Steppin' Out Adventures - Trips

Cuba
Exploring music, art, culture, and more!

Next Set Departure: 3/23/2023 - 4/2/2023

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Cuba is complicated and enticing. The Caribbean Island is located where the northern Caribbean Sea, Gulf of Mexico, and Atlantic Ocean meet. Going there is truly a step back in time. A simpler way of life. Fewer comforts, but more dance, music and smiles. It’s an inspiration for artists and musicians. A getaway for gangsters. A home of a revolution. There you can experience natural beauty, history, art by day, tap your toes to Caribbean rhythms by night, and wash it all down with a mojito.

I love to visit the gorgeous beaches and hike in tropical forests, but what is really enticing is meeting extraordinary people from interesting walks of life and hearing their stories. We have spent time with different members of Cuba's Jewish community and shares a Shabbat service and meal and visited with an independent film maker, a world-famous photographer, a horse whisperer trainer, a tobacco farmer from Pinar Del Rio, the home of the world's best tobacco, one of Havana’s architect and an award winning acapella group, and musicians all over whose music combine aspects of West Africa and European styles. with just to name a few.

Travel to Cuba for tourist activities remains prohibited. There are, however, categories of authorized travel. The Department of the Treasury’s Office of Foreign Assets Control (OFAC) has issued general licenses that offers opportunities for U.S. travelers to go to Cuba under the government regulation titled “Support for the Cuban People.” Discover the island’s vibrant culture through interactions with locals and by supporting independent artisans, musicians and community projects. Meet the rising entrepreneurs in this extraordinary country now before it changes forever.

Steppin Out offers opportunities to travel legally to Cuba under the new OFAC Regulations published June 5, 2019. Following the General License category “Support for the Cuban People,” Steppin Out programs include activities intended to strengthen civil society in Cuba.

Check out one of our itineraries to Cuba.. Can't make that date or want your trip to be a specific focus? Email us about a custom trip at [email protected]

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Meet At
Havana Airport José Martí International Airport, Havana, Cuba (HAV)
Arrive by 2:00 pm
Depart From
Havana Airport José Martí International Airport, Havana, Cuba (HAV)
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The first few days will be spent in Havana. We will be exploring the town, taking tours, learning about the history, and enjoying the art and music Havana has to offer. From Havana, we will head for Pinar Del Rio where we will speak with and learn about Cuban lifestyle, take in the history, marvel at the architecture, check out a cigar factory and even roll our own cigars! There will be opportunities for biking, hiking, and horseback riding.
From Pinar Del Rio, we will head back to Havana where we will learn Salsa from the experts, meet with the Federation of Cuban Women and learn about the history of gender rights in Cuba, visit the home studio of Cuban Photographer Roberto Salas, and check out a neighborhood turned art gallery.
Then off to Cienfuegos where we will explore the city and visit the Cienfuegos Synagogue.
From Cienfuegos, we head to Trinidad where we tour the town, check out art studios and galleries, visit a local cigar factory and meet Cuban artists, exchange with provincial representatives of Cuban Institute of Friendship with the Peoples, check out photographer Julio Munoz's home, and kayak at a local beach. Early morning hike in the Escambray Mountains before heading back to Havana.
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Itinerary
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Lodging
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Not Included
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Travel Documents Required
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Preparing For Your Trip
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Additional Information
50 Easy Classical Guitar Solos
Andrew York

Your Experience Includes

A legal license to travel to Cuba under People to People exchange
10 Nights at 3 and 4 star hotels
All breakfasts- lunches and dinners as indicated in the itinerary
Special meetings arranged with artists, historians, musicians, filmmakers, community leaders
Entrance Fees to museums like the Fine Arts Museum and to beaches, etc.
Private transportation with own charter bus and English-speaking guide throughout.
Guided hikes as indicated
Guided biking as indicated
Donation to organizations that we visit
Shabbat dinner for the Jewish community that we will join
A classic car ride!

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Voices From Our Community

"I have been blessed to have had many opportunities with Steppin' Out to see and experience the world in such off-trail, non conventional and unique ways."
Steve, Adventures: Tanzania, Peru, Thailand, Mexico, Bhutan, Nep

"We were able to become closer with the local culture on her trips such as traveling to a Swaziland orphanage, where we created a Christmas party luncheon and brought toys and games for kids, and taught the hokey pokey."
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"You can tell that a lot of effort goes into every detail of the trip. You don't have to think about anything. Robin takes care of the things you don't even think of. Plus Robin has a photographic memory and connects everyone. She knows who has met whom on what trip and continues to remember. It's because of her that I believe that I have met some of my closest friends."
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