Curated Cuba
November 24-29, 2026
Immerse yourself (legally!) in a world few Americans will have the chance to experience on this 6 day, 5 night cultural immersion in Cuba.
From the vibrant and colorful streets of La Habana to the lush rolling hills of Viñales and beyond - we'll explore rich culture and history of this beautiful Caribbean gem.
Arrival + Welcome
Fly into Havana (HAV) by 1pm local time to meet your group, where we'll arrive in style as classic cars transport us back in time (and to our boutique accommodations!) After settling in, we'll meet for a rooftop welcome drink and review our itinerary for the week before heading to a local Cuban-fusion restaurant for our first group dinner.
Connecting with Cuba's Past, Present, and Future
After breakfast, we'll begin our deep dive into understanding Cuba's cultural context with an exclusive conversation with a local independent journalist. This is where our (optional!) pre-trip book club comes to life - with the unique opportunity to ask questions and learn directly from our hosts and local experts.
Next up - we'll explore Havana by foot, building on our understanding from the morning's info session and Q&A.
Explore the Tobacco Farms of Viñales
After breakfast in Havana, we'll hop back into the iconic classic cars for our transfer to Viñales - where all new adventures await! After checking into our accommodation for the next few nights, we'll head to the neighboring national park where we'll ride horses to a local tobacco farm. On the farm, we'll enjoy a delicious traditional lunch, sample local honey, coffee, and rum, and get an up close look at how the country's famous hand rolled cigars are made!
Sunrise Hike + Authentic Farm Feast in Viñales
Waking up before the sun has it's advantages - especially in Viñales! For our early birds, enjoy an approachable all-levels hike to a nearby rural settlement that culminates with a breathtaking view of the sun rising over 3 lush valleys (with a coffee in hand, of course!) After a proper breakfast and a bit of downtime to explore the nearby national park (or to squeeze in a quick nap) we'll enjoy a particularly authentic local experience - a proper Cuban roast with a local family! More than just a chance to experience some of the best local cuisine, we'll have the opportunity to learn firsthand about navigating some of the country's unique challenges when it comes to cooking - from the ration booklet to power cuts, we'll leave with full bellies and a deeper understanding of some of the nuances of real Cuban life.
Mixology + Cooking Class
After one last lunch in Viñales, we'll head back to Havana for an extra special treat - a rooftop cocktail making workshop and cooking class with a Cuban celebrity chef! Learn the secrets of crafting the perfect local dishes to impress your friends back home, and enjoy one last rooftop meal (for now!) with your new friends from the trip. Our time together may be coming to a close, but the connections we've made will endure long past the flight home.
FAQs
Is it legal for Americans to travel to Cuba?
Yes! There are currently 12 designations under which Americans are permitted to travel to Cuba - 100% legally!
What's included?
Nearly all meals (2 opportunities for lunch on your own!), bilingual local guides, all transportation within Cuba, accommodation, and entry to all scheduled activities
What's not included?
Flights, travel insurance, drinks/personal expenses, any donations (first aid products, OTC medications, period products, and other items difficult for Cubans to access) that you may wish to bring to support the local community
Pricing
Shared room: $2,450
**Private room: $2,950
Deposit: $350
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**Please note private rooms are limited and available on a first come, first served basis - register early to secure your space!
Launch Promo:
$50 off with code:
CUBALAUNCH50
Registration & Billing
Reserve your spot by completing our registration form, and you'll receive an invoice to submit your $350 deposit within 2 business days. Payment plans are available - email kelcie@wanderwildlyretreats.com to learn more!