From Havana's Heart to Viñales Vistas:
A Journey Through Cuba's Historic Past and Entrepreneurial Present

Day 1 – Wednesday, February 7

Upon your arrival in Havana, meet your driver who will take you to your accommodations. Check-in at a charming, luxurious boutique hotel. Enjoy a light lunch, and take time to get settled in at Elvira Mi Amor Old Havana.

After lunch, join the group for a conversation with Cuban economist and entrepreneur Oniel Diez, who will provide us with a succinct overview of the current state of the Cuban economy, as well as a recent reforms and how they may shape the country’s future.

Next, we will savor some sumptuous local flavors at La Guarida, one of Havana’s oldest and most prestigious paladares (private eateries).

This was the setting for the groundbreaking film Strawberries and Chocolate (1993). From the rooftop, we can enjoy 360-degree views of the city, accompanied by a unique blend of its sounds and smells.

After dinner, we can explore Michifu, situated down the street from La Guarida (optional activity). This eclectic night spot boasts art, amazing drinks, and a vibrant crowd of locals.

HOTEL: Elvira Mi Amor, Old Havana

Day 2 – Thursday, February 8

On our second day, we’ll begin by listening to and conversing with Miguel Coyula, Cuba’s “Explainer in Chief.”

As we listen to this renowned professor recount the past 500 years of Cuba and Havana’s evolution, we’ll gain a foundational understanding of the forces that have shaped contemporary Cuba.

Given his background as an architect and urban planner, he will provide us with deep insights into the architectural, cultural, and political influences on display in Havana.

Next on the itinerary is a visit to a children’s home in Old Havana, which plays a significant role in the local community. We’ll tour the center, engage with educators and children, and there will also be an opportunity to make donations to the home.

For lunch, we’ll visit Ivan Chefs Justo, a cozy paladar nestled in an old colonial house dating back to 1866. It boasts a diverse menu filled with excellent starters, entrees, and desserts.

In the afternoon, we’ll embark on a behind-the-scenes walking tour of Old Havana. We’ll delve into its historic center, gaining insights into the history and architectural significance of this UNESCO World Heritage Site (recognized as such since 1982).

After our tour, we’ll return to the hotel for a brief break before the evening’s activities.

Come nightfall, before our dinner, we’ll savor the sounds of local musicians’ jam sessions on a charming rooftop. We’ll immerse ourselves in the rhythms and vibe of Cuban jazz, courtesy of Degnis’ band, all while overlooking the mesmerizing city of Havana.

Our dinner will be at Sensacioones Restaurant – a gourmet paladar in the Playa neighborhood of Havana.

We will also stop for a drink at La Floridita, a cocktail bar famous for its daiquiris, and for having been one of Hemingway’s favorite hangouts in Havana.

For those wishing to explore Havana’s nightlife further, music and drinks await at El Bleco.

Situated just off the Malecón, this bar occupies the rooftop of an otherwise unassuming two-story building. With its roof replaced by an open-air balcony, it’s the ideal spot from which to observe the city’s nocturnal activities.

HOTEL: Elvira Mi Amor, Old Havana

Day 3 – Friday, February 9

On our third day in Havana, we will visit the National Museum of Cuban Fine Arts. Accompanied by an art historian, we’ll gain an overview of Cuban art and artists spanning the last four centuries.

Next, a roundtable discussion awaits with a number of leading Cuban entrepreneurs. Here, we’ll gain insights into the new regulatory reforms, along with a deeper understanding of the Cuban private sector – straight from the leading entrepreneurial minds in Cuba.

Our conversation with local entrepreneurs will continue over lunch at Paladar San Cristobal. Situated in the heart of Central Havana, this spot boasts an excellent reputation for its atmosphere and local cuisine.

In the afternoon, we’ll dive into the rhythm of percussion and dance with the local dance group, Habana Compas. Founded in 2004 by Liliet Rivera, a protégé of the famed List Alfonso Dance Company, Habana Compas Dance aims to reclaim and preserve Cuba’s rich dance heritage, rooted in Spanish and African traditions.

Afterwards, we’ll return to the hotel for a brief break and to freshen up before our evening activities.

Later that night, we’ll indulge in a private tasting and masterclass where a cigar specialist will unpack the history and cultural significance of this Cuban staple.

Dinner will be served at El Cocinero, a charming restaurant located in a former factory. Immersed in Havana’s vibrant culture, you might feel as though you’re in Soho or Madrid.

For those wishing to extend the evening’s festivities, we can immerse ourselves in art, music, and dance at Fabrica de Arte Cubano.

Conceived by Afro-Cuban musician X-Alfonso, this establishment stands out as one of Havana’s premier cultural venues. A hub for intellectuals and artists alike, it attracts scores of both Cuban and international visitors. Here, we can wander through the multi-media gallery spaces and even catch a live performance.

HOTEL: Elvira Mi Amor, Old Havana

Day 4 – Saturday, February 10

On Saturday morning, after breakfast, we will depart for the Viñales region.

Many consider this region to be the most beautiful place in Cuba. The Viñales Valley National Monument boasts stunning vistas, and the area is renowned as the premier tobacco-growing region in the world.

En route from Havana, we’ll make a stop at El Laguito Cigar Factory in the Miramar neighborhood. Here, we’ll take a private tour and get a rare, first-hand glimpse into the cigar-making process.

For lunch, we’ll pause at Finca Tungasuk in Artemisa, a mere 15-mile drive from Havana, before continuing to Viñales. We’ll spend time with the farmhands, exploring the farm both on foot and on horseback. There, we’ll gain insight into local production methods and cap off the visit with an organic farm-to-table meal.

Upon arrival in Viñales, we will check into casas particulares (small bed and breakfasts). You can then join a group yoga session overlooking the beautiful valley, or take a nap before dinner.

In the evening, a traditional pig roast dinner with community members awaits our group. This will be a great opportunity to discuss life in the countryside, the casas particulares, local paladares, food supply, and agriculture in this special region of Cuba.

ACCOMMODATION: Local Bed & Breakfast in Viñales

Day 5 – Sunday, February 11

In the morning, we will stroll through the valley to learn about tobacco — one of the region’s most vital crops — and meet with the farmers and their families.

We will visit a tobacco farm to gain insight into the cultivation and production processes, followed by a cigar rolling demonstration.

Upon our return to Havana, we will enjoy a late lunch at Otramanera, a home turned internationally recognized paladar situated between Playa and Miramar neighborhoods.

En route, we’ll make a stop at the iconic Fusterlandia, which is a community project spearheaded by ceramic artist Jose Fuster. Here, we will discover its impact on the local community, and learn about the project’s inception and ongoing contributions to the Cuban people.

We will then check in at Claxon Hotel, a boutique hotel in the Vedado neighborhood.

As the sun sets, we will attend a jazz performance at Malecon 663. Located on a rooftop, it offers a unique cityscape, with a panoramic view of the renowned seawall.

Malecon 663 tempts visitors with its live music and a creative menu featuring a blend of traditional Cuban recipes and contemporary fusion cocktails..

Dinner will be served at Eclectico, housed within the picturesque colonial Paseo 206 boutique hotel. Here, traditional Italian and Mediterranean flavors are blended seamlessly with the robust fragrances of the Caribbean.

Post-dinner, consider a visit to the legendary Hotel Nacional to enjoy a drink in its famous bar, the “Hall of Fame”.

As a National Monument embodying Cuban history, culture, and identity, the Hotel Nacional hosted numerous dignitaries during their Cuban sojourns.

Notably, it was the venue for annual Mafia meetings in the 1950s, and its enchanting grounds are a timeless sanctuary.

HOTEL: Claxon Boutique Hotel, Vedado Neighborhood, Havana

Day 6 – Monday, February 12

On one of our final days in Havana, you will have the opportunity to select your desired activity for the first half of the day.

After breakfast, sports enthusiasts can visit the local Rafael Trejo gym to witness boxing with local Cuban champions. At this venue, you’ll have the chance to hone your fighting skills alongside some of Cuba’s finest boxers.

If boxing isn’t your thing, consider exploring Havana by bicycle: Get ready to experience a memorable guided bike tour that winds through the heart of this enchanting capital city.

For lunch, we’ll reconvene at the local paladar, La Corte del Principe – an Italian and Mediterranean restaurant nestled in the Miramar Neighborhood.

In the afternoon, we’ll head to the Nostalgic Cars restoration garage to meet its owners, Nidialys Acosta and Julio Alvarez. This dynamic husband-and-wife duo represents the new face of entrepreneurship in Cuba, capitalizing on recent economic shifts to lovingly restore and operate these classic American vehicles.

Next on the agenda are behind-the-scenes visits to the studios and galleries of emerging Cuban artists, hosted at Taste Cuba Spirits in Havana. Specialist Ariel, a fervent enthusiast of both Cuban culture and Cuban rum, will be eager to share his passions with you.

Our day will culminate in a memorable farewell dinner at a Cuban residence, complete with a private chef.

Here, we’ll savor traditional Cuban cuisine, all while enjoying the company and music of our local hosts and the local Cuban friends we’ve made during our journey.

HOTEL: Claxon Boutique Hotel, Vedado Neighborhood, Havana

Day 7 – Tuesday, February 13

After breakfast, we will check out of the hotel and head to the famous Finca Vigía. Once the home of Ernest Hemingway, it still houses his expansive collection of books and other personal artifacts, as well as his boat, El Pilar.

Please note that this is an optional tour. If your flight departs early in the morning, a transfer will take you to the airport ahead of time. You should plan to be at the airport approximately 2.5 hours before your departing flight.

Departures are scheduled throughout the day.

Per US regulations, traditional hotels are not compliant in Cuba. One of the initiatives of US Policy on Cuba travel is that there is an intention to support the private sector vs. state-owned entities.

We will be using beautifully restored colonial mansions turned into private, boutique hotels. The hotels are not only incredibly charming, but they also boast phenomenal service.

Our trip is designed to have you stay in two different parts of Havana during the trip. The first stay is in historic, Old Havana, and the second stay is in the beautiful Vedado neighborhood. 

Room types vary, and during registration you’ll be asked if you’d like a standard room or one of the executive rooms.

February 7-10: Elvira Mi Amor boutique in Old Havana

February 10-11: Viñales Valley Bed & Breakfast

February 11-13: Claxon Boutique Hotel in Vedado, Havana

• 6 nights’ accommodations in Cuba
  • 5 nights in Havana in luxury boutique hotel
  • 1 night in Viñales Valley in countryside bed and breakfasts
• Local ground transportation for listed activities
• Airport transfers (pick up and drop off)
• Daily breakfast
• Meals (as specified in the itinerary)
• Meal reservations (as specified on the itinerary)
• Professional, bilingual guide for listed activities
• Pre-trip departure information
• Compliance with U.S. Treasury Department regulations
• Speaker fees
• Cuban Visa processing
• Admission to all museums and public buildings mentioned in the itinerary.

• Round-trip airfare
• Meals and activities other than listed on itinerary
• Individual house or hotel expenses
• Tips for local guides, drivers, restaurant service, etc.

Is it legal to travel to Cuba?

Travel to Cuba is restricted by U.S. regulations that require travelers to meet certain requirements during visits to the island. Travel to Cuba was expanded under the Obama Administration, tightened by the Trump Administration, and recently expanded again by the Trump Administration. The Treasury Department’s Office of Foreign Assets Control (OFAC) oversees Cuban sanctions, including rules governing U.S. travel to the island. Our local partners in Cuba have over a decade of experience offering legal, fully compliant travel to Cuba for U.S. travelers with specific permission from OFAC.

Your trip to Cuba is fully legal and will be accompanied by all the necessary paperwork, which will include a travel affidavit for OFAC, a travel letter on the local partners’ letterhead, specifying your category of travel, and full-time agenda that complies with OFAC regulations.

There are several categories of legal travel to Cuba, including journalism, religion, professional meetings, and people-to-people travel. Your trip will take place under the people-to-people category, which requires that you maintain a full-time program of activities that involve meaningful interaction with the Cuban people.

Is it safe to travel to Cuba?

Yes, Cuba is one of the safest countries in the world for tourists. In 2018, Cuba was given the “Safest Country to travel to” title at Madrid’s International Tourism Fair., as tourism is highly valued and highly protected. Gangs, guns and drugs are non-factors, severely limiting violent crime and social problems linked to it. The Cuban people are very friendly and open, and show lots of love and gratitude to visiting Americans despite the complicated relationship between governments. Safely wandering the streets of Cuba and visiting people’s homes is one of the most special elements of visiting the country.

Why Cuba?

Cuba is rich in culture, history, and people. It’s also incredibly unique. One of the last communist-run countries on earth and the most-sanctioned nation in the world, visiting Cuba is an intellectually stimulating journey that often leads to more questions than answers. 

Visiting Cuba allows us to learn from and share with our neighbors, and leads to out-of-the-box thinking as we explore different and unique challenges in a society, very different from our own, as well as issues of mutual concern and interest.

What should we expect in terms of logistics and the travel experience?

Expect balance and diversity. Expect to hear different points of view and diverse viewpoints on a range of issues. Expect unique experiences that are luxurious in content (top musicians, decision-makers and thought leaders) as well as the opportunity to explore backstreets, get into living rooms and meet and hear from average Cubans.

Cuba is luxurious in what it has to offer in culture, architecture, and history, and we’ll fully tap into it. Cuba is also severely challenged in infrastructure, technology, and other areas. You’ll have a luxurious, high-end experience, while also exploring and tapping into the shortcomings to get a fair, honest view of Cuba and Cuban society, as well as the impact of its relationship with the U.S.

What should we expect regarding lodging?

The Trump Administration enacted several new sanctions against Cuba that have not been reversed by the Biden Administration. One of them being a ban on U.S. travelers staying in any hotel run by or associated with the Cuban Government. This puts all the large hotels on the island out of reach of U.S. travelers. Fortunately, the expansion of the private sector in Cuba over the last decade has led to a flurry of small, boutique properties that are fully owned and operated by entrepreneurs not affiliated with the Cuban state.

Our local partners in Cuba was already giving priority to these properties and utilizing them over state-owned hotels as a way to support private sector growth, and because of the customer service and traveler experience. These properties are smaller – normally 6 to 12 room boutique hotels, housed in colonial-era mansions – and more efficiently run by Cuban and foreign entrepreneurs. They have all the necessary amenities of a boutique, luxury property and tend to exceed the state-run hotels in charm and experience.

Will our credit cards work in Cuba?

Due to the U.S. embargo and internal banking challenges – your credit cards and ATM cards will not work in Cuba. You will want to bring adequate cash (either USD or Euros) so that you have enough money for your stay. Our local Cuban partners will assist with currency exchanges and will also advise on navigating paying for any additional meals, tips, etc. During pre-trip communications, the local partners will provide additional information about currency and suggestions for how much cash to bring to the island.

Do I need health insurance?

Basic health insurance is included with any US air carrier’s ticket. If you have an underlying health concern, and you think you need additional health insurance, please let us know, and we will put you in touch with our local partners for further advise.

What do I need to travel to and from Cuba?

Cuba requires entering travelers to have a visa, health insurance, and valid passport (must not expire within 6 months of returning to the U.S.). For your trip, the local partners will provide your entry visa, and as outlined above, the airline ticket includes your required health insurance.

The United States requires travelers to have a letter of authorization, a signed travel affidavit, and a detailed, written agenda that is compliant with OFAC regulations. You will first receive an electronic version of your travel affidavit at time of registration, and local partners will provide your letter of authorization and the travel agenda prior to your departure.

Is there a US Embassy in Cuba?

Yes. The U.S Embassy in Havana was formally reopened in 2016. It is fully functioning and provides consular services and other assistance to U.S. travelers. Our local partners has a great relationship with the U.S. Embassy as well as the State Department and is in constant communication about current events and special projects.

Climate and Weather

February typically boasts the island’s most agreeable temperatures, and minimal rain. High temperatures in Havana average 78°F (25°C), with most days being sunny. The continued cool temperatures overnight mean the average low temperature for the month is about 63°F (17°C).

While slightly cooler, the lower evening temperatures are perfect for enjoying a cocktail in one of the Havana’s paladares, as long as you bring a light jacket or a sweater with you!

And you may also want to pack a light raincoat in case of some unexpected rainfall – although again, February is considered a dry month on the island.

Weather in Viñales in February is quite similar to that in Havana, although temperatures in the valley during the day can be slightly higher, around 82°F (28°C) during the day. During the night, the temperature can also be a bit higher, at around 69°F (20°C).

Clothing

Lightweight cotton and linen clothing and a cardigan will work for the days in Havana and the Viñales Valley, which we’ll visit in Cuba in February. 

However, you will want to pack some warmer clothes for the cooler evenings in Havana, like a sweater or a lightweight jacket.

Mosquito Repellent

Although February is considered a dry month, don’t forget to pack mosquito/bug repellent with you, since it is tough to find it in Cuba, and you may still need it in the evenings or when in the Viñales Valley.

Electrical Outlets

In Cuba, the majority of the places should have the US “A-type” plugs, although there might be other spots with the European “C-type” plugs. To be on the safe side, be sure to pack a regular travel adaptor. 

We are so excited to see the interest in this trip, and worked hard to negotiate the best price on all of these high-end experiences, exclusively for our members.

Please note that due to the nature of the trip and the size of the group, we can only allow cancellations if we can find a replacement for your spot.

Please remember to check your calendar first… Cancellations/refunds will only be issued if a replacement is found with ample time before the trip, as travel-related document issuance should be taken into account.

• Standard Rooms (in Havana): $4,900 per person (total of $9,800 for two people)
• Executive Rooms (in Havana): $5,200 per person (total of $10,400 for two people) 

• Standard Rooms (in Havana): $5,500 per person
• Executive Rooms in Havana: $6,200 per person