Best Things to Do in Trinidad and Cienfuegos: A 3-Day Cuba Itinerary

I just returned from another heart-stirring trip in Cuba — the island where my family is from — and this time I traveled to Trinidad and Cienfuegos, to see more of the beautiful country whose people have been suffering for over 70 years now.

It’s important for me to relay accurate, safe, and legitimate information to travelers, especially from the U.S., so that you not only comply by the rules in place, but so that you understand what the people there have to go through, and that Cuba is much more than just old cars and crumbling colonial charm.

If you want a unique experience to see a different side of Cuba, with Caribbean nature, fresh seafood, vibrant culture, and a little adventure, this three-day excursion between Cienfuegos and Trinidad delivers.

As a solo female traveler who seeks extreme adventures and embraces local culture, I found this route safe, soulful, and full of the best things to do in Trinidad and the best things to do in Cienfuegos!

First things first though:

Please be aware of the rules and regulations for U.S. travelers! You cannot go to Cuba for tourism purposes, and you cannot spend any money at government owned places (like hotels and restaurants.

Read my other posts for more information!

How to Get a Visa for Cuba

15 Travel Fails to Avoid in Cuba

10 Tips for Traveling Solo in Cuba

The REAL Cuba: In Their Voices [VIDEO]

If you’d like help planning a completely legal and legitimate trip to Cuba, and especially if you’d like to help bring food/medicines, please get in touch! info@Mylifesamovie.com

Day 1: Best Things to do in Trinidad!

Leave Havana early to get to Trinidad through the scenic Escambray foothills and check into a casa particular near Plaza Mayor. Walking Trinidad’s cobblestone streets, visiting Museo Romántico, and pausing at Iglesia Parroquial de la Santísima are essential items on any “best things to do in Trinidad” list.

Explore pastel houses, artisan shops, rum bars, and live-music corners; let yourself wander and enjoy impromptu performances. If you’re feeling up to it, climb up the bell tower for a panoramic view of the city!

In the evening, take part in a cooking lesson, salsa class, or drum session, followed by an authentically cooked meal, and one of the famous local drinks, “canchancara”! You’ll get to stay at a beautiful casa particular, likely that used to be owned by a wealthy Spanish colonizer.

FYI! Trinidad is home to one of the most famous nightclubs in the world! BUT, it’s government owned, so U.S. citizens can’t go there. If you’re not a U.S. citizen, feel free to check out Disco Ayala — it’s located inside of a cave!

Day 2: Hike to Waterfalls in Parque Guanayara

Early in the morning you’ll head to the mountains to take a guided hike to Parque Guanayara arranged by a local agency. You’ll use what they call a “Russian limousine”, which is an old war truck, to go up the steep hill to the park’s entrance. It’s a bumpy ride, but better than walking!

The trail climbs through jungle and farmland to sweeping views of the Valley of the Sugar Mills, with a stop at a gorgeous waterfall and natural swimming pools for a cooling dip (very cooling, in fact, freezing).

The hike is rewarding and strenuous in parts, so wear sturdy shoes and bring water and insect repellent! End the hike at a jungle cafe and enjoy a delicious lunch, and celebratory mojito, before heading back to Trinidad.

Return to Trinidad for sunset drinks and another delicious meal!

Day 3: Best of Cienfuegos: Kayaking, Castillo de Jagua, and Lobster Lunch

Another early start so that you can make the long drive to Cienfuegos for a guided kayaking tour on the Bay of Cienfuegos, that includes a stop at Castillo de Jagua. Paddle across warm turquoise water, glide next to mangroves, and land at the 18th-century fortress that once guarded the bay entrance.

Guides share colonial history and pirate lore, and the fort offers great photo vantage points. The kayak-to-Castillo Jagua trip ranks among the best things to do in Cienfuegos because it combines active adventure with local storytelling. After exploring the castle, paddle back down the bay to a fun outdoor restaurant, where you can enjoy a lobster lunch by the bay — grilled with garlic and lime, served with rice and plantains.

Afterwards, head back into the town in Cienfuegos and check into a centrally located casa particular or boutique guesthouse near the Paseo del Prado. Start at Parque José Martí, the lively city square with neoclassical architecture, Teatro Tomás Terry, and local life that’s perfect for photos. Walk the Paseo del Prado toward the Malecón and visit Punta Gorda’s seaside mansions for panoramic bay views.

For anyone searching for the best things to do in Cienfuegos, the city square, Yacht Club photo ops, and a sunset stroll along the bay should top the list. Stop for lunch at a paladar near the square and order the day’s catch — Cienfuegos seafood is simple and superb.

Spend the evening enjoying a delicious dinner and an early night.

Practical Travel Tips for U.S. Citizens Traveling to Cuba

U.S. citizens must travel to Cuba under an authorized category such as people‑to‑people exchanges, support for the Cuban people, family visits, or professional research; pure tourist travel is not permitted. The simplest, least stressful option is booking an authorized group trip or working with a U.S.-based travel organizer who provides the required itinerary and documentation.

Keep daily schedules, receipts, and local contacts on hand. Obtain a Cuban Tourist Card (tarjeta) for entry and exit — some airlines provide it at check‑in, but verify beforehand. Bring enough cash for the entire trip because U.S. bank cards and ATMs often do not work.

You can use U.S. cash in most places, but it’s good to exchange some into Cuban pesos for things like souvenirs. Using euros or other currencies is currently not ideal as they give the same rate as the U.S. dollar!

Purchase travel/medical insurance, some airlines or vendors sell Cuban coverage or include it in the fare. Data connection is limited in Trinidad and Cienfuegos but the wifi worked decently in most casa particulars—you can buy a buy a Cubacel sim card if you have a sim card slot, but don’t bother with eSIMS, they don’t work.

Use registered taxis, keep valuables discreet, learn basic Spanish phrases, and avoid sensitive political debates with strangers.

Trinidad and Cienfuegos Packing Essentials and Safety

Pack sturdy hiking shoes, reef-safe sunscreen, a wide-brim hat, reusable water bottle, insect repellent, a small first-aid kit, portable battery pack, photocopies of passport and tourist card, and lightweight quick-dry clothing.

Carry small bills for tipping casa hosts, guides, and drivers; gratuities are expected. Trinidad and Cienfuegos are welcoming and generally safe for solo women, but exercise usual precautions: avoid poorly lit streets at night alone, use registered taxis, and ask your casa host for neighborhood safety tips.

Ready to Book a Legal, Customized Cuba Trip?

I help connect travelers with tour companies who offer legal Cuba itineraries for U.S. travelers — custom solo routes or small-group people‑to‑people trips that comply with U.S. requirements. We can design a 5–10 day Cuba adventure, arrange casas, vetted guides, transfers, and the kayaking plus Parque Guanayara day! Send your travel dates and style preferences and I’ll draft a tailored itinerary and pricing to make your Cuban adventure unforgettable! info@mylifesamovie.com

OR! Join our next Support for the Cuban People Group Trip to Cuba — Click Here and fill out the 2027 poll to get notifications!

Please don’t forget! I work extremely hard to produce these free travel guides and posts! If it helped you, or you enjoyed it, PLEASE give it a share on social media, and follow me to keep up with more posts! You’re two minutes of effort truly helps keep my business running! Thank ya!

xx, Alyssa