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How to Pick the Perfect Cuban Destination For You

July 19, 2016
11 min read
How to Pick the Perfect Cuban Destination For You
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Just back from a three-week trip to Cuba, TPG Contributor Lori Zaino highlights some of the best places to visit so you can decide where to go first. (All photos are by Darrel Hunter unless otherwise specified).

Cuba offers so much beyond its capital city of Havana, and thanks to new flights launching this September on Silver Airways and American Airlines — which you can even use AAdvantage miles to book — you can fly nonstop to several incredible destinations around the country. However, deciding where to go can be difficult, as there are so many wonderful spots to choose from. Here's my cheat sheet for things to see in each of Cuba's major cities, with helpful tips for where to stay and how to get there.


Who Should Go: Hemingway fans who want to see Papa's old stomping grounds and people looking to party with the locals.

Havana is the perfect place for a city break.
Havana is the perfect place for a city break.

How to Get There: Keep an eye on flights that might soon be heading to Havana from the US later this year. Otherwise, starting September 11, you can fly into Juan Gualberto Gómez Airport (VRA), located between Matanzas and Varadero, twice daily from Miami (MIA) on American Airlines. From there, you can contract a driver or rent a car to take you to Havana, an hour and 45-minute drive away. I highly recommend Ivan and you can contact him here: or +53 52900743.

Where to Stay: Hotel Saratoga is perfect for those looking for luxury amenities like a rooftop pool or free Wi-Fi, which is a rare find here. If you're in the mood for something a little more local, this Airbnb rental features a traditional colonial-Cuban style look, and Ms. Osmary, the host, will ensure you have a perfect stay. If points-hotels are more your style, redeem a free stay at the Four Points by Sheraton Havana for 20,000 Starpoints per night.

While You're There: Throw back a refreshing happy hour mojito on the rooftop of the Hotel Ambos Mundos in Old Havana, one of Hemingway's old haunts, then head over to the Paladar San Cristobal for some traditional Cuban food — President Obama ate here during his recent trip to Cuba and was a big fan of the sirloin steak.

Cuban fare at San Cristobal. Try the sirloin steak (it's what President Obama ordered).
Cuban fare at San Cristobal. Try the sirloin steak — it's what President Obama ordered when he was here.


Who Should Go: Honeymooners and anyone else seeking an all-inclusive retreat or beautiful beaches with amenities like lounge chairs and beach bars.

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Varadero's fine white sands and crisp turquoise waters.
Varadero's fine white sands and crisp turquoise waters.

How to Get There: Starting September 11, 2016, AA will fly into Juan Gualberto Gómez Airport (VRA) twice daily from Miami. From there, grab a taxi or rent a car for the 40-minute drive to Varadero.

Where to Stay: The Meliá Las Americas is a swanky, adult-only resort that's perfect for a romantic getaway. For a more family-friendly option, try one of the many Iberostar properties located in Varadero.

Varadero is perfect for the traveler who wants to simply lounge by the pool or beach.
Varadero is perfect for travelers who want to simply lounge by the pool — if you can bring yourself to leave the beach.

While You're There: Spend some time relaxing on the fine, white sand of this 12-mile stretch of beach and admire the crystal blue waters of Varadero. While most hotels and resorts in Varadero are all-inclusive, it's worth it to spend a day outside the resort area and get a sense of real Cuba. Rent a moped and explore nearby cliffs and beaches, then chow down on some fresh lobster at La Gruta del Vino for lunch.


Who Should Go: Cienfuegos was colonized by the French, so those who love a nice European architectural influence will appreciate not only the city's brightly-colored buildings, but also the neoclassical, gothic and Mudéjar art reminiscent of the Alcazar Palace in Seville, Spain. Hipsters and artsy types will love the random street art found throughout the city.

A view of the stormy sky from the Palacio de Valle in Cienfuegos.
Stormy skies as seen from the Palacio de Valle in Cienfuegos.

How to Get There: Hop an American Airlines nonstop flight from Miami (MIA) to Cienfuegos (CFG) starting September 7, 2016, or a daily nonstop flight on Silver Airways from Fort Lauderdale (FLL) starting October 21, 2016.

Where to Stay: Spend the night at Hotel Palacio Azul, the most iconic hotel in the city, located next to the Cienfuegos Yacht Club.

Explore Cienfuego's architecture and street art.
Cienfuegos is full of funky street art, like this.

While You're There: Wander around the city to get a feel for the architecture, then pay a visit to the Spanish-inspired Palacio de Valle and Teatro Tomás Terry, a beautiful, old fashioned theater dating back to 1889.


Who Should Go: Salsa lovers and anyone looking for creative inspiration, bold colors and quaint streets.

How to Get There: Fly into Cienfuegos (CFG), as I detailed above. From there, it's about an 80-minute drive to Trinidad.

Trinidad is a feast for the senses.
Trinidad is one of my favorite cities in Cuba, a true feast for the senses.

Where to Stay: A homestay or casa particular, is the way to go in Trinidad. I recommend staying in Casa de Fidel y Yesenia, an Airbnb property that offers a private rooftop and great views of the city.

Trindad at dusk from Fidel and Yesenia's Airbnb rental.
Trindad at dusk from the Casa de Fidel y Yesenia's Airbnb rental.

While You're There: Explore every nook and cranny of this charming city, and when it's so hot you can't take it anymore, grab an iced coffee from Café Don Pepe and chill out in its picturesque garden patio. There's live salsa music and dancing in Plaza Mayor every night starting around 10:00pm, so kick back with a Cristal cerveza and enjoy the music or get in on that bailando action.

Playa Larga and Playa Girón

Who Should Go: Anyone in search of an off-the-beaten-path adventure, snorkelers and divers, nature lovers and history buffs who want to visit the site of the Bay of Pigs Invasion or explore nearby Museo de Playa Girón.

How to Get There: Head to Cienfuegos (CFG), as described above, then drive (or ride) about 90 minutes to reach these two spots.

You can see some incredible marine life while snorkeling around the rocky areas of Playa Larga.
Snorkel around the rocky areas of Playa Larga for a look at some of the local underwater wildlife.

Where to Stay: This area is still pretty under-the-radar, so you'll most likely have to book a B&B or stay in a casa particular homestay. I especially liked Casa Frank, which had a great rooftop restaurant and bar attached.

While You're There: Swim and snorkel in Cueva de los Peces, a natural, salt water cenote that's 200 feet deep and filled with tropical fish. Entry is free, but you can also contract dives that will lead you from the cave system out to the ocean. Nature enthusiasts can visit the swamp-like Ciénaga de Zapata National Park, a UNESCO World Heritage site where you can spot egrets, crocodiles and flamingos. Check out the Museo de Playa Girón for more info on the Bay of Pigs Invasion — everything is presented in Spanish but offers a solid dose of history, Cuban-style.

Spend a relaxing day snorkeling at Cueva de los Peces, a natural, salt water cenote.
Spend a relaxing day snorkeling at Cueva de los Peces, a natural, salt water cenote.

Santa Clara

Who Should Go: Cigar aficionados, college students for its university town vibe and anyone who loves Che Guevara.

How to Get There: Silver Airways will operate one daily nonstop flight from Fort Lauderdale (FLL) to Santa Clara (SNU) starting September 1, 2016, while AA will offer two nonstop daily flights from Miami (MIA) starting September 9, 2016.

People watching in Santa Clara is an interesting activity.
People watching in Santa Clara is an interesting activity.

Where to Stay: There aren't a ton of hotel options in Santa Clara, so it's best to stay at an Airbnb, like Amarillo B&B, which has nice garden views. Whereas you won't find luxe digs in Santa Clara, Hostal D'Cordero II is also a nice option if you'd like something that feels a bit more regal than usual.

While You're There: The Che Guevara Monument is one of the town's main attractions, complete with a mausoleum holding Guevara's remains. Cigar lovers should visit the Constantino Perez Cigar Factory, which offers insights on how some of the top brands like Montecristo and Romeo y Julieta are made.

The Che Guevara Mausoleum definitely warrants a visit. Photo courtesy of <a href=";clicksrc=download_btn_inline&amp;id=88508956&amp;size=medium_jpg&amp;submit_jpg=" target="_blank">Shutterstock</a>.
The Che Guevara Monument definitely warrants a visit if you're in the Santa Clara area. Image courtesy of Shutterstock.

Santiago de Cuba

Who Should Go: Those seeking a less touristy urban experience than Havana will love Santiago de Cuba, the country's second-largest city — because it's much closer to Haiti and the Dominican Republic than the rest of the country, its got not only a Cuban, but also a very Afro-Caribbean history and feel. Carnaval is also a big deal here, so visiting during that festive time of year is a great way to experience the culture. Nature lovers will want to check out eclectic ecosystems surrounding the city.

How to Get There: Silver Airways will start flying to Santiago de Cuba (SCU) from Fort Lauderdale (FLL) on November 3, 2016.

Santiago de Cuba is Cuba's second-largest city after Havana.
Santiago de Cuba is the country's second-largest city after Havana.

Where to Stay: Those looking for the most luxurious option can stay at the Meliá Santiago de Cuba, which has a refreshing pool area when you need a break from the heat.

While You're There: UNESCO World Heritage site Castillo de San Pedro de la Roca, also know as El Morro, is a massive castle perched on a hilltop just outside the city that definitely warrants a visit. While there's plenty to see within the city limits, like the Parque Céspedes historic area, Santiago de Cuba's nifty location between the Baconao Park and Biosphere Reserve, the Sierra Maestra mountains and the beach makes the area a great base for taking day trips outside the city.

Baconao Park and Biosphere Reserve is a beautiful, protected area located just outside Santiago de Cuba. Photo courtesy of <a href=";clicksrc=download_btn_inline&amp;id=377096026&amp;size=medium_jpg&amp;submit_jpg=" target="_blank">Shutterstock</a>.
Baconao Park and Biosphere Reserve is a beautiful, protected area located just outside Santiago de Cuba. Image courtesy of Shutterstock.

Final Tips

Note that current travel restrictions mean American citizens technically can't travel to Cuba strictly for tourist purposes just yet. You'll have to sign an affidavit stating that you're traveling there for one of 12 reasons approved by the US government, and lounging in an all-inclusive resort isn't one of them — Cuba doesn't care, it's the US that does, so it might be worth tacking a few days of relaxation onto a guided, people-to-people tour just to be safe.

If you're interested in cruising to Cuba rather than flying there, read TPG Senior Editor Kaeli Conforti's review of the Fathom cruise or check out these posts from her time in Havana, Cienfuegos and Santiago de Cuba. These posts about 9 essential things to pack and 10 essential tips for traveling to Cuba are also worth a look.

Have you been to Cuba yet? Which areas are you most excited about visiting? Let us know, below.

Featured image by Darrel Hunter