Cross the entire island

Cuba Vacations

Did you know that Hemingway spent the last 20 years of his life in Cuba? Havana is 500 years old? Hotel Nacional was built by an architecture firm from Boston? Ropa Vieja literally translate to dirty clothes?

All our trips to Cuba are safe and legal. The itinerary is carefully designed to meet the category: “Support for the Cuban people”.

Highlights of Cuba Vacations

  • 3 cities: diverse Havana, French influenced Cienfuegos and Spanish colonial Trinidad
  • Breathtaking countryside of Viñales with tobacco plantations and cigar rolling workshop
  • Idyllic eco village of Las Terrazas with artist studios and best coffee on the island
  • Legendary Cuban music concert
  • Ride on Malecon in convertible cars
  • Pristine Playa Ancon

Dates & Cost



COST (double / single)

February 13th – 23rd, 2021

12 days

$2795 / 3295

Cuba Itinerary

Day 1

Welcome to Havana! A magical city full of friendly people and warm weather. You will have the opportunity to exchange the currency (at official bank rate). In the evening we will head to Paladar San Cristobal – one of the famous restaurants in Havana that once hosted President Obama, Beyonce and Jay Z and over 20 other presidents. We will shake hands with the legendary owner -Carlos Cristobal and have a welcome dinner (with rum and cigar) and a guided tour of this spectacular establishment.

All day             Arrivals at the airport and hotel. Check-in to casas and welcome drinks and orientation, money exchange. Sunset at La Guarida (with 360 view from the rooftop). Dinner at  Paladar San Cristobal (where Obama had dinner). Music Concert at Havana Jazz Festival

Meals included: dinner

Day 2

Morning      Architecture tour of Old Havana with focus on colonial history of the City. Visit to all four squares: Plaza Vieja Plaza de La Catedral Plaza de Armas Plaza de San Francisco Calle Obispo Calle Mercaderes , Capitolio and Parque Central, Bacardi Building , Ambos Mundos Hotel (Hemingway room), Theatre Alicia Alonso, Floridita (Hemingway bar), Lunch at Mama Ines – run by chef Erasmo that cooked for Fidel

Afternoon   Visit to Custodio San Angel (where Jose Marti was baptised), artist galleries, old book market, Clandestina (first Cuban designer boutique). Dinner at  Doña Eutimia – one of the oldest Paladars with best ropa vieja in Havana

Evening     Jazz concert at  FAC (Fabrica de Arte Cubano)

Meals included: breakfast, lunch, dinner

Day 3

Morning      On the way to Viñales visit to Fusterlandia (art community). Viewpoint Los Jazmines. Visit to tobacco farm, drying houses, cigar rolling lesson. Lunch with guajiros (campesinos) at the farm

Afternoon   Hiking through the Valley of Silence dotted with yuka, tobacco and coffee plantations. Dinner and sunset at Balcone del Valle

Evening       Dance and music workshop

Meals included: breakfast, lunch, dinner

Day 4
Las Terrazas

Morning      Drive from Viñales to Las Terrazas. Tour Las Terrazas, eco-community of artists, coffee growers, etc. Lunch at Las Terrazas – El Romero – Cuba first vegetarian and eco cafe

Afternoon   Visit artist studios: Lester Campa, Ariel, Henry Loma. Visit to old coffee plantation with discussion on Cuba coffee industry. Coffee tasting at Café de Maria. Visit to spectacular Hotel Moka. Swim in baños.

Evening       Dinner at La Catedral in Havana

Meals included: breakfast, lunch, dinner

Day 5

Morning      Revolution Day in Havana – modern history of Cuba. Visit the Museum of Revolution  with discussion on Cuban revolution and its leaders. Lunch at II Rustico – Cuban first authentic Italian restaurant

Afternoon   Stroll through Malecon, drinks in gardens of Hotel Nacional. Convertible car ride with stops at Universidad de Havana, Plaza of the Revolution, Havana Forrest

Evening        FREE TIME – Our team can help with booking individual activities (additional cost), for example: Baseball game (if available), Jazz concert, FAC (Fabrica de Arte Cubano), Tropicana cabaret or other

Meals included: breakfast, lunch

Day 6

Morning      Visit to Finca Vigia – Hemingway house. Visit to Muraleando community project. Lunch with Muraleando community

Afternoon   Drive to Cienfuegos. Tour of Cienfuegos – focused on French architecture. Santeria drumming if available

Evening       Dinner at Las Mamparas. Sunset cocktails on the rooftop of Palacio de Valle at Punta Gorda

Meals included: breakfast, lunch, dinner

Day 7 

Morning      Drive to Trinidad via Playa Larga. Tour of Trinidad with workshop on Santeria religion, colonial architecture and history, tasting the local drink canchanchara. Lunch at Finca

Afternoon   Free time in Trinidad

Evening       Live music and dance

Meals included: breakfast, lunch

Day 8 
Sancti Spiritus and Camaguey

Morning      Drive to Sancti Spiritus. Tour of the Old town. Lunch at Papo’s Boulevard 

Afternoon   Departure to Camaguey. Tour of Camaguey

Evening       Dinner at Casa Austria. Drive to Holguin

Meals included: breakfast, lunch, dinner

Day 9 
Holguin/ Baracoa

Morning      Historic tour of Holguin. Coastal ride via Playa blanca, Playa Pesquero, Guardalavaca. Lunch at the beach coast.  

Afternoon   Drive to Baracoa

Evening       Dinner at Restaurante La Terraza – Casa Nilson. Music at Casa de la Trova

Meals included: breakfast, lunch, dinner

Day 10 
Baracoa and Guantanamo

Morning       Cocoa plantation tours, chocolate tasting, isolated sea coast tour. Lunch at Finca

Afternoon    Drive to Punta de Maisi – very end tip of the island of Cuba. Lunch at Punta de Maisi. Drive to Guantanamo

Evening        Drive to Santiago de Cuba

Meals included: breakfast, lunch 

Day 11 
Santiago de Cuba

Morning      Historical tour of Santiago: El Tivolí, Museo de la Lucha Clandestina, Padre Pico steps, Balcón de Velázquez, Parque Céspedes, Casa de Diego Velázquez, Catedral de Nuestra Señora de la Asunción, Cuartel Moncada. Lunch at Rumba Cafe.

Afternoon   Visit to Santa Ifigenia Cemetery, where Jose Marti and Fidel Castro are buried. Drumming lesson.

Evening       Goodbye dinner at Company Gallo

Meals included: breakfast, lunch, dinner

Day 12 
Santiago de Cuba

All day         Free time. Departures

Meals included: breakfast

Tour Operator

Sylvia  +1 617-301-1237  Jorge +53 5-344-2776

Emergency Telephone Numbers

Country Code for Cuba +53

Police 106

American Embassy: (+53) 7-839-4100 Address: Calzada St between L&M

Asistur English speaking tourist information: 7-866-8527 (regular hours), 7-866-4121 (24h emergency)

Hospital: Clínica Central Cira García Hospital in Miramar, +509 34 86 8761

Panataxi: 7-55-5555


We stay in 4/5 stars boutique hotels that best reflect the local architecture and flavors.

Air condition

Towels and soap

Hair Dryer


Example from past accommodations


What’s included?

  • Cuban Visa
  • Flights between countries
  • All activities listed on itinerary
  • Accommodation
  • All Breakfast and lunches, 8 dinners
  • Guides
  • Tickets to all scheduled sites
  • Ground transportation
  • 24h bilingual tour director support
  • Pre-departure Q&A

What’s not included

  • Airfare
  • 3 dinners
  • Alcohol
  • Additional health & evacuation insurance
  • Optional airport pick up and drop off - 45 USD (both ways) per person


Register now!

Steps to enroll:

  1. Download registration form below, fill it out and send to or mail to Colibri Boston, 210 Broadway, Suite 201, Cambridge, MA 02139.
  2. Send us a copy of your passport and deposit check.
  3. Pack your bags and enjoy!

Small group:

8 - 20 ppl

Physical rating:


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While Cuba is a fascinating country, it wouldn’t have been nearly as wonderful without your commentary, creativity, and enthusiasm. I was so utterly impressed with your knowledge of Cuba’s history, your remarkable ability to navigate the Cuban bureaucracy, and your unending flexibility and willingness to make our requests come to fruition. I don’t think that there was a detail that you didn’t attend to. Add to that your wonderful sense of humor, sensitivity and great spirit – and you are hard to beat! I would follow you on any trip you plan knowing it would be just as exciting, informative and fun as Cuba vacations was.

Gail G. of Brookline, MA

As a recent participant on a Cuba Study tour through UMass Bosont guided by Colibri Boston, I have nothing but high praise for Colibri’s preparations and follow through for all phases. As a frequent foreign traveler who avoids group tours I can say I was pleasantly surprised by their ability to cater to those folks who needed more guidance while leaving us solo types to explore as we wished. The local contacts they made for guide and driver were excellent. Our accommodations were far from spartan yet allowed people to soak up local flavor through the Cuban equivalent of Bed and Breakfasts. Finally, as on all trips, both solo, and group, unforeseen logistical problems arose which Sylvia handled with professional competence and aplomb. Kudos to Colibri.

Joe M. of Seattle, WA

We want to thank Colibri Boston for organizing our Cuba vacations with great meals, and the excellent tour leaders, Jorge and Alex, who made the whole trip a truly unforgettable experience! It was absolutely superb in every way. The organization of the itinerary was excellent and accurate on every detail. Our group was lucky to have the most amazing, intelligent and funny tour directors ever - Sylvia. She provided valuable insight into the Cuban politics and the daily lives of the Cubans. What we loved about this travel company is that they gave us as much as they could in the time frame allotted but also gave the option of having our own personal time and helped arranged activities that we wanted.

Pete J. of Portland, MA

Sylvia was a country where things may not go as planned, Sylvia made everything appear seamless. Her knowledge of Cuba is astounding. She's unflappable...if plan A doesn't work she has a plan B, C and D and does it with a smile. What my wife and I experienced was eye opening, what Sylvia showed us, where she took us, what she taught us, made the trip more than we ever envisioned.

Doug S. of Jamaica Plain, MA

We had a great experience with Colibri Boston. They were super quick to respond to every email we sent prior to our trip. All details were set and we knew exactly where to meet our driver at Havana Airport. Jorge was wonderful! His knowledge of the Cuban history was incredible and his English was perfect!

Dan B. of Manchester, NH

This is my 5th experience with Colibri Boston, and once again, it failed to disappoint. I went to Cuba last year and Vietnam, Thailand, Japan, Poland the previous years. As usual, a wonderful time was had by all, and big thanks to Sylvia and her staff for being prompt and accommodating. You are highly recommended!!

Adriana S. of Chicago, IL

Colibri Boston is awesome! Our guide Jorge was warm, welcoming, smart, fully knowledgeable and spoke excellent English. We enjoyed deep conversations, as we were very curious about daily life in Cuba. As for accommodation, we stayed in stunning villas in Havana and charming “campesino” fincas in the countryside. We loved every bit of our Cuba vacations.

Maria & Tony C. of Boston, MA