Cuba
Guided By Tim Tendick
Gain a different perspective on art, joy, and the past five centuries.
Eight nights in Havana plus two nights at the beach.
“Travel in Cuba really feels like learning about life. Plus, I’ve never known another place more likely to have live music drifting on a warm breeze. I don’t know if it’s something in the food or the genes, but Cubans dance like joy itself.” —Tim Tendick
Cuba
11 Days / 10 Nights
10–15 Travelers
$5995 per person (double occupancy)
+$1000 single supplement
A $1000 deposit reserves each spot
Balance due 90 days before
February 13—23, 2026
(Fri–Mon)
Highlights
Cienfuegos
Live Music
Topes de Collantes
Havana Cathedral
Neighborhood
Walking Tours
Classic Car Ride
Itinerary
Playa Ancon, Trinidad
Tour starts and ends in Havana.
Day 1–We’ll meet at our hotel in Cuba’s Old Town for an orientation meeting and the first mojito of the tour. Salud! Then we’ll take a ride in Havana’s famous classic cars to cruise the seaside malecon in style on our way to dinner together at one of the city’s famous restaurants formed in people’s homes, the paladares. Afterward you can hit the hay or stroll the promenade in the warm Caribbean breeze. Welcome to Cuba!
Day 2–There’s a lot to learn about this caricatured country and unique city, so we’ll get our bearing with local architects, a non-governmental organization planning Havana’s future, and (after lunch) a walking tour of Old Town. After dinner we know the best places for live jazz to really bring you in.
Day 3–What better way to start a Cuban day than morning salsa lessons? We’ll leave the ballet to the professionals of the National Ballet School, but there will be plenty more chances to get your boogie on. That evening we’ll head up to the fortress for the ceremonial firing of the cannon, sunset views, and dinner together.
Day 4–Few countries rival Cuba’s photogenic appeal, so today is about the camera. We’ll tour the Vedado neighborhood before meeting with famed photographer Roberto Salas, who can tell us firsthand what it was like to document the Cuban Revolution. That afternoon we’ll join a local photographer for a story-filled walk through the side streets of Havana before a free evening.
Day 5–Time to hit the road for the southern coast! We’ll stop in beautiful Cienfuegos, and get a chance to hear the award-winning local choir before heading to our seaside resort near Trinidad, where we’ll spend the next two nights in luxury.
Day 6–Optional morning trip to Topes de Collantes nature preserve to hike among the peaks and waterfalls. (It’s okay if you prefer to lounge around the resort, swim in the blue crystal Caribbean, or get good and sandy on the nearby Playa Ancon beach.) For the afternoon we’ll head into beautiful Trinididad, a city best known for the preservation and restoration of its 17th & 18th century Spanish colonial architecture, and vibrant salsa dancing. We’ll add a community arts and knitting project, and meet more of the locals who make Cuba what it is.
Day 7–I’d hate to have to choose between hiking OR beach, so we’ll enjoy a free morning for sand, sun, and sea before heading back to Havana. Along the way we’ll check out the Valley of the Sugar Mills and learn about this important piece of Cuban, colonial, and world history.
Day 8–Cuba is rightfully famous for its art scene, and today we’ll check out the National School of the Arts and a community project I’ve loved since my first visit over a decade ago. After dinner you can wander the galleries, make purchases if any walls back home could use a little zazzing up, or take another stroll on the malecon.
Day 9–Today we get to meet with a local film maker, watch one of her shorts, and have a Q&A about race and gender in Cuba. In the afternoon we’ll continue our dive into the country’s culture with a visit to a church that’s central to the island’s Santeria heritage, and meet with a friend who can tell us more about this faith tradition. There’s more to learn more about Afro-Cuban history, we’ll have a nice cup of Cuban coffee, and see about chances for more live music or even a baseball game.
Day 10–Global politics are not abstract in the lives of the Cuban people, and today we’ll learn about Cuba’s relationship with the United States, effects of the embargo, and their approach to the future. Our Cuban adventure will have flown by, but we made sure to include one more ride in those classic cars before our farewell dinner together.
Day 11–Tour over after breakfast. We’ll help arrange transportation to Havana International Airport or further travels in Cuba.
Tour itinerary subject to change.
What’s Included
Meet Artists, Thinkers & Everyday People
What’s Included:
A small group experience of 10-15 people
Ten nights accommodation, including breakfast
All breakfasts and two group dinners
All entrance fees and honoraria with local experts and guides
Transport by private mini bus
Pre-tour travel consultation and updates with Tim
All required paperwork to qualify for a legal visit to Cuba
Optional limited currency exchange of USD to Cuban pesos
Not Included:
Airfare & airport transfers to and from tour hotels
Activities, meals, and hotel extras not included with the tour
Travel insurance
Conditions:
Tour itinerary and What’s Included details subject to change. Future substitutions will be approximately equal or better in value.
This tour needs 10 travelers booked by October 1, 2025 to be viable.
FAQ
Old Havana
What is the legal status of travel to Cuba?
Travel “for tourist activities” remains prohibited for US citizens. However, there are twelve categories of authorized visits, one of which is educational activities and people-to-people exchanges, which is exactly what we do.
This is perfect for us, since we’re not going just to lie on the beach (though we’ll find time for that too). We are going to Cuba to learn about the island, its history, its culture, its people, its future, to meet locals, see things for ourselves, maybe learn how to dance or sharpen our skills, and more. To my mind, these requirements are not a barrier, they’re redundant conditions that would be fulfilled naturally anyway. They’re a good thing!
One of these requirements is that we work with a licensed provider and wouldn’t you know it, I know the best one. I am honored and delighted to work with the long-time Cuba expert who first took me to the island over a decade ago. With her insider knowledge and expertise, we have put together a truly remarkable visit to this truly remarkable place.
Is there anything I have to do to qualify?
Yes, there’s an online e-visa you’ll have to get, but we’ll help you with this simple process at the right time. (We’ll go over all of this with you when we get closer to the tour.)
How do we even get there?
At present there are direct commercial flights from Houston, Tampa, and Miami. If this changes between now and then, we will keep you up to date on any necessary adjustments.
Can we use Cuban ATMs to withdraw money?
Nope. Bring cash. We will talk about a budget, and can help you change US dollar (or euros) to Cuban pesos at the best possible rate.
Do they still have the CUC, the special currency for foreigners?
Nope, they got rid of all that. Just pesos now.
Is there wifi in Cuba?
Yes, kind of. Your phone will likely work pretty much as it normally does overseas, and our hotels will have wifi, but it will be very slow. Think 3G. For me, it’s a good chance to pretend it’s not there at all and disconnect for a little vacation. Family can reach you if they need to, but you can leave the news behind for 10 days. If you want.
What if I don’t speak Spanish?
No problem at all. I’ve probably seen more English language barriers in London than Havana, just because of the accent.
Will the current US administration block this trip?
My crystal ball ran out of batteries years ago, but whenever the US has changed its rules, already established reservations have always been honored and allowed. That’s why I have our hotels for 2026 and 2027 already booked. After that? We’ll see. This may be a vanishing opportunity, and I don’t want to miss out!
Is travel insurance hard to get for Cuba?
Nope. I’ve had good experience with World Nomads. They can cover things like tour cancellation and medical evacuation coverage. There’s a required Cuban health coverage that is automatically included in the ticket if you fly from either the US or Europe.
Is Cuba safe?
While this is always a subjective question, to my mind Cuba is intensely safe. A buddy system is a good idea anywhere, but I have walked around lots of Cuban cities and towns by myself at all hours with a fancy camera in my hand and never had any problem.
If I want to bring some kind of donation, can you help me figure out what to bring and who to give it to?
Absolutely! One of the things I appreciate about my collaborator on this tour is her insight into where and how we can most benefit our hosts. We can talk about that before we go.
Can I get a packing list? What’s the weather like?
Yup! We’ll send you a recommended packing list before the tour. The temperature in February is usually sunny and pleasantly warm, 77 F average, ranging 65 to 81. Try not to lord it over your family back home TOO much.
How’s the food?
In Cuba, as in many places like France and Italy, what used to be considered peasant food has become sought after cuisine. I can’t wait to dig into a plate of “ropa vieja” again, the stewed pork that seems to me like a Caribbean cousin of boeuf bourguignon.
Vegetarianism is not common in Cuba, but just let us know when you sign up and we’ll make sure you always have plenty to eat.
What questions am I not asking?
We’ll provide an orientation packet that goes over everything you need to know, and have an online call to go over everything with our Cuban expert. But rest assured, Cuba is not the forbidding land many of us were once told it was.