Undiscovered Cuba Tour

13 Days / 12 Nights

Havana | Santa Clara | Remedios | Caibarién | Camagüey | Bayamo | Baracoa | Santiago de Cuba | Holguín


The intriguing island nation of Cuba is roughly 780 miles long. It’s a rich, geographically disparate stretch where virgin forests hug rustling tobacco fields, colonial cities sprout from the foot of rugged mountains, and rivers reach blue tentacles around fertile valleys. We wouldn’t blame you if you wanted to see it all.

In fact, that’s exactly why we’ve introduced our 13-day Undiscovered Cuba Tour. For those of you with a real zest for adventure and a desire to leave no stone unturned, this is the ultimate excursion. 

From the moment you touch ground in Havana, your Cuban guide is here to not only help navigate country roads and labyrinth streets, but to offer a unique perspective and understanding of the place they call home. Experience Cuba as an active participant, coming to know lifelong locals through small-group discussions and behind-the-scenes excursions. This cross-country tour, along with the rest of Insight Cuba’s people-to-people journeys, offers unique access to people and places the average tourist rarely sees.

Your trip begins in Old Havana, a famous UNESCO heritage area swathed in Hispanic-Andalusian architecture. Immerse yourself in Cuban culture from the very onset, as you get to know Cubans across multiple generations.

From Havana, it’s off to Cuba’s central province of Villa Clara, where you’ll have the chance to discuss political expression through alternative art and music with local artists in Santa Clara. Nearby, the carefully preserved town of Remedios beckons with a historic square overlooked by a Baroque cathedral. Since good things come in three's, our third stop in this province includes Caibarién, known as Villa Blanca, for its white sands. 

As you journey east, stops include Camagüey, where your guide will help navigate winding, maze-like streets flanked by red-tiled Colonial houses and historic churches. 


Then its on to Bayamo and then Santiago de Cuba, the second-largest city in the country and birthplace of the Cuban Revolution. Santiago is Afro-Cuban to the core, witnessed by the white clothing of Santeria initiates and the fast-talking nature of its residents.

Next, make your way to Baracoa. Wrapped in tropical forests and hugged by the sea, Baracoa will leave a photograph on your mind. As the oldest city in Cuba, its way of life is refreshingly simple; many people make a living fishing and cultivating coconut and banana. You’ll see strong work ethic in action on a private tour of a cucurucho (sugar and coconut candy) factory. The pride the locals have in creating this unique island delicacy is a treat unto itself.

You’ll then return to Santiago de Cuba to immerse yourself one more time in this soulful city before heading to Holguín and then back to Miami.

For us at Insight Cuba, this cross-country expedition is about far more than taking you from Point A to Point B. It’s about seizing the beauty, spirit and soul of Cuba and its people, while making personal connections and feeling the island’s beat of life. We look forward to going the distance with you.

Scroll down to see what's included, the sample itinerary, departure dates, and pricing

What's Included

  • One night at Sofitel Miami Hotel, Including breakfast and airport transfer. New

  • Private welcome reception and pre-tour briefing. New

  • Full schedule of guided people-to-people activities

  • Superior accommodations at the Melia Cohiba in Havana. New

  • Superior accommodations at the Melia Santiago when in Santiago de Cuba

  • Standard accommodations in the provinces

  • Insight Cuba exclusive-guided programming, including; unique handpicked people-to-people activities; insider access to Cuba's famous places and those rarely seen; and private visits and lectures with Cuba's renowned experts. New

  • Experienced Insight Cuba Tour Leader

  • Expert Cuban guide

  • All meals while in Cuba, except for two paladar evening dining experiences on your own

  • U.S. Department of the Treasury license and Insight Cuba letter of authorization

  • Small group size (usually 16 or fewer guests; never more than 24)

  • All entrance fees to scheduled activities and events

  • Flight package (cost additional) including; round-trip charter air from Miami to Cuba; priority check-in at Miami International Airport; and baggage fee for first checked bag. New

  • All in-country ground transportation, and airport transfers

  • Travel health insurance, emergency medical evacuation, and trip cancellation coverage (up to $1,000)

  • Fresh bottled water while touring

  • Insight Cuba Travel guidebook

  • 24 hour emergency customer service hotline

  • Gratuities for luggage handling, restaurant service, and programmed activities throughout tour* New

*Customary end-of-tour gratuities for the Cuban guide, driver, and tour leader are left to the guest’s discretion and should be based on your satisfaction with the level of service received.

New Tour addition as of Dec 4, 2013.

Sample Itinerary

*A significant portion of your in-country programming is customized for each group to maximize your cultural experience. Many of the places we visit are not tourist destinations and are thus not always available. Therefore, this program should be considered as a sample only – please keep in mind that your particular tour may vary. Final itineraries are sent to guests one to two weeks prior to departure.

Days 1-2: Miami / Havana

Your trip begins at the Sofitel Miami Airport hotel with an early evening briefing and reception. Following breakfast, you’ll board your charter flight to Havana. After clearing immigration and customs, get your first taste of this island nation at one of our favorite restaurants. Then, it’s a short drive to Jaimanitas to meet artist Jose Fuster. Known as the Picasso of the Caribbean, he has turned his home and community into a living art gallery that has transformed old facades into colorful murals. After, you’ll check in to our hotel in the heart of Havana, then meet for an orientation and a welcome dinner. 

Meals Day 1 | Enjoy dinner on your own, at your leisure
Meals Day 2 | Breakfast, Lunch, Dinner


Day 3: Havana

Take a walking tour of historic Old Havana on your way to meet students and professors from La Escuela Taller Gaspar Melchor de Jovellanos. After lunch, visit Angela Landa primary school, where the children’s smiles will warm your heart. End the day with dinner at La Floridita, one of Hemingway’s favorite daiquiri spots.

Meals | Breakfast, Lunch, Dinner

Day 4: Havana

Meet the editor of a popular Cuban newspaper for a presentation on Cuban social, economic and policy issues. Visit a local farmers market and experience firsthand Cuba’s dual currency. After lunch, you’ll meet with a professional children’s theater group to watch them rehearse and get to know them.

Later, meet the teachers and headmistress of La Casa del Niño y la Niña, an after-school program. Tonight, you’ll dine on your own at a paladar, a private, family-owned restaurant. Your Insight Cuba tour leader, who is an expert in the dining scene, will make the best recommendations.
Read More

Meals | Breakfast, Lunch

Days 5: Havana/ Santa Clara

Today, you'll journey to the colonial town of Santa Clara. Your first stop will be a community project where residents have converted a defunct industrial area into a nature park. After lunch, you'll visit the Che Guevara Memorial before heading to a special meeting with members of a traditional music troupe, who will demonstrate their unique genre of music, a style common in theatrical performances and silent movies at the beginning of the 20th-century. Afterwards, you’ll check in to your hotel in Santa Clara.

Meals | Breakfast, Lunch, Dinner

Day 6: Santa Clara / Remedios / Caibarién

After breakfast, you’ll visit the town of Remedios to meet with a historian who will discuss the town’s unique history. Afterwards, you’ll travel by bicycle taxi (great fun!) to a warehouse where parade floats are made and stored for Remedios’ famous street celebration called Las Parrandas, which has occurred every December since the eighteenth century.

After lunch in Remedios, you’ll take a short trip to the town of Caibarién, where you’ll visit a traditional printing house still using nineteenth-century machines.  Next, you’ll make your way along the Caibarién Malecón to learn about the town’s sailing history before you visit an artist’s community project. Afterwards, you’ll return to Santa Clara for dinner.
Read More

Meals | Breakfast, Lunch, Dinner

Days 7: Santa Clara / Camagüey

Early this morning, you’ll depart for Camagüey, where you will have lunch. Afterwards, meet with a sculptor and painter in his studio. In keeping with the days artistic theme, you'll meet with a local dance group. Tonights, you'll dine at Camagüey’s best paladar, a private, family owned restaurant. 

Meals | Breakfast, Lunch, Dinner

Day 8: Camagüey

On your second day in Camagüey, meet the creative people at the National Union of Writers and Artists of Cuba before visiting an inspiring community project for children. After lunch, visit with musicians at the Casa de la Trova before taking another bicycle taxi with a local historian.

Meals | Breakfast, Lunch, Dinner


Day 9: Camagüey / Bayamo / Santiago de Cuba

Depart for Santiago de Cuba, stopping in historic Bayamo, where you’ll meet the singers at the Professional Choir of Bayamo before visiting artists at the Muñequería y Artesanía community project. You’ll arrive in Santiago de Cuba in time for dinner.

Meals | Breakfast, Lunch, Dinner

Days 10: Santiago de Cuba / Baracoa

The day begins with a presentation from an expert on Afro-Cuban culture and traditions. Afterwards, visit the Plaza Delores with a historian.

Take in a breathtaking view over lunch at El Morro de Castillo before journeying to Baracoa, where you’ll check in to your hotel. After breakfast, visit a Baracoa music-dance ensemble. After lunch, begin your journey back to Santiago de Cuba.

Meals | Breakfast, Lunch, Dinner

Read More

Day 11: Baracoa

Your first morning there will include a visit with a renowned historian to learn about Baracoa's unique history and traditions. Afterwards, take a short boat ride up the Rio Toa. After lunch, visit the Fabrica de Cucuruchos, where they make a local sweet from palm leaves, coconut, sugar, and pineapple.Tonight, you’ll dine on your own at a paladar, a private, family-owned restaurant. Your Insight Cuba tour leader, who is an expert in the dining scene, will make the best recommendations.

Meals | Breakfast, Lunch

Day 12: Baracoa / Santiago de Cuba

After breakfast, you’ll have an exclusive visit with Insight Cuba’s friends in their homes for a taste of Cuban hospitality, warmth, and learning about daily life in Cuba. Later this morning, you’ll visit with a Baracoa music-dance ensemble, followed by lunch.  After lunch, you’ll begin your journey back to Santiago de Cuba. 

Meals | Breakfast, Lunch, Dinner

Day 13: Santiago de Cuba / Holguín / Miami

After breakfast, you’ll depart for Holguín and visit an artist community, where you'll gather with local painters. After lunch, bid farewell to Cuba and board your flight to Miami from Holguín's Frank País Airport.

Meals | Breakfast, Lunch

Tour Dates & Prices

Undiscovered Cuba Tour

DateDouble Occupancy (per person)Status
Feb 23, 2014 – Mar 7, 2014$5,995  Sold Out
Mar 16, 2014 – Mar 28, 2014$5,995  Sold Out
Apr 6, 2014 – Apr 18, 2014$5,995  Sold Out
Apr 27, 2014 – May 9, 2014$5,995  CALL NOW
May 18, 2014 – May 30, 2014$5,695Only 5 spots left! Book Now!
Jun 15, 2014 – Jun 27, 2014$5,695Only 7 spots left!Save $300!Book Now!
Jun 29, 2014 – Jul 11, 2014$5,695  Sold Out
Jul 27, 2014 – Aug 8, 2014$5,595  Book Now!
Sep 21, 2014 – Oct 3, 2014$5,595 Save $300!Book Now!
Nov 16, 2014 – Nov 28, 2014$5,695  Book Now!
Dec 21, 2014 – Jan 2, 2015$5,995  Book Now!
Dec 28, 2014 – Jan 9, 2015$5,995  Book Now!
Jan 18, 2015 – Jan 30, 2015$5,995  Book Now!
Feb 8, 2015 – Feb 20, 2015$5,995  Book Now!
Mar 8, 2015 – Mar 20, 2015$5,995  Book Now!
Mar 29, 2015 – Apr 10, 2015$5,995  Book Now!
Apr 26, 2015 – May 8, 2015$5,795  Book Now!
May 17, 2015 – May 29, 2015$5,795  Book Now!
Jun 7, 2015 – Jun 19, 2015$5,795  Book Now!
Jun 28, 2015 – Jul 10, 2015$5,795  CALL NOW
Jul 19, 2015 – Jul 31, 2015$5,795  Book Now!

Single Supplement: For single-occupancy pricing, add $500.

Pricing From

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Flight Package

Undiscovered Cuba Tour

  • Air from Miami to Havana
  • Cuban visa
  • Air from Santiago de Cuba or Holguín to Miami
  • Baggage fee for first checked bag
  • Priority check-in at Miami International Airport


Jan 8 - Dec 19$635
Dec 20 - Jan 7$725

-Flight Package Prices are subject to change unless accompanied by confirmed booking

  • “I feel fortunate to have selected Insight Cuba. They are experienced, very helpful, knowledgeable and a professional tour company. It was an excellent trip; I highly recommend InsightCuba.”

    Virginia T.

  • “Highly professional staff, an interesting selection of tours. Insight Cuba took care of everything so we could enjoy our experience and get what we wanted from it.”

    Elizabeth R.

  • “Next stop Havana! It's legal so let's go!!! ”

    Crystal K.

  • “If you have the opportunity to go with Insight Cuba, don't miss out! This is a very exciting time to visit Cuba!”

    Ellie Z.