November 5-9, 2025
$1,695 per person
Explore the soul of Cuba in style with a “30s-ish” small group experience, curated by Cassie in Cuba.
Your trip includes:
🇨🇺 Four nights in chic, upscale accommodations in the heart of Havana. Some of the finest stays the city has to offer.
🇨🇺 All meals. 4 breakfasts, 3 lunches, and 4 dinners at Havana’s trendiest restaurants
🇨🇺 Full-time local bilingual host
🇨🇺 All listed activities, tours, transportation, and cultural experiences
🇨🇺 Pre-trip orientation call, plus ongoing guidance
Day 1: Welcome to Cuba!
🇨🇺 Airport pickup – private transfer in classic vintage cars
🇨🇺 Welcome drink & trip orientation
🇨🇺 Dinner at one of Havana’s most popular private restaurants
🇨🇺 Night out to celebrate
Day 2: Culture & Connection
🇨🇺 ‘Welcome to Cuba’ discussion with a Cuban author: Explore the past, present, & future
🇨🇺 Guided walking tour of Old Havana
🇨🇺 Lunch at local hidden gem
🇨🇺 Free time with optional experiences: salsa, boxing, San Isidro community, shopping
🇨🇺 Bici-taxi to private rooftop cocktail class with a Cuban TV personality + celebrity chef
🇨🇺 Dinner at a famed private restaurant visited by President Obama, Madonna, and Beyoncé
Day 3: Viñales Day Trip Experience
🇨🇺 Horseback riding through Viñales National Park
🇨🇺 Private cigar rolling experience at Cassie’s family tobacco farm
🇨🇺 Authentic farm-to-table Cuban lunch
🇨🇺 Explore Cueva del Indio, a stunning natural cave
🇨🇺 Dinner at a top restaurant on Havana’s foodie scene, where modern flair meets traditional Cuban flavor
🇨🇺 Nightlife with live Cuban music
Day 4: Havana Uncovered
🇨🇺 Convertible Classic Car City Tour + Mafia History Tour
🇨🇺 Optional: Afternoon at Santa Maria del Mar Beach
🇨🇺 Bici-taxi to private rooftop cocktail class with a Cuban TV personality + celeb chef
🇨🇺 Fun Coco-taxi to our final dinner at iconic, trendy Cuban restaurant
🇨🇺 Night out at Fabrica del Arte Cubano, Havana’s top cultural venue
Day 5: Departure
🇨🇺 Morning at leisure depending on flight time
🇨🇺 Airport transfer
FULL PAYMENT REQUIRED, AS WE ARE WITHIN 60 DAYS OF THE TRIP
VERY LIMITED AVAILABILITY REMAINING
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Give Back While You Travel: Bring supplies to donate directly to Cuban families in need
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Elevate Your Escapes is proudly donating planning services for this trip, ensuring the full trip cost goes directly to the experience and donations for the Cuban people —no added fees or markups.
el@elevateyourescapes.com
The logistics:
Accommodation is double-occupancy, either with your chosen roommate or paired with another traveler of the same gender. Private accommodations are available for an additional $300 (recommended for comfort).
You’re welcome to extend your trip before or after the main itinerary—we’re happy to help coordinate extra nights for an added fee.
Not included: Flights to/from Cuba, mandatory travel & medical insurance (we’ll help with that at no cost!), drinks, gratuity
Operated by Cassie in Cuba. Any alterations to an itinerary are at the sole discretion of the supplier. Elevate Your Escapes bears no responsibility for any changes.
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Can’t make it this time?
See our Riviera Maya January 2026 20s/30s Voyage here
&
Caribbean Ladies Escape January 2026 Voyage Info
