Grand Tour of Cuba: Havana to Santiago de Cuba

12 days
Revolutionary and restrictive, colorful and crumbling, well-versed in hard times and yet ineffably vibrant—the best way to learn about this complex country is from the people who call Cuba home. Meet with locals at every step as you travel from Havana to Cuba’s eastern shores, discovering the indelible cultural heritage and history that makes this island nation like none other.

Let us handle the details

Expert Tour Director

      Local       cuisine

Handpicked hotels

Sightseeing with local guides

Private transportation

Personalized flight options

Tour group size: 15 - 26 travelers

Tour pace: You will walk for about 3 hours daily across moderately uneven terrain, including cobblestones and unpaved paths, with few hills or stairs.

Let us handle the details

Expert Tour Director

      Local       cuisine

Handpicked hotels

Sightseeing with local guides

Private transportation

Personalized flight options

Your tour includes

  • 11 nights in handpicked hotels

  • Breakfast daily, 10 lunches, 9 three-course dinners with beer

  • Multilingual Tour Director and Local Cuban National Guide

  • Flights from Fort Lauderdale to Havana and Santiago de Cuba to Fort Lauderdale

  • Private deluxe motor coach, guided sightseeing and select entrance fees

  • Cuban Visa

Miami, Florida 1 night

Day 1: Arrival in Miami

  Included meals: Dinner

Welcome to Florida! Arrive in Miami and make your way to your hotel. First, review important information with your Tour Director. Then, set out on a short tour of Little Havana, the Cuban cultural neighborhood of Miami, before sitting down to a welcome dinner and drinks with your fellow travelers.

Havana 3 nights Hotel info

Day 2: Arrival in Havana

  Included meals: Breakfast, Lunch

This morning, board your flight from Fort Lauderdale to Havana, Cuba. Upon arrival, head out with your group and discover the city with a local guide. (Please note: flight times are subject to change.)

• Engage with locals as you visit Havana’s historic districts, including El Cerro, El Vedado and Miramar

• See Metropolitan Park, the beautiful green space along the Almendares River, before making your way down the Malecón, a five-mile-long waterfront esplanade

• Enjoy open discussions about important restoration projects as you view the historic National Capitol Building, Revolution Square, Plaza Vieja and more

After lunch, meet with locals across Havana to learn about Cuban culture.

• Meet a local artist for an interactive discussion about what life is like in Cuba 

• Walk through the tunnels below the Hotel Nacional de Cuba while you discuss the Cuban Missile Crisis, then taste a traditional mojito

Day 3: Old Havana

  Included meals: Breakfast, Lunch, Dinner

Get to know the UNESCO-recognized neighborhood of Old Havana, the heart of the city, with a local architect leading the way.

• Engage in open discussions about recent restoration projects in Havana as you walk along the colorful main streets

• Pass through Plaza de Armas, Plaza de San Francisco, Plaza de la Catedrale and Cortina de Valdés, home to the city’s ancient arsenal

After lunch, visit the Museum of the Revolution, a collection of exhibits devoted to the revolutionary war of the 1950s, housed in the former Presidential Palace. Then, interact with community representatives at the Callejón de Hamel. You’ll learn about Afro-Cuban religion and ceremonies as you watch performers in a traditional dance. 

Tonight, sit down to a dinner of local specialties at a traditional paladar restaurant. Then, engage with musicians and locals at a Buena Vista Social Club performance to get a taste of the lively Cuban music culture.

Day 4: Finca Vigía & Cojímar

  Included meals: Breakfast, Lunch, Dinner

Today, get a look at some of Cuba’s world-famous cultural touchstones, including cigars, Hemingway’s writing retreat and antique cars. 

• Interact with staff at a local cigar factory to see how Cuba’s most famous export is made from start to finish

• Take a salsa dancing lesson taught by the masters and engage with the performers at a demonstration

• Meet with a local historian at Finca Vigía, where Ernest Hemingway wrote and discuss the importance of Hemingway’s work both in Cuba and the U.S. 

• After lunch, visit with local fishermen at the nearby village of Cojímar, where Hemingway kept his boat, Pilar

This afternoon, head back to Havana to engage with local artisans at the Almacenes San José Artisans’ Market.

Cayo Santa María 2 nights Hotel info

Day 5: Cayo Santa María via Cienfuegos & Santa Clara

  Included meals: Breakfast, Lunch, Dinner

Say adiós to Havana this morning as you make your way to Cienfuegos. Get to know the city nicknamed “the Pearl of the South” with a local as your guide.

• Interact with locals as you discuss the culture and traditions of Cienfuegos, a UNESCO-recognized city 

 • Make your way through José Martí Square and view the Cathedral of  the Immaculate Conception, then pass by Teatro Tomás Terry and the neo-Gothic Palacio de Valle

Then, continue on to the beautiful island of Cayo Santa María, home to pristine coastal scenery and azure waters. En route, stop in Santa Clara to discuss Cuba’s revolutionary history at the Che Guevara Mausoleum.

Day 6: Caibarién & Remedios

  Included meals: Breakfast, Lunch, Dinner

Head out to the agricultural and cultural center of Caibarién this morning.

• Engage with a local artist to learn about Cuba’s vibrant creative scene 

• Discuss the tools and machinery used in sugar production at the sugar factory-turned-exhibit, Marcelo Salado Sugar Mill Museum 

Then, board a steam train to Remedios, the eighth-oldest city in Cuba, and interact with the conductors en route.

• Learn about the famous Parrandas festival, one of the Caribbean’s largest and oldest traditional carnivals, with roots stretching back to the 18th century

• Hop on board a bicycle taxi for a tour of Remedios, heading into the main square where you’ll meet the drivers and share coffee

Camagüey 2 nights Hotel info

Day 7: Camagüey via Sancti Spíritus

  Included meals: Breakfast, Lunch, Dinner

This morning, travel to the city of Sancti Spíritus for a guided walk. 

• Stroll through the charming historic center and enjoy an open discussion about restoration projects in the city 

•Visit the Sancti Spíritus School of Art, an elementary and middle school for talented youth, and engage with the students to learn about their studies and interests

Then, continue on to Camagüey, a historic city settled by the Spaniards in 1528.

Day 8: Camagüey

  Included meals: Breakfast, Lunch, Dinner

Discover Camagüey’s rich cultural heritage as you explore the city’s famously winding streets. 

• Interact with performers from the Ballet of Camagüey at the Teatro Principal and learn about traditional Cuban dance

• Take a bicycle taxi tour of the city’s UNESCO-recognized center, stopping at Plaza de los Trabajadores, Plaza del Carmen, Parque Ignacio Agramonte and the colonial Plaza San Juan de Dios 

• Meet with local artisans at a leather workshop to discuss their craft

• Visit the Casanova Pottery Studio to learn about the region’s famous tinajónes, or earthenware jars, as you discuss clay pot-making with locals in the studio 

Take a short rest at your hotel before heading to the Martha Jimenéz Gallery. There, you’ll meet with locals and discuss Cuba’s growing contemporary art scene.

Guardalavaca 1 night Hotel info

Day 9: Guardalavaca & Holguín

  Included meals: Breakfast, Lunch, Dinner

Make your way to Guardalavaca, stopping in the cities of Las Tunas and Holguín to interact with local artists and craftspeople. 

• Stop in the center of Las Tunas, nicknamed “The Sculpture City” for its collection of public artwork 

• Visit a mechanical organ factory in Holguín to meet and interact with the craftspeople, learning about the traditional instruments they build 

Continue on to your hotel in Guardalavaca, a beachy city along the coast.

Santiago de Cuba 2 nights Hotel info

Day 10: Santiago de Cuba via Birán

  Included meals: Breakfast, Lunch

Learn about some of Cuba’s most iconic figures as you travel to Santiago de Cuba, the second-largest city in the country. 

• Visit the birthplace of Fidel Castro, in Birán, to learn about the head of the Cuban Revolution and discuss the controversial leader’s legacy 

• Discuss the works of José Martí, a revolutionary author and philosopher, at his mausoleum in Santa Ifigenia Cemetery 

• View the Plaza de la Revolución and learn about Santiago de Cuba’s role in the country’s fight for independence 

• After dinner, listen to traditional trova music and interact with the local musicians who play it

Day 11: El Cobre, Santiago de Cuba & El Morro

  Included meals: Breakfast, Lunch, Dinner

Uncover both modern and colonial Cuba as you explore the region with a local as your guide. 

• Meet with locals in the town of El Cobre to discuss what life is like in Cuba today 

• Learn about Cuban culture at Our Lady of El Cobre, a shrine dedicated to the country’s patron saint 

• Follow your local guide through Santiago de Cuba’s historic center

• Visit the San Pedro de la Roca Castle, the UNESCO-recognized fortress built on the rocky cliffs of El Morro, overlooking the bay 

• Enjoy a traditional performance by a vocal quartet and engage with the singers 

Tonight, celebrate your trip with your fellow travelers at a local paladar restaurant.

Day 12: Departure

  Included meals: Breakfast

Transfer to Santiago de Cuba Airport (or Holguín Airport depending on flight schedules) for your flight to Fort Lauderdale, where you will be driven to Miami airport to connect to your flight home.

(Please note: Due to changing flight schedules, your flight to Fort Lauderdale may depart from the airport in Holguín. Depending on your home destination, you may spend the night in Miami before flying home on the morning of day 13.)

Go Ahead Tours is pleased to offer educational and cultural exchanges to Cuba. Go Ahead Tours qualifies for the people-to-people general license established by the Office of Foreign Assets Control of the U.S. Department of the Treasury (“OFAC”). Under this license, Go Ahead Tours will offer educational and cultural exchanges and conversations with the people of Cuba. The itinerary is subject to change based on day of the week and availability, but a complete people-to people itinerary will always be maintained.

How's the weather?

  • Miami, FL
  • Havana, Cuba
  • Cayo Santa María, Cuba
  • Camagüey, Cuba
  • Guardalavaca, Cuba
  • Santiago de Cuba, Cuba
Temperature Precipitation
  • JAN
  • FEB
  • MAR
  • APR
  • MAY
  • JUN
  • JUL
  • AUG
  • SEP
  • OCT
  • NOV
  • DEC

Passport & visa requirements

  • In order to enter Cuba, U.S. and Canadian citizens need a valid passport with an expiration date extending at least six months beyond the date of reentry.
  • We recommend having at least two blank passport pages for entry stamps.
  • Go Ahead will provide U.S. citizens with a visa and all other documentation needed to enter Cuba. It is important to note that we will take care of all aspects of your Cuba visa application. 
  • As part of federal requirements, you should keep a copy of your Cuban travel itinerary and airline ticket receipt on file for five years. 
  • If you are not a U.S. citizen, you must contact your country’s consulate for specific entry requirements.
  • The Cuban government does not recognize the dual nationality of those who are Cuban-born or the children of Cuban parents. * Cuban-born citizens and the children of Cuban nationals may be required to hold a Cuban passport and/or HE-11 visa, and will be responsible for any additional costs incurred. If you were born in Cuba or are the child of Cuban nationals, please contact our Customer Experience Team at your earliest convenience. 

Documents & paperwork

You will receive all documents and paperwork necessary for travel to Cuba through the mail. All forms must be completely filled out and returned to Go Ahead at least 45 days prior to your departure date in order to participate on this tour. The forms that you will be receiving are:

  • Travel Affidavit
  • People-to-People Reservation Form and Operator-Participant Contract
  • Visa Application Form

  • You will receive finalized copies of your travel documents at your hotel in Miami, where a briefing will be conducted in the afternoon prior to your departure to Havana.

  • Please note: The Cuban visa forms will need to be filled out correctly and cannot be lost. Should you need a new Cuban visa form, a charge of $150USD will be assessed on tour. Additionally, you will be required to provide Go Ahead with a copy of your passport. 

Tour pace

  • You will walk for about 3 hours daily across moderately uneven terrain, including cobblestones and unpaved paths, with few hills or stairs. 
  • Travelers should be in reasonable health to take our included walks.
  • You should feel comfortable managing your own baggage at all times. 
  • Please note that the summers can get very hot and this is a very full itinerary.
  • If you have any mobility concerns or physical restrictions, please contact our Customer Experience Team so that we can review all necessary information with you.

Transportation & arrival information

  • Round-trip flights booked through Go Ahead arrive in and depart from Miami International Airport. A Go Ahead representative meet you at the airport and escort you to the shared shuttle service, which will bring you to your first hotel. Please remain in the arrival lounge, as the representative might be escorting one of your fellow travelers to the shuttle at the time of your arrival. 
  • Your flight to Cuba will depart from Fort Lauderdale and arrive in Havana, and your return flight will depart from Holguin Airport (or Santiago de Cuba Airport, depending on flight schedules) and arrive in Fort Lauderdale.
  • Once you arrive in Cuba, all included transportation is by private motor coach.
  • Taxis are the best way to get around on your own. However, if you choose to take a taxi, please note that drivers will most likely speak only Spanish. You should make a point to agree on the cost of the fare before getting into the cab. Additionally, cab fare may be paid in USD.
  • Please note: If you are making your own flight reservations, you will need to be in Miami no later than 3pm on day one of the tour and should plan to depart from Miami no earlier than 8:30pm on day 12. 

Baggage allowance

Commercial flights to and from Miami:

  • Airlines have varying weight restrictions on baggage. Some airlines may impose additional charges if you choose to check any baggage; be advised that you are responsible for any such costs. 
  • Contact your airline for baggage size and weight restrictions for your flight, but please note that Go Ahead travelers are restricted to one checked bag per person due to storage limitations on motor coaches and other transfers, which may include train connections or flights. 
  • One carry-on bag of 45 total inches (length + width + height) is also permitted.
  • Make sure you label your baggage and keep valuables, medication and documents in your carry-on bag.

Flights to and from Cuba:

  • We recommend traveling with one suitcase and one small carry-on bag (such as purse or small backpack) per person.
  • Each passenger is allowed up to 44 total pounds of checked baggage. A fee of $2USD per additional pound will be charged for any baggage that exceeds this limit. Your small carry-on (a personal item or purse) will not count toward total baggage weight.
  • On your flight from Cuba to Fort Lauderdale, there is no charge for baggage that is less than 50 total pounds per person.

Clothing & packing tips

  • We recommend packing lightweight, loose-fitting clothing that can be easily layered to accommodate varying temperatures, as well as a light jacket or rainwear.
  • A sturdy pair of walking shoes or sneakers is recommended for sightseeing.
  • In addition, we recommend packing insect repellent, sunglasses, sunscreen, a bathing suit, a sun hat, and hand sanitizer, as well as washcloths as most hotels do not provide them. You may also want to bring your own toilet tissue for use in public restrooms. 
  • Please note that it is preferable not to visit churches or other religious sites with bare legs or shoulders (entrance may be denied on this basis).  


  • Emergency medical insurance is included for those traveling from the U.S. to Cuba through our flight service. 
  • Coverage is limited to $25,000 medical and $500 dental. If you wish to increase your coverage, please contact our Customer Experience Team. 
  • There are no major health risks associated with traveling to Cuba. 
  • At least 60 days prior to departure, check with your doctor or healthcare provider for the latest updates and entry requirements, or visit the Center for Disease Control and Prevention website at
  • We strongly recommend speaking with your doctor prior to your departure to review any medical concerns.
  • If you have medication that you take daily, be sure you have enough for each day of the tour as well as any possible delays encountered.
  • Bring a small first aid kit that includes antacids, anti-diarrhea medication, and any other medications you regularly need.
  • If you have dietary restrictions and/or food allergies please notify Go Ahead at least 30 days prior to your departure by logging in to your account and updating your traveler info. To update this information closer to your departure date, please call our Customer Experience Team.
  • Drink bottled water. Aside from the hotels where you will be staying and the restaurants you will be visiting, where water is purified, it is not advisable to drink tap water.  


  • As a result of Spain’s historical colonization of the country, Cuban cuisine is known for its Spanish influences. 
  • African and Caribbean flavors also play an important part in traditional dishes. Common foods often include pork, chicken, yucca, plantains, beans and rice. Cuban coffee is also popular and is known for being strongly brewed.                     


  • There are two currencies used in Cuba. The first is the Cuban Peso, which is used primarily by the locals for basic staple products. The second is the Cuban Convertible Peso (CUC), mostly used by tourists. The currency you will be using for your tour is the CUC.
  • In Cuba, you can exchange USD or CAD for CUC at the Havana airport, hotels, exchange bureaus, and in some banks. Currently, there is a 13% surcharge fee for exchanging USD to CUC.
  • When exchanging currency, your passport will be required at the time of transaction. It is also important to note that most places will not accept torn or marked bills when converting to CUC.
  • Credit cards, debit cards, and ATM cards issued by U.S. banks are currently unusable in Cuba. As such, purchases and payments for services must be made in local currency. You should plan on bringing enough cash with you for meals that are not included and anything else you may wish to purchase.
  • Although some small businesses and taxi drivers will accept USD, paying in CUC is strongly encouraged.

Electricity & air conditioning

  • Cuba generally operates on 220 volts. However, there may be both 220- and 110-volt outlets in some hotels. The outlets will work with Types  A, B, C, or L plugs with two or three prongs. An adapter will be required. 
  • The strength of the air conditioning in Cuban hotels is often not as strong or as cool as what you might be used to in the U.S. or Canada. When air conditioning is available, it is usually regulated seasonally and controlled centrally by the hotel.
  • Your hotels may provide hairdryers, irons and other small appliances. However, these amenities cannot be guaranteed.


  • Even with the purchase of an international service plan, U.S. cell phones will not currently work in Cuba. 
  • If necessary, you may use the phone in your hotel room by arranging payment with the hotel front desk. However, placing a call to the U.S. can be expensive, sometimes costing more than 2.50CUC ($2.50USD) per minute. Connection charges may also apply.
  • While Cuba is a technologically developing country with Wi-Fi not readily available at all hotels, some hotels may have business centers where internet service is available. Charges for use may be up to 2CUC ($2USD) per hour.

Time zones

  • Cuba is on the equivalent of U.S. Eastern Standard Time (EST).
  • When it’s noon in New York, it’s  also noon in Cuba.


  • In addition to your Tour Director, you will be accompanied by a Cuban National Guide for the duration of your trip. Your Cuban National Guide is there to assist with any and all matters, including providing a local’s perspective and offering assistance with any issues or emergencies. 
  • Tips for the Cuban National Guide have already been covered by Go Ahead and additional tipping is not required.


  • At the conclusion of your tour, it’s customary to offer your Tour Director a gratuity in local currency. Please keep current exchange rates in mind.
  • We recommend tipping the equivalent of $7USD/CAD to $10USD/CAD per person per day for your Tour Director. 
  • In Cuba, tipping is an important part of the local economy. Local salaries are extremely low and many Cubans depend on tips for their livelihood. 

For your convenience, your Tour Director will collect tips in Miami for the following components of your tour in Cuba:

  • Local guides
  • Speakers
  • Community project staff
  • Musicians
  • Bus drivers

  • Please budget up to $147USD/CAD per person to cover these tips for this tour. 

  • Tips can only be paid in cash. 

Items to give or trade

  • If you’d like, it is okay to bring small items such as pens, markers, coloring books, or small toys to give out to local children. 
  • It is very important to note: If you are asked at the Cuban customs area, these gifts are not to be called “donations.” A “donation” requires prior authorization and is usually given in large quantities and is not (and should not be) what you are bringing. Instead, you should refer to these items as “small gifts to hand out.”    

U.S. Customs

  • Per U.S. regulations, you are allowed to bring back $400USD worth of goods for personal use.
  • Travelers returning from Cuba may be asked questions by Customs and Immigration officers. It is possible that you may need to provide a copy of the authorization letter provided to you and undergo additional screening in the Customs area.


  • As part of the people-to-people agreement, U.S. law requires that all travelers participate on all of the tour’s scheduled activities. Deviation from this itinerary, even in part, is not permitted. 
  • Specific itinerary inclusions such as meetings with individuals and visits to organizations and homes are dependent on outside factors and may sometimes be substituted or changed while on tour. 
  • It is important to go into this experience with a very open mind! Your guide will be good at swapping out activities for others when needed and your flexibility is appreciated.

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