One of my more important lessons as a traveler came early—when I was 19 and backpacking around Europe with my best friend—and it’s never failed me: deviations from your planned itinerary, whether chosen or forced, always result in unexpected and delightful experiences, if you are open and allow them to unfold.

So, when my partner Nick and I arrive at a bus station during our tour of Cuba and find that all departures from Havana to Santiago de Cuba are booked for days, I sit back and realize that this is certainly going to be one of those “happy accidents” (as I like to call them).

The woman behind the counter says we can board a bus to Trinidad in 30 minutes or wait three days for a bus to Santiago. Without hesitation, I hand her our money and we get on our way. The itinerary we sketched out for our month-long Cuban adventure didn’t include a stop in the exquisitely preserved colonial city of Trinidad, but throughout the last week, I had started wishing it did because every local we met told us we couldn’t leave Cuba without at least spending a few days in Trinidad. It seemed that fate agreed.

Trinidad is sort of on the way to Santiago, so we decide to spend a night there and then “get back on track,” but we fall in love with the city immediately. Enamored with this quaint, colorful community, rich in cultural and historic attractions and surrounded by stunning natural areas, we stay for four days and even then, we are reluctant to leave. Though we love every moment of our time in Trinidad, these following experiences stand out.

Casa de la Musica

We arrive in early evening and the first thing I notice after stumbling off the bus is the Cuban music wafting through the darkness. We settle into a casa particular—a private homestay—and then venture out to find food. Instead, the festive notes floating from maracas, drums, guitars and an array of other instruments, draw us to Casa de la Musica, an outdoor venue set on a sweeping staircase right off the Plaza Mayor, the remarkable square situated in the heart of old town. Every night, locals and tourists gather at Casa de la Musica to enjoy Caribbean rum in its many forms, to experience high-caliber music and of course, to celebrate life by dancing until all hours of the night. Even if you’re not ready to strut your salsa skills, grab a seat, a mojito (or two or three) and get ready to absorb the palpable and contagious energy.

Playa Ancon

After enjoying a delicious breakfast accompanied by a local soundtrack—the clip-clop of hooves on the cobblestones and native birds chirping with delight—we hop on our bikes and head through the colorful streets toward Playa Ancon, a sparkling white sand beach where we catch some rays and snorkel in the warm, salty waves. Though you can take a taxi here, we rent bikes and enjoy the 37-kilometer loop ride, a magnificent, enjoyable and leisurely adventure that heads back along the rugged, rocky coast near the small seaside village of La Boca. This return route rewards riders with a spectacular sight (especially at sunset): the turquoise waters of the Caribbean shimmer in the foreground while the lush Sierra del Escambray (Escambray Mountains) tower on the distant horizon.

Biking Playa Ancon Cuba

© Chris Kassar

Topes de Collantes

Nick and I huff and puff uncontrollably as we pedal up the steepest road in creation (or at least that’s how it feels) as we ride upward toward Gran Parque Natural Topes de Collantes, a protected nature reserve that encompasses verdant mountain slopes vegetated with thick pines, ferns, bamboo and eucalyptus. I understand now why our Cuban hosts responded so incredulously when we said we were going to ride here today; the road is straight up and unrelenting for miles, so it’s not the most enjoyable bike ride, but it is beautiful. Regardless of how you get here (we recommend a taxi or shuttle!), no visit to Trinidad, Cuba, is complete without exploring a bit of the 90 kilometer-long Sierra Escambray, the island’s second largest mountain range.

An extensive network of hiking trails mean you can immerse yourself in the area’s varied ecosystems, discover the park’s biodiversity and experience the immense natural beauty of Cuba. Shower in a waterfall, plunge into a cool pool or rushing stream, delve deep into a cave, or see how many bird species you can see and hear while rambling through lush forests buzzing with wildlife activity.

This story and photos were shared by Chris Kassar, an outdoor adventurer and a freelance travel writer for Nat Hab.