Project Description

Cuba holidays for mature couples. City & Beach. A Captivating Cuba™ sample Itinerary

Multi-Centre Holiday  | for Mature Travellers

Carefully designed by destination experts

  • Havana + Trinidad + Varadero

  • Recommended for 7, 10, or 14 nights

At Captivating Cuba, we organise many holidays each year for mature couples and solo travellers. If feeling vital  is part of your travel experience, and you enjoy culinary experiences, beach resorts and natural wonders, the sample itineraries we suggest here might be for you.

We’ve taken good care in selecting the three destinations consistently favoured by our mature clients. Havana, rich in history, architecture, and a vibrant culture. Trinidad, a UNESCO heritage colonial town surrounded by the Caribbean Sea, forests, and mountains of outstanding natural beauty. And Varadero, with its 20 miles of beach line and some of the best resorts in Cuba, perfect for a bit of relaxation at the end of your trip.

Where possible, we’ve chosen hotels with lots of history and character. Hotels with remarkable architecture that have witnessed key events in Cuban history, from dark connections to the American mafia before the Cuban Revolution to famous events after 1959 such as the Cuban missile crisis.

We’ve also included some activities that we believe you might like, including a guided tour around Havana onboard a vintage American car, for many the highlight of their trip.

Bear in mind however that these are mere suggestions. Every traveller is different an, as a tailor-made Cuba specialist, we have plenty of experience and expertise in helping our clients plan and organise journeys to Cuba around their every specification. Speak to one of our Cuba Experts and we will take care of everything for you.

Itinerary at a Glance


Recommended minimum stay: 3 nights

Luxury City and Beach Cuba Holidays by Captivating Cuba.
  • Direct or connecting flight to Havana in Economy or Premium Economy

  • Meet & Greet with a Captivating Cuba Representative at the Airport

  • Direct transfer to your Hotel or Casa in Havana

  • Accommodation in your chosen hotel, Hotel Sevilla, Hotel Nacional, Iberostar Parque Central, Hotel Raquel, or a Casa Particular

  • Alternate accommodation in beach Resort Memories Jibacoa near Havana

  • Lots of activities to choose from, including a leisurely walking tour of Old Havana and a tour onboard a Classic Old American Car


Recommended minimum stay: 2-3 nights.

Luxury City and Beach Cuba Holidays by Captivating Cuba.
  • Private transfer to Trinidad from Havana

  • Luxury stay at Iberostar Grand Hotel in Trinidad

  • Alternative accommodation in our recommended Casa Particular

  • Leisurely walking tour of Trinidad

  • Great choice of city, beach, or nature activities


Recommended minimum stay: 4-10 nights.

Luxury City and Beach Cuba Holidays by Captivating Cuba.
  • Private or Shared transfer from Havana or Trinidad  to your choice of Beach Resort in Varadero

  • Deluxe  accommodation at Melia Las Americas, Sol Palmeras, or Paradisus Princesa del Mar

  • Representation Service in Varadero to look after you

  • Choice of excursions including fishing experiences or a boat trip to nearby islands

For mature couples and solo travellers, we’ve hand-picked these three destinations. How you mix them is entirely up to you.

Some of our clients prefer a longer stay by the beach; others prefer to skip Varadero altogether to spend more time in Trinidad. Trinidad is such a charming colonial town surrounded by verdant mountains and the  sea, that is not uncommon our clients ask us to make the arrangements for them to stay there a few nights and enjoy the lively town culture.

When you speak to us, we can discuss your interests and expectations and suggest the best itinerary based on your plans for this trip

Matthew Osullivan, Captivating Cuba

Create your own destination mix

City and Beach combinations we’ve created for our clients in the past include some of the following variations. Depending on your preferences, we can create the right mix for you.

  • Havana + Varadero
  • Havana + Trinidad

  • Havana + Trinidad + Varadero Favourite

Itinerary Map

Essential Cuba Tour Map

Itinerary Complexity

Call us on 01438 419111

Start Planning your Dream Holiday

Interested in a free, no commitment quotation? Ready to start tailoring your Cuba adventure with the top specialists in the UK? Give us a call or send us an email and we promise we will exceed your expectations.

We are an ATOL bonded Cuba specialist with over 20 years of experience exclusively devote to organising authentic journeys to this fascinating Caribbean nation. Our expertise and dedicated travel consultants are entirely at your disposal.

Call us on 01438 419111

Experience Cuba like no one else. Detailed Itinerary Suggestions

Here’s our idea of what this journey could be. With hundreds of accommodation choices, activities, excursions, and the dedicated service of a professional team with more destination expertise than any other tour operator, the possibilities are limitless.

Virgin Atlantic Upper Class Cabin. Book with Captivating Cuba

Coming to Cuba

Fly Virgin Atlantic  direct to  Havana with our excellent  Premium Economy or Economy fares. Use your local airport in the UK and save the journey to  Gatwick and fly via Paris , Amsterdam or Madrid.

On arrival to Havana International airport, we’d recommend the services of our airport fast track service, with a welcome directly from the aircraft , a fast track through airport formalities and enjoy a Cuban coffee or cocktail while your bags are collected by the porter team .

At the arrivals lounge, look for the Captivating Cuba Representative carrying our branded sign. After a very brief meet and greet our representative will take you to your transfer so you can start enjoying your holiday straight away. Your transfer (choice of private or shared transfer), will take you from the airport to your hotel or Casa in Havana.

To find out more about our flight fares or the airport fast-track service in Havana, please give us a call on +44(0) 1438 310099

To learn more about flights to Cuba with Virgin Atlantic , follow this link. The article explains in detail the cabins, services, and the experience Virgin Atlantic makes available to you.

Virgin Atlantic Upper Class Cabin. Book with Captivating Cuba

Your Stay in Havana

Havana is a fascinating city for you to explore in search of some cultural understanding to complement a well deserved time away from it all. It’s history, music, and architecture stimulate the mind and allows for some care-free fun as well. Unsurprisingly, Havana is in the bucket list of many mature travellers due to it’s wide offering of galleries, museums, landmarks, and sites you will soon find both new and different.

For a place to stay that is thoroughly enjoyable, we’ve selected a handful of hotels with lots of character, history, and mind blowing architecture. The Hotel Nacional, for instance, is Cuba’s most iconic hotels, with direct links to some of the most important historical and cultural events in Cuba’s past. Hotel Sevilla not only boasts amazing architecture, but dark links in its past to the American mafia that, at one point, had deep roots in Havana.

We would recommend at least three nights in Havana so you are able to fully appreciate the city and explore aspects of its history, art, and culture.

To ensure you make the most of your time, we suggest a few excursions added to your itinerary. A leisurely walking tour of the historic centre of Old Havana, and a guided excursion of the city onboard a vintage 1950s American car come highly recommended. If you are a nature lover, just over an hour outside Havana there’s a UNESCO heritage site, Las Terrazas. It’s awe inspiring scenery and magnificent orchid gardens make for a great day out.

The beach, of course, is a favourite among most travellers to Cuba. Many of our clients prefer to stay at a great beach resort just outside Havana, the Memories Jibacoa. The resort allows for a very relaxing beach experience whilst close enough to Havana to enjoy sightseeing day trips or quick visits to the best bars and restaurants in Havana.

When are able to pre-book for you all sorts of activities, from dinner reservations at some of the best restaurants in Havana to making arrangements for special occasions like a birthday or anniversary celebration. When you speak to your Captivating Cuba travel consultant, please let us know exactly the kind of experience you’d like to live in Cuba. If it works, we can make it happen.

When you speak to your Captivating Cuba™ travel consultant, please let us know if you have specific interests. We can offer you a Specialist Guide to cover areas of interest (music, architecture, history, etc.). We will also help you with restaurant bookings and guidance. Our team in Havana keeps us up to date on the best, most trendy, and best value for money restaurants, bars, and venues in Havana.

For more information on our suggestions in terms of accommodation and excursions in Havana, please follow the links below:

Multi-Centre Cuba Holidays for Mature Couples

Trinidad, Cuba’s Living Museum

After enjoying Havana and before heading to our recommended beach hotels , take the chance to visit Trinidad travelling there  privately of course on our exclusive sightseeing transfer with your own private guide and visit some fascinating sites en route.

For a luxury experience at this charming colonial town, stay 2 or 3 nights at the Iberostar Grand Hotel in the very centre of the small city. Alternatively, for a very authentic experience, why not stay at one of our highly recommended Casa Particulars such as Casa Real 54 , Casa Buri Nesti, or Casa Osmary Alberto. Casa Particulars in Trinidad are renowned for their hospitality, authenticity, cuisine, and quality of services and facilities.

There’s plenty to do with Captivating Cuba™ in Trinidad. We would recommend a leisurely walking tour of the town’s historical centre, or perhaps a tour of Sugar Mill Valley, rich in history of Cuba’s colonial past, slavery, and sugar industry. Maybe even a ride in a steam train!

For further reading on our accommodation suggestions and activities in Varadero, please follow the links below.
Virgin Atlantic Upper Class Cabin. Book with Captivating Cuba

Head to Varadero Beach

Head to Varadero on a private transfer and stay at the Paradisus Princessa Del Mar , perhaps  enjoying the additional benefits , greater luxury and butler service of the dedicated  Royal Service area . Feeling more inclined for a livelier stay then head to the Melia Las Americas and enjoy perhaps its famed  golf course.

Pre book any excursions that might be on your agenda and enjoy the opportunity for extra privacy and comfort by allowing us to arrange them on an exclusive basis for you. Perhaps a catamaran trip to a nearby secluded island, or some snorkelling in the crystal clear waters of Varadero, or even a round of Golf at Cuba’s only golf course.

For further reading on our accommodation suggestions and activities in Varadero, please follow the links below.

However specific your requirements, we are here to help. Speak to us and we will give you unbiased advise for your trip, priceless tips based on direct destination knowledge and nearly twenty years of experience organising authentic journeys to Cuba.

Jo, Senior Travel Consultant