Book With Confidence

If you’re looking to explore some of Latin America’s most iconic destinations in 2022 or beyond, now is the perfect time to plan ahead. Plus, take advantage of our new Flexible Booking Policy when booking before 31 December 2021.

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.

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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.

Accommodation

Browse our unrivalled portfolio of accommodation . Every option has been carefully chosen by our team of travel experts, so you can rest assured that you’ll relax in utter comfort.

What our clients say

97% of our clients rated their experience with us as Excellent or Good.

"This was our second trip with you and we have again been very pleased with the whole experience: if we are going to spend such a lot of money on a holiday, we want to know that the company are real experts, and that everything will be done efficiently and professionally. Thank you."

LK, Gerrards Cross

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.

Chris Rendell Dunn
Chris Rendell-Dunn - Travel Expert

Anglo-Peruvian Chris grew up in Lima and spent much of his adult life in between London and Cusco as a tour leader, before settling permanently in our London-based Tailor-made and Group Tours sales 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.

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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

Real Latin America Experts

  • Lina Fuller
    Lina Fuller - Travel Expert

    Lina's passion for the continent where she was born really took off when she moved to Córdoba (Argentina) to study, spending the holidays travelling between Argentina and her native Colombia.

  • Mary Anne Nelson
    Mary Anne Nelson - Travel Expert

    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 Holidays and Group Tour sales team.

  • Kathryn Rhodes
    Kathryn Rhodes - Travel Expert

    Kathryn backpacked across Argentina, Chile, Bolivia and Peru before joining us. She has a degree in Philosophy and French and is a keen netball player.

  • Hannah Waterhouse
    Hannah Waterhouse - Travel Expert

    Hannah had an early introduction to Latin America when her family moved to Ecuador and she returned to study in Buenos Aires for a year before backpacking across the continent.

  • Sophie Barber
    Sophie Barber - Travel Expert

    Sophie lived in Chile before joining us and has travelled extensively across Latin America, from Mexico to the furthest tip of Patagonia and beyond to Antarctica.

  • Paul Winrow Giffen
    Paul Winrow-Giffin - Travel Expert

    After graduating in Computer Science, Paul spent seven months travelling from Colombia to Argentina and came home hooked on Latin America.

Meet the team