Tolve Travel
person with cigar on stairs




A collaboration trip led by
Del Caiman & TOLVE
Passionate, proud, SULTRY, rich in tradition, & creatively ingenious. Cuba’s style evokes an essence and sway unlike any other.

DATES: Two Options
Dec 30-Jan 6, 2023-24
March 2-9, 2024

8 days, 7 nights

Starting at $4800

Group size: 8 travelers

If your soul has an untamed and insatiable curiosity for the exotic (as ours does) then likely you have had the desire to travel to CUBA. A country that stands still in time, a postage stamp of culture insulated from the rest of the world, and “heartbreakingly beautiful” as Bourdain puts it. We travel to the island in collaboration with Del Caimán, a non-profit founded by Cubans to empower diverse artists with a platform and connection to the global community. “Cuban ART is a monument to perseverance”, a word that could easily describe much of the culture and way of life in CUBA.

Perseverant, yes. Also, passionate, proud, sultry, rich in tradition, & creatively ingenious. Cuban’s style evokes an essence and sway unlike any other. Their kindness is infectious, music & art a form of storytelling, and rum an elixir of the gods that makes for the perfect daiquiri. Havana, the capital, is rich with architectural buildings of a bygone era, lingering facades, stunning in form and beauty, remnants of once colonial opulence. Cars from the ‘50s and plumes of smoke from hand rolled cigars off the lips of elders have vibrant presence, while outside the capital bleached out beaches and glistening shorelines contrast the islands interior of rugged terrain and tobacco fields as far as the eye can see.

Curious to journey deeper into the essence CUBA? We visit Cuba through the eyes of Cubans.

Beginning in Havana we spend three nights at a Casa Particular (well-appointed guest house) immersing in the most iconic landmarks, wandering the plazas, & driving the streets from the vantage point of a classic car. While the sun dips into the horizon we tuck into acclaimed restaurants and bars, once frequented by the likes of Ernest Hemingway, often accompanied by dance and local music.

On the fourth day we drive up the coast to Cojimar and the estate of Ernest Hemingway, exploring the grounds of the most famous writer associated with Cuba, and onward to the Varadero Peninsula as we drift away from the city and into natures elements. The beaches are pristine. Moments of tranquility and reflection amidst the expansive Caribbean blue. After two evenings by the sea, we journey into the countryside for a Cuban style roast at a local family farm reveling in a style of living authentic to Cuba’s interior before our return to the capital and international flight home.

Experience Profile


  • Casa Particulares / Guest houses  
  • History, Culture & Art, Immersive, UNESCO sites
  • Walking explorations, Photography, Beaches, Caves, Tobacco farms
  • Modern and Traditional Cuban
  • Salsa dancing, Vintage car cruising, Local art studios, Rum
musicista salsa

We visit Cuba through the eyes of Cubans.


  • Roundtrip Airfare to Havana Cuba from major US cities*
  • All accommodations
  • All transportation on island
  • Airport pick-up/drop off
  • Required Cuban Visa & Health Insurance
  • Local bilingual guides (in partnership with Del Caiman)
  • Daily breakfast & group meals
  • Cuban Cafecito (always on us)


  • Gratuities
  • Alcohol
  • Leisure spending



  • 1 Booking: $4800
  • 2 Bookings: $8640
  • (based on double occupancy)
  • *Please review attached document: CUBA travel FAQs
  • *Note: Your deposit secures your reservation and we will proceed to book your airfare promptly. However, if the price of airfare rises/falls drastically from estimate to actual cost at time of booking we will notify you and submit a separate invoice for the difference in cost/credit accordingly.

    Looking to book as a group, family, business retreat?
    Love the itinerary however dates don’t work?
    Contact for custom options, we want the best in travel experiences for you!


    tobacco farm cuba
    food stop
    drying shed
    beach cuba
    cuba, oldcars, havana

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