Cuba – Havana Weekend Getaway

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Signature Journey

4 Days / 3 Nights

$2,695 Adult / $2,495 Child

Escape to Havana for a weekend of art, music and exploration. Experience the best of this vibrant city!

The Experience

Havana is a city that is alive. From the narrow alleyways in Old Havana that echo jazz to the bustling seaside boardwalk known as the malecon, a weekend in Havana is a getaway you’ll never forget. Over the course of four days, you’ll step right into the stream of day-to-day life in Havana experiencing everything the city has to offer. More importantly, you’ll explore Havana like a local by meeting some of its most notable residents and witnessing first-hand a country in transition.

Spend a morning uncovering Ernest Hemingway’s old haunts at his house in Cojimar, a charming seaside town. Take a stroll through the cobblestone streets of Old Havana learning about its colonial heritage. Enjoy a performance from an Afro-Cuban dance company and test out your salsa dancing skills. Visit Havana’s Museum of Fine Arts, home to Cuba’s largest collection of contemporary art. Venture to a factory that has been transformed into a center for Cuban culture, arts and nightlife. Like a walking museum, the depth of history in Havana is unlike any other city in the world.

Legal, Immersive Travel to Cuba

Discover Corps offers a legal way to travel to the island of Cuba. We operate under the Support for the Cuban People license which ensures that you are traveling with an itinerary that will help support Cuban micro-entrepreneurs. Visit our Cuba FAQs page for more information.

Our Impact

Times are fast changing in Cuba, and Havana lies at the cusp of this new era. This could be a final chance to view a city largely preserved in time, before the onset of increased tourism.

This trip is designed to support the Cuban people and locally-owned businesses. Spend four days getting a taste of life in Havana and the art, music, and history that makes the city burst with such intense energy. Eat at family owned restaurants, or paladars, and stay in family-owned casas particulares instead of hotels.

Where You’ll Stay

During your trip, you’ll have the unique opportunity to stay in casas particulares, which literally translates as “private homes”. Casas are essentially family-run bed & breakfasts (think AirBnB’s with private breakfast in the morning). Families invest in making sure their houses are up to international quality standards, and they greet you with Cuban hospitality – but also give you the privacy and comfort you desire.

While houses vary in style from eclectic to classical, they all provide a comfortable glimpse into Cuban life. Our portfolio of casas particulares are hand selected with prime locations that will put you right in heart of the action and have private bathrooms, air conditioning & a fresh breakfast each morning.

Itinerary Overview

Arrive in Havana and settle into your casa particulare in the city. Venture to Finca Vigia, the former home of Ernest Hemingway. Discover the Cuba’s past with a visit to Havana’s colonial squares. Around one corner, Spanish-style cathedrals grace open-air plazas where live music echos across the buildings.

Around another, the heroes of the Cuban Revolution, Che Guevara and Fidel Castro, adorn the sides of buildings looking over the city. Explore the city’s art scene and engage in meaningful exchanges with the hosts of your casas particulares, or local bed & breakfasts. See the real Havana before it changes for good.

Traveler’s Journal

Havana is a place that epitomizes Cuban joie de vivre, or joy of life. In the streets, life just emanates out of every corner. Whether it’s the music, art or the depth of history, Havana never ceases to amaze me. I cannot wait to come back.
Havana Vacation

Mimi A.

Burlington, VT

Read More Discover Corps Reviews

Rating: 5/5 stars

Dates and Prices

Our trips are inclusive of all activities, lodging, transport and most meals to make your experience hassle-free.

$2,695 Adult

$2,495 Child

  • Double Occupancy Price. Children’s pricing applies to travelers 16 years old and younger sharing a room with an adult
  • Single Room Supplement = $250. This will guarantee you your own, single occupancy room for the entirety of the trip. If you are a solo traveler and would like us to match you with a roommate of the same gender, please book as double occupancy. See full details here.
  • Have questions about the logistics and legalities of traveling to Cuba? Contact us at (619) 758-3030.

What’s Included:

  • Bilingual expert Cuban guide & private Cuban driver
  • All meals in Cuba – Breakfast, Lunch and Dinner at restaurants or in Cuban families’ homes
  • 3 nights accommodation in casas particulares in Havana
  • All scheduled activities
  • All in-country ground transportation and airport transfers via air-conditioned van
  • Tips for luggage handling, restaurants, and programmed activities throughout tour
  • Legal documentation of your support for the Cuban people program
  • 24-hour Discover Corps emergency hotline & turnkey service

What’s Not Included:

  • Tips for Cuban guide and driver
  • International airfare
  • Cuban visa


Our intimate, small-group departures consist of like-minded travelers. Don’t see a date that works? Want to make it private? Schedule a personal travel consultation and we’ll make it happen.

2024 Dates

September 20-23, 2024 STS

October 4-7, 2024 STS

December 28-31, 2024

December 30, 2024-January 2, 2025

2025 Dates

January 3-6, 2025 STS

February 21-24, 2025

March 28-31, 2025

June 13-16, 2025

July 4-7, 2025

Sept 12-15, 2025 STS

October 3-6, 2025 STS

December 30-January 2, 2026

2026 Dates

January 2-5, 2026 STS

February 20-23, 2026

March 27-30, 2026

June 12-15, 2026

July 3-6, 2026

September 11-14, 2026 STS

October 2-5, 2026 STS

December 30-January 2, 2027 off dates

Want to learn more?

Alumni & Family Discounts, Monthly Payment Plans, and More

Repeat travelers and groups are eligible for discounts. Looking for a payment plan to help manage your trip? Learn more here.

Customized Private Trips

Let us create a custom trip for your group. Learn more about custom group travel.