What to expect on ‘Hola Cuba’, by Americans who have been on the trip

written by Bex Shapiro August 7, 2017
Hiking Vinales Cuba

There are less than 100 miles separating parts of the US from Cuba.

To say the two countries are so close but so far would be one hell of an understatement. And to call their political situation tricky would be one too. But here at Intrepid, we firmly believe that travel changes the way people see the world. We’re all about breaking down barriers by talking to locals, learning about different cultures through real life experiences, and trying to gain an understanding of our world by actually seeing it.

These are just some of the reasons why we’re so proud to run our ‘Hola Cuba’ trip, a people-to-people tour for US citizens that’s legal, educational and, importantly, fun. During the local-led 9-day trip, you visit a tobacco farm, try your hand at salsa, enjoy a cookery demo, hike to a waterfall, stroll around the picture-perfect Trinidad and Havana – and that’s just for starters. You experience a lot and you learn even more (yep, from Cubans themselves).

Vinales Cuba

Visiting a tobacco farm in Viñales

As a company, we think this is awesome. As a person, I think this is awesome. And as the Intrepid blog’s North America editor, I thought it’d be nice to not have to take our word for it. So, at the end of a recent Hola Cuba trip, I asked a selection of American passengers just two questions: what the highlight of their trip was and what they wish they’d known prior to setting off.

The answers are useful, they’re illuminating, and they explain why we do what we do:

Jill and Kent

Brief bios: Jill is a wonderful think tank owner (and dance enthusiast) who lives in Oakland, California. Her father, Kent, is an entrepreneurial investor (and absolute sweetheart!) based in Quincy, Illinois.

Vinales Cuba

Jill and Kent taking a selfie in Viñales

What was the highlight for you of Hola Cuba?

Jill: I had an unexpectedly spectacular night dancing at The Cave (Trinidad’s nightclub in a cave)! I had anticipated a more humble setting but it was one of the most incredible places I’ve ever danced in.
Another highlight was the warmth of the Cuban people – a constant thread throughout the trip and also a big surprise. Given the history of our countries I didn’t anticipate such genuine warmth and openness.

Kent: One of the most delightful aspects was the tour leader Dady’s enthusiasm for her work and for teaching us about her world. She alleviated our fears and trepidation from the very beginning, and did a marvelous job! The Intrepid trip – and Intrepid more generally, I’ve discovered – takes you right into the heart of the country. I’m going to look up Intrepid again and say, “Where in the world do I want to go?”
It was my first time traveling somewhere so developing and I found the places we stayed in to be very pleasant. I think all Americans should be encouraged to come.

What do you wish you’d known before the trip?

Jill: Not to over pack! And to take light clothing!

Kent: How unprepared I’d be for the heat. Traveling in July was very hot and I wish I’d brought less clothes with me – particularly because we had to move our baggage over cobblestone streets. Dady always encouraged us to drink lots of water but I think you need to start hydrating yourself before you even arrive. Bringing a 1.5 liter bottle is a good idea!


Aisha and Mia

Brief bios: Aisha (left) came to Cuba to celebrate finishing her medical training. The newly-qualified surgeon is from LA, is currently based in Philly, and was undoubtedly the funniest person on the tour. Her inspiring best friend Mia (right) works in education and lives in Houston.

Las Terrazas Cuba

Aisha and Mia looking out over Las Terrazas eco-village

What was the highlight for you of Hola Cuba?

Aisha: Developing a love for the country, free of the preconceived notions that Americans often have. When you get to Cuba you see that people are proud of their country and culture, that they want good relationships with the US. It’s important for people here in America to understand. The lack of wifi was also a really nice break – the fact it wasn’t omnipresent made the trip even better.

Mia: I think Dady was the highlight – I loved her enthusiasm and knowledge! I really like I got an authentic experience here. You can go on a tour and it’s just a tour, but this was different, this was really heartfelt. I really felt like I learnt a lot and that’s important to me. I have nothing negative to say at all! The food was great and fresh; not eating meat was not a problem. Everyone was nice and I felt safe – everything important to me as a female traveler was catered for.

What do you wish you’d known before the trip?

Aisha: To be honest, everything people said was difficult about Cuba wasn’t really problematic. I had heard a lot about the food not being good but we enjoyed it on the tour. You get used to the pure taste of food here, without the salt and sugar that is everywhere in America. I had also been told to bring toilet paper with me, but there was endless toilet paper in Cuba!

Mia: Not to bring a rain jacket! I was pretty prepared – I read the trip notes! It’s worth bringing a supply of snack bars because Cubans seems to eat dinner later than many Americans do.



Brief bio: Linda is a hilarious, warm-hearted Casting Director based in LA. She had been to Bhutan with Intrepid prior to Hola Cuba!

Vinales Cuba

Linda dining at Balcon del Valle, just outside Viñales

What was the highlight for you of Hola Cuba?

The people. The instant friendship and hospitality of the Casa (guesthouse) owners. Every single one was absolutely gracious. I felt no harm against Americans – you get more attitude traveling in the States than you do here! I’m amazed by Cuba and how the Cuban people do things: their creativity in utilizing the little they have, the organic food, all of it.

What do you wish you’d known before the trip?

I was working so much before the trip I didn’t get a chance to read the trip notes properly. I didn’t need to bring the toilet paper I brought with me! I wish I’d known the best way of making a difference. The one thing I walked away with is how much I want to help. I looked at the shelves of the supermarkets and it’s clear that the Cuban people are lacking, though they don’t show it.


Vivian and Dan

Brief bios: Vivian and Dan are lovely retirees living in Florida. She used to be a teacher and was a total trooper when hiking with a bad knee; he loves steak and collects old cars.

Trinidad Cuba

Vivianne and Dan hiking in El Cubano National Park, near Trinidad

What was the highlight for you of Hola Cuba?

Vivian: The accommodation. I didn’t expect the Casa owners to be so friendly and accommodating!

Dan: The architecture of Old Havana. It’s full of surprises!

What do you wish you’d known before the trip?

Vivian: I wish I’d known more Cuban history before coming. It happened in my lifetime and I assumed I was up to speed, but I wasn’t. I had been worried about the money system before coming but I had no issues.

Dan: I wish I’d known more Spanish.


Anne and Jeremy

Brief bios: Anne and Jeremy are an adventurous couple based in Seattle; they’ve traveled everywhere from Borneo to Ethiopia. She is a Bridge Engineer with a penchant for baking; he works in real estate and gets to enjoy Anne’s baking.

Viñales Cuba

Anne and Jeremy at Finca Agroecologica El Paraiso (organic farm) in Viñales

What was the highlight for you of Hola Cuba?

Anne: Seeing everything in Cuba for real. Dady did a great job of giving insight into local Cuban life and we found out things that you wouldn’t be able to look up online in the US. I was pleasantly surprised by the food – there’s more variety than people give it credit for, and it’s literally farm-to-table.

Jeremy: The cocktails! The Mojitos! Rum in the morning! I enjoyed visiting the tobacco farmer in Viñales and seeing how cigars are made, seeing how people live their lives in general.

What do you wish you’d known before the trip?

Anne: To bring really comfy shoes! I’d advise people to be flexible and not to be afraid. The heat was tough at times but it’s important for Westerners to get out of their comfort zone. They need to know what the rest of the world is like – that there are often fewer creature comforts and that many places are hot and have a less varied cuisine than what we’re used to!

Jeremy: I’m not sure, really. I hadn’t known how much music is in the blood here – everyone seems to dance! I’d tell Americans to limit their preconceived notions.


Risa, Nikki and Grant

Brief bios: Risa is the sweetest nurse around, and lives in San Jose, California. Her two hilarious children, Nikki and Grant, study Spanish and Environmental Policy and Economics respectively.

Las Terrazas Cuba

Risa (middle), Nikki and Grant at Las Terrazas

What was the highlight for you of Hola Cuba?

Risa: The sweetest host (Casa owner) in Viñales! She took us in and we honestly felt like part of the family, like we were at home. Her daughter even put on plays for us!

Nikki: I liked the waterfall. I like hiking and it was nice to learn about ecology and the area’s environmental problems from the local guide. Plus, the waterfall itself was pretty and I got to swim! You come here and you see everyone and they’re just living. It made me realize how much time I waste online and it kind of inspired me to delete some apps.

Grant: Going to The Cave nightclub in Trinidad. It was pretty packed and everyone was having a good time.

What do you wish you’d known before the trip?

Risa: How hot is was going to be! I should have read the trip notes more. And I hadn’t realized how temperamental the wifi would be. It worked for me the first time and then not at all.

Nikki: Not to bring any heavy denim! As an introvert I didn’t realize the trip would be as social as it was, but it was great.

Grant: I wouldn’t have worried about not knowing Spanish. Just travel with Intrepid and you’ll be fine!



Brief bio: Dady is a Cuban local who has been expertly leading Intrepid tours for nearly 10 years. She is from Trinidad, loves to dance (of course) and is pretty much the warmest, loveliest human around. Oh, and she knows all the best spots for foodies and shopaholics. Read her story here.

Havana Cuba

Dady at Plaza del Cristo in Havana

What was the highlight for you of leading Hola Cuba tours?

The Americans themselves! I’ve led American tours for over a year; I expected some difficult groups – it’s a busy itinerary!– but found only the most interested, interesting people. Honestly, Cubans didn’t know what to expect from American travelers, but I’m very grateful for the great groups I’ve led.

What do you wish Americans knew before going on the trip?

I call Cuba the land of inconsistency, but that doesn’t mean travelers need to stress about cash, tipping or their safety. Their leader will help them out. And if travelers can go without internet on the tours it will save themselves a lot of hassle!
Also, us Cubans have never been communists. Cuba was socialist until the 90s and now we are not socialists but not capitalists either.

Cuba is a beautiful country. The charisma, the people, the charm. It’s just lovely.

Travel changes the way people see the world. There’s no place this is more obvious than on our Hola Cuba tour. If you’re an American interesting in seeing Cuba through local eyes, check it out!

(All images c/o Rebecca Shapiro)

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