First Time in Cuba

By now we’ve all heard the buzz about Cuba — the fabulous and recently accessible island country that transports travelers back in time with vintage cars and premium cigars galore! However, for most Americans, it’s also a destination shrouded in mystery. If you’re anything like me (before my visit), your knowledge of Cuba is limited to Cold War tensions and Fidel Castro. We understand — Cuba’s been under the radar for more than half a century; how could you know?

Since September 2016, a handful of the Extraordinary Journeys team has visited the country, each delighted with their discoveries. Over the winter holidays, I was thrilled to finally go myself and explore the island with my husband Chris. And let me tell you, Cuba deserves the hype.


Like most visitors, we flew straight into Havana. Unlike many EJ destinations, traveling to Cuba spares you the jet lag so you’re ready from the get-go. When we touched down, I was nervous. (Yes, even a travel professional like me.) I didn’t know what to expect. As soon as we exited the airport though, we were surrounded by warm friendly faces, classic vintage cars and essentially enveloped “back in time” — it was all excitement from there! In the taxi from the airport, we passed iconic building after iconic building with images of Che and other historical figures. It was amazing to finally see these sites with my own eyes. Half an hour later, we arrived at our “casa particular” (private home) in Vedado, the vibrant heart of the city. The energy here envelops you immediately, and Chris and I were totally enchanted.

At the airport, we had opted not to exchange money to avoid lines so when we arrived at La Reserva, we asked directions to the nearest bank (only three blocks away). None of the bank tellers spoke fluent English, and neither Chris nor I speak much Spanish. This was our first interaction with locals and I’m still astounded at how friendly and accommodating everyone was. Bank tellers and locals helped keep our place in line and translate at the counter. No one seemed frustrated by our lack of Spanish or, more surprisingly, that American tourists were slowing down the line. We felt this sense of community and acceptance every day throughout our visit.

**Travel Tip: If you’re like me with “un poco” high school Spanish, don’t sweat it. My Spanish is terrible but I try to speak it anyway (with the aid of a handy language app). The universal rule of thumb: As long as you make an effort, people respect the attempt and are happy to help.

In Havana we split our time between private tours and exploring the city on our own. Our guide William took us for a half-day colonial tour of Old Havana; from the cobblestone streets to the bustling bodegas to the lively main squares, we were hooked. Having a guide was so helpful because he provided context – the history and culture — and we were able to ask questions, solicit his opinion and dialogue about the current state of Cuba. Another favorite was touring the area in a private vintage car. (Opt for the convertible; it’s worth it.) Our guide expounded on city sites, Hemingway and other prominent figures from Cuba’s past.

**Travel Tip: Chris and I researched Cuba’s history before the trip, but I wish I’d read more. There’s so much to this little country — the more knowledge you have to start, the more you take away!

While we appreciated the expertise and company of guides, don’t underestimate the magic of spontaneity and exploring on your own too. There’s so much to experience — let yourself uncover some of it at your own pace between the more “planned” activities. Some of our fondest memories are walking to Calle 23 to catch taxis into Old Havana for dinner or a night on the town. Again, the language barrier exists, but we always managed to communicate (often with plenty of laughter in the process) and it was important to us to experience Cuba like locals. From shared taxis to walking the streets at night, we really wanted to live it and it made us fall even more in love with the city. Obispo Street in Old Havana was one of my favorite areas, where we happened upon a small gallery run by a charming older couple. We even purchased some art of our own (with a bit of haggling) that’s now hanging in our home in Denver.

**Travel Tip: Don’t overly worry about pickpockets or safety. As with anywhere, you want to keep your wits about you but I never felt unsafe exploring the streets of Cuba.


I almost didn’t want to leave Havana. How could anywhere match its magic? Then we arrived in Trinidad and fell in love all over again. To me, it’s the gem of the island. While Havana is old-world charm with a gloss of fresh paint and a more recent influx of money for infrastructure upgrades, Trinidad retains rougher edges from years past and the narrow cobblestone streets are lined with small, colonial houses. (Side note: I mean it when I say cobblestone here! It can make for difficult walking, so save your high heels for Havana.)

We decided not to arrange tours because Trinidad is perfect for exploring on your own. No destination, no problem: simply pick a direction and start walking to encounter the thrum of everyday life. Street markets sell beautiful fabrics, galleries feature local art and hole-in-the-wall bars and restaurants offer refreshments and music. One of my favorite memories from Trinidad was an evening spent at “Casa de la Musica”, a beautiful outdoor space perfect for people-watching and alive with music and dancing. Every night, live bands perform in the square while guests can snag a seat at the tables and chairs or recline on terraced stairs to soak it all in. As soon as we arrived that night a server was on hand to help us find seats with great views of all the action and run drinks to guests throughout the night. (Try the mojito!) Eventually, we continued to a small restaurant nearby with a balcony overlooking the streets. The music and laughter floating around us were infectious and made for an unforgettable night.

**Travel Tip: If you’re a night owl, try joining in the revelry and salsa dancing at Casa de la Musica. The energy is electrifying, and you’ll really feel like a local!

We only spent two nights in Trinidad but we could have stayed longer. We split time between perusing the city on foot and exploring nearby Playa Ancon. If you’re looking for a little R&R getaway, this nice, clean white sand beach is the obvious choice. Populated by both locals and tourists, the beach never felt overly crowded and was a nice break before our last stop.

Vinales Valley

Just like leaving Havana, I couldn’t imagine how Vinales Valley would match up against Trinidad…but again, we weren’t disappointed. You may have seen pictures of the enormous, alien-like rock structures in Vinales. Trust me, in real life it will take your breath away.

After spending days in cities, the valley offered both a change of pace and a sense of rural life in Cuba. One of our favorite experiences was the horseback expedition. We spent hours on dirt paths through tobacco plantations with stunning views of the surrounding area. While Chris and I aren’t exactly horseback experts, this was the ultimate (and more authentic) way to explore Vinales.

When eventually we had to leave Cuba, I was heartbroken. My greatest takeaway wasn’t the art, or the beauty of the valley, or even the charm of the cities. For me, Cuba is about the pervasive kindness of the people. It has the same spirit of kindness that first captured my heart in Africa and still fuels my passion for my work. Even after opening to American tourism, Cuba retains its heart and soul, sharing it freely with those eager to experience it.

Ready to go? Now is the time!