4 Day Cuba Tour - Havana Weekend

Starting at US $1290 / person See Tour Dates

Tour Summary

group size 2 travelers minimum, 12 travelers maximum
single supplement Single Room for the tour - $403 USD extra (read more)
accommodation 3 nights in privately owned deluxe 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; Art gallery visit; Discussion of race and gender with community leader; Mafia History tour; Havana Classic Convertible tour; Fusterlandia and Muraleando Community Projects; Meet & Greet at a Local businesses - part of the 'new Cuba' movement; Maridaje ceremony (cigar & rum pairing).
other inclusions All breakfasts, 3 lunches, 3 dinners, & cocktails included in specific activities listed above.  Airport arrival transfer. Wifi card, English-speaking Cuban tour leader throughout
Tourists at Fusterlandia

Itinerary Summary

Day 1 Arrival Day Havana (10 a.m. start time)
Day 2 Havana
Day 3 Havana
Day 4 Departure

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. Activities and time tables may change based on factors such as availability, season, and weather or to take advantage of other unique opportunities.

Tour requires a minimum of 2 passengers to depart. Please do not book international flights to Cuba until the tour is guaranteed. 

See tour dates

Tour Description

If you only have a few days in Cuba but want to go beyond the usual tourist experience, this is the tour for you! It encompasses a little bit of all that makes Havana one of the most unique cosmopolitan cities in the world. In a short time, 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.

This tour encompasses three action packed days, each with a full schedule of interactions with private business owners, community leaders, and artists and is designed to comply with US legal travel regulations. For that reason, you won’t see chill beach time instead you’ll find a fun and diverse selection of activities that we have cultivated to give you the most multidimensional understanding of Havana within a short time.  If you have more time we recommend extending your trip to the 5 day tour: Havana Weekend + Viñales to see the breathtaking vistas and organic farms of the rural Pinar del Rio province. Feel free to stay as long as you want, 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 a local gallery, a cultural project with the aim of providing a space to bring together art & the community through performances, workshops and exhibitions.

Tonigh we will have dinner at one of Havana's classic paladars.

Included Activities: Walking tour of Old Havana, Cocktail lesson, Galleria 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. Founded by a local hip hop artist and an expat photographer/filmmaker, the goal of ReglaSoul 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. Note: This activity is seasonal, alternative is visit to a family-owned fashion brand tackling issues of self-esteem and empowerment in their community, followed by a Afro-Cuban meal in the home of the late founder of Callejon de Hamel.

Later we board classic convertible cars (weather permitting) for a panoramic tour of Havana’s less touristy neighborhoods. Then we’ll learn about the fascinating 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, you’ll see why as we tour the oil factory turn arts complex. 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, Afro-Cuban meal, Mafia History tour, Panoramic city tour in Classic Car, Fabrica de Arte Cubano

Included Meals: Breakfast, Lunch, Dinner

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 - 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 an extra day, you could take the 5 day Havana weekend that includes a full day in Viñales.

Tour Dates & Availability

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Flexible Bookings!
With our flexible bookings policy, you can book your place on a tour for only $100 and change your departure date anytime at no cost. Read more...

Budget for additional costs

Spending money for snacks, souvenirs, tour leader gratuity, and additional gratuities: US$200-300

Medical Insurance (Required by Cuban Government): US$16
Note: Insurance is included in airfare for direct flights to Cuba from the U.S.

Roundtrip flights from Miami to Havana (including medical insurance): US$300-600. 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 in above itinerary
  • Drinks (1 non-alcoholic drink included with meals)
  • Gratuities for tour leader and optional activities
  • Airport departure transfer (approx 25EUR in taxi)
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