December 5-13, 2019

Trip Highlights

Enjoy rooftop views, listen to jazz and rumba, and seize the opportunity to engage in historical and colorful conversations with the welcoming Cuban people to reflect on the island’s remarkable history and fascinating future. Join Next Step Travel for either  a weekend adventure to Havana (the “Hidden Havana” program) or a week-long exploration of the island (“Explore La Isla” program) – or both and receive $100 off!

  • Immersive History - Learn about Cuba’s history and architecture through hidden local gems and World Heritage sites.

  • Artist Interactions - Join artists in their studios and on the streets and discover Cuba's impressive and evolving art scene and subcultures.

  • Latin Beats - Dance to uniquely Cuban musical styles, from son to rumba and jazz.

  • Optional Extension - See the Bay of Pigs, Cienfuegos, Trinidad, and Santa Clara. Learn more about Che Guevara’s guerilla army during the 1958 liberation, visit the Valle de los Ingenios to dive deeper into the sugar industry, and chat with villagers in Manaca Iznaga.


Prices are based on double occupancy. Accommodations include Cuban homestays (similar to B&Bs, where each room has a private bath and shower) and charming 3-star hotels. Private accommodations are available for a $399 single supplement for the Hidden Havana program and $399 supplement for the Explore La Isla program. As a solo traveler, if you prefer, we can also pair you with another traveler (two twin beds, requiring no single supplement, based on availability).


This trip is accessible for most travelers. That being said, please note that the trip can involve long days, a good amount of walking (including stairs, varied elevations, and uneven surfaces), exposure to the sun, and potentially hot temperatures. If you have any medical conditions or other concerns, there will be opportunity for you to make us aware of them, and then we can determine if the trip is appropriate for you.


  • Accommodations as described in the itinerary (based on double occupancy)
  • All meals as outlined in the itinerary
  • Transportation by private, air-conditioned motor coach as well as transfers for the group as appropriate
  • English-speaking guides
  • Comprehensive cultural information and reading materials
  • All gratuities for participants and staff to cover drivers, wait staff at group meals, guides, and tour directors


  • Cuban visa, which will be processed by Insider Expeditions at an additional fee of $100
  • Flights to and from Havana’s José Martí International Airport (HAV) (for the “Hidden Havana” program) or to Havana’s José Martí International Airport (HAV) and from Santa Clara (SNU) (for the “Explore La Isla” program, or if choosing both programs). A group flight may be available and additional details will be provided after booking.
  • Expenses of a personal nature (including cab fares, laundry and other personal items, room service charges, etc.)
  • Transportation of luggage in excess of weight allowance
  • Travel insurance (we strongly advise that each participant arrange for their own travel insurance)
  • Alcoholic beverages
  • Meals not noted in itinerary
  • Medical expenses
  • Passport application fee
  • Costs associated with trip interruption or modification due to weather, travel conditions, political/civil disputes, medical emergencies or other causes beyond our control


Cancellation by Traveler

The $250 trip deposit is non-refundable.

  • 25% non-refundable 120 days or more prior to departure
  • 50% non-refundable 119 to 90 days prior to departure
  • 75% non-refundable 89 to 60 days prior to departure
  • 100% non-refundable 59 days or less prior to departure

If a traveler leaves the trip for any reason after it has commenced, we are not obligated to make any refunds for unused services. If a travelers fails to join a tour, join it after departure, or leave it prior to its completion, no refund will be made.

Cancellation by Trip Operator - Insider Expeditions (IE)

IE may cancel a trip at any time prior to departure due to terrorism, natural disasters, political instability, or other external events if it is not viable for us to operate the planned itinerary. If IE cancels the trip, traveler can transfer amounts paid to an alternate departure date or receive a full refund. In circumstances where the cancellation is due to external events outside our reasonable control, refunds will be less any unrecoverable costs. We are not responsible for any incidental expenses that you may have incurred as a result of your booking including but not limited to visas, vaccinations, travel insurance excess or non-refundable flights.



Hidden Havana

December 5-9, 2019

Day 1 - Explore Havana

Enjoy the sunset from a gorgeous, breezy rooftop before starting your evening with an engaging Q&A on life in Cuba with a former diplomat.

Lunch and dinner will be provided.

Day 2 - Cigars, Art, and Architecture

Meet with aficionados at a cigar factory and visit a local association to learn more about community organizations in Cuba and how they support the people and culture of the island. Enjoy dinner with a local family, before visiting Fábrica de Arte, a factory converted into a warehouse of emerging art and live music.

Breakfast, lunch, and dinner will be provided.

Day 3 - Santería, Rituals, and the Malecón

Tour a famed Cuban ceramicist’s wondrous studio. Enjoy a special lesson in spirit and cigar tasting from an expert sommelier. Then, meet with Santería practitioners before cruising the Malecón oceanside promenade in classic convertibles.

Breakfast, lunch, and dinner will be provided.

Day 4 - Cuban Countryside

Leave the city limits and discover Cuba’s scenic countryside at Las Terrazas, the pioneering eco-village that is now a UNESCO Biosphere Reserve. Discuss conservation efforts with a sustainability expert, and wander through one of the country’s oldest coffee plantations, with stunning views of the lush green valley and the Caribbean Sea in the distance. Finish the night with a celebratory feast and listening to the Grammy-awarding winning hits of the Buena Vista Social Club.

Breakfast, lunch, and dinner will be provided.

Day 5 - Departure or Extension

Depending on final flight times, relish a final morning of self-exploration in old Havana, featuring several options that will be presented to you by our local guide. Or join us for the “Explore La Isla” program to venture to the Bay of Pigs, Cienfuegos, Trinidad, and Santa Clara.

Breakfast will be provided.


Explore La Isla

December 9-13, 2019

Day 5 - Bay of Pigs

Head to the hilltop village of San Francisco de Paula for a private visit to Ernest Hemingway’s Finca Vigía, the eclectic house where he lived for 20 years—now a museum displaying his library, manuscripts and personal effects. Then drive through Cuba’s country side to the Bay of Pigs, the location of the failed military invasion undertaken by the CIA on April 17, 1961. Stop and enjoy the views and hear locals reflect on the Cold War, and bring your bathing suit for a dive into the profound natural beauty of this historic site. Those arriving today just for the “Explore la Isla” program will have a private airport transfer to join us at the Bay of Pigs.

Lunch and dinner will be provided.

Day 6 - The Pearl of the South

Visit Cienfuegos, another UNESCO World Heritage site, learn about Cuba’s ocean life and environmental stewardship at the Delfinario de Cienfuegos dolphin center, before heading for a splash in the Guanaroca Lagoon. Visit the Castillo de Jagua, an ancient fort that allowed the city to withstand the pirate attacks once common in Cuba, and learn about the burgeoning private economy.

Breakfast, lunch, and dinner will be provided.

Day 7 - The Potter’s Wheel

Take a guided tour of Trinidad’s main plaza and museums before visiting a potter’s studio that has been operated by the same family for decades. In the afternoon, visit the local library and learn about the library system in Cuba, including censorship and how the facilities are supported.

Breakfast, lunch, and dinner will be provided.

Day 8 - The Legacy of Sugar

Another of Cuba’s many UNESCO World Heritage sites and Cuba’s best-preserved colonial city, enjoy lunch in Trinidad, which was founded in 1514. Learn from local professor and visit the nearby Valle de los Ingenios and the sugar district. Chat with villagers in Manaca Iznaga while enjoying a glass of cold mango juice or guarapo.

Breakfast, lunch, and dinner will be provided.

Day 9 - Santa Clara

Famous for being the site of the last battle of the Cuban revolution which marked the end of the Batista regime, climb the 579-foot peak to reach Loma del Capiro, the ideal spot to look out and learn about this regional capital. Visit the mausoleum and memorial, and learn about Che Guevara’s immortalized legacy from locals. Then say your final farewells before heading out for afternoon flights from the Cuban province of Villa Clara, Santa Clara (SNU).

Breakfast will be provided.

A Note on the Final Itinerary:

Itineraries and pricing are subject to change. This particular tour has been designed with specific events in mind, and schedules and availabilities may change in coming months. If any activity or person that is advertised is missed or not available, it will be replaced with an activity or person of equal interest and value. A final itinerary and briefing packet will be ready two weeks before the trip.


december 5-9, 2019

$2,299 ($399 single supplement)

Cuba - Havana Reservation
Purchase Reservation

december 9-13, 2019

$2,299 ($399 single supplement)

Cuba - La Isla Reservation
Purchase Reservation

december 5-13, 2019

$4,498 ($789 single supplement)

Cuba - Both Trips Reservation
Purchase Reservation

Reservation fee will be credited towards full ticket.

This trip is coordinated by RPCV Mary Bruce of tour operator Insider Expeditions.