Jazz Plaza

The Owlsong Jazz Plaza 2020 Tour

Join the Alan Lewine Xtet this January in Havana
Presented by Owlsong Productions and Cultural Island Travel


Special Curated Group Tour with the Alan Lewine Xtet

Alan-red-T-shirt copy

Presented by Owlsong Productions and Cultural Island Travel

Architecture walking tour of Old Havana, Jazz Festival shows, visit to the Cuban countryside, Special exclusive music performances, classic cars, dine at Havana’s best paladares, Hemingway house, and Havana’s world famous nightlife!





Do you want an authentic experience of Cuba’s music and culture?

Owlsong Productions in partnership with Cultural Island Travel offers the perfect trip for you! Havana’s Jazz Festival is the most exciting time of the year for music in Cuba, when many artists living abroad return home and multiple indoor and outdoor venues are overflowing with live music.

On this tour, you will experience the old-world charm of Havana and scenic rural Pinar del Rio province, while also enjoying delicious food at Havana’s top restaurants, and be totally immersed in the rich history and culture of Cuba. At night you can go to any number of festival shows at venues all over Havana.

Our mission is to immerse you in this passionate culture to truly have you experience Cuba just like a local. ‘Support for the Cuban People’ travel allows even the most seasoned travelers to view Cuba through the lens of the musicians, dancers, artists and locals – an experience that is difficult to find anywhere else in the world.

*This trip to Cuba is legally compliant with current OFAC regulations*

Will you please let us know how you heard about Owlsong Jazz Plaza Tour?


Sample Itinerary


DAY 1 / January 14, Tuesday USA-Havana

• Check-in for your flight from your departure city

• Arrive at Jose Marti International Airport in Havana at 1:30 PM, pick up your luggage and meet your tour leader at the arrival area

• Lodging check-in and orientation

• Visit the historic Hotel Nacional and enjoy a cocktail while overlooking the ocean

The upscale Hotel Nacional is one of the country’s most famous landmarks, with a fascinating and storied history, ranging from a Mafia meeting in the 40’s that took place on-site to tunnels in the garden used during the Cuban Missile Crisis. The common spaces, including the lobby and the ocean-view gardens. are gorgeous, casting light on Havana’s golden age of Cuban hospitality, nightlife and entertainment. Some past famous guests include Frank Sinatra, John Wayne, Winston Churchill, Mickey Mantle, and Marlon Brando!

• Experience a ride in a classic convertible car around Havana City

Havana is beloved by American visitors with its collection of thousands of vintage American cars, manufactured before the Revolution and subsequent US embargo. In the absence of automobile imports, these living relics are preserved by Cuban mechanics or improvised fixes by the owners themselves. Experience an hour in a classic convertible Chevy, Ford or Oldsmobile!

• Nighttime suggestion: Enjoy the various shows of the Jazz Festival at the main theater or other indoor and outdoor venues throughout Havana


DAY 2 / January 15, Wednesday Havana

• Visit Old Havana and learn about Havana’s world-renowned UNESCO heritage designated architecture on an expertly guided walking tour (around 2 hours)

There is no better introduction to Havana than a walk through Old Havana, where the streets are full of life – vendors, musicians, performance artists are everywhere. On this walk, you will explore Old Havana’s five major plazas and see the interiors of cathedrals and other important buildings. UNESCO designated Old Havana as a world heritage site in 1982. Although today Havana is a sprawling metropolis of more than two million people, the old center retains an interesting mix of Baroque and neoclassical monuments, beautiful balconies and courtyards.

• Visit Taller de La Grafica lithograph collective

Located in the heart of the old city, Taller de la Grafica de la Habana is one of Havana’s most revered artistic attractions, featuring lithograph artists who create and sell their own experimental work on site. Visitors are treated to explanations of the collective’s equipment and techniques from the artists themselves and can purchase art directly from the Taller.

• Lunch at El del Frente paladar (a staff and client favorite – try the daiquiris!)

• Visit the newly renovated Grand Theater of Havana for a tour of one of Havana’s most beautiful architectural treasures. It is currently home to the Cuban ballet.

• Visit the home studio of Cuban painter Andy Rivero

• Nighttime suggestion: Enjoy the various shows of the Jazz Festival at the main theater or other indoor and outdoor venues throughout Havana.

• Meals: Breakfast, Lunch


DAY 3 / January 16, Thursday Havana

• Meet with Jewish community leaders in Havana and enjoy a tour of Havana’s Jewish sites, including synagogues, the Hotel Racquel, Menorah Park

• Lunch at Cocina Lilliam

• Visit Fernando, the mechanic from the Discovery show, “Cuban Chrome”

• Visit Finca Vigia, Ernest Hemingway’s estate

Peek into the Cuban home of celebrated novelist Ernest Hemingway, where the writer penned "The Old Man and the Sea" and "For Whom the Bell Tolls." On this guided tour you will get a sense of the writer’s life in Havana and see his collection of books, trophies and other memorabilia. Outside you will be able to view the gardens, pool, pet cemetary, and Hemingway’s boat, Pilar.

• Meals: Breakfast, Lunch

Alan Lewine Xtet-Cubano performing at Club Iris Jazz, Santiago de Cuba, Festival Cubadisco. 2017

Alan Lewine Xtet-Cubano performing at Club Iris Jazz, Santiago de Cuba, Festival Cubadisco. 2017

DAY 4 / January 17, Friday Havana 

• Visit the famed Abdala Recording Studios for a tour and a private jazz performance

• Visit Fusterlandia, the home and gallery of Jose Fuster, the Picasso of the Caribbean

Inspired by works he saw by Gaudi in Spain and Brancusi in Romania, this self taught artist devoted himself to creating a more colorful and creative atmosphere for himself and his neighbors. The result is unlike anything you have ever seen!

• Lunch at VIP Havana and enjoy a rehearsal performance with Alan Lewine Xtet

• Enjoy an amazing guitar ensemble performance by the children of Clave de Sol

• Nighttime suggestion: Enjoy the various shows of the Jazz Festival at the main theater or other indoor and outdoor venues throughout Havana

• Meals: Breakfast, Lunch


DAY 5 / January 18, Saturday Havana-Vinales Valley in Pinar del Rio

• Travel to the countryside (~2 hours travel time)

• Meet a fourth generation farmer in Cuba’s famed tobacco fields

Cuba’s lush western province is among the most fertile grounds for growing tobacco in the world. On a tour of the Montesino tobacco farm you will learn about the tobacco growing process, enjoy a cigar rolling demonstration, and meet the fourth generation farmers responsible for some of the most famous cigars in the world. You will also enjoy the stunning scenery of this region, known for its distinct hills called mogotes.

• Enjoy a delicious organic farm-to-table lunch at Patio Pelegrin

• Explore the farm, gallery, and community project Patio Pelegrin

Often called the secret garden, Patio Pelegrin is not only an organic farm but also a community hub for dance, literature, debate, music, and theater for local residents to cultivate their artistic and intellectual interests.

• Visit the lookout point in Vinales Valley and see why the NY Times called Vinales one of the top 10 places to see in 2017

• Return to Havana

• Nighttime suggestion: Enjoy the various shows of the Jazz Festival at the main theater or other indoor and outdoor venues throughout Havana

• Meals: Breakfast, Lunch


DAY 6 / January 19, Sunday Havana

• Visit Bellas Artes (Fine Arts) Museum with a private guide*

Enjoy as an art expert guides you through the Cuban wing of this beautiful museum, providing rich historical detail and context. The displays are chronologically ordered, so you will be introduced to classic works such as La Gitana Tropical (The Tropical Gypsy) sometimes referred to as Cuba’s Mona Lisa, and then taken through a visual exploration of Cuban identity and political expression over the course of several galleries.

*OR Visit the Revolution Museum

Located in the Presidential Palace of former dictator Fulgencio Batista, the Museum of the Revolution is a must for anyone curious about the history of Cuba. Filled with relics from revolutionary battles and Cuban historical figures, you will learn a great deal about how this important historical event unfolded and how its narrative continues today.

• Lunch at Al Carbon paladar for excellent Cuban food and ambiance (the chef was Fidel Castro’s former personal chef!)

• Visit the San Jose craft market

San Jose is the largest craft market in Havana, with more than 300 stalls offering all kinds of souvenirs: guayaberas, t-shirts, wooden sculptures, leather accessories, jewelry and more. Prices are negotiable, so bargaining with sellers becomes part of this unique experience.

• Nighttime suggestion: Enjoy the various shows of the Jazz Festival at the main theater or other indoor and outdoor venues throughout Havana

• Meals: Breakfast, Lunch


DAY 7 / January 20, Monday Havana-USA

• Head to Jose Martí Airport for your return flight (air transfer included)

• Adios Cuba!

• Meal: Breakfast


A Paladar is a privately owned restaurant, as opposed to regular restaurants that are owned and operated by the Cuban government. Paladars compete with each other and most of them are quite beautiful and creative with great food and flare. Eating at paladares also helps encourage private enterprise in Cuba. We include as many paladares as possible in our program to help local business and to provide you with the best Cuban restaurant experience.

What's Included

Included items in the price of your tour:
  • Compliance with U.S. Treasury Department regulations
  • Pre-trip departure information on Cuba travel
  • Daily breakfast in Cuba (at your accommodations)
  • Lunch as listed on the itinerary (all meals include one drink)
  • Admission to all museums and public buildings listed in your itinerary
  • Coordination of all listed activities on the itinerary and admission to those activities (this includes private music concerts, dance performances, artist visits, etc.)
  • Superior accommodations
  • Expert CIT tour leader
  • Havana Jazz Fest all-access pass
  • Superior accommodations
  • Expert CIT tour leader
Not Included:
  • Cuban visa*
  • Round trip airfare
  • Airline baggage fees
  • Individual hotel/accommodation expenses (mini bar, room service, laundry fees, etc.)
  • Dinner and after dinner activities
  • Tips for tour leaders, local guides, wait staff, and cleaning personnel (you will receive a detailed tipping guide long with your final itinerary)

*For a $75 fee the Cuban visa can be added to your package. Otherwise, you can purchase it at check-in from the airline. Visa fee varies by airline from $50-100.

If you have any questions or to sign up for this tour, please contact Teresa Sanchez at (917) 882-4195 or email her at OwlsongJazzPlaza@gmail.com.

Tour Dates & Prices

Contact Teresa Sanchez at (917) 882-4195 or email us at OwlsongJazzplaza@gmail.com for all your inquiries regarding this tour.