The Details

This is a travel experience for the culturally curious and the adventurers at heart. This trip won’t be a typical, relaxing island getaway and it’s not for everyone. Check out the details below to learn more about this unique opportunity to engage with the land and people of this truly incredible country.


There’s so much to see and do in Cuba. Lucky for you, we’ve curated an itinerary based on our favorites. Get ready to:

  • Explore 2 distinctly different locales: Havana and Viñales

  • Eat the BEST food the island has to offer

  • Tour tobacco fields, organic farms, and the architecture of historic neighborhoods

  • Be inspired by local art and the artists who carry on the rich traditions

  • Ride horses, roll cigars, shop, connect, wander...and more!  



Enjoy 4 nights at our handpicked accommodations in the heart of Old Havana.
**All rooms are double occupancy. Single occupancy rooms may be requested for an additional fee.**




  • Roundtrip flights from BWI to Havana

  • Travel Visas (Required to visit Cuba)   

  • Airport transfers and ground transportation in Cuba


  • Four nights stay in our charming Cuban B&Bs and private homes

  • A shared room with one other person. A single occupancy room may requested at an additional fee.


  • ALL meals -- Breakfast, Lunch and Dinner -- sampling the BEST Cuban food the island has to offer

  • Alcoholic beverages are not included


  • Locally guided architecture, city and farm tours

  • Curated itinerary that includes concerts, horseback riding, shopping, free time and more



  • You have a genuine interest in Cuba, it’s culture and making connections with its people.

  • You love meeting and hanging out with new people.

  • You seek off the beaten path activities and have a “go with the flow” attitude.

  • You enjoy walking, eating and trying new things.


  • You have a restricted diet. We’ll be eating Cuban food everyday (yum!). There will be very limited vegetarian options and we can’t guarantee accommodation of other restrictions or food allergies.

  • You need internet access to stay sane. We may encounter wifi hotspots at various points, but you should plan on being internet-free for this 5 day adventure.

  • You’re looking for a leisurely sand and sun island vacation. This experience is action packed!

  • You find walking difficult, as much of our exploring will be done on foot.

  • You require luxury amenities to be comfortable away from home.

  • You don’t enjoy stepping outside your comfort zone.