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Cuba and the Cold War 9-day Tour

Contact to Arrange Dates!

Monthly departures starting at $2985 per person Group Pricing

Pack your bags and take the trip with Cuba Up Close now!

We have created a Worry-Free Travel Experience to Cuba!

Cuba Up Close All-inclusive Package Includes:

  • Travel Visa, Health Insurance and mandatory documentation required to enter Cuba
  • Meals and Accommodations in Premium Restaurants and Hotels per Itinerary
  • Daily Happy Hour at Legendary Bars
  • Private Driver and Guide
  • Expert-led Lectures and Private Tours of Sites
  • Transportation in Air-Conditioned Vehicles
  • Access to the REAL Cuba through behind-the-scenes meetings with artists, musicians, professors, doctors, farmers and Cuban officials.

Our Tour Price does not include: Driver and Guide Gratuities

Cuba and the Cold War, Bay of Pigs, Guantanamo and Havana 9-Day Tour

During our 9-Day immersion into Cuba, the last vestige of the Cold War between the United States and Russia, we will travel and tour to learn about one of history’s most tense and exciting conflicts.

  • Dine in top, chef-owned Paladars and take in the sights and sounds of a vibrant country in transition
  • Gain first hand knowledge of individual perspectives on past, present and future relationships between nations
  • Visit prominent sites that pay homage to this historical conflict
  • Discuss the Bay of Pig invasion, the Cuban missile crisis and how this conflict has shaped the lives of Cubans
  • Get a glimpse of the unique practices of the Cuban Santeria religion and traditional Afro-Cuban dance techniques.

Through our exploration of the Bay of Giron (Bay of Pigs), Revolution Square where all the major speeches of the revolution occurred and even The Hotel National’s secret underground tunnels, we will explore this conflict in history through a unique perspective in twentieth century times. Join us!

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Sample Itinerary

Day 1 | Miami

Arrive in Miami in time for a welcoming hors d’oeuvre/cocktail reception and orientation where we will talk about our exciting upcoming travels and departure the following morning to Cuba!

Day 2 | Havana

  • We will be processed at Miami International Airport and board our private charter flight to Havana.
  • After hotel check in we will enjoy a welcome reception and quick program orientation during our motor coach tour of the city before dining at our paladar restaurant, rumored to be former President Obama’s favorite.
  • After dinner, we will be guided through the cobblestone streets of Old Havana for a leisurely stroll as we begin to see why the city was designated a UNESCO world heritage site and once considered the Rome of the Caribbean.

Day 3 | Old Havana

  • After breakfast we will tour the Bellas de Artes Museum, Parque Lenin, the tree lined streets of Vedado and the embassy district and then on to a drive-by of Punta Zero (Point Zero), the very private and protected compound of Fidel Castro.
  • Lunch will be at stately favorite paladar mansion before we tour a cigar factory and see the process in action. We will have a chance to purchase the freshly rolled product and hear historical anecdotes of the time pre-Cold War when Cuba and the US were friends.
  • Happy Hour finds us at the legendary Sloppy Joe’s bar for a refreshing Pina Colada and its namesake hors d’oeuvres before jaunting back to the hotel to recoup for dinner.
  • Dinner tonight is at a lively revolutionary themed paladar restaurant with the coldest beers in Havana. After dinner we will have the chance to hear many of the legendary jazz ensembles at the jazz clubs that dot the streets of Havana.

Day 4 | Old Havana

  • Our bus will pick us up in the morning and we will visit the impressive Morro Castle and Fort, see an exhibit of the Soviet missiles which were transported to Cuba, triggering the Cuban missile crisis and visit the city of Regla, across the bay of Havana to get a glimpse of the unique practices of the Cuban Santeria religion and traditional Afro-Cuban dance techniques.
  • For lunch we will dine overlooking the Malecon sea wall and the fortress protecting the harbor before we tour the home of the famous revolutionary, Che Guevara.
  • Mid-afternoon finds us at the Hotel National and its secret underground tunnels, which were used by Fidel and his men during the overthrow of Batista.
  • Happy Hour is sipping mojitos on the expansive manicured lawn of the hotel overlooking the sea before we head back to the hotel to regroup.
  • Dinner is a dinner-theater show with traditional Cuban fare, rum cocktails and the sounds of the Buena Vista Social Club celebrating Cuba’s traditional musical elite.

Day 5 | Bay of Pigs

  • Will depart in the morning to visit Playa de Giron (the Bay of Pigs), the site of US CIA backed invasion during the Kennedy era. We will visit the Bay of Pigs museum and then relax in the afternoon at a unique waterfront restaurant of a local fishing family who will grill us freshly caught fish and shrimp at their beach restaurant and have chilled beer waiting upon our arrival.
  • We will have the chance to take a dip in the warm Caribbean waters and relax before we depart back to Havana and our hotel. An evening of leisure of choice await after we return.

Day 6 | Old Havana

  • We will start our day with a walking tour of the cobblestone streets of Old Havana, stop into galleries and explore the various shops before settling into the famous Dona Eutemia restaurant for lunch.
  • After lunch we will visit the gallery and workshop of the “Picasso of the Caribbean” where we will meet Jose Fuster and explore the neighborhood, which he has transformed through his art.
  • For dinner we will dine at a new stylish rooftop restaurant in a converted oil factory then go to the renovated art and dance space next door for a nightcap, shopping and optional jazz clubs to continue the evening of fun.

Day 7 | Vedado

  • After our breakfast buffet at the hotel in vibrant Havana, we will visit the up and coming Vedado neighborhood and the embassy district, including the Russian embassy and its unique architecture.
  • Lunch is at a Ranchon owned by a popular contemporary musician who will also give us a tour of his studio and talk to us about the business and creative opportunities he now has because of a thaw in the embargo.
  • After lunch we will meet at Hemmingway’s haunt, La Floridita, famous for daiquiris and to listen to a great rendition of “Guantanamera” by the house band.
  • For dinner we will gather at a top paladar, considered a favorite by President Obama, then have a nightcap at a glassed in rooftop bar overlooking the city while listening to live music.

Day 8 | Cojimar

  • After breakfast we will depart for Finca de Hemingway, the author’s beloved home where we will tour the grounds and see the property which he was forced to relinquish when relations between Cuba and the United States were severed in the mounting tensions involving Russia, the United States and the Cuba.
  • We will travel on to Cojimar and dine at the restaurant where Hemingway penned The Old Man and the Sea and while we enjoy lunch and mojitos overlooking the water, we will be reminded of the inspiration the infamous author reaped from living in this intriguing country.
  • After we head back to the hotel to change, dinner and dancing await as we are chauffeured in classic American cars from the hotel for a final tour of Old Havana to the our paladar farewell dinner.
  • After dinner we will meet at a legendary jazz lounge for live entertainment, a nightcap, and more dancing with a chance to experience the evening sights and sounds of our final night in Havana.

Day 9 | Havana to Miami

After breakfast we will stroll the streets of Old Havana for the last time, checking back into favorite shops to purchase rum, cigars and gifts as well as a stop at a favorite bakery for savory individual mini quiches, pastries and coffee before heading to the airport for our departure to Miami.

*Cuba is a country in transition. Our itinerary can change due to forces beyond our control. In such an event, rest assured that we would improvise and partake in a similar activity or event.

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