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.
Outline itinerary
Day 1
Transfer from the airport to your hotel in Jibacoa
Day 2-3
Relax on the beach at Jibacoa
Day 4
Drive to Cienfuegos, optional visit to Che’s Mausoleum near Santa Clara
Day 5
Walking tour of Cienfuegos and optional kayaking in the bay
Day 6
Free day for optional day trip to Trinidad or waterfall jeep safari
Day 7
Drive to Las Terrazas, with an afternoon to explore
Day 8
Full day excursion in Pinar del Rio and Viñales
Day 9
Optional Guided Walking Tour of Havana
Day 10
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.
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.
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.
Papagaio
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 InspirationHolidays Trailblazer Cuba
From expertly designed Pre-designed Holidays to trail-blazing Group Tours, browse our range of carefully crafted holidays.

Private Journeys
Cuba
Active Cuba: Bike, hike, kayak
14 days from £1,948pp

Private Journeys
Cuba
Family Cuba: Salsa, beach and vintage cars
15 days from £3,076pp

Private Journeys
Cuba
Luxury Cuba: Colonial classics and coast
10 days from £2,260pp

Group - Discovery
Cuba
Parakeet: Cuba Beyond the beach
15 days from £3,014pp