Custom Trips

Cuba

Your dates, your group From $4,600
Cuba
Robin Connects You With The World!
Here are a few examples of places we travel to and Robin's take on the locaton. We've included a sample itinerary of each (some are part of our set departures), but don't let that stop your imagination of what we can provide. The best part of the countries we visit is the relationship we've established with the local operators who have become our friends. In the unlikely case they can't arrange something, they know someone who can. If the location is not on our upcoming list, ask about custom departures.

About This Trip

Cuba is complicated and enticing. Going there is truly a step back in time, a simpler way of life. There are 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 and history. You can look at 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 shared a Shabbat service and meal. We have visited with an independent film maker, a world-famous photographer, a horse whisperer trainer, a tobacco farmer, one of Havana’s architects, and an award winning acapella group - just to name a few.  

Traveling 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.

Your Experience Includes

  • 9 Nights

Trip Details

Activity Description
Cultural exploration. We do walk around a decent amount, but this is not one that is physically active. It is more about the people you meet and the traditions you learn. 
Activity Level
Easy with some moderate options. 
Highlight

We will be in Havana for the first few days. 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 Trinidad making a stop in Cienfuegos. We will explore museums and art galleries and at the end of the trip head back to Havana for a farewell. 

Be sure to login and checkout the itinerary for more details on what to expect on the trip!

Additional Information

Trip Photos

Example Packages

9 nights

Every custom trip is tailored – this is a starting point.
Single Occupancy Starting At$5,200
Double Occupancy Starting At$4,600

Need a different type of itinerary?

We'll build a trip around your dates, your group and your interests.

Contact us for a custom itinerary
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 Additional Information
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."
Heather, Adventures: South Africa, Mexico, Dominican Republic, S
"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."
Harold, Adventures: Cuba, Peru, Thailand, Skiing
"Her trips are like a summer camp for adults where you make lifelong friends with the Steppin' Out family."
Lisa, Ski Trips
"Robin planned an awesome trip for my friend and me and our two daughters. Every last detail was taken care of. All the adventures that Robin suggested and scheduled for us were exciting and fun. We felt so safe and taken care of due to the incredible planning by Robin. "
Jenny, Adventures: Costa Rica
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Copyright 2026 Steppin' Out Adventures. All Rights Reserved.