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Weekend in Havana

Itinerary Overview

  • 3 nights in deluxe casa particular or hotel accommodations in Havana.
  • Private airport transfers with VIP assistance.
  • English-speaking private guide & driver for all included cultural activities.
  • Advance itinerary customization and restaurant reservations, as well as 24/7 in-country support. 

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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.

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.

Day 1

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 privately-owned boutique 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.)

Day 2

Exploring Havana

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 how 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.

Day 3

Further Exploration of Havana

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.)

Day 4

Until Next Time!

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

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.

Private Journey PricingPer Person

Pricing Level
From Price Per Person
Deluxe Itinerary: 2 Guests Traveling Together


Deluxe Itinerary: 4 Guests Traveling Together


Premium Itinerary: 2 Guests Traveling Together


Premium Itinerary: 4 Guests Traveling Together



  • 3 nights in Havana: Deluxe casa particular (Deluxe) or Premium casa particular (Premium). Lodging upgrade options available at additional cost.
  • Breakfast daily.
  • Private arrival and departure transfers (assumes all guests on same flights.) English-speaking guide included when specified in itinerary.
  • VIP Airport service in Havana on arrival. (Departure service also included with Premium experience.)
  • Private, local English-speaking host guide for all transfers and activities (supplemented by expert guides for Premium experience) as described in the program.
  • Visas.
  • Private air-conditioned prepaid taxi (modern rental vehicle for Premium experience) for all included activities and transfer, with bottled water daily.
  • Round-trip transfers for dinners and included evening performances.
  • Cost of entrance for all sights and experiences specifically included in your program.
  • Local concierge service to assist with any special requests before and during your journey.
  • 24/7 local emergency contact during your journey.
  • Full-service advance tailoring of your itinerary and assistance with restaurant reservations.

Not Included

  • Air travel.
  • Lunches, dinners and alcoholic beverages unless otherwise specified in your program.
  • Gratuities to guides, drivers, hotel porters, etc. unless otherwise specified in your program.
  • Travel or medical evacuation insurance.
  • Any other items or services not specifically included in your itinerary.

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