Overview & Highlights
Our covid-conscious holiday visits the highlights of Cuba from the palm-shaded beaches of Jibacoa, to the charming colonial city of Cienfuegos and lush countryside east of Havana. This self-drive itinerary discovers Cuba’s most inspiring places, and if driving’s not your thing, it can be organised with private services throughout.
- Half day guided walking tour of Cienfuegos
- Full day excursion exploring Pinar del Rio and the valley of Viñales
- Optional Visit to the Che Guevara Museum in Santa Clara
- Optional half day kayak tour to Jagua fortress
- Optional half day walking tour of Trinidad
- Optional half day walking tour of Old Havana
Be among the first to blaze a trail back to Cuba. We’ve designed this trip to include all the iconic highlights and heady atmosphere of Cuba, while remaining entirely covid-conscious in our choice of arrangements. You’ll be staying in just three hotels, especially selected for their location and secluded settings. Travelling by hire-car, you’ll relish the sense of adventure as much as the flexibility to travel at your own pace, although if you would prefer not to drive yourself, the trip can be easily adapted to include exclusively private transfers.
You’ll begin your travels by unwinding on the paradise beaches of Jibacoa, where the soft, palm-shaded sands are lapped by azure waters.
Driving on to the historic port city of Cienfuegos, you’ll have the chance to kayak in the calm waters of the bay to round imposing fortresses and sunken ships, admire elegant balconied mansions and sample delicious seafood at your quaint oceanside guesthouse on the outskirts of town. You might choose to visit the Che Mausoleum in Santa Clara, the gushing waterfalls in El Nicho Natural Park or take a walking tour of charming colonial Trinidad.
The tropical forests of Las Terrazas are your final stop, where you’ll be nestled amongst acres of protected woodlands in the Sierra del Rosario Nature Reserve. From here you’ll explore the dramatic, fairytale landscapes and sleepy towns of Pinar del Rio and Viñales, and if you choose, spend your final day taking in the romantic splendour and bustling street life of Havana.
Transfer from the airport to your hotel in Jibacoa
Relax on the beach at Jibacoa
Drive to Cienfuegos, optional visit to Che’s Mausoleum near Santa Clara
Walking tour of Cienfuegos and optional kayaking in the bay
Free day for optional day trip to Trinidad or waterfall jeep safari
Drive to Las Terrazas, with an afternoon to explore
Full day excursion in Pinar del Rio and Viñales
Optional Guided Walking Tour of Havana
Drive to the airport
Things to do
We proudly offer the widest range of activities, excursions and one-of-a-kind experiences across all our destinations, tried and tested personally by our travel experts.
What our clients say
97% of our clients rated their experience with us as Excellent or Good.
Very efficient with the booking process and very helpful with his service throughout. Adam was always prompt and helpful in answering all our questions prior to departure.IR, London
Our Trailblazer holidays
As the world begins to open up again, we have put together a selection of covid-conscious itineraries specifically designed for travels in these times. Our Trailblazer Cuba holiday stays in carefully selected locations that avoid the crowds, allowing you to see the highlights whilst always staying within your comfort zone.
Carrie Gallagher - Travel Consultant
A former JLA tour leader, Carrie brings a wealth of on-the-ground experience to our London-based Escorted Groups team.
Inspired by this trip
Our exciting range of articles on Latin America explore everything from iconic destinations and lesser-known cultural gems to delicious traditional recipes. You’ll also find exclusive travel tips, first-hand client reviews and the chance to get your personal questions answered by our travel experts.
Your edit for Latin American inspiration
Our exciting range of articles on Latin America explore everything from iconic destinations and lesser-known cultural gems to delicious traditional recipes. You’ll also find exclusive travel tips, first-hand client reviews and the chance to get your personal questions answered by our travel experts.View Extraordinary Inspiration
Holidays Trailblazer Cuba
From expertly designed Pre-designed Holidays to trail-blazing Group Tours, browse our range of carefully crafted holidays.
Active Cuba: Bike, hike, kayak
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Luxury Cuba: Colonial classics and coast
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Group - Discovery
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Real Latin America Experts
Paul Winrow-Giffin - Travel Consultant
After graduating in Computer Science, Paul spent seven months travelling from Colombia to Argentina and came home hooked on Latin America.
Ben Line - Travel Consultant
Ben fell in love with Latin America on a six month backpacking trip from Colombia to Mexico in 1995. Since then he has explored most of South America, including living in Peru for a year. He is now Manager of the Tailor-made Department.
Mary Anne Nelson - Travel Consultant
Born in the Atacama Desert in northern Chile, Mary’s insider knowledge and dry sense of humour make her a highly valued member of the Tailor-made team.
Hannah Donaldson - Travel Consultant
Having spent part of her childhood in Colombia and worked in Brazil and Costa Rica, Hannah's ties to Latin America run deep. Hannah is an invaluable part of our Group Tours team.
Evie Oswald - Travel Consultant
It’s hard to believe that Evie has had time to cram so much in to her life so far. Having lived as a child in the Americas and Europe she found herself immediately attracted to Latin America.
Sophie Barber - Travel Consultant
Sophie lived in Chile before joining us and has travelled extensively across Latin America, from Mexico to the furthest tip of Patagonia.