What I'm Working on: Cuba - May 20, 2026
A vibrant Cuban journey filled with culture, music, and unforgettable local experiences!
Cuba – 8 Days
This month, I’m working on an incredible trip through Cuba for clients who want to truly experience the heart and soul of the island - and who are interested in the political & economic history in particular. From the colorful streets of Havana to the charm of Trinidad and the vibrant countryside in between, this itinerary blends history, culture, music, and local connections — with plenty of time to soak it all in along the way.
Itinerary
Day 1 - Welcome to Havana
They’ll arrive in Havana and be greeted with VIP airport service before heading to their beautiful townhouse in Old Havana. After settling in, they’ll meet their local concierge, enjoy a welcome cocktail, and ease into the evening with live music and a great dinner in the city.
Day 2 – Colonial Havana & Culture
The day begins with a guided walk through Old Havana, exploring its historic squares and colorful streets. Later, they’ll dive into local life on a food tour, cruise the city in a vintage convertible while learning about Cuba’s history, and wrap up the night with live music and Havana’s buzzing nightlife.
Day 3 - Nature & Local Connections
The morning kicks off with a walking tour of Old Havana’s plazas and historic streets, followed by a hands-on food and cocktail experience at a local market. In the afternoon, they’ll cruise the city in a vintage car, spotting landmarks and learning about Havana’s history, before having a heart to heart with a Cuban economist.
Day 4 – Cienfuegos & Trinidad
The journey continues with a drive to Trinidad, stopping in Cienfuegos for lunch and a walking tour through its beautiful colonial streets. Once in Trinidad, they’ll check into their boutique hotel and enjoy a salsa lesson in the late afternoon. The night ends with dinner and a taste of local music.
Day 5 – Trinidad & Escambray Mountains
After breakfast, they’ll explore Trinidad’s UNESCO-listed historic center on foot. The afternoon is spent in the Escambray Mountains, hiking to secret waterfalls, swimming in pools, and learning about the area’s unique flora and fauna. In the evening, they’ll dine at a charming local restaurant and enjoy traditional Cuban music or salsa dancing.
Day 6 – Leisure in Trinidad
A full day to relax and soak up Trinidad’s charm. They might enjoy a beachfront lunch, wander the cobblestone streets, or take in a casual music performance at a local venue. The evening is perfect for sampling tapas and cocktails in a relaxed café or enjoying live music late into the night.
Day 7 – Santa Clara & Havana
They’ll head back toward Havana, stopping in Santa Clara to visit the Che Guevara Memorial and learn about Cuba’s revolutionary history. After lunch, they’ll continue to Havana and check back into their city accommodation. The evening is free to enjoy the city’s nightlife, rooftop bars, or a final stroll through Old Havana.
Day 8 – Goodbye Cuba!
On their final day, they’ll have a leisurely breakfast and some free time for last-minute wandering or souvenir shopping before their private transfer to Havana’s airport, bringing their Cuban adventure to a close.
Does this type of trip appeal to you?
Remember, each of the trips I plan I customize to meet my traveler's specifications, so if this type of trip appeals to you, I can duplicate it, or I can change it up to include things that are more appealing to you!
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