Havana & Vinales, Cuba

6 Days, 5 Nights

Experience Cuba! This beautiful country, which is a cobblestoned Caribbean gem, has so much to offer! The rum is plentiful, the smiles infectious and dancing is essential. Wind your way from sultry Havana and its crumbling churches, and on to the beautiful farmlands and mountains of Vinales. Along the way you’ll get to know tobacco and rum experts, celebrated local chefs, historians and salsa dancers that understand where Cuba came from, where the country sits now and, more importantly, where it’s going.

Support the local people by experiencing Cuba on this legal trip for US Citizens. Due to the new regulations, all of these tours are included and required by all guests. We’ve tested them all and they’re both fun and interesting, with a variety of the best things to do in Cuba!

Fly in/out of Havana. Please try to arrive before 5pm on Day 1 so you don’t miss any group activities.  You may leave any time on the last day as we’ll already be in Havana.  If you need help with flights, reach out!

Itinerary subject to change based on the discretion of trip leader or tour operator, due to weather or other extenuating circumstances.

November 2nd-7th, 2022

April 21st – 26th, 2023

Deposit $650

Trip Total $2999

*flexible payment options available for balance- to pay monthly or in a few equal installments
  • Personal Concierge at the airport upon arrival. Private transport to the hotel.
  • Bi-lingual Cuban Guide throughout the entire trip who has an in-depth knowledge of culture, history, and everything there is to do!
  • Welcome dinner (authentic Cuban dinner included)
  • City Walking Tour of Colonial Havana
  • Hemingway and Mafia Tour in Classic American Car
  • Salsa Lessons with cocktails included!
  • Dinner at one of the best Cuban restaurants (dinner included)
  • Cigar and Rum Tasting at the National Hotel (rum and cigar included)
  • Horseback riding, trekking, or cycling in the mountains of Vinales
  • Authentic tobacco tour in Vinales
  • Surfing Lessons or Beach day with a local Cuban guide outside of Havana.
  • Farewell dinner at the famous Cuban Art Factory (dinner included)
  • Live music and club outings with local guide every night.
  • 3 nights accommodation in Havana including 3 breakfasts.
  • 2 nights accommodation in Vinales including 2 breakfasts.
  • 4 dinners included
  • Private transport RT between Havana and Vinales and at all times during tours/included activities and dinners.
  • Verified/Legal itinerary prepared and insured
  • Cuba is a developing country. Normal amenities you have come to expect will not always be available, including wifi. We think this is a good thing but want you to be mentally prepared for a different, disconnected experience.

Deposits are non-refundable (but are transferable to another person or Legit Trip). Any additional payments can be refunded if canceled more than 90 days prior to the trip start date.  Deposits may only be transferred one time and incur a $100 rebooking fee.

Please be sure to read the complete booking terms and conditions at checkout.

We recommend a travel insurance plan to help protect you and your travel investment against the unexpected.
For more information on our recommended providers click here.

Fast Facts About CUBA


Cuba is often called El Caiman or El Cocodrilo (Spanish for alligator), which is what the island looks like from an aerial view.

Local People

Cuba is the most populated country in the Caribbean, with more than 11 million residents. In addition, the people are some of the friendliest in the world!


Cuba has a 99.8% literacy rate, which is one of the highest in the world.


Flights to Cuba are still very inexpensive from all over the US. You will need a visa which we will help you obtain but you do not need it before locking in your flight.

Day 1


VIP Arrival in Cuba, meet and greet with travel mates and trip hosts. 

Dinner at Fabrica de Arte with the option to stay for live music afterwards. 

Group travel to Cuba - Solo travel - Legit Trips

Day 2


The day begins with a tobacco tour with our expert (lunch incl), followed by horse riding in Vinales Valley. 

We’ll relax and unwind and then join together for tapas and live music!

Legal Travel to Cuba - Book a trip with friends - Legit Trips

Day 3


We’ll go into the Cuban countryside with a local documentary film maker & see firsthand a disappearing way of life of the country people.

Swim in a cave or relax in the countryside.

Travel to Cuba - Group itineraries - Legit Trips

Day 4


Start with a walking tour in the footsteps of Havana’s colonial past.

In the evening we’ll have a group salsa lesson followed by dinner, cigar & rum tasting & live music at our fave local spot.

Group Travel to Cuba - Legal travel to Cuba - Legit Trips

Day 5


We’ll begin with a Hemingway Tour and Mafia Tour in vintage American cars then spend the afternoon on the beach with an option to try surfing lessons.


Legal group travel to Cuba - Book with friends - Legit Trips

Day 6


Say goodbye to all of your new travel buds and friends in Cuba. 

Transfers back to the Havana airport.

Group travel to Cuba - Legal Travel to Cuba - Legit Trips

Ready to get started?

Your Cuba trip to Havana and Vinales is Just One Click Away!