santa Maria, Remedios and Camaguey. We enjoyed a Cuban rodeo and bar-b-cue at the King Ranch among other activities, and yes formerly part of the Texas King Ranch. Next trips in March are to Havana and the UNESCO World Heritage site of Trinidad. The second most visited city on the island. So many places to visit, thats why so many people return again. Its the people, artists, musicians in each place that the group gets to meet that makes the trips so personal.

  3. Douglas Miller

    My partner and I are leaving for a month of cycling in the Pinar del Rio region/province of Cuba. Our long time friends at Wow Cuba have recommended this as being one of their favorite areas in Cuba, especially for riding.
    We’ll stay in casa particular for the most part, maybe some of the 32 days in a beach side hotel in a quiet area out of the hustle of tourism. We’ve experienced the south eastern part of Cuba in the past both cycling and in resorts.
    We expect to see changes in that 4 year gap.
    Last year we cycled/traveled in Belize. We will blog our Cuba trip as we did in Belize.

  4. The Gentleman Backpacker

    I’ve been to Cuba via Grand Cayman and I had a wonderful time. Amazing photo opportunities as well. I happened to go for the 50th anniversary of the Revolution (1959-2009) so they had a number of events on. Happy to share any tips, etc. I didn’t use a guide and was perfectly fine. :-)

  5. Eileen

    Just back from a trip to Cuba with Geographic Expeditions and loved it! A perfect blend of talks with economists, dance, art and overnight trip to Vinales. Jennine Cohen is the contact at Geo Ex- highly recommended!

  6. Joslin Fritz

    Hi Wendy,

    I was bitten by the Cuba travel bug three years ago, when I started working as a U.S. Representative/Tour Leader for company offering People-to-People exchanges. Now, with over twenty trips to the Carribean country, working with multiple travel companies as a Tour Leader, I’ve started consulting individuals and companies on possible itineraries and logistical help with US licensing. I’m excited about these upcoming changes between the US and Cuba, and look forward to continuing to provide unique and authentic experiences for my participants and groups. Viva Cuba!

    1. Kay Showker

      I’m belong to a writer’s group some of whose members are interested in visiting Cuba this year. Can you please email me your contact information.
      Thank you, K. Showker

  7. fred husserl

    Just got back a mo ago and ready for a rtc trip to havana….
    ck out photo alliance nola for show end of jan

  8. Dave

    We traveled to Cuba on a Jazz tour with Insight Cuba. We found them to be an excellent provider. Very good logistics, accommodations and program. The local guide and American guide were both very knowledgeable.

    Insight Cuba also had the editor of Jazz Times accompany us on the trip. They have been doing Cuba tours for a long time so know their way around the country.

  9. lucila silva

    My partner and I traveled to Cuba over Christmas, 2011. I am a brazilian so legally entered CUBA albeit through Cancun. Our first three nights were booked through Montreal, Canada, the remaining 11 nights we totally winged it and stayed in other hotels, and pensione particulares. It was a fantastic vacation! Great food, freedom to travel where we wanted. To the west to Vinales (stay at the hotel there), back to Havana, to Santa Clara, Sancti Spiritus, Trinidad, Cienfuegos and back to Havana. We traveled twice by very comfortable and clean buses, and then took taxis from city to city!! The country side is BEAUTIFUL, people lovely, food delicious. Best fly fishing in the southern marshes. Havana Musuem of Modern Art is incredible, worth the trip just for the museum. Enjoy the cigars, leave your phone, ipad at home, you will not be able to hook up:) Truly a magnificent vacation.

  10. Your mother

    I know quite a few people who have gone and None of them booked through a tour. Money grubbing opportunists. Wolves in sheep clothing!

  11. Joan Russell

    Wendy – World Affairs Council of Philadelphia has held licenses under both the Clinton and Obama Administrations, We work with excellent TSPs (Treasury approved travel service providers) and have years of experience with people-to-people itineraries; the best accommodations; and special meetings. We bring special insights on the politics, economics and learn from Cubans across the social spectrum. Cuba is perfectly suited to educational travel. I also just had a family group of five return from a New Year’s trip and they loved it!
    Joan Russell, World Affairs Council of Philadelphia

    1. Kay Showker

      I saw your comment re Cuba on Wendy Perrin’s site. If the World Affairs Council of Philadelphia is planning a Cuba trip in 2015, I would be very interested in learning about it. Can you please email me the information.
      Thank you, kay Showker

  12. Lee

    Hello Wendy,

    There is such excitement on travel to Cuba. I have been following you and your advice for a long time. As a Travel agent specializing in personal/unique experiences, I have worked with many of your recommended travel specialists. I am currently partnering with DMC in Miami who are licensed and specialize in travel to Cuba. Having recently traveled to Havana with them through their People to People license, I can definitely attest that it is a wonderful destination and absolutely agree the time to go is now! If I can be of any assistance, please let me know.
    Lee Lennon, CTC
    Travel by Design, Inc.

  13. KathyK

    It’s funny that you ask for info on Cuba travel specialists, because when I also decided (quite spontaneously) to fit in a Cuba trip in 2015, my first stop WAS your WOW list ;-) I went with well reviewed and regarded People to People exchange operator, Insight for the Jazz in Havana trip. It seems like the perfect marriage for my family, with interests in photography, jazz and art. So far they’ve been incredibly responsive and helpful. I had 3 personal calls from them to insure they had answered all my questions and we had all the information we needed. I will let you know how it goes!

    I appreciate your straight advice. I have a well traveled friend who said to me on a forum that they would “wait till they rebuild Havana, when the service will be better” , so there are travelers for whom a trip this year might not be for them. Im glad you reminded poeple that it’s important to know what they want out of the experience!

    Thanks for keeping us updated on what you hear about changes…I’m curious how soon before ground is broken for that first US hotel or cruise ships start port of calls!

  14. Kim-Marie Evans

    I went to Cuba last year with cazenove+loyd out of the UK. We went the “authorized” way in that I was on a people to people visa however I experienced a Cuba that could not have been experienced without the guiding hand of c+l. They arranged the best hotels and Fincas, sent me to off the map restaurants and arranged for private meetings with artists. I was even able to purchase art through a curator who handled all the details for me. I cannot speak highly enough of their attention to detail and on the ground knowledge. Happy to put you in touch.
    Luxury Travel Mom

    1. Robin Gracey

      Please tell me about the folks who helped you with your trip to Cuba. I’d love to go. Is it safe enough?

  15. kayla

    Wendy, thanks for this very timely post, as you know I’ve been scouring for some of this info and trust you as a source! It’s on my 2015 travel list so I’ll be sure to report back! :)

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