Cuba Explorer popular tour Havana Extravaganza for Americans

Cuba discovery sojourn tour

A Cuba expedition focused on people-to-people education, nature and cultural exchanges. The program is geared to naturalists, and lovers of the arts, history and architecture. The tour has a very diverse itinerary and features comfortable accommodations and tasty Cuban cuisine.

Tour introduction and overview of activities

Dan Rutherford picture
Dan Rutherford

This most popular Cuba tour is inspired by Dan Rutherford, a former 25-year international vice president of a Fortune 100 Company, extensive world traveler, and accomplished state legislator and constitutional officer. His first visit to Cuba was in 1999. His Midwest charisma and charm makes for knowing how to put together a fun adventure abroad.

Together with Josh Lanning, a youthful Cuban expert, the two have created an experience within the ever changing US-Cuban relations. The Global Relations Cuba Discovery Tour is meticulously structured and adamantly adhere to the legal expectations of the U.S. Department of Treasury, Office of Foreign Asset Control.

Josh Lanning picture
Josh Lanning

Global Relations Cuba Discovery Tour – well into its multi-year edition – is geared to people who seek to engage with everyday Cubans. It’s for Americans who want to learn about island culture, its people and society. The Tour is an opportunity to visit an exotic foreign country and absorb a culture different than most. It is a tropical paradise.

This highly inclusive Tour is ideal for history buffs, lovers of art, music, culture and architecture. The Tour’s diverse itinerary goes to western Cuba from the metropolis of Havana to the mountain jungles of the Viñales Valley where Cuba’s famed tobacco is grown. The Tour sports comfortable accommodations and tasty Cuban cuisine.

What is the difference between this and other tour opportunities? Email us directly and we will send a very detailed itinerary for the Tour of your interest: DanRutherford@GlobalRelations.US

Dan, Josh and the Global Relations Travel Club Team warmly invite you to Discover Cuba!


Cuba discovery sojourn tour map

On this tour you’ll visit
Cuba is big. It’s larger than Connecticut, Massachusetts, New Hampshire, Rhode Island and Vermont combined.

Day 1 • Saturday • Arrive Cuba / Welcome dinner

  • Depart to Havana via your own arranged flights.You should plan arriving Havana by mid-afternoon. It may take you some time to clear Cuban Immigration, get your bag and go through Customs. You will be met in the arrival hall, after clearing Customs, by our Cuban representative holding a ‘Cuba Explorer’ sign to take you to your hotel. They will have your name and will be monitoring your flight arrival in case there is a delay. Your first tour activity will be the welcome dinner and your guide will finalize details with you on arrival to your hotel.
  • Havana’s International Airport arrival hall does have bathrooms. They may not have seats or tissue. This is normal in Cuba’s public places, so you may wish to bring packets of tissues. It is suggested to use the restroom on your flight before landing.
  • On arrival at Havana’s José Martí International Airport proceed through Immigration. There is a combined Immigration, Customs and Healthcare form which needs to be filled out electronically and your airline will send you a link to it. Your carry-on will once again be scanned.
  • Collect your bags and go through Customs.
  • You will be welcomed at the airport exterior lobby after you exit Cuban Customs. Look for the person holding signage of ‘Cuba Explore.’Tour participant’s arrival times may vary throughout the day. Individualized Airport transfers will be arranged.Quote from Lonely Planet:  “No one could have invented Havana. It’s too audacious, too contradictory and – despite 60 years of withering neglect – too damned beautiful. How it does it is anyone’s guess. Maybe it’s the swashbuckling history still almost perceptible in atmospheric colonial streets; the survivalist spirit of a populace scarred by two independence wars, a revolution and a US trade embargo; or the indefatigable salsa energy that ricochets off walls and emanates most emphatically from the people. Don’t come here with a long list of questions. Just arrive with an open mind and prepare for a long, slow seduction.”
  • Private transfer to your hotel for check-in with assistance from your guide.
  • Free time to settle in and get oriented with your hotel.
  • Welcome Diner at Mojito Mojito private restaurant, great Cuban food and just off Plaza Vieja in Old Havana. You will enjoy a wonderful meal, live music, and friendly staff. (Included)

Day 2 • Sunday • Old Havana tour / Vintage American cars/ Craft market & shopping / Evening free to explore

  • Breakfast at your hotel. (Included)
  • Walking tour of Old Havana (it will be leisurely and have rest stops), a UNESCO World Heritage Site. You will visit the historic plazas that make Havana unique in the Western Hemisphere. It contains the largest collection of remaining colonial-era architecture. Meet the private street vendors selling souvenirs out of their homes. This is a private tour led by your Cuban guide. (Included)
  • Cathedral Square, the most beautiful and private 18th century colonial plaza on the island. Named after the masterpiece of Cuban baroque architecture: the Catedral de San Cristóbal de la Habana, was built by the Jesuit order. Christopher Columbus’ remains were kept in the cathedral between 1796 and 1898 before they were taken to Seville Cathedral, Spain.The Cathedral of Havana celebrates mass Sunday at 10:30 am and 6 pm on Thursday. Let your guide know the night before if you wish to attend Sunday mass so that the walking tour may take that into consideration.
  • San Francisco Square, one of the oldest plazas in the historical quarter. The square is named after magnificent Iglesia y Monasterio de San Francisco de Asís dating from the 16th century. The basilica is a striking example of Cuban baroque architecture.
  • Plaza Vieja, the only civic square of colonial times. Absent are churches and government buildings and is in contrast surrounded by opulent aristocratic 17th century residences.
  • Square of Arms, a military parade ground for Spanish soldiers, surrounded by impressive colonial buildings.
  • As you stroll through the historic cobblestone streets of Old Havana you will experience the sensations Ernest Hemingway felt and those of the colonialists’ centuries earlier.
  • Lunch at El Template overlooking the Bay of Havana in Old Havana. (Included)
  • You will have the opportunity to caravan in iconic 1950’s Vintage American cars, a fascinating experience of nostalgia. You will cruise the Malecon (a broad esplanade, roadway, and seawall) and stop for photos. (Included)
  • Opportunity to shop for souvenirs at Centro Cultural Antiguos Almacenes de  Depósito San José, a large crafts market housed in renovated maritime warehouse. Offerings are garish-colored paintings by local artists, guayaberas (short-sleeve, open-neck Cuban shirts), sculptures, leather goods, jewelry and various trinkets & gadgets bearing the image of Che Guevara. The metal-framed structure is retro and Art Deco. (Included, Optional)
  • Return to hotel. Independent Time.
  • Dinner (Not included). This is a perfect evening to explore Cuba’s famed paladares or visit one of the many cafes within easy walking distance of your hotel.
  • Your guide can help arrange tickets to a Buena Vista Social Club type entertainment if you like. We suggest informing your guide soon on arrival to ensure tickets. (Optional)
  • Attend El Canonazo with Cubans, a Havana tradition which first started hundreds of years ago. At 9 o’clock, a cannon was fired from the ancient Fortress of San Carlos de Cabana to indicate the gates of the Old City were about to close. A large chain was then raised from the water and put across the entrance to the Harbor to keep pirates from sailing in. You will go to the fort for the ceremony where the tradition continues, other than the chain which is no longer used. (Included)

Day 3 • Monday • Valley of magnificent mogotes & the national park / Meal in country-side paladar / Staying casa particular

  • Breakfast at your hotel. (Included)
  • Hotel check-out.
  • Morning departure to the western agricultural province of Pinar del Río.
  • In route you will have a discussion with your Cuban guide about the distribution of food to restaurants, the slaughter of the cattle and the food ration book for Cuban citizens.
  • Brief stop at Las Barrigonas, a clean, staff friendly rest stop with fresh squeezed fruit juices, one of the best Pina Coladas around, a snack grill and gift shop.
  • You will drive through the Vinales National Park. Many consider this the most beautiful nature spot on the island.
  • Lunch at private restaurant Balcón del Valle (Balcony of the Valley and you will see why when you get there), one of the most spectacular views of the entire trip. (Included) You will have the opportunity to visit the kitchen, chat with the cook’s preparing food over charcoal fire; it is rustic and wonderful.
  • Check into your Casa Particilar, located on the edge of the small colonial town, overlooking the mogotes.
  • Tour of the property and relax with a refreshment.
  • Dinner (Not included). Evening is free to take a stroll in the colorful main street of Vinales. There are several Paladares that will welcome you or enjoy a wonderful meal at your Casa. All will be using ingredients from their organic garden.

Day 4 • Tuesday • Explore the Viñales Valley on horseback or horse drawn cart / Tobacco farming / Paladar dinner

  • Breakfast at your Casa. (Included)
  • Morning horseback riding or horse drawn cart ride in the valley of the National Park (Included)
  • Lunch in the National Park for those with horses. (Included)Those not riding horses or horse drawn cart will have independent time in the morning. One may visit Jardin Botanico de Vinales, Botanical Garden, a lush, well established, enclave of native plants, sunbathe, or stroll the main street of Vinales.
  • Meet at the Casa in early afternoon.
  • Visit a privately owned small tobacco farm that produces the leaves for the world-renowned Cuban cigar. You will need to walk part of the way for horse or oxen are the only other means of transportation. Meet the owners, third generation women who run the small farm. You will have a personal demonstration of hand rolling a Habano cigar and discuss with the ladies about the government oversight of the tobacco production and sales. Learn the Cuban government’s process for pricing and delivery of the leaves. (Included) You may purchase excellent hand rolled cigars that the three generations of women in the family prepare in the evenings. (Optional)
  • Tour the Vinales Valley in your motor coach and see the mogotes. They are irregularly shaped steep-sided hills that can rise as high as 985 feet and have bases as much as a mile in length. The mogotes were once underwater and during the Jurassic Age, about 200 million years ago, they were the first formations to emerge from the Atlantic Ocean during the creation of Cuba.
  • On return to your Casa you will stop at a small grocery store to have an opportunity to get bottled water, wine, rum, coffee, and snacks.
  • Dinner at El Campesino paladar, located on the edge of an agriculture field with the mogotes as a backdrop. You will enjoy a wonderful meal of Cuban country-style cooking from the kitchen supervised by the mother, Nino. (Included)

Day 5 • Wednesday • Havana return / Visit Casablanca & the statue of Christ

  • Breakfast at your Casa. (Included)
  • Drop by an open-air craft market as you depart Vinales. (Included)
  • Lunch: To save time on the return to Havana to-go sandwiches will be provided on the coach ride. (Included)
  • A stop at Las Barrigonas to stretch your legs, and shop for souvenirs, organic honey, or Cuban rum.
  • Visit Casablanca, a quaint village to the north of Havana accessible by ferry. The hamlet was established in 1762 by shipbuilders and carpenters who serviced Spanish galleons and merchant vessels dispatching the spoils of South American conquest to the royal court of Spain. This UNESCO World Heritage Site is home to the giant marble sculpture Christ of Havana, and the National Weather Observatory. The panoramic view across the bay to metropolitan Havana is mesmerizing.
  • The magnificent statue of Cristo de La Habana is by Cuban sculptor Jilma Madera. She won a 1953 design contest organized by the wife of dictator Fulgencio Batista for this work. Madera created the statue in Italy and shipped the marble pieces to Havana. It is carved from 67 blocks of White Carrara Marble (each blessed by Pope Pius XII), stands 74 feet tall from its base, and weighs 320 tons. It’s the most massive statue created by a female artist.
  • Check into your hotel.
  • Dinner at the paladar La Casa, private restaurant, one of the earliest established in Cuba and still in the original home. (Included)
  • OPTIONAL EXCURSION: Experience the acclaimed Tropicana Cabaret, located in a lush, tropical six-acre garden estate. Built in 1939 and over time the Tropicana helped to spread Cuban culture on a level never seen before. The showgirls created the showgirl-era. The lavish costumes and vibrant performance styles quickly spread from Cuba to Las Vegas, New York, and Paris. A full orchestra, loud colors, sultry rhythms, and a stunning production with more than 200 singers and dancers will entertain you. (Not Included – details on booking will be sent to you)

Day 6 • Thursday • Hemingway by the sea / Organic gardening / Private cooking lesson / Hemingway’s home / Last night in Habana

  • Breakfast at your hotel. (Included)
  • Travel to Cojimar, a small fishing village east of Havana. It was Ernest Hemingway’s favorite fishing port in Cuba and the basis for Old Man and the Sea. This is the harbor where Hemingway’s boat Pilar was moored and where Papa and Gregorio would depart to marlin fish or hunt German Submarines. On water’s edge see Hemingway’s bust made from metal, donated by the local fishermen, and get photos in front of the 17th century Spanish Lookout Fort. (Included)Much of the inspiration for The Old Man and the Sea came from Hemingway's time in Cojimar. LaTerraza, is a fisherman’s bar on the Bay of Cojimar where Hemingway docked his boat, Pilar. The bar is where he spent many an afternoon drinking with the fishermen, one being Gregorio Fuentes, the Captain of Pilar. Many believe him to be the model for the character Santiago—the old man of the sea. Some say the young boy in the story, Manolo, was based on the young son of the owner of La Terraza, Manolito.
  • Visit the small organic garden of Jesus and Julio where they show you how herbs, vegetables and fruits are raised for the private restaurant where you will be cooking later. Up close see mangos, bananas, plantains, squash, avocado, coffee and maybe even the Cuban Bee Hummingbird, the smallest bird in the world, endemic to Cuba. See how organic gardening in a residential neighborhood produces private income and supplies a local business. (Included)
  • TOUR HIGHLIGHT: Cooking & mojito making lesson at paladar (private restaurant) El Ajiaco followed by lunch, which you helped prepare. This is a unique experience; in the kitchen, with the chef and staff preparing multiple dishes (seafood, ropa vieja & el ajiaco soup) and then at the bar learning how to properly prepare a Cuban mojito. It is a humble paladar visited by food networks from around the world and several notable celebrities such as Kevin Bacon and Sigourney Weaver. (Included)
  • Visit Finca Vigía, home and farm of Ernest Hemingway, southeast of Havana in the small town of San Francisco de Paula. He lived longer in his Cuba residence than any of his other homes. It was here he accepted the Nobel Peace Prize for Literature and wrote portions of A Moveable Feast, For Whom the Bell Tolls, Islands in the Stream and much of The Old Man and the Sea.  Now a museum, you will meet the docents and curators who affectionately maintain his library, manuscripts, and personal belongings. His boat Pilar (made famous, in part, from Papa’s Marlin fishing and hunting German submarines off the northern coast of the island) and the graves of some of his dogs are all on the grounds. (Included)
  • Return to hotel.
  • Dinner (Not included). With all the great food you have experienced, this is your chance to re-visit a favorite privately owned restaurant or one you may have heard about. Your guide will be of assistance in helping you select a good private paladar.
  • Your last night in Cuba; enjoy!

Day 7 • Friday • Havana / Home

  • Breakfast at your lodging. (Included)
  • Transfer to José Martí International Airport in Havana for flight home. (Included)
  • Airlines recommend you be at your departure airport 3 hours before takeoff. Please prepare accordingly. Your guide or driver will meet you in the lobby of your hotel.
  • After you clear Cuban Immigration, you will be screened and your carry on will be scanned. In the departure hall there is a duty-free shop, places to buy snacks and drinks, as well as souvenirs.
  • When arriving to your U.S. entry airport you will need to clear U.S. Immigration and U.S. Customs. If asked by an Immigration Officer about your trip to Cuba, note that you were on a sanctioned Support of the Cuban People tour. If asked what you did, tell the truth, and explain it was an opportunity to directly engage and support the Cuban people, learn about their life and country. To be clear: You were not on a vacation.
  • Memories of a wonderful visit to the Pearl of the Antilles: Cuba! (Included)
While in Cuba, our attentive island team ensures your trip is magical and memorable.While in Cuba, our attentive island team ensures your trip is magical and memorable. Activities subject to change if Covid-19 prevention measures demand.

Reserve your tour now. Take 48 hours to shop and compare.

Sep 9 - Sep 15, 2023$ 2999

Included in Cuba tour package cost

IMPORTANT: for entry into Cuba, one must have a valid passport with expiration no earlier than two weeks from scheduled Cuban departure. A Cuban Visitor Visa is also required for entry into Cuba.

  • A dedicated website having your itinerary, pricing, FAQ, and registration will be produced. Sharing the link will make it easy to provide tour participants relevant information.
  • A Certificate of Legal Cuba Travel, per participant, in accordance with the US Department of the Treasury, Office of Foreign Assets Control (OFAC) section 31 C.F.R. § 515.572(a)(1) will be provided.
  • You will receive briefing e mails before departure to assist you in preparing for the trip.
  • All amounts are quoted in U.S. dollars.
  • Fly to Havana and you will be met at the airport and transferred to your lodging. On the last day of the tour the transfer to the Havana airport is also included.
  • Your Cuban Visa is included.
  • Airport departure tax from Cuba and the Cuban mandatory Emergency Insurance coverage during your island stay is covered in the cost of airfare with U.S. carriers.
  • All breakfasts, lunches, and dinners, as per your itinerary.
  • All activities and services, as described in your tour itinerary, except those noted as “Optional” or “Not included”.
  • Air-conditioned transportation and a Cuban professional driver dedicated to you.
  • Cold bottled water on transport.
  • An English-speaking Cuban guide who will also serve as interpreter.
  • Gratuity for your Cuban tour guide, driver, chambermaids, restaurant staff, porters, etc. for group activity is included.
  • Emergency call access to the United States while in Cuba.
  • You will receive travel support from the Global Relations team before, during and after your stay.

Tasty meals included each tour day


Not included