Havana's Music, Art & Culture

Cuba Long Weekend Cultural Walking Adventure

4 DaysStarting at $4,495


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.

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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


Days 1-4 Havana
Your long weekend full of fascinating insights begins at a local market where you can chat with the locals as they shop. At Fusterlandia, you meet the artists who founded the neighborhood project that has filled the streets with vivid murals and art installations. Then you head out for a walking exploration of Havana Vieja (Old Havana) with a local historian. After dinner in a privately-owned restaurant (paladar), you can cap your day with a daiquiri at El Floridita, one of Hemingway's favorites bars.
You’ll be welcomed into a traditional cigar-making factory where a friend who is an aficionado fills you in on the role of the trade in Cuban life. Then you get an up-close look at Cuba-U.S. relations and the Revolution from the U.S.S. Maine to Hotel Nacional. Later, meet the husband-and-wife team whose independent small business specializes in restoring classic cars. Then their craftsmen take you for a tail-finned spin through the streets of Havana.
Throughout, you also have chances to cook with a Cuban chef, visit a local private Afro-Cuban dance company, chat with a photojournalist who documented Castro’s life, meet local artists alongside an art curator, and get in a salsa lesson. Your time in Havana is capped with a visit to Finca Vigia, Ernest Hemingway’s Cuban home that is now a museum.
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  • Starting Point:

    Havana – 10:00 am – Lobby of La Reserva
  • Ending Point:

    Havana – 3:00 pm – José Martí Airport

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.

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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.
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What’s Included

  • 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 hotels, 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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