Caribbean

History & Hidden Gems of Cuba & Jamaica

12 Nights
Scenic, Historic, Cultural
A 12-night cultural journey through Cuba’s vibrant Havana and Trinidad, paired with Jamaica’s Blue Mountains, beaches, and reggae heritage.
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Cuba (Havana & Trinidad): 6 Nights
DAY 1 1
Cuba (Havana & Trinidad)

Arrival in Havana

  • Arrive in Havana and transfer to your boutique hotel in the historic center.
  • Enjoy a welcome mojito on a colonial rooftop terrace.

DAY 2 2
Cuba (Havana & Trinidad)

Private Havana City Tour & Classic Cars

  • Explore Havana’s Old Town with a private guide, followed by a classic car ride along the Malecón and into the modern quarters of the city.

DAY 3 3
Cuba (Havana & Trinidad)

Cuban Rum & Cigar Experience

Discover the secrets of Cuba’s finest exports with a guided tasting tour of a Havana rum distillery and a traditional cigar workshop.

DAY 4 4
Cuba (Havana & Trinidad)

Salsa Dancing & Live Music Night

  • Join a private salsa class with local instructors and spend the evening enjoying live Afro-Cuban jazz or traditional trova in a lively venue.

DAY 5 5
Cuba (Havana & Trinidad)

Transfer to Trinidad & City Tour

  • Journey to the UNESCO World Heritage town of Trinidad with its pastel buildings and cobblestone streets.
  • Check into a charming casa particular.

DAY 6 6
Cuba (Havana & Trinidad)

Topes de Collantes National Park

  • Explore the lush nature of Topes de Collantes with a guided hike through waterfalls and coffee plantations.

Jamaica (Blue Mountains & Kingston): 3 Nights
DAY 7 7
Jamaica (Blue Mountains & Kingston)

Fly to Kingston, Jamaica & Blue Mountains Transfer

  • Arrive in Kingston and transfer to a secluded eco-lodge in the Blue Mountains for nature, coffee, and cooler climes.

DAY 8 8
Jamaica (Blue Mountains & Kingston)

Blue Mountains Coffee & Hiking Tour

  • Take a guided hike in the Blue Mountains, followed by a private tour of a coffee plantation with tastings of Jamaica’s world-famous brew.

DAY 9 9
Jamaica (Blue Mountains & Kingston)

Kingston City & Bob Marley Museum

  • Visit the Bob Marley Museum, Devon House, and Kingston’s vibrant art scene with a private guide. Evening at leisure with local live music.

Jamaica (Negril): 3 Nights
DAY 10 10
Jamaica (Negril)

Transfer to Negril

  • Travel to Negril’s famous Seven Mile Beach and check into a beachfront resort.

DAY 11 11
Jamaica (Negril)

Rick’s Café & Cliff Diving

  • Relax on the beach and visit Rick’s Café for iconic sunsets and the thrill of cliff diving.

DAY 12 12
Jamaica (Negril)

Leisure Day & Private Beach Dinner

  • Enjoy a free day at your resort with an optional spa treatment.
  • In the evening, celebrate the end of your trip with a private beach dinner under the stars.

DAY 13 13
Jamaica (Negril)

Departure

  • Private transfer to Sangster International Airport in Montego Bay for your flight home.

History & Hidden Gems of Cuba & Jamaica
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Ludovica Natalini
I was born and raised in Rome and with my family, I have visited all the regions of Italy and traveled to the best and most renowned places. We love food and wine and I have explored many wineries and eaten typical and local products.Growing up, my love for traveling brought me to Ireland, where I spent two amazing years studying, working, and traveling. When I returned to Rome I decided to work in the luxury travel industry, and I spent the last years working for 5-star hotels. I traveled all over Europe, learning about different cultures and lifestyles.I am an avid hiker and climber, and I love beautiful landscapes, cities, history, and museums—each one is unique. My current job allows me to work from anywhere I want, and I love it!
DESTINATIONS SPECIALITIES
Sports Tourism

KendlerFamily - Elm Grove, WI

My favorite experiences in Lake Como were hiking with Francesca in Lake Como then boating with Giovanni

Charles - Jacksonville, FL

Ludovica and her team did a wonder job beginning with the travel planning to execution.

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