5-Nights Havana In-Style from $5,499

Itinerary Details

Day 1: VIP Arrival Service in Havana

Upon arrival at the airport, you'll be met and escorted to the VIP Lounge where you can wait comfortably while your luggage is unloaded. After claiming your bags and passing through customs, you'll be warmly greeted by our Airport Representative and escorted to your private vehicle for the chauffeured transfer to your hotel. All of our boutique properties have been carefully selected for their historic charm, modern comfort and ideal locations close to the historical center of Old Havana. With only 3 to 19 guestrooms, these intimate, privately-run hotels create a perfect retreat that immerses visitors in the rich cultural tapestry of Havana. This evening, we'll take you to Cinco Sentidos for dinner. With spectacular seafood dishes, an outstanding wine list and exceptional service, this is one of the best new restaurants in the capital. If you wish, your Tour Concierge can suggest some nearby venues where you can experience Havana's legendary music scene. Meals D

Day 2: Havana, Old + New

After breakfast, join your private guide for an immersive exploration of the Cuban capital, from its wealth of Colonial architecture to its modern-day vitality. Stroll along charming cobblestone streets and through centuries-old public spaces like Plaza Vieja in the heart of Old Havana #WHS# as your guide offers insight into Cuban history and culture. With just you and your personal guide, you'll have myriad opportunities to engage with friendly city residents for a genuine look into their daily lives and traditions. Enjoy lunch at El del Frent where, weather permitting, you might dine on their inviting rooftop terrace. Later this afternoon, you'll spend time with two artists in their studios. Please let us know in advance if you are interested in specific media such as photography, sculpture or painting and whether you prefer to engage with established or emerging artists. We will try to confirm your visits accordingly but actual appointments will of course depend upon the artists' availability during your stay. This evening, we've arranged for you to meet Carlos Alzugaray, a highly-regarded author, essayist, diplomat and professor. Mr. Alzugaray's numerous credentials include Full Academician of the Cuban Academy of Sciences and distinguished member of the National Union of Writers and Artists in Cuba. Over cocktails, your discussions with the professor will be fascinating, enlightening and memorable. Then enjoy the fine cuisine at at La Cocina de Liliam. Meals B+L+D

Day 3: Of Hemingway, History + The Arts

After breakfast, a chauffeured vintage American convertible will take you to Finca La Vigía. Built in 1886 in the pleasant San Francisco de Paula district south of central Havana, this handsome estate was the home of Ernest Hemingway for two decades. Explore the grounds and peer through the large open windows to see the rooms where he wrote two of his most famous works, For Whom the Bell Tolls and The Old Man and the Sea. As your private guide shares insights into Hemingway's time in Cuba, you'll see hundreds of his personal possessions almost exactly as he left them when he departed Cuba for the last time in 1960. On the drive back to Havana, you'll visit Cojimar, the picturesque fishing town that inspired Hemingway to write The Old Man and the Sea. In 1954, he dedicated his Nobel Prize in Literature to the fishermen of Cojimar, and today you'll see a bust of the author cast from fishing boat propellers that town residents donated after the author's death. End your morning tour at El Morro Fortress, an impressive 16th-century fortress that offers spectacular views of Havana. After a traditional Cuban lunch at Ajiaco Café, your private touring continues along Callejón de Hammel. Filled with vibrant murals and fanciful sculptures, this colorful street is a great way to appreciate the city's devotion to public art, much of it inspired by the island's Afro-Cuban traditions. Late afternoon finds you and your personal guide exploring the bustling streets of Centro Habana. Though still in the heart of the city, this part of town has not seen the investment dollars that have poured into Old Havana. With fewer tourists and many of the Colonial-era buildings showing their age, the faded grandeur of Centro Habana is a photographer's paradise and offers a truly genuine experience of modern-day life in Habana. This evening, you'll dine at Costa Vino. Opened by a renowned Cuban sommelier and under the direction of chef Boris Prieto, this stylish new restaurant is known for its fusion cuisine and fresh seafood. After dinner, we've arranged for your VIP Entry to Fabrica de Arte Cubano. Set in century-old factory, this arts and culture venue opened in 2014 and has remained one of Havana's most popular night spots—an exciting space where you can experience art exhibits, live music, film and dance. Meals B+L+D

Day 4: Personalize Your Exploration

Today we offer two different touring options, one focusing on the agrarian lifestyle and traditions of the World Heritage Viñales Valley and the other offering a deep dive into the world of Cuban rum, cigars and farm-to-table dining. We invite you to choose one of these included privately-guided cultural excursions based upon your personal interests and style: Option 1 - Farm Life in the Viñales Valley: Spend the day with your private guide immersed in the countryside life of the beautiful Viñales Valley #WHS#, recognized as a UNESCO World Heritage Site for its enduring agricultural traditions and the authentic architecture of its farms and villages. It's a spectacular region with pastoral fields encircled by mountains and interspersed with rugged limestone outcrops that soar as high as 900 feet above the surrounding terrain. With narrative insight and translation from your guide, you'll engage with farmers to learn about their cultivation methods and to experience the rhythms of their life and work. At a tobacco plantation, you can see the entire production process from cultivation and drying to the hand-rolling of fine Cuban cigars. A delicious lunch of traditional countryside cooking is included and throughout the day, you'll have myriad opportunities to share your own experiences as you learn about the lives and livelihoods of the valley's friendly residents. Option 2 - Cigars, Rum and Organic Farm Experience: An unforgettable day unfolds this morning as you tour one of Havana's oldest and most renowned cigar factories. You're sure to be mesmerized as you watched these skilled torcedores at work, handcrafting world-famous Montecristo and Cohiba cigars. Using different types of tobacco leaves for the filling, binder and cap, it's a multistep process that requires speed, agility and even grace! Midday finds you at Finca Tungasuk, a 32-acre organic family farm about 25 miles from downtown Havana. Run by Alfredo, a former UN election monitor from Peru and Annabelle, a Paris-trained Nicaraguan chef, they are united by their passion for food, sustainable farming and country living. Learn about the operation of this bucolic agricultural estate, enjoy its idyllic setting, and sit down to a delicious farm-to-table lunch prepared by Annabelle. This evening, our cigar expert will join you for a rum + cigar pairing. With their expert guidance and knowledgeable insights, you'll enjoy your choice of cigar paired with a tasting of two fine Cuban rums. After your chosen excursion, you'll have time to refresh before dinner at Otra Manera. Set in a beautifully refurbished 1950's mansion, this stylish restaurant has emerged as one of Havana's finest restaurants, renowned for its fine cuisine and exemplary service. If you wish, our Tour Concierge can offer suggestions and assistance for you to experience more of the city's vibrant music and nightlife scene. Meals B+L+D

Day 5: Modern Cuban Life + Revolutionary History

There are a variety of ways for Cubans to acquire and pay for their daily staples: from state-issued ration books and government-run bodegas and markets to mercado libre where goods can be purchased with the Cuban peso. For the American visitor, it can all be a bit bewildering! But accompanied by your personal guide, this morning's visit to a local produce market will be interesting, instructional and insightful, as you mingle with Havana residents going about their daily life and learn about the island's economy. For lunch, we'll take you to Jibaro. Learn to make an authentic Cuban mojito before enjoying the eclectic cuisine of this stylish, somewhat Bohemian restaurant tucked away in Old Havana. Just around the corner, you can stop to see Iglesia de Las Mercedes, a lovely Baroque church founded in 1630. This afternoon's touring begins along the Malecón, the picturesque waterfront esplanade that stretches for nearly 5 miles along the coast in Havana. Graced with monuments to important figures from the Cuban War of Independence, it's a great place to learn more about the island's pre-revolutionary history. Then visit the Museum of the Revolutions, set in the former Presidential Palace, before continuing to the Hotel Sevilla, an infamous gathering place for mobsters who exerted a great deal of influence in Havana throughout the 1950's. You'll also see a bodega where city residents shop with their ration books before ending your sightseeing in Revolution Square, an impressive symbol of the Cuban Revolution. Late in the day as the sun dips toward the Atlantic horizon, your guide will take you back to the Malecón to join city residents who are out to enjoy the sunset. It's another wonderful opportunity to engage with local Cubans and experience daily life in Havana. Tonight, you'll dine at the landmark La Guarida. Opened in 1996 and set in an elegant if somewhat faded century-old residence, this is one of Havana's oldest paladars and it continues to be one of its most notable dining establishments. Meals B+L+D

Day 6: Depart Havana

After breakfast, your private car and driver will take you to the airport for your homeward flight. Meals B