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Havana, Cienfuegos & Trinidad

Cuba Cultural Walking Tour

7 DaysStarting at $5,895
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Overview

For all you’ve heard about life in post-revolution Cuba, one of the country’s great surprises is how much of its pre-Castro history has been preserved—and how that past and present coexist today. This fascinating expedition includes the colorful colonial cities of Trinidad and Cienfuegos, where you explore cobblestoned streetscapes, walk in lush mountains and snorkel on the tropical coral reef in the Bay of Pigs. In Havana, you wander in the 500-year-old city and out to Hemingway’s home. As you travel Cuba with us on foot, you’ll interact closely with coffee-growers, artists, dancers, historians, and everyday Cubans from all walks of life. Ultimately, you’ll gain a sense of Cuba from its sugarcane-fueled colonial days right up to the latest moment. Join us on a trip to Cuba and you will be rewarded with an engaging, well-rounded understanding of Cuba that’s second to none.


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Watch the three-minute documentary: A Traveler’s Tale in Cuba

One of “50 Tours of a Lifetime” & one of the most authentic, immersive, sustainable, & best-guided tours.”
National Geographic Traveler

Itinerary Highlights

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• See Old Havana on foot at eye level on a walk that precedes a visit to Fidel Castro’s personal photographer in his home to share stories and anecdotes over iconic images.

• Meet the husband-and-wife and their team of automobile craftsmen whose small business specializes in restoring classic car and select your favorite candy colored the tail-finned masterpiece for a ride of a lifetime to Revolution Square.

• Step into Ernest Hemingway’s shoes at his Cuban home, Finca Vigia, on a private visit with the curator and then sip a daiquiri at Hemingway's favorite bar.

• Learn how much your hips can sway in a memorable salsa dancing lesson in a private studio.

• Tour a traditional cigar-making factory with an expert roller, who explains the process and its important role Cuban life and then later in the week learn about Churchill and Castro’s shared passions during a fascinating and fun cigar and rum tasting with a sommelier.

• Shop a local fruit and vegetable market, then join a chef who pauses her TV show to welcome you into her personal kitchen for an instruction and lunch.

• Enjoy conchonchera cocktails with a diplomat who shares a fascinating 60 years of geopolitics in 60 minutes in an ‘only with Classic Journeys’ sit down.

• Savor a gourmet lobster bake on the beach at the Bay of Pigs followed by snorkeling with naturalist guides on its pristine coral reef.

• Share footpaths with farmers going to market in the cinematic and historic Valley of the Sugar Mills.

• Clip clop on a horse and carriage ride on a guided tour of 500-year-old Trinidad and then on foot with a historian in Cienfuegos, the pastel city known as the “Pearl of the South.”. 

• Walk past jaw dropping waterfalls in the Escambray Mountains to meet a family of coffee growers who welcome you to their plantation to share how their coffee is grown and to share a tasting with you.

Havana Jazz Festival


Join us on the Havana Jazz Festival dates (below) and enjoy all of the experiences in this itinerary against the backdrop of music throughout your days and evenings in Havana. You’ll also enjoy three extraordinary ‘only with Classic Journeys’ experiences: sit down for drinks and a discussion with a musicologist (a personal friend of our guides), a private jazz session with a group of musicians who take you on a journey through different elements of Cuban music, and special access tickets to a concert so you get to the performance without having to arrange the details yourself.  

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Map

  • Starting Point:

    Havana – 10:00 am – Lobby of first night’s accommodation

  • Ending Point:

    Havana – 5:30 pm – José Martí Airport
Itinerary Map

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Walking Level

  • Daily Mileage Options: 2-7 miles

  • Route Notes:

    The terrain on this trip includes a mix of paved and cobblestone streets in Havana, Trinidad, and Cienfuegos; as well as well-maintained mountain, countryside and coastal trails of compressed dirt and stone that offer a selection of level, rolling and hilly terrain; with some elevation gain and loss.
To See Mileage Daily, Download Full Itinerary

Dates & Prices

The earlier you book, the more options you’ll have and the lower your price. Secure your spot with a deposit of just $500 per person at the time of reservation. Plus, you can always change your mind — there’s no fee to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887.

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Family Departure

Select our “Family Departure” to travel with other families.

Hotels

We spend years cultivating personal relationships with our hoteliers to provide you thoughtfully selected accommodations that reveal the true character of the region. Here is a sampling of our favorite hotels on this tour. 

La Reserva

In the heart of Havana’s El Vedado, this exquisitely renovated colonial mansion has luxury rooms, a tropical garden with bar, and an in-house art gallery featuring contemporary Cuban artists.

Claxon, Havana, Cuba

Claxon

Located in an elegant mansion on Paseo Avenue, Claxon is a beautiful boutique hotel in downtown Havana. Enjoy a comfortable room with modern amenities and a drink on the garden patio during your relaxing stay in the heart of the capital.

Mansion Alameda

Mansion Alameda is a charming boutique inn located in Trinidad, the heart of central Cuba. This restored manor house is where Fidel Castro’s wife grew up, offering authentic historic accommodations for a memorable stay.

La Distancia, Havana, Cuba

La Distancia

Casa La Distancia is a privately owned boutique residence in the quiet Vedado neighborhood. Located within walking distance to the Malecón, this revitalized colonial mansion offers modern conveniences, an outdoor patio, and Cuban music-themed decor.

Casa Brava, Havana, Cuba

Casa Brava

Enjoy Havana’s serene Vedado neighborhood at Casa Brava boutique hotel. Relax in your comfortable room with modern amenities, sip a drink in the private bar, and experience the warm Cuban hospitality in this family-owned colonial house.

La Casona

A colonial ranch on the edge of Santa Rosa Valley, La Casona’s terraced rooms are decorated with local art. The large garden and yard look out on the ruins of a colonial fort.

What’s Included

  • Meals: Six breakfasts, six lunches, and four dinners.
  • Hotels: Award-winning boutique properties, thoughtfully selected for their exceptional location, design, history, and regional character.
  • Tour Leader(s): Expert guides who are your well-connected local friends and provide you access to people and places you wouldn’t find on your own.
  • Supplemental Experts: Additional regional guides and specialists on select tours.
  • Transportation: All land transportation as listed in the daily itinerary, including fares for trains, ferries, and other modes of travel.
  • Privileged Access Events: One-of-a-kind access to remarkable people, places, and experiences arranged just for you, as noted in the daily itinerary.
  • Admissions & Entry Fees: Entry to tastings, historic sites, and other scheduled activities listed in the daily itinerary.
  • Baggage Transfers: Upon arrival, we whisk you and your bags directly to your room—no waiting, no tipping.
  • Gratuities : All gratuities at hotels, restaurants, and for baggage handling.
  • Dedicated Guest Services Coordinator: Your pre-trip concierge and tour expert, available to answer questions and ensure you’re fully ready to get the most out of your tour.
  • Equipment: Premium gear and expert guides for kayaking, rafting, glacial hiking, and snorkeling as outlined in the daily itinerary on select tours.
Not Included: Tour Leader gratuities, travel to and from your trip’s start and end points, and any meals or activities taken independently.

Why Choose Classic Journeys

We believe in creating authentic connections by immersing you into the history and culture of a people and place. So we find the most well-connected local guides who share their relationships and knowledge with us. And with them, we handcraft walking tours in cinematic settings that allow you to see the world on foot and at eye level. It’s why Travel + Leisure magazine has named Classic Journeys as the #1 World’s Best Tour Operator multiple times, and the editors of T+L say, “Classic Journeys provides unbeatable access to experiences around the globe.” Here’s what that access means for you every time you travel with us.
  • Experience Cuba on foot and at eye level. Each day, join your guide on the most cinematic footpaths in the cities, towns, villages, countryside and coasts of this fascinating island.
  • Exceptional full-time local guides who become your well-connected friend. Our guides are with you throughout each day sharing their lifelong connections as well as engaging anecdotes about the history and culture of the fascinating island and its people.
  • Small groups that provide you unrivaled access. An average of 10 guests per departure means we can offer you special ‘only with Classic Journeys’ access to experiences like a visit to Hemingway’s home with the curator and visits with Castro’s personal photographer and a diplomat for in-depth discussions into geopolitics.
  • Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive privately owned accommodations on the island where we know the owners personally and they treat you like invited guests.
  • Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of Cuba. From gourmet lobster bakes at the Bay of Pigs to a cooking instruction with a famous chef in her kitchen, our meals offer you opportunities to explore native food traditions and fine dining.
  • Handcrafted itineraries with all activities included. With our long-term friendships, we know Cuba more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of Havana, Cienfuegos, Trinidad, the Bay of Pigs and the spectacular coastline and countryside.
  • Regenerative Travel that supports the history, culture, people and places you’re visiting with us in Cuba. We put our local currency into the pockets of the people who live where we travel. It’s your guarantee that you’ll have authentic, up-close experiences on your trip. Best of all, our person-to-person approach helps sustain their ways of life.

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FAQs

Is it legal for U.S. citizens to travel to Cuba on this tour?

Yes—your Classic Journeys tour is operated under the “Support for the Cuban People” general license (31 CFR § 515.574) authorized by the U.S. Department of the Treasury. This means your journey is not only fully legal, but also designed to maximize authentic cultural exchanges with local entrepreneurs, artists, and communities. All compliance details are seamlessly handled on your behalf, so you can focus on enjoying Cuba with confidence and peace of mind.

What makes a walking tour of Cuba different from other tours?

Exploring Cuba on our walking tour allows you to experience it all on foot and at eye level—strolling through Old Havana’s plazas, meeting artists in their studios, and joining locals in lively markets. Unlike bus tours or big groups of tourists, this style of travel emphasizes close, authentic encounters rather than surface-level sightseeing, giving you a richer sense of Cuba’s daily life.

What is the level of physical activity on the Cuba tour?

Our Cuba walking tour is considered easy to moderate, with an average of 2-7 miles per day. Your curated walks include guided strolls through cities, cultural sites, and countryside settings. Walks are at a relaxed pace, with plenty of stops for exploration, conversation, and refreshment along the way. The terrain on this trip includes a mix of paved and cobblestone streets in Havana, Trinidad, and Cienfuegos; as well as well-maintained mountain, countryside and coastal trails.

What kinds of accommodations and meals can I expect in Cuba?

You’ll stay in carefully selected boutique accommodations and casas particulares (privately owned and beautifully restored mansions) that reflect Cuban character and hospitality. You’ll eat like (and with) the locals as your meals feature a mix of paladares (family owned restaurants), chef-hosted experiences, and curated group dinners. This ensures both comfort and immersion in Cuba’s traditions while being in full compliance of the U.S. Treasury Department’s Office of Foreign Assets Control (OFAC), pursuant to the general license in 31 CFR § 515.574, Support for the Cuban People.

How many travelers are in each small group in Cuba?

Classic Journeys keeps groups small—an average of 12 guests and never more than 18, with a remarkably intimate 6:1 guest to guide ratio—ensuring you get incredible access, flexibility, and genuine connections. This ensures personalized attention from your expert local guides as well as genuine camaraderie with your travel companions while exploring Cuba on foot at eye level.

What about the guides in Cuba?

Your expert local guides, who will become your well-connected friends, will open doors to private homes, introduce you to artisans, and get you access to places and people few travelers ever see or meet. Their stories, humor, and deep knowledge bring Cuba’s culture to life as they welcome you to their island. They are also happy to assist with any questions, logistics or translating that may come up along the way.

Do I need a visa to go to Cuba?

Yes—traveling to Cuba requires U.S. citizens to obtain a Cuba Tourist Card, also known as an eVisa. The process is simple, and your Classic Journeys Guest Services Coordinator will take care of all the details to make it quick and hassle-free. For your convenience, you can review official visa information and begin your application via the U.S. Department of State’s website here: Cuba Visa Services – Apply for a Cuba Tourist Card with our Cuban Visa online application before your travel to Cuba. Rest assured, we’ll guide you through every step to prepare you for an unforgettable Cuban experience.

How do I fly to Cuba? Do I have to fly on a charter flight?

Charter flights aren’t necessary to visit Cuba. Many major U.S. airlines run regular, nonstop flights into Havana from hubs like Miami, New York, Houston, Dallas, and Atlanta. You have options like American Airlines, Delta, United, Southwest, and JetBlue at your fingertips. Your Classic Journeys team will assist in selecting flights that best suit your travel schedule, ensuring smooth and convenient transport to Cuba’s vibrant capital.