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Cuba Guided Tours: Exploring the Island’s Past, Present & Future November 2021

Cuba Guided Tours: Exploring the Island’s Past, Present & Future November 2021

$2100 per person
8 days 7 nights | Group size: 6 - 12

Join us on one of our Cuba Guided tours and get to know Cuba on a deeper level. The island is easily one of the most unique and interesting destinations to visit in all of Latin America, if not the world. While you may come to Cuba looking for answers you’re more than likely to return home with even more questions. With a complex history from pre-colonial times all the way up to the present day global political climate and economic situation, Cuba is a history and poly sci buff’s paradise. Not only that, Cuba’s vibrant culture is reflected in its art, music, dance, food, drink and overall ambiance felt as you cruise the streets of la Habana Vieja or spend a leisurely afternoon smoking a cigar on a family run tobacco farm in Viñales Valley.

Our Cuba guided tours immediately immerse you into everyday life in Cuba as you settle into your “casa particular” owned and run by a Cuban family. From there you will jump into learning about Cuba’s historic and cultural past and present while traveling throughout both urban and rural Cuba. Our in-country host families, local guides, and drivers are all friendly, warm, and excited to share the real Cuba with you.

We invite you to join us on one of our Cuba guided tours to learn about this beautiful and resilient nation and the people who call it home. And also.. get ready for rum, cigars, classic cars, nonstop music and dancing, and delicious farm-fresh meals!

We look forward to sharing this adventure with you!

Itinerary subject to small changes at the discretion of The Heart of Travel guides in order to provide you with the safest, and most comfortable and enjoyable travel experience possible.


Saturday, November 13th to Saturday, November 20th, with the option to extend for 5 nights to visit Trinidad & Cienfuegos and depart on Thursday, November 25th.



Lodging in casa particulares (bed & breakfasts) - each room with private bathroom, hot water, clean sheets + towels, pillows, soap, mini-fridge, and many with a safe

7 breakfasts, 5 lunches, 5 dinners

Entrance fees and tickets for all activities included in the itinerary

Ground/water transportation to all points of interest included on the itinerary

Bilingual local guides

24/7 access to support and assistance from bilingual Heart of Travel guide

5-night add-on: Lodging, transportation, activities, guide, and 5 breakfasts 5 lunches and 3 dinners

Not Included

Airfare to/from Havana (estimated $550 - $750 depending on point of departure)

Visa (approximately $50 - $100 purchased individually at airport, depending on airline)

Trip Insurance

Additional beverages

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Tour Plan


Airport pick-up: Upon arriving at the airport, one of our Program Directors will be waiting to escort you to our headquarters in La Habana Vieja. Once in La Habana Vieja, you will be checked into your bed and breakfast (casa particular) and given a brief orientation of the city. If you need any assistance with errands or visits to a nearby point of interest, your guides will be more than happy to accompany you. In the event, you arrive early in the morning and would like to coordinate any specific activities during the day just let us know so we can accommodate your requests.

6:30 pm: Welcome Dinner (included)

We will all meet at the bed and breakfast headquarters to enjoy a homemade welcome dinner & cocktails during which time travelers can get to know one another and the guides better as we discuss the itinerary for the following days.

8:00 pm: Cocktails and Live Music (1 drink included)

Get into the spirit of Havana with cocktails and live music at one of Havana’s most iconic bars just steps from the capitol!

DAY TWO: SUNDAY, NOVEMBER 14th: B, L & D included

8:00 am: Breakfast at the casa particular (included)

9:00 am - 12:30 pm: Walking Tour of Old Havana

Join us on a personalized walking tour of Old Havana with your bilingual local guide. This tour stops at all major plazas and points of interest giving you a good lay of the land for future independent exploration as well as a general overview of Cuba’s history and current political and economic climate. We will also point out some of our favorite hidden gems such as shops, restaurants, bars, cafés, and galleries!

12:30 pm - 2:00 pm: Lunch (included)

Lunch in Old Havana to try traditional Cuban cuisine!

2:00 - 6:00 pm: Free time

Downtime for rest or independent exploration including visits to the Museum of the Revolution or Modern Art Museum which we highly recommend checking out on this day. Many people find touring the art museum is enhanced by paying 2 CUC extra for a guided tour in English. If you’re interested in doing this please let us know as soon as possible so we can try and reserve a museum guide.

6:30 pm: Dinner (included)

Departure from Habana Vieja to the posh Vedado neighborhood to enjoy a delicious dinner at La Fabrica’s VIP restaurant Tierra!

8:00 pm: Night out at La Fábrica de Arte Cubano

Join us for an incredible mixed media art and bar experience. You will view everything from photography to sculptures, to fashion to architecture, as well as film, live music and much more. There are no words to describe this amazing place which is popular with locals and visitors alike!

This is a perfect chance to meet and interact with people from Cuba as well as many other parts of the world! Plus, live music will start at 10:30 pm and that’s when the party really gets going on the main dance floor. Of course, if you’re looking for something more laidback there are quiet lounges, the upstairs theater and various patios for a breath of fresh air. This is one party in Havana that many tourists don’t get to experience, but once you do you’ll be dying to come back!

*Most people choose to stay out late at Fabrica, located in Vedado, therefore your tour leaders will be happy to arrange taxis to take participants home in waves if some of you decide to head home before others*

DAY THREE: MONDAY, NOVEMBER 15th: B & L included

8:30 am: Breakfast at the casa particular (included)

9:30 am: Travel to Viñales Valley

After breakfast, we will begin our drive to the Cuban countryside to visit Viñales Valley, a UNESCO World Heritage site, known as the heart of the tobacco and coffee-growing region in Cuba.

10:00 am: Visit Fusterlandia

Fusterlandia is a community-based art project located on the outskirts of Havana where you can admire Cuban artist José Fuster’s childlike rough shapes and bright colors in his untrained mosaic compositions. This project began with artist José Fuster turning his residence into a living museum which little by little attracted visitors to this small fisherman's neighborhood. Fuster went on to become a world-renowned artist and now many of the surrounding houses, walls, and even the public bus stop in this neighborhood have been decorated in the same fashion making this area a popular destination for visitors which has allowed the community to increment their earnings.

1:00 pm: Organic Farm Tour and Lunch (included)

Upon arriving in Viñales we will head to Finca Paraíso, a beautiful hillside organic farm. Here we will enjoy a large family-style lunch before taking a tour to learn more about sustainable agriculture in Cuba.

3:30 pm: Visit to Viñales Mural de la Prehistoria

Next, we’ll visit the Viñales Mural de la Prehistoria, or the Prehistoric Mural. This massive mural painted on the side of a large “mogote” showcases a unique interpretation of pre-historic life. However, the main highlight of this stop is by far the piña coladas, considered by many to be the best in all of Cuba!

5:30 pm: Free Time

We will check into our casa particular for the evening and enjoy some downtime to rest and relax or to explore the small town of Viñales.

7:30 pm: Optional group dinner (not included)

Meet at the headquarters for an optional group dinner in town!

DAY FOUR: TUESDAY, NOVEMBER 16th: B & D included

8:00 am: Breakfast at the casa particular (included)

9:00 am: Visit the la Cueva del Indio

Take a short boat ride through an impressive cave that once served as a dwelling for the indigenous community that inhabited the area prior to the arrival of Spanish colonizers. This quick trip allows you to appreciate the limestone caves and interesting rock formations common to caves in the area. Additionally, there is a small handicraft market upon exiting the cave that is fun for browsing!

10:00 am: Visit a tobacco and coffee farmer’s home

After our short tour of the cave, we will continue a day of outdoor adventure with a light hike or horseback ride throughout Viñales Valley to learn about flora and fauna. Here we will visit a tobacco and coffee farmer’s home. This is a great opportunity to try and purchase cigars, snap an iconic photo and sip on a delicious local beverage known as canchanchara!

While here, your tour leaders, along with the farmer, will explain the Cuban tobacco industry in greater detail as well as the overall way in which the Cuban economy works in order to deepen your appreciation of the work that goes into creating products and experiences for tourists and the way in which your visit to the country can have a positive impact on the lives of individuals.

We highly recommend waiting to buy cigars until you get here as you will be directly supporting individual farmers and putting more money into their pockets unlike buying boxed and branded cigars from the government-run shops back in Havana.

1:00 pm: Lunch (not included)

You’re free to eat wherever you’d like back in town and we are happy to provide recommendations. Keep in mind that we will be enjoying a delicious and abundant pig roast later that day so a light lunch is encouraged!

2:00 - 5:00 pm: Free time

Downtime for rest or independent exploration. We are happy to help coordinate various activities depending on your interests just let us know!

6:00 pm: Delicious pig roast & party (included)

Live a true “guajiro” experience with music, drinks, food and cross-cultural interaction on a family farm!


8:30 am: Breakfast at the casa particular (included)

9:30 am: Return to Havana

After breakfast, we will hug our Cuban host families goodbye and begin the journey back to Havana, making a quick stop at the impressive Jazmines lookout which allows you to appreciate expansive panoramic views of the valley.

12:30 pm: Lunch at Los Antojos (included)

Upon arriving back in La Habana Vieja we will grab lunch on the patio at Los Antojos. Located on one of the cutest streets in all of Havana, Los Antojos serves delicious Cuban recipes in a fresh and modern way. Our personal favorites are the pork ribs and the beef picadillo, but you’ll find a variety of seafood and vegetarian options as well that are sure to delight the palate!

2:00 pm: Free time

After lunch, we will check back into our bed and breakfast and you will have some downtime before an optional visit to the market.

4:00 - 5:30 pm: Shopping!

We’ll visit the largest market in Havana featuring local arts, crafts, clothing, gifts, etc. This is a great opportunity for some souvenir shopping for loved ones back home. A lot of the different stalls offer similar items but if you’re interested in something more unique we’d love to show you D' Brujas Jabones Artesanales. This is a female-led cooperative that makes artisanal soaps and is an awesome, and rare, example of female-powered entrepreneurship within Cuba’s emerging private sector.

For those not interested in shopping, this is also a good opportunity to visit any museums of interest that you haven’t seen yet, or to grab a beer at the brewery located next to the artisan market.

5:30 - 8:00 pm: Free time

Downtime for rest/relaxation.

8:00 pm: Dinner and a show (included)

Meet at the casa particular headquarters to go to dinner and a show, which could be a musical performance or modern ballet depending on the season.

DAY SIX: THURSDAY, NOVEMBER 18th: B & L included

8:00 am: Breakfast at the casa particular (included)

9:30 am: Departure to Mégano Beach

We’ll head to Mégano for a day on the beach, arriving at approximately 10:30 am. Here you can enjoy a relaxing morning on the beach, go for a dip or even do some snorkeling. For those looking to take care of the environment, we will have trash bags and gloves available to do an optional beach clean up.

12:30 pm: Lunch (included)

Enjoy a picnic lunch on the beach!

3:00 pm: Depart Mégano Beach

We’ll depart from Mégano and return to Havana to freshen up before dinner!

6:00 pm: Optional Group Dinner (not included)

We will enjoy a delicious group dinner at the fun and funky El Dandy! Located close to our casa particular headquarters, this small corner restaurant serves delicious cocktails and international cuisine. Fan favorites are mojitos, the sweet potatoes fries, and their pasta arrabbiata.

Located right around the corner from El Dandy is one of our favorite places to shop in all of Havana, Clandestina. We highly recommend squeezing in a visit before dinner!

Clandestina was established in 2015 and is the first Cuban urban fashion brand made up of a collective of designers, artists and creators selling products in Cuba and abroad. All products are designed in Habana and Clandestina believes in the sustainable fashion industry and strives to see the industry become more fair and ethical. They reuse and repurpose garments, fabrics and many other materials and their designs are inspired by the upcycling and zero waste movements. Clandestina is also a female-founded and extremely inclusive company with employees of different races, genders, religions, sexual orientations, etc.

7:30 pm: Visit the Fortress of San Carlos de la Cabaña for the Cannon Ceremony

After dinner, we will hop in our pre-reserved cabs and cross the bay to visit the fortress of San Carlos de la Cabaña (UNESCO World Heritage site). Here we will attend the nightly Cannon Ceremony and visit the Che Guevara museum. Every night at 9:00 pm in Havana they reenact the cannon ceremony which was performed every morning and evening during colonial times to symbolize the opening and closing of the city’s port.

DAY SEVEN: FRIDAY, NOVEMBER 19th: B, L & D included

9:00 am: Breakfast at the casa particular (included)

10:00 - 12:00 pm: Classic Car Tour

Classic car tour around Havana allowing the group to see a variety of different Havana neighborhoods and sites including the Revolution Square, Vedado, Miramar, the Havana Forest & El Mirador del Cristo de la Bahía. This is a great day for photos so wear something comfy but cute! Also, the sun can be strong in the convertible cars so sunscreen and a hat are recommended.

12:00 pm - 1:30 pm: Lunch (included)

We’ll grab a delicious meal at Jíbaro, known for its innovative cocktail menu!

2:00 pm: Tour of Havana Club Rum Museum (included)

Guided tour of the Havana Club Rum Museum, where we’ll have the opportunity to experience the process of making rum in detail and learn about the origin of Cuba’s most popular distillate!

4:00 pm 7:00 pm: Free time

Head back to casa particular for downtime before dinner.

7:30 pm: Farewell dinner in Más Habana (included)

Enjoy a delicious meal and round on drinks as we celebrate another successful Heart of Travel adventure and share our personal trip highlights with one another!


8:00 am: Breakfast at the casa particular (included)

On our final day, we will have breakfast at our casa particular before heading to the airport to catch our return flights. For those doing the extension, we will hit the road to Cienfuegos and Trinidad shortly after breakfast.


DAY EIGHT: FRIDAY, MAY 8th: B & L included

9:00 am: Drive to Cienfuegos

12:00 pm: We will make a stop at the Bay of the Pigs where we can swim, snorkel or just take in the ocean views at this historic site.

1:00 pm​: After finishing up at the beach we will stop for lunch at Alexis’ local paladar for fresh seafood cut and prepared on the grill right in front of us! This is one of our most fun and delicious meals so it’s the perfect way to break up the day’s drive! (​included​).

2:30 pm: ​Not too far from Alexis’s restaurant we will stop in Girón to visit the Museum of the Invasion, a very interesting look into Cuba’s perspective on this sad event in history which helps to continue contextualizing Cuba’s history and complex relationship with the United States.

5:00 pm: Free time!

Upon arriving in Cienfuegos, we will check into our casas particulares and you’ll have some downtime to rest and freshen up before an optional group dinner.

7:00 pm: Optional group dinner (not included)

Optional group dinner at Ozniel’s rooftop, where he has a variety of traditional dishes and drinks!

DAY NINE: SUNDAY, NOVEMBER 21st: B, L & D included

8:00 am: Breakfast at the casa particular (included)

9:00 am: Walking Tour of Cienfuegos

Walking tour of Cienfuegos before visiting the Palacio del Valle and enjoying rooftop drinks.

12:00 pm: Travel to Trinidad and lunch (included)

We’ll begin our journey to the coastal town of Trinidad, stopping for lunch on the way.

3:00 pm - 6:00 pm: Walking Tour of Trinidad

Upon arriving in Trinidad, we will check into our casa particular and take a brief break before enjoying a walking tour of the city including a visit to a temple to learn more about Afro-Cuban culture and santeria.

7:30 pm: Group dinner (included)

Group dinner at our favorite place in Trinidad, La Redacción.

9:00 pm: Opportunity to listen to live music and dance at Casa de la Música!

DAY TEN: MONDAY, NOVEMBER 22nd: B, L included

8:00 am:​​ Breakfast at the casa particular (included)

9:00 am: Sugar Cane Plantation Visit

After breakfast, we will visit a local market at what was once an old sugar plantation to learn more about Cuba’s history and economy and how it relates to the Haitian slave revolt. This is also an opportunity to shop for some unique items not found in Havana.

11:00 am - 4:00 pm: Playa Ancón and Lunch (included)

Afternoon at Playa Ancón for a picnic lunch ​(included)​ and swim! A highlight for many, Playa Ancón is a gorgeous beach and the perfect place to relax and appreciate Cuba’s natural beauty plus your tour leaders and drivers have put together an awesome picnic for you.

4:00 - 6:00 pm: Free time

Downtime to freshen up before the evening’s salsa class!

6:00 - 7:00 pm: Salsa class (included)

No trip to Cuba would be complete without learning some basic moves!

7:30 pm: Optional group dinner (not included)


8:00 am: ​​Breakfast at the casa particular (included)

10:00 am - 4:00 pm: ​​Horseback Ride to Natural Swimming Pools (included)

Horse ride or hike to a beautiful waterfall and natural swimming pools that are popular with locals and visitors alike. We will have lunch at a nearby local paladar and enjoy a relaxing day in nature ​​(included).

4:00 - 8:00 pm:​ ​Free time to relax, rest or explore independently!

8:00 pm:​ ​Group dinner ​​(included)


8:00 am: Breakfast at the casa particular (included)

9:00 am: Begin the journey back to Havana!

12:30 pm: Lunch on the road (included)

3:30 pm: Arrive in Havana

Arrive back in Havana and get settled into the casa particular with downtime to rest/freshen up. Your guides will be available to assist you with any last-minute shopping or activities.

7:30 pm: Dinner (included)

Dinner in Vedado with the option to visit a live music venue afterward!


8:00: Breakfast and Departure

On our final day, we will have breakfast at casa particular (included) before heading to the airport to catch our return flights.

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