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Celebration in Havana

Private Havana Adventure

Custom Expeditions
Celebration in Havana

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Private Havana Adventure

Allow yourself to be swept away by the profoundly original traditions of Havana! This journey includes stopping to chat with artists in their studios, surveying Hemingway’s former home and favorite bars and discovering the history of Cuba's famed cigars and rum.

Meet Cuban Entrepreneurs

Highlighting the journey are opportunities to mingle with Cuba’s new generation of entrepreneurs – restaurant owners. Family run paladars offer the best cuisine, plus chances to discuss the changing face of Cuba’s economy with private business owners.

International Expeditions' private Cuba travel programs include private guide and private driver along with air arrangements, accommodations and most meals.

The sample itinerary below can be customized to take full-advantage of your travel time and interests.

Experience the Complete Cuba

Daily Itinerary

Private Havana Adventure

  • Day

    Welcome to Cuba!

    Fly to Havana, where we are met by our Cuban guide. Hop into vintage classic American cars. Cruise along the Paseo del Prado in Centro Habana passing a variety of landmarks, including the Bacardi Building, Central Park, the Grand Theater and Capitol. Stop at the 17th Century Morro Castle for sweeping views across Havana Bay. Cap-off our introduction to Cuba at Sloppy Joe’s Bar, where history and cocktails easily mix. Sloppy Joe’s became a haven for American tourists during U.S. Prohibition, hosting celebrities such as John Wayne, Spencer Tracy and Clark Gable. Enjoy dinner tonight at a privately owned restaurant (paladar). Paladars offer the best variety of fresh, inventive cuisine. Plus, our time here is the ideal opportunity to chat with this new generation of entrepreneurs about this “new” Cuban economy. Tonight at dinner we also meet and enjoy chatting with a Cuban dignitary about the changing face of Havana. Looking for an incredible night out in Havana? Consider spending your night at Fabrica de Arte Cubano (FAC), where Cuban youth and famous artists gather. Inside FAC there are art galleries, a theater, concert venues and quiet venues to enjoy a drink and chat. Cocktails are at your own expense. (D)

  • Day

    Exploring Havana

    Discover 500 years of history and architecture while exploring Havana. Our day begins with a fresh juice at La Vitrola (the Jukebox), a popular spot in Plaza Vieja. Stroll along the meandering streets to Plaza de San Francisco, stopping to pay your respects to the bronze statue of El Caballero de Paris (the Gentleman of Paris) and learn about the interesting story of why he was immortalized. In Plaza de Armas your guide discusses the city, founded here in 1519. Continue a leisurely stroll through the main squares of Old Havana. See Hotel Ambos Mundos, where Ernest Hemingway kept a room for years. The hotel served as a refuge for writing such works as For Whom the Bell Tolls and as a base for frequenting his favorite bars. You have a moment to see the room where Hemingway worked if you wish before sampling a mojito at the rooftop bar. From the City Museum (the former Captain General's residence) to the street vendors trading authentic books and memorabilia that commemorate the Revolution, Plaza de Armas is one of Havana's greatest treasures. You continue on to Plaza de la Cathedral, the fourth of Havana's wonderful squares. The picturesque plaza usually provides an opportunity to snap a photo with local Habaneros dressed in traditional costumes. At historic Hotel Nacional, sip drinks on the verandah overlooking the bay and tour the extensive grounds, the playground of dignitaries, royalty and celebrities for decades. Enjoy cocktails and dinner at another trendy paladar. While these eateries are gaining acclaim with celebrities and world travelers alike, take a few moments while here to consider the challenges facing these entrepreneurs in a country where trade is severally hampered by the U.S. embargo. (B,L,D)

  • Day

    Day Trip to Soroa & Vinales

    Wind into the countryside, seeing the breathtaking landscapes and tobacco farms of Pinar del Rio. Visit the exquisite orchid gardens of Soroa — Cuba’s largest botanical garden — hosted by an expert horticulturist, who shares stories of the challenges the garden has faced, and the wonders of the botanical species they've managed to raise in Cuba's tropical climate. Continue into the famed Viñales Valley with it’s the rugged mogotes — limestone karst outcroppings with caves and rivers running through. Take in stunning vistas from Los Jazmines lookout: the mogotes, red soil and lush vegetation in perfect harmony. Delve into the cigar-making process while calling on a tobacco farm, where owner proudly shows you his farm and discusses the intricacies of growing tobacco and selling it to his only authorized buyer: the Cuban government. Savor time in the picturesque town on Viñales, observing beautiful countryside houses painted in exuberant Caribbean colors and local markets. Stop at a CUC store and a bodega — a ration book store where locals buy subsidized goods in Cuban pesos — to understand the contrast between the two currencies and the products you can buy with each. Following your stop in town you enjoy lunch at a local organic farm. As we head back to Havana, watch for horse-drawn carriages alongside the speeding cars on the national highway…a gentle reminder of how simple many Cuban's lives are to this day. Dinner is offered tonight at your boutique hotel. The evening is your to take in the world-renowned cabaret at the Tropicana or allow our guides to make arrangements at another famed nightclub (at your own expense).  (B,L,D)

  • Day

    Hemingway’s Havana

    Venture out of the city to the seaside village of Cojimar, which served as the inspiration for Ernest Hemingway's The Old Man and the Sea. After seeing his monument, sample drinks at one of Hemingway’s favorite bars, La Terraza. You may also join a local chef for a cooking lesson before lunch at Ajiaco. This paladar renowned for their ajiaco stew, a Cuban staple created using farm-to-table ingredients. Continue paying homage to “Papa” Hemingway at his former home Finca Vigia, preserved as it was on the day of his death, and discuss his life with Cuban experts and researchers. Savor the hospitality and warmth of those who have but a smile and delicious home cooked meal to share. Although the embargo has limited what the residents of Cuba have at their fingertips, there is no denying that their food is as comforting and as tasty as any offered in a home kitchen in America. Your guide will act as interpreter and help you ask all the burning questions you may have about living in Cuba. The people of this country speak freely and share openly. Your meal is homemade, authentic Cuban food that the locals enjoy on special days with the family. After-all, it isn't every day they get to chat up an American! Head to Casa Blanca and the ramparts facing the Havana Bay for the cannon-firing ceremony. If dinning with a Cuban family is not on your bucket list we can also provide you with great suggestions for an evening on your own. (B,L,D)

  • Day

    Havana’s Traditions

    A visit to Havana's Fine Arts Museum, Bellas Artes, is a must for those who want to learn about the country's past through the eyes of its artists. Spend your morning perusing the famed pre- and post-Revolution collections. Perhaps nothing is more symbolic of Cuba than cigars, and our morning is spent at a factory learning about the country's coveted tobacco and the artisanal process by which they are rolled one by one in a process that hasn't changed for centuries. See the famed classic cars of Cuba at a local garage, learning how Cubans keep these classics on the road despite limited resources. Enjoy lunch at Club Habana. Built in the 1920s as the Biltmore Yacht & Country Club, Club Habana features a beach, swimming pools, tennis courts and one of the city’s best cigar shops. This is also your chance to contrast the cuisine and service received at this state-run restaurant with the private restaurants where you’ve enjoyed meals. This evening, delight in a sunset drive in a classic convertible along the sea-side Malecon to a rum and cigar tasting. An expert in both vices leads the tasting, uncovering the nuances of these indulgences and regaling you with the role rum and cigars have played in Cuban history. After your tasting, enjoy a chef-prepared meal of fresh seafood, roasted pork and local produce, along with handcrafted cocktails. Your driver and guide make themselves available if you want to enjoy one last night out in Havana. (B,L,D)

  • Day

    Depart Cuba

    Sadly, all good things must come to an end. Our Cuba tour ends as we return to the airport for your flight back to the U.S. (B)


Hotel Parque Central

Parque Central

Located on beautiful Central Park in the heart of Havana, the Parque Central comprises two buildings, a colonial section and modern tower. The tower is sleek, chic and contemporary, with a wood, glass and steel design theme set off by bright colors and textured fabrics. The colonial part is classic elegance: what you’d expect to find in a five-star hotel in any global capital city.  All rooms feature air conditioning, balcony or terrace, private bath, satellite TV and a coffee/ta maker.


Melia Cohiba

Meliá Cohíba

Located in Vedado, a modern district in Havana, just steps from the famed  Malecón, the Meliá Cohíba offers stunning views of the city and sea. Fully air conditioned, the hotel provides comfort and an elegant, modern design with Cuban marble and references to the world of cigars and the famous Cohíba brand.

Custom Havana Accommodations

Based on your budget and travel style, your Cuba Travel Planner may recommend a variety of accommodations. Your preferred accommodations will impact the price of your journey.

From: $3,999 per person
6 Days, 5 Nights
Trip Type
Travel Style
Expedition Destinations

Trip Highlights

  • Available to book anytime!
  • Absorb the colonial charms of Old Havana.
  • Savor a home-hosted meal with a Cuban family.
  • Peruse Cuba's most famous museums & galleries under the guidance of local art experts.
  • Mingle with paladar owners, Cuba's newest entrepreneurs.
  • Discover the transformative power of art during in-studio discussions with Cuban artists.