Vintage car on a street in Old Havana, Cuba

YPO Pacific Expeditions

OLD HAVANA
CALLING

In Hemingway's Footsteps

January 20 – 24, 2027 · Havana, Cuba

"My mojito in La Bodeguita, my daiquiri in El Floridita."
— Ernest Hemingway

You Are Invited

An Exclusive Journey for Visionary Leaders

YPO Pacific Expeditions · January 2027

Travel to Havana with your fellow YPO Pacific Expedition members and enjoy unique, impactful, behind-the-scenes experiences curated by Cuba Educational Travel. Explore the rich culture and history of Cuba — connect with Cuban artists, musicians, entrepreneurs, and activists.

This is not a conference. This is an experience.

  • Explore the backstreets of Old Havana and its beautiful plazas
  • In-depth panel discussions with top Cuban thought leaders
  • Support important community and entrepreneurial projects
  • Intimate small-group experiences: boxing, biking, art, and music
  • Private music and dance performances with Cuban artists
  • Walk in Hemingway's footsteps at the legendary Finca Vigía

Join us in Havana for this Only in YPO Experience

Backstreets of Old HavanaCuban musicians performing in Havana

Day by Day

Five Days in Havana · January 20 – 24, 2027

★

Day OneWednesday, January 20

3:00 PM

Arrival to Havana. Meet your local hosts and transfer to lodging. Check-in at Boutique Hotels. Light lunch upon arrival.

5:30 PM

"21st Century Cuba: Economic Reform and Private Sector Growth" — a conversation with Oniel Diaz, a leading mind on the Cuban economy.

7:00 PM

Welcome dinner at La Guarida — the legendary Concordia mansion. Private music performance by Primera Linea, a youth band fusing music from Cuba and New Orleans.

★

Day TwoThursday, January 21

9:00 AM

Architecture, urban-planning and family economics. Presentation by urban planner Miguel Coyula on housing, infrastructure, investment, and restoration programs.

10:30 AM

Old Havana on Foot. Explore the historic center and UNESCO World Heritage Site. Venture to the side streets to witness Cuban life first-hand.

1:00 PM

Lunch at Old Havana Paladares in small groups.

3:00 PM

Performance by Datway Dance Group. Briefing with senior official from MINREX (Ministry of Foreign Affairs).

7:30 PM

Dinner at Atelier, one of Cuba's first female-led paladars. Post-dinner: Choose your Cuban Vice — Rum Tasting or Cigar Tasting.

★

Day ThreeFriday, January 22

9:30 AM

Percussion and dance with Habana Compas Dance. Founded by Liliet Rivera, protégé of the renowned Lizt Alfonso Dance Company.

10:30 AM

Panel discussion with private business entrepreneurs on new reforms and the private sector.

12:00 PM

Buffet lunch on site at Estudio 50.

1:00 PM

Havana Deep Dive — Choose Your Activity (see Activities section below).

6:00 PM

Havana rooftop jam session. Get down with Cuban music and watch the sunset while jamming with local musicians.

8:00 PM

Dinner at Paladar Yarini in the San Isidro Art District. Nightlife: Havana Nights.

★

Day FourSaturday, January 23

9:00 AM

Conversation with Cristina Escobar — journalist and political reporter on Cuban television for 13 years, one of the most important analysts of Cuban reality and foreign policy.

11:00 AM

Visit Ernest Hemingway's old stomping grounds — an insider look at Finca Vigía, the history-filled compound where he spent much of his time.

Afternoon

Coastal reception at a private residence in the beautiful Miramar neighborhood. Live music, salsa dancing, food, drink, and a fashion show hosted by Cuban brands.

8:00 PM

Dinner at El Cocinero. Private concert by Cuban legend Carlos Varela. Nightlife: Fabrica de Arte Cubano.

★

Day FiveSunday, January 24

Morning

Check-out of lodging and depart for airport — allow 2½ hours prior to your flight. (Pending individual flight information.)

Friday Afternoon · Day Three

Choose Your Cuban Adventure

Select your activity when registering

Salsa Lessons

Learn the moves of Cuba's most famous dance with a private instructor in an intimate setting.

Behind-the-Scenes Art Tour

Visit the homes and studios of independent Cuban artists for an exclusive look at their creative process.

Museum of Cuban Art

An art historian guides you through four centuries of Cuban art at the Museum of Cuban Art.

Ruta Bikes Tour

Bicycle through Havana with Ruta Bikes, a privately owned company operated by private employees.

Finca Vigía, Ernest Hemingway's home in Havana

A Literary Pilgrimage

Walk Where Hemingway Lived

Finca Vigía, Havana · Saturday, January 23

On Saturday morning, your group receives an exclusive insider tour of Finca Vigía — the history-filled, beautiful compound where Hemingway spent much of his time in Cuba. Explore the rooms where he wrote, the gardens he loved, and the views that inspired some of the 20th century's greatest literature.

"There is no friend as loyal as a book."
— Ernest Hemingway

Culinary Experiences

Dining in Havana

Cuba's finest paladares and private dining experiences

Private dinner setting at a Havana paladar

Welcome Dinner · Wednesday

La Guarida

The Legendary Concordia Mansion

Set inside a crumbling but magnificent Havana mansion, La Guarida is one of Cuba's most celebrated restaurants. Your welcome dinner here includes a private music performance by Primera Linea, a youth band fusing music from Cuba and New Orleans.

  • Private music performance included
  • Historic Concordia neighborhood setting

Closing Night · Saturday

El Cocinero

Private Concert by Carlos Varela

Your final evening in Havana culminates at El Cocinero with a private concert by Cuban legend Carlos Varela. The night continues at Fabrica de Arte Cubano — Havana's most celebrated cultural venue.

  • Private concert by Carlos Varela
  • Late-night at Fabrica de Arte Cubano

Evenings in Havana

Havana Nights

Music. Dancing. Unforgettable Evenings.

🎵

Live Music Nightly

🍹

Rum & Cigar Tastings

🌙

Fabrica de Arte Cubano

Each evening in Havana brings a new experience — from a private concert by Carlos Varela to a rooftop jam session at sunset, from the vibrant Fabrica de Arte Cubano to intimate dinners in historic paladares.

January 20–24, 2027

Havana, Cuba

Dates

Jan 20–24, 2027

Location

Havana, Cuba

Membership

YPO Gold Pacific Expeditions

Spaces are limited. This journey is offered exclusively to YPO Pacific Expedition members and their partners. To confirm your place, please contact your YPO chapter coordinator.