Long Weekend in Cuba

Havana Cultural Walking Tour

4 DaysStarting at $4,695


In the first half of the 20th century, Americans loved to hop down to Havana for a long weekend, spiced with the climate and culture of the tropics. Now that idea is back with this 4-day/3-night cultural exchange program created to connect you with the irresistible rhythms and vivid art of Cuba. In one concise, complete weekend you'll connect with the city's artists, musicians and dancers at an extraordinary level. You will chat with the city's most creative people, applaud their performances, and even get in a salsa lesson. To get a feel for everyday life, you’ll shop in a farmers’ market with the locals, cook lunch with a Cuban chef, meet a family that restores classic tail-finned cars, and more. From your ideally located accommodations, you are close to every essential site from a working cigar factory to Ernest Hemingway's home. Throughout, you'll eat at some of the city's finest privately-owned restaurants, explore historic landmarks, and hear firsthand stories from the Cuban people about the art of living in Havana – for a long weekend you'll never forget.

Havana Jazz Festival: Join us on the Havana Jazz Festival date (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 ‘only with Classic Journeys’ experiences: sit down for a meal with the director of the Jazz Festival (a personal friend of our guide), a private jazz session with a group of musicians who share with you how they create music, and in-demand tickets for concerts each of the evenings in Havana so you get access to the best performances without having to arrange the details yourself.

>> You can still travel legally to Cuba with Classic Journeys! Click to read about the latest news on Cuba travel restrictions

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


Download Full Daily Itinerary

• 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.

Download Full Daily Itinerary


  • Starting Point:

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

    Havana – 3:00 pm – José Martí Airport
Itinerary Map

Click map to enlarge

Walking Level

  • Daily Mileage Options: 2-5 miles

  • Route Notes:

    The terrain on this trip includes a mix of paved and cobblestone streets in Havana. Generally, the walks are level, with very little elevation gain and loss.

Dates & Prices

The earlier you book, the more choice you’ll have and the lower your price. And you can always change your mind — you won’t be charged to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887.

Talk to an expert
Family Departure

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

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 the world on foot and at eye level. Each day, join your guide on the most cinematic footpaths in the region.
  • Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, share their lifelong connections as well as engaging anecdotes about the history and culture of the region.
  • Small groups that provide you unrivaled access. An average of fewer than 10 guests per departure means we can offer you special access to sites like Stonehenge so you experience the stone circle when it’s closed to the general public, a guided visit to Zion Narrows that other companies cannot arrange because of larger group sizes, and vineyard walks with a count and countess in Tuscany.
  • Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in the region you’re exploring, including rainforest lodges, 16th century villas, and award-winning properties that show up on World’s Best and Gold lists.
  • Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of the places you visit with us. From gourmet picnics to coveted local restaurants, 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 our walking tour regions more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of the villages, organic farms, archeological sites and the people who know them best.
  • Sustainable travel that supports the places you’re visiting. 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.


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 the vibrant 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.

Elvira Mi Amor

Elvira Mi Amor is a beautiful boutique hotel located in the center of the old Havana district. A restored 1920s building, this unique property showcases modern design and a gallery of Cuban artwork.

What’s Included

  • Boutique accommodations that provide you unlimited access to the people and places, culture and history you came to experience
  • 3 breakfasts, 3 lunches, and 2 dinners
  • Full-time experienced guide(s) who are with you throughout the trip and handle behind-the-scenes logistics
  • Admissions to tastings, historic sites and other scheduled events as noted in the detailed daily itinerary
  •  Gratuities for accommodations, meals, and baggage
  • All land transportation during the trip

Above & Beyond Benefits

Privileged Access Events

  • One-of-a-kind access to remarkable people, places and activities arranged just for you.

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