Cuba Group Travel Dates




Wed, July 3, 2024 – Sun, July 7, 2024



Fri, August 30, 2024 – Tue, September 3, 2024


2 Spots Left

Wed, December 4, 2024 – Sun, December 8, 2024



Thu, February 13, 2025 – Mon, February 17, 2025



Wed, July 2, 2025 – Sun, July 6, 2025



Thu, December 4, 2025 – Mon, December 8, 2025




Important Note for U.S. Citizens

It is still illegal for U.S. citizens to visit Cuba for general tourism and/or recreational activities.  However, the U.S. Treasury Department Office of Foreign Assets Control (OFAC) has issued 12 categories of legal travel to Cuba under a General License, one of which being “support for the Cuban people”.  Travendly is able to offer a legal trip to Cuba under the General License of Support for the Cuban People.  Our itinerary provides a full-time schedule of activities designed to result in support of local businesses and individuals in Cuba.  United States law requires that all participants on our trip adhere to the full-time schedule of our itinerary.

Where We Go

Cuba group trip Havana map



Places Visited

  • City of Havana
  • Vinales


  • Experiencing local life of a Cuban by staying in a casa particular
  • Learning how to salsa dance
  • Taking in the decaying beauty of Old Havana through a historical walking tour
  • Getting your culinary game on in cooking class on the rooftop of a building in Old Havana
  • Visiting a working tobacco farm in Vinales
  • Cruising through Havana in convertible classic cars

Trip Inclusions

Trip Rankings

Physical Intensity
Free Time
Culture / History
Very High
Food / Cuisine

Flight Information

Airfare is not included in the price of our Cuba group travel trip. When purchasing airfare please do so as follows:

  • Arrival: Fly into Havana (airport code: HAV) by 4pm on the first day
  • Departure: Fly from Havana (airport code: HAV) at anytime on the final day

Is This Cuba Trip Right for You?

  • Cuba is a developing country and modern day amenities and luxuries you might be used to at home are not available in Cuba. Grocery stores are often scarce with limited supply and items, common household goods such as toilet paper and everyday pharmacy supplies (i.e. toothpaste, Advil, etc.) are hard to find, and A/C in a vehicle is considered a luxury. It’s important to put all this into perspective to fully appreciate the resourcefulness of local Cubans and just how different their daily lives are from yours.
  • You will stay in privately owned homes (casa particulars) for the duration of this Cuba trip. The casas we use are nice (for Cuban standards) but they are probably not what you are used to at home. The beds can be old, shower pressure can be low, hot water might not be working, and power outages could occur. It is important that we stay at privately owned casas to support the individuals of Cuba and, further you will get the real, authentic experience of life in Cuba.
  • While there is WiFi access in Cuba it’s not always available and, even when available, the government run network doesn’t always work. It’s best to approach this trip thinking you will be without the internet for the duration of the trip.
  • The pace of life in Cuba is very slow. For example, it’s not uncommon to wait for well over an hour at a restaurant for your food. Patience is very important when visiting this island.

Frequently Asked Questions

The group leader on this Cuba group tour will be a local from Cuba! His/her job is to ensure the safety and well being of everyone on the trip and to show everyone the most amazing time ever! Since there is a strong cultural component for this trip your local Cuba group leader will also be educating you on the culture, history and customs of Cuba. Best of both worlds!

A passport is required for this Cuba trip. It is strongly recommended that your passport have at least 6 months validity (from the time you leave Cuba) to avoid any problems. Further, a tourist visa is also required. You will pick up your visa at your airline’s check-in desk (in the U.S.) upon arrival at the airport; the visa will cost about $50. No further paperwork is required.

You will be staying in casa particulars for the duration of this Cuba group travel trip. Casa particulars are privately owned homes that have been converted into rooms for rent. You can think of a casa particular like a Bed and Breakfast. Each room is set up with a private bathroom and has air conditioning; a simple breakfast (eggs, fresh fruit, bread and jams, coffee) is served each morning in the kitchen area. Please understand that the people of Cuba do not have much and the majority have been cut off from the outside world for over 60 years. While the casa is extremely clean, safe and in a beautiful neighborhood the infrastructure and decor is very old and dated.


It’s extremely important that we stay in casas (and not hotels) as all the hotels in Cuba are government owned while the casas are privately owned; your dollars will go directly to the locals in Cuba. The casa we use is located in the Vedado neighborhood of Havana – a residential neighborhood home to old mansions and beautiful, old architecture. The casa is walking distance from many great restaurants and night venues.

In order to budget properly please consider the following items which are not included in this Cuba group trip:

  • Tipping 
    • Local drivers and guides and restaurant staff: Tipping is not compulsory but can make a big difference to individuals in Cuba. Therefore, we recommend budgeting around $50 for these services.
    • Group leader: Tipping your group leader is completely discretionary. For outstanding service you may consider tipping your group leader ~$10/day.
  • Visa: A tourist visa is required for entry to Cuba. You will pick up your visa at the (U.S.) airport upon departure. Budget around $50 for the visa.
  • Travel insurance: Travel insurance covering our minimum requirements ($100k+ in medical coverage including emergency evacuation) is compulsory for all participants. Budget anywhere from $50 to $130 for travel insurance (from a 3rd party) depending on your specific coverage inclusions.

The single room supplement on this Cuba trip is $299. You will be able to select your preference for a single room supplement when filling out the application. If you are applying for this trip within 3 months of the departure please contact us for single room availability before applying.

Your group leader will be waiting for you at the airport in Havana! Upon meeting your group leader he/she will help you exchange money then get you set up with your airport transfer. After arriving at the casa you will have free time until around 6pm upon which you will meet the group at the casa. Then you will walk to a nearby spot for drinks/dinner as you begin to get to know one another!

While you will not physically meet your group mates until the evening of the first day you will be in contact with everyone well ahead of time in the group WhatsApp chat and, in addition, we will provide you with everyone’s traveler bios so you’ll already know each other a little before physically meeting!

You will need cash only for this Cuba trip. If you hold a credit card from a U.S. based financial institution please know it will not work in Cuba as there is no relationship between the Cuban government and U.S. financial institutions. Cuban currency (CUP) is a closed currency which means you will only be able to obtain it in Cuba. Therefore, you will exchange all your USD to CUP when you arrive at the airport in Havana. Your group leader will help you obtain local Cuban currency upon arrival at the airport in Havana.

We recommend bringing a carry-on sized suitcase for this trip. The waiting time for a checked bag (to come on the carousel) in Havana can be unpredictably long so we recommend a carry-on only bag to avoid this.

WiFi is available at hotels, public parks, and recently in some casa particulars. The WiFi in Cuba is cumbersome, expensive ($2/hour) and logging into the government owned network is not always possible. It’s best to approach this trip thinking you will not have WiFi for the duration of this trip. For a more complete understanding of WiFi in Cuba check out our article about WiFi in Cuba.

Cuba has come a long way in recent years and you will find some nightlife options in Havana though certainly much different than what you will find in the U.S. While there are a handful of bars in Havana most of the nightlife revolves around music and dancing salsa!

We’ve heard the beaches in Cuba are absolutely breathtaking but, unfortunately, you will not be allowed to go to the beach on our Cuba group travel trip. We operate a legal trip to Cuba for U.S. citizens under the Support for the Cuban People license in which we must provide a full-time schedule of activities designed to result in support of local businesses and individuals in Cuba. It is still illegal for U.S. citizens to visit Cuba for recreational purposes (like visiting the beach). But don’t worry – you will love our itinerary and be able to experience the real Cuba before it changes forever.

Depending on your cell service provider you might get cell phone (roaming) service in Cuba. Please note that if you indeed get service it will be roaming and the fees are extremely expensive (as high as $3/minute and $2/MB of data). Therefore, we recommend putting your phone in airplane mode for the duration of your trip to avoid these fees.

Cuba Group Travel Itinerary

  • Excited to be one of the first people to visit Cuba (from the U.S.) since travel restrictions were loosened? It all begins today! For those of you on an early flight into Havana you’ll have some time to join your group leader for a walking exploration of our neighborhood, Vedado, with some magnificent and large houses that’ll surely leave you in awe.


  • Tonight our group will sit down to a welcoming dinner over classic Cuban food at a local paladar (a privately owned restaurant).


Daily Inclusions:

  • Lodging: Casa particular in Havana (double occupancy)
  • Meals: Dinner
  • Transportation: Private airport transfer
  • It’s time to take in all of (Old) Havana today. After breakfast, we’ll embark on an educational historical tour of beautifully decaying Old Havana. Buildings with faded and crumbling facades in Old Havana are a nostalgic reminder of the earlier magnificence of the baroque and neoclassic architecture and style of this unique area. Our guide will take us back in time, while we explore the Plaza de Armas, Plaza de la Catedral, Plaza Vieja and Plaza de San Francisco. We’ll learn about Cuba’s tumultuous past, the revolution, and its hopes for the future. And, to top it off, we’ll have the unique opportunity to meet with Cubans along the way so we can learn, first hand, about the daily life in this charming city.


  • After lunch we’ll get our Cuban dance on with some Salsa dance lessons at a dance school. Not only will we learn (Salsa) moves but we’ll also learn about the importance this Latin American dance has on the Cuban culture.


  • In the evening we’ll stop by our casa to relax for a bit before heading out to paladar with excellent local Cuban cuisine.


Daily Inclusions:

  • Lodging: Casa particular in Havana (double occupancy)
  • Meals: Breakfast, Lunch, Dinner
  • Activities: Old Havana walking tour, Salsa class lesson
  • Transportation: Classic car ride
  • Today we will go on a full day trip outside the city of Havana to Viñales, a beautiful and lush valley in the Pinar del Rio province of Cuba known for its breathtaking scenery and world renowned tobacco farming. We’ll head West to Viñales where, upon arriving, we’ll have lunch at a local organic farm with some breathtaking views. After lunch we’ll head to a nearby tobacco farm and meet a tobacco farmer to learn more about the farming way of life in Cuba and, of course, the infamous Cuban cigar industry.


Daily Inclusions:

  • Lodging: Casa particular in Havana (double occupancy)
  • Meals: Breakfast, Lunch, Dinner
  • Transportation: Private transfer to/from Viñales
  • Sleep in a bit this morning as we’ll start our day in the late morning by heading to Old Havana for a unique cooking class experience.  Upon arrival in Old Havana we’ll head to a market where we’ll select fresh ingredients (for our class in just a bit) then make our way to the rooftop of a beautiful building in Old Havana where we’ll learn about traditional Cuban food and, with the help of chefs, make our own delicious lunch!


  • After enjoying the fruits of our labor and relaxing for a bit (on the rooftop) we’ll walk to a nearby artists’ studio where we’ll learn about their work, the local art scene in Havana and the struggles they have in obtaining basic art supplies. Lastly, we’ll finish off our day by heading to the town of Jaimanitas, often called Fusterlandia. Fusterlandia, named after its creator Jose Fuster, is a truly remarkable and unique pace. This art complex is a magical, colorful place of mosaic creations with art at every imaginable twist and turn. We’ll learn about the significant impact Fuster’s art has had in reviving this Cuban community.


  • Tonight, we’ll meet up for a farewell dinner.


Daily Inclusions:

  • Lodging: Casa particular in Havana (double occupancy)
  • Meals: Breakfast, Lunch, Dinner
  • Activities: Artist studio visit, cooking class, Fusterlandia exploration
  • Transportation: Private transfers all day
  • Today, sadly, is our last on our Cuba group travel trip for young professionals. While you will be going home today the experience on the trip and friendships made will last a lifetime! You’re free to depart from Havana at any time today.


Daily Inclusions:

  • Meals: Breakfast
  • Transportation: Private airport transfer (to Havana airport)
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