How to spend one week on the red-hot island.

By Frank Roffers

With its faded beauty and history intact, Cuba fuses a unique blend of Caribbean and Latin. It leaves you shocked, perplexed, confounded and with a feeling of sensory overload. The largest island in the Caribbean offers stunning architecture, wide-open spaces, picturesque mountain villages and pristine stretches of beautiful coastline. The country presents a heady mix of music, arts, gastronomy and stunning natural beauty.

 


 

SATURDAY

Living History
Check into Hotel Nacional, a bastion of luxury located in Havana’s Vedado neighborhood. Dating back to 1930, this elegant establishment recalls another era. Adorning the walls are vintage images of famous regulars, including Winston Churchill, Marlene Dietrich and Frank Sinatra.

The Vista al Golfo bar is an excellent place to grab a mojito or Cuba libre while taking in the Havana vibe. Just off the bar is a small museum focused on the 1962 Cuban Missile Crisis. During the conflict, Fidel Castro and Che Guevara set up their headquarters here.

Old Havana

Habana Vieja is a step back in time, with its colorful Spanish architecture, weathered buildings, narrow cobblestone streets, colonial plazas and historic cathedrals. Couples walk the sweeping ocean-side Malecón, with its picture-perfect view of El Morro castle across the bay.

Channeling Hemingway
Ernest Hemingway’s two favorite watering holes, El Floridita and La Bodeguita del Medio, are near each other in Old Havana. A small plaque hanging in El Floridita offers this quote from the famous author: “My mojito in La Bodeguita, my daiquiri in El Floridita.” Papa still holds the record at the latter for drinking 16 daiquiris with no sugar and double shots of rum.

Best Chicken in Town
El Aljibe is a traditional Cuban paladar in the Miramar neighborhood and is known for the most delicious creole-roasted poultry in Havana. The same family has been operating this institution since the 1940s, and it’s an authentic rustic dining experience. For $15, you get all the chicken, rice, black beans and French fries you can eat. Surprisingly, El Aljibe has one of the most outstanding wine cellars in town.

Sequins and Feathers
The most venerable show in Havana, the Tropicana cabaret is a Vegas-style, open-air spectacular that has been performing continually since 1939. Voluptuous and scantily clad showgirls descend from palm trees to dance Latin salsa under bright lights. The club is located at Villa Mina, a six-acre estate with lush tropical gardens. Ask your hotel concierge to arrange a prime seat as some have restricted views.

 


 

SUNDAY

Fore
Built in 1953, the Havana Golf Club (formerly the Rovers Athletic Club) is one of only two courses on the island. It is both a time capsule and a paradox. Flagsticks are fashioned from bamboo poles and red flags. The bar, Hole 19, features vintage photos of Castro playing the course in combat boots and military fatigues. Club rental is available; some are classic, meaning actually from the 1950s.

Tobacco Temple
Cuban cigars are known to be some of the best in the world. Entering through the wide doorway of the Partagas factory, you are hit with the earthy, intoxicating smell of unlit cigar tobacco. It is now the site of one of the finest cigar shops in Havana.

Primo Paladar
Located on the second level of a magnificently decayed, early 20th century palace, La Guarida is a massively popular restaurant serving some of the best food in Havana. Don’t let the entrance fool you; after you walk up the broken marble stairs, a romantic dining room is revealed. Reservations are a must.

Shake It Up
Take a short cab ride to Fábrica de Arte Cubano for a quirky mix of nightclub and art gallery, all situated in a former cooking-oil factory. When you arrive, the doorman hands you a ration card, which bartenders mark each time you order a drink. You settle up your bill on your way out at the end of the night. The building has two floors that transition between music, photography, fashion, dance, film and theater. Fábrica opens for three-month stretches then closes for a few weeks so the space can be reimagined.

 


 

MONDAY

Old Man and the Sea
There’s no better place for top-notch deep-sea fishing than the Gulf Stream off Cuba’s northern coast. Head to Club Nautico Internacional at the Marina Hemingway seven miles west of Havana. For $120, an experienced captain and first mate will take you out for four hours of fishing marlin, sailfish and tarpon with the city skyline as the backdrop.

Sushi Speakeasy
The best sushi joint in Cuba is on the way back into Havana. The hard-to-find Santy Pescador looks and feels like a speakeasy shack in a small village at the end of a dusty street on a backwater inlet. The menu changes daily, and reservations are necessary.

Everyman’s Tropicana
Casa de la Música is a mainstay for outstanding salsa music. Housed in a beautiful old mansion, this nightclub features a vibrant, non-touristy ambiance for people of all ages. It can be crowded and smoky, as this is where the locals go to party. The experience is like a local Tropicana show, only with better people watching.

 


 

TUESDAY

Beach Bound, 57 Bel Air Style
Almendrones, as Cubans call them, are 1950s Buicks, Cadillacs, Chevys and Fords still on the road thanks to the genius of Cuban mechanics. Some two hours east of Havana sits Varadero. Technically Americans are not allowed to go to this beach; however, many tour operators offer at least a day trip. The turquoise water and white-sand beaches are among the most beautiful in Cuba and the most pristine in the Caribbean.

Live Like a du Pont
Located in the beachfront area of Varadero is the exclusive estate of French-American millionaire Irénée du Pont. In 1927, he retired at age 49 from his chemical empire and bought a peninsula with five miles of virgin beach to build a four-story manse and private golf course, dubbing it Xanadu. It was expropriated during the revolution, and the estate now operates as a luxury six-room inn, carefully restored in the style, design and décor of the 1930s.

Drink Like a du Pont
On the top floor of Mansion Xanadu is Bar Mirador Casa Blanca, the finest bar in Varadero. Featuring long views and remarkable sunsets, it’s best reached by the tiny, steep staircase. Ask for Guzeman.

 


 

WEDNESDAY

Wide Open Spaces
The countryside of Cuba feels like the Wild West. The 162-mile drive from Varadero to Trinidad is like riding on a narrow roller coaster while sharing the rails with oversize trucks. Flat tires are common, and with very few road signs, it’s easy to get lost.

Colonial Trinidad
Trinidad is a UNESCO World Heritage Site and the most perfectly preserved colonial city in Cuba. The architecture is defined by multicolored, pastel-hued buildings with rust-red roofs. Take a walking tour with a local guide to learn the town’s history. Trinidad makes Havana feel like Manhattan. Multigenerational families live under the same roof and seem to spill out onto cobblestone streets.

Welcome to Paradise
On the edge of Trinidad sits one of its oldest houses: the unique Finca Kenia. Enter through the tall wooden doors off an insignificant street into an unexpected world. Give in to the soothing sense of calm and let time fall away at this charming bed and breakfast.

 


 

THURSDAY

A Private Pied-à-Terre
Upon your return to Havana, check into Penthouse Ydalgo, a luxury residence juxtaposing the art deco style of 1950 with today’s modern conveniences. Outdoor terraces provide unmatched views of the city and the sea. VIP service comes standard, complete with airport pickup, salsa lessons, drivers, translators, laundry and massage.

Revolutionary Photographer
Seeing the studio of Roberto Salas is a must. In 1957, he caught the attention of Castro, who was in New York raising money for the revolution. At just 16 years old, the photographer had an iconic image of the Statue of Liberty draped in a Cuban flag published in LIFE.

In 1959, upon the political leader’s urging, Salas began serving as a photographer for the Cuban government newspaper, Revolución. For nearly 50 years, he has lived on the Carribean island and taken exclusive photos documenting the stories of the nation, including some never-before-seen images of Castro. By appointment only.

House Hunting International
Only since 2011 have Cubans been allowed to buy and sell real estate. Today, there is a gold rush for investment property, with many foreigners becoming silent partners. But buyer beware: Until the embargo is lifted, a U.S. citizen investing in Cuban property is subject to criminal penalties under the Trading with the Enemy Act.

The process is very informal, and some of the best properties remain pocket listings between private agents and the government. Homes start at $20,000. Right now, you can buy a small flat in Havana for less than $100,000 or a luxury penthouse apartment in an architecturally significant building with sweeping views for $1.2 million.

 


 

FRIDAY

Tobacco Land
The rolling green hills of Pinar del Río province are worth a day trip. At the center of Cuba’s tobacco industry is Viñales, the perfect place to witness growers and harvesters at work. Oxen are used in place of tractors to plow the fields. See the famous drying houses while a farmer demonstrates how to roll a cigar.

 


 

SATURDAY

Homage to Hemingway
Finca Vigía, Ernest Hemingway’s home, sits in a modest village some 10 miles east of Havana. Visitors can peer through the windows to get a look at a 1950s time capsule. This is where the author penned two of his most celebrated novels, For Whom the Bell Tolls and The Old Man and the Sea. No trip to Finca Vigía is complete without stopping for a cocktail at Hemingway’s third favorite hangout, La Terraza.

Last Call
Cuban musicians are known for crafting some of the best jazz in the world. And La Zorra y el Cuervo is one of the top places to hear it live in Havana. There is not a bad seat in the house.

 


 

If You Go

Getting There: U.S. citizens can legally visit Cuba under one of 12 broad categories of purposeful travel. Your best bet is to go with the pros. Our top picks? Altruvistas (altruvistas.com) creates custom travel programs built on the pillars of experiential education, philanthropy and social responsibility. Black Tomato (blacktomato.com) is known for creating unique travel itineraries with exclusive experiences. InsightCuba (insightcuba.com) is a nonprofit specializing in people-to-people travel to Cuba.

When to Go: Peak tourist season runs from mid-December to mid-March and all of July and August. Cuba has a hot, tropical climate with an average temperature of 75 degrees. The winter is considered the dry season, when the mercury can drop as low as 60 degrees. The wet season occurs from May to October, when strong rainstorms come down hard and fast. The summer months are scorching hot.

What to Bring Back: Americans can now bring back up to $400 worth of souvenirs, including $100 worth of cigars.

What is Yet to Come: The Federal Aviation Administration is reportedly in talks with Cuban authorities to allow American carriers to offer regularly scheduled commercial flights. Currently, there are only three ports of entry: Miami; Tampa, Florida; and New York’s John F. Kennedy International Airport. Travel to Cuba via cruise ships is next; several lines have announced intentions to sail to Havana.

Cuba has a shortage of high-end hotels, an issue that will become even more dire as more Americans visit. Airbnb started offering service on the island last spring and now has more than 3,000 homes there.

Read the article as it appears in the magazine.

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