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Weekend in Havana

An in-depth, cultural experience with private guiding and transportation


Almaz Journeys operates private journeys to Cuba in compliance with the U.S. Department of Treasury’s general licenses for Cuba travel. Our custom journeys include the required full daily schedule of cultural exchanges, while still being tailored to your interests and giving you some flexibility. We use our favorite private sector guides, and you will generally dine only in our favorite privately-owned restaurants (paladares) – all to ensure you’re supporting Cuba’s burgeoning private sector as much as possible. Throughout your stay, you will meet many Cubans from different professions, ages, and experiences in order to witness in-depth this period of profound change in Cuba and promote greater understanding between the U.S. and Cuba. Please note that this is not a tour, and under the general licenses you are required to participate in all activities on your schedule.


Arrival From the US

Welcome to Cuba!

Upon arrival this afternoon (flight not included), your local Almaz Journeys representative will meet you outside for your private arrival transfer.

Any trip to Cuba must begin with the majestic faded glory of Havana. Located on the northern coast of Cuba just 105 miles from the U.S., Havana was founded in the 16th century by the Spanish and quickly became a jewel in its New World holdings as a strategic trading stop between Spain and its colonies. Although the colonial days are long gone, Old Havana is still home to one of the largest number of Spanish colonial buildings and therefore a UNESCO World Heritage site.

With investments in ongoing restoration since the 1990s, the faded facades of colonial buildings, the fountain-filled plazas, and the oceanfront promenade known as the malecón are all slowly returning to former glory. Havana (and Cuba overall) is one of the most exciting destinations in the world today, offering the chance to witness yet another period of change through the eyes of everyday Cubans.

After check-in at your casa particular or hotel, you'll have a little time to settle in before dinner.

We suggest you begin your stay with one of our favorite long-running private restaurants (paladares) housed in a historic mansion slowly reclaiming its former glory. If you still have energy after dinner, there are lots of options for live music and dancing we can suggest based on your interests. (Cost of dinner and transportation for evening activities not included.)


Services: Private vehicle, driver & guide
Lodging: Casa particular, Melia Cohiba or Hotel Saratoga
Meals: None included today



After breakfast this morning, walk in the footsteps of Havana’s colonial past as you explore the four key squares of Old Havana, a UNESCO World Heritage site, with your expert local guide offering insightful history throughout. Please wear comfortable shoes for this walking exploration! (For the Premium experience, this visit is led by a specialist architecture guide.)

For the Deluxe experience:

This afternoon, you have your choice of the following activities led by your host guide:

  • Learn about the Cuban revolution through a visit to the Revolution Museum, and discuss with your guide how Cubans today view it.
  • Visit Hemingway's former home, Finca Vigia, and discuss with your guide the changes Havana has seen since the era of Hemingway.
  • Explore the Cuban wing of the Fine Arts Museum with your guide, and discuss artists have and continue to express themselves in the post-Revolutionary period.

For the Premium experience:

After lunch (not included), you’ll explore Hemingway’s Havana in a classic 1950s American convertible! Gertrude Stein once commented that Hemingway had a good nose for finding good places to live and eat, and his villa outside Havana proves her point quite well.

Hemingway’s house is perched on a hill, with a terrific view of Havana in the distance and surrounded by lush tropical vegetation, so it's no wonder that quite a few celebrities made their way here in the 1940s and 1950s. The house you find today is perfectly intact, just as the famed author left it in 1960 with his personal effects, his favorite fishing boat, and lots more. You’ll have a look around the grounds with your specialist guide, who can offer you fascinating insight into Hemingway’s life in Cuba.

After the visit while heading back to Havana, you’ll want to stop at the picturesque Cojimar fishing village, the inspiration for Hemingway’s novel “The Old Man and the Sea” – so much so that he later dedicated his Nobel Prize to the village’s fisherman.

Dinner reservation at one of our favorite privately-owned restaurants (paladars). For the Premium experience, tickets to the famous Tropicana are included after dinner.

Services: Private vehicle, driver & guide
Lodging: Casa particular, Melia Cohiba or Hotel Saratoga
Meals: Breakfast



This morning, meet your guide and driver for an overview drive around Havana including an essential stop at El Morro, the fortress at the mouth of the harbor, for panoramic views of the entire city. Your introduction this afternoon will take you along the seafront boulevard (malecón), to Revolution Square, and past important landmarks including the impressive Bacardi building and numerous former Mafia haunts including Meyer Lansky’s Havana Riviera.

Then, you'll have a lunch reservation (cost not included) at one of our favorite privately-owned restaurants.

For the Deluxe experience:

Your guide will take you this afternoon to visit some privately-owned shops to support and learn about entrepreneurship and its unique challenges in Cuba.

Then, to cap off the afternoon, we've arranged a special cigar and rum tasting experience.

For the Premium experience:

You'll explore the thriving local arts scene with visits to the studios of several emerging or established artists. Every exploration is tailored for you, whether you have a very specific interest or simply wish to get a taste of Havana’s thriving artistic community. Please speak with your Almaz Journeys expert about what types of art and artists you’d like to include this morning.

Then, you'll cap off the afternoon with a premium cigar and rum pairing experience in a private location, featuring a few rare rums and top quality cigars.

Additional options you may consider for today include but are not limited to(costs vary):

  • For foodies, visit some of Havana’s best local markets this morning with a specialist guide to learn about urban farming and innovative solutions to food supply issues in Cuba, as well as a deeper insight into food history. Your guide may give you a shopping challenge to understand firsthand the challenges faced by everyday Cubans. A cooking class can also be added onto this activitiy.
  • For those interested in dance, you won't want to miss a rehearsal of one of the top companies such as the National Ballet, Carlos Acosta Dance, etc.
  • Visit a mechanic who has built his own small business restoring and maintaining classic American cars, for a great look at Cuban entrepreneurship and their can-do spirit.
  • Private salsa dancing lesson, followed by a visit with your instructors to a salsa matinée to test out your new dancing skills among an all-Cuban crowd - a very local experience.

To close out your stay in Havana, we suggest an al fresco dinner on the roof of a former factory, located adjacent to one of the most exciting contemporary art spaces in Havana. After dinner, head next door to hear live music and see works by some of the island’s avant garde artists. (Cost of dinner and transportation for evening activities not included.)

Services: Private vehicle, driver & guide
Lodging: Casa particular, Melia Cohiba or Hotel Saratoga
Meals: Breakfast



Return To The US


Morning check out and transfer to Havana airport for your flight back to the U.S. (Air not included.)

Services: Airport transfer
Lodging: Casa particular, Melia Cohiba or Hotel Saratoga
Meals: Breakfast


Looking to spend a few more days on this magical island? How about exploring the colonial charm and surrounding natural beauty of Trinidad as well as the lush Viñales valley, the heart of tobacco production in Cuba? Our Taste of Cuba itinerary is a great starting point for a longer 8-day exploration. Contact Almaz Journeys for more options.


Tailoring Your Journey

This is just a brief sample visit to Cuba, which can be completely tailored to suit your needs and specific interests. Below are just a few of the countless possibilities that can be incorporated in customizing your journey to Cuba:

Private visits to studios of emerging or established Cuban artists

Drop in during a rehearsal of a top Cuban dance company

Meet emerging Cuban entrepreneurs - designers, classic car restorers, paladar owners and more

Work up a sweat with private salsa dancing lessons

Visit the island's largest Jewish community

Enjoy a private dinner and exchange in the home of a Cuban artist

Private Journey Pricing

Based on double occupancy (rates vary by season and itinerary)

2 Guests Traveling Together
Deluxe experience from $2,400 per person
Premium experience from $4,200 per person

4 Guests Traveling Together
Deluxe experience from $2,100 per person
Premium experience from $3,500 per person


  • Accommodations in Havana for 3 nights:
    • Deluxe experience - Privately-owned, deluxe casa particular, with optional upgrade to premium casa particular, Melia Cohiba - The Level or Hotel Saratoga (additional cost applies)
    • Premium experience - Junior Suite at Melia Cohiba - The Level, or Double room at premium casa particular
    • Supplements apply for single occupancy rooms, varying by type of accommodation.
  • Breakfast daily
  • Private arrival and departure transfers with English-speaking guide and VIP arrival assistance (VIP departure assistance included with Premium experience)
  • English-speaking host guide for all transfers and daily activities. (Supplemented by expert specialist guides with Premium experience.)
  • Private vehicles for all included daily activities and evening transfers, with bottled water. Deluxe experience includes dedicated taxi/taxivan transportation, and Premium experience include modern rental sedan, van or taxi Sprinter based on group size.
  • Entrances for all sights and experiences specifically included in your itinerary
  • Evening performance (Premium experience).
  • Cuban tourist card (visa).
  • Full advance customization of your itinerary based on your interests and in compliance with U.S. travel rules.
  • Local concierge service to handle all dinner and evening reservations, and 24/7 emergency contact in Cuba.


  • Air travel
  • Lunches or dinners. We will assist you in selecting and reserving the best dining options, based on your needs and taking into account the rapidly change dining landscape in Cuba.
  • Gratuities
  • Medical or travel insurance. (Mandatory health insurance is typically included with the purchase of any flight between the U.S. and Cuba)
  • Any other items or services not specifically included in the itinerary

Excited to learn more?

Get in touch with us with us today to start planning!

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