5 Day Cuba Tour - Havana Weekend (+ Viñales)

Starting at US $1450 / person See Tour Dates

Tour Summary

group size 12 travelers maximum
accommodation 4 nights in privately owned luxury class Bed & Breakfasts (casas particulares), double occupancy.
transport Private transportation in air conditioned bus.
license This tour complies with the general license category Support for Cuban People (515.574). The tour provides the basis and support for your compliance with the law.
Included Activities Walking tour of Old Havana; Cocktail lesson; Boxing Studio visit; Galeria Taller Gorria visit; Meeting with community project in Regla; Afro-Vegan cooking demonstration; Mafia tour in Classic Car; Murals and Mosaics local art communities tour; Meet & Greet at a Local business - part of the 'new Cuba' movement; Maridaje ceremony (cigar & rum pairing), Day Tour to Viñales including: Visit to tobacco farm, Indian caves, and Prehistoric Mural.
other inclusions 4 breakfasts, 4 lunches, 4 dinners, cocktails in activities as listed above.  Airport arrival transfer. Private local Cuban tour leader throughout, some local specialist guides.
Women in Red Car

Itinerary Summary

Day 1 Arrival Day Havana
Tour starts at 10am
Map 5 Day Tour
Day 2 Havana
Day 3 Havana
Day 4 Viñales
via Jaimanitas
Day 5 Departure Day

This tour begins at 10am on Day 1, so we encourage you to arrive the night before the tour. We are happy to book pre-tour accommodations for you, or you may reserve them on your own. If you can’t arrive by 10am Day 1, try to arrive in time for the group dinner around 7pm.

The purpose of this itinerary is to give you an idea of the types of activities you will engage in during this tour of Cuba, however, it may change based on factors such as season, availability, and weather.

Tour requires a minimum of 4 passengers to depart. Please do not book international flights to Cuba until the tour is guaranteed.

See tour dates

Tour Description

The Havana Weekend + Viñales package takes you to visit the rural side of Cuba with a day tour to see the breathtaking vistas and organic farms of the Pinar del Rio province.  

It encompasses a little bit of all that makes Cuba one of the most beautiful countries in the world. The first three days we spend exploring Havana one of the most unique cosmopolitan cities in the world. We cover several aspects of the culture and history of Cuba, from its mafia past, to its present blossoming private sector. You’ll learn about the societal impact of the revolution and the social challenges that Cuba currently faces. On this tour you won’t find museum visits, we want you to immerse yourself in Havana with discussion, exchange, and hands-on experiences sure to create lasting memories.

Then we journey east to rural Viñales, unforgettable for its views and charming inhabitants. Here you’ll learn from farmers about Cuban agriculture and how it is affected by Cuba’s political climate and relationship with the United States.

If you only have a few days in Cuba but want to go beyond the usual tourist experience, this is the tour for you! This tour encompasses four action packed days, each with a full schedule of interactions with private business owners, community leaders, artists, and farmers and is designed to comply with US legal travel regulations. If you need a shorter trip, take our 4 day tour: Havana Weekend. If you’ve got more time to spend, there is so much more to do in Havana! Add on some extra days for museum visits, day tours, visit the beautiful beaches of Eastern Havana, or take classes in Spanish, Dance or Percussion.

Day 1 - Havana: Start time 10am

We start our group tour in Havana at 10am today with an orientation meeting followed by a tour of Old Havana, a UNESCO World Heritage site. This 2-hour walking tour encompasses the four principal plazas of Old Havana, you’ll also learn about the ration system with a visit to a local bodega. Following the tour, we’ll have lunch at a paladar (privately owned restaurant) and learn how to make traditional Cuban cocktails. Once fed and watered, we will explore the hip art district of San Isidro, including stops in a well-known boxing studio and a visit to Galeria Taller Gorria, a cultural project with the aim of providing  a space to bring together art & the community through performances, workshops and exhibitions.

Tonight we will have dinner at one of Havana’s classic paladars.

Included Activities: Walking tour of Old Havana, Cocktail lesson, Boxing Studio visit, Galeria Taller Gorria visit

Included Meals: Lunch, Dinner

Day 2 - Havana

Today we cross the bay to Casablanca and Regla to see the Havana skyline and visit with community project ReglaSoul for a discussion on gender and race issues in Cuba. ReglaSoul is a community project formed by a local hip hop artist and an expat photographer/filmmaker, their goal is to promote wellness in the Afro-Cuban neighborhood through free concerts and workshops. For lunch we’ll be treated to a Today we cross the bay to Casablanca and Regla to see the Havana skyline and visit with a local community project in the town of Regla for a discussion on gender and race issues in Cuba. The aim of this project is to promote wellness in the Afro-Cuban neighborhood through free concerts and workshops. For lunch we’ll be treated to a homemade Afro-Vegan meal.

Later we board classic convertible cars (weather permitting) for a panoramic tour of Havana in which you will learn about the history of the American Mafia and the role it played in pre-revolutionary Cuba. We end the tour at the notorious Mafia headquarters and the lodging of choice for America’s royalty.

Tonight’s dinner is at a ‘small plates’ restaurant, with a post dinner visit to the famous Fabrica de Arte Cubano. Named one of Time Magazine’s World’s 100 Greatest Places. Featuring five salons showcasing various types of art, from textiles, to architecture, music, dance, and eye-catching installations, plus bars and pop-up shops; you’ll marvel at the innovation and talent of New Cuba.

Included Activities: Meeting and discussion with local community members of Regla, Afro-Vegan Cooking demo, Mafia History tour in Classic Car, Fabrica de Arte Cubano

Included Meals: Breakfast, Lunch, Dinner

Pink Cars Parked

Day 3 - Havana

How do you take an impoverished neighborhood known as the ‘Ugliest Street in Havana’ and turn it into a successful community project that catches the notice of President Obama? Today we’ll learn about how individuals used their talents to fuel positive change in their neighborhoods on a special tour with Havana Adventures. Don’t forget your camera, you’ll visit two of the most artistically remarkable neighborhoods in Havana.

After lunch we cover the topic of ‘cuentapropistas’, entrepreneurship in Cuba. Beginning in 2011 the Cuban Government began opening the private sector and legalizing private businesses not seen since the 1959 revolution. Private businesses face a unique set of challenges to succeed in Cuba, from government bureaucracy to advertising bans to scarce resources. In order to survive and thrive they have to show remarkable creativity and tenacity. We will illustrate this topic with a visit to one of Havana’s successful new businesses to hear their story and perhaps get a special demonstration of their manufacturing process.

In the evening we will have the opportunity to experience a “maridaje” ceremony - the pairing of Cuban rum and Cuban cigars.

Included Activities: Murals and Mosaics local art communities tour with lunch and cocktail, Meet & Greet at a Local business - part of the 'new Cuba' movement, Maridaje ceremony (cigar & rum pairing)

Included Meals: Breakfast, Lunch, Dinner

Day 4 - Full day in Viñales

We depart very early in the morning to head off towards the mountains and the province of Pinar del Rio. On arriving in the town of Viñales we will meet with a specialist local guide who will take us through the tobacco fields to meet local farmers & visit a farm, learn about growing tobacco, how to roll cigars, taste some local coffee and experience real life in the small country town, After our light trek through the Viñales valley we visit an organic farm for a fantastic farm-to-fork lunch.

We will have a light orientation tour around this small town, and time permitting we’ll visit take a boat ride through Cuevas del Indio (Indian Caves). You will also see the controversial Prehistoric Mural where you can decide for yourself whether it is art or an eye-sore. We’ll end our day with a cocktail in a small local bar (perhaps with some local musicians) before heading back towards Havana for our final night and farewell meal.

Included Activities: Day trip to Viñales - visit to tobacco farm, organic farm, Indian caves (time permitting) and Prehistoric Mural.

Included Meals: Breakfast, Lunch, Dinner.

Work in Tobacco Farm

Day 5 - Depart Havana

Today you can depart at any time. There are no included activities, however, your tour leader will be around at least until midday in case you have a few extra days planned in Havana and need some pointers or recommendations. An airport departure transfer is not included in the tour package. You can hire your own taxi or otherwise ask your tour leader for assistance.

Included Meals: Breakfast
If you have a little less time consider taking the 4 day Havana weekend

Summary of Travel Time

Havana to Vinales - 3 hours


Prices start at US$1450 person. 

Optional Single Supplement US$450. We welcome solo travelers! You don't pay a single supplement unless you want to guarantee your own room.  Read more about the single supplement.

We require a US$400 per person non-refundable deposit to reserve your place on the tour. The remaining balance is due 60 days before the tour departs. Tours can be booked up to 10 days in advance, full amount would be due at booking.

Budget for additional costs

Spending money for meals, souvenirs,  additional gratuities: US$200-300

Medical Insurance (Required by Cuban Government): US$36
Note: Insurance is included in airfare for direct flights to Cuba from the U.S. 

Roundtrip flights to Cuba from Cancun to Havana: US$375-450

Roundtrip flights from Miami to Havana (including medical insurance): US$200-300. Read more here.

Cuban Tourist Visa (Tourist Card): US$50 - 100

Travel insurance: Price Varies. We highly recommend you purchase travel insurance in case of unforeseen circumstances that cause you to cancel or delay your trip.  We don't sell travel insurance but you can shop for insurance policies online at www.insuremytrip.com

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Not included in the Tour

  • International airfare (Tour starts and ends in Havana)
  • Cuban Tourist Visa (aka Tourist Card) - Read more HERE
  • Mandatory medical insurance (included in flights from USA)
  • Meals not included - 3 lunches, 3 dinners
  • Drinks
  • Gratuities for guide and optional activities
  • Airport departure transfer (approx 25 CUC in taxi)
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