Project Description


Five-Star Luxury| The Best Possible

A City & Beach Holiday Experience in Cuba for discerning travellers

This itinerary was designed by senior travel consultants at Captivating Cuba for those who want to experience five-star luxury and the best possible holiday experience in Cuba. Quality, exclusivity, and the highest standards of service are at the core of this itinerary. If you like to do exactly what you want, when you want it during your holidays, have everything taken care of, and enjoy the finer things in life, this city & beach journey to Cuba could be a good place to start. For complete customisation around you interests, time, and personal preferences, a dedicated Cuba specialist will be put at your disposal as soon as you get in touch with Captivating Cuba.

  • Hand-Picked Destinations for Discerning Travellers

  • Dedicated Senior Consultant to Tailor your Trip

  • Top Hotel choices, with exclusive upgrades

  • Complete flexibility to customise around your time and interests

  • We take care of absolutely everything

  • Great choice of activities, including dining and cultural exploration

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 Premium Economy or Upper Class
  • Airport Fast-Track Service to expedite leaving the airport

  • Meet & Greet with dedicated Captivating Cuba Representative

  • Journey to Havana on Classic American Car

  • Luxury Accommodation at Hotel Saratoga, Kempinski Manzana, or boutique Casa Loma del Angel

  • Dedicated guide service to help you do exactly what you want


Recommended minimum stay: 4-10 nights.

Luxury City and Beach Cuba Holidays by Captivating Cuba.
  • Private chauffeured transfer from Havana. You decide what to do on the way, including a stop at Cuba’s tallest bridge.

  • Luxury accommodation at the Royal Service in Paradisus Princesa del Mar Resort and Spa.

  • Exclusive area and butler service during stay at Paradisus Princesa

  • Alternative accommodation at the Diamond Club, Royalton Hicacos

  • Dedicated Representative with wide choice of adventures including sailing to idyllic nearby cayos.

Santa Maria

Recommended minimum stay: 4-10 nights.

Luxury City and Beach Cuba Holidays by Captivating Cuba.
  • Private sightseeing transfer to Cayo Santa Maria. Points of interest along the way include Remedios, one of Cuba’s oldest colonial settlements.

  • Luxury stay at Melia Buenavista, Royal Service.

  • Butler service and exclusive area within the Melia Buenavista

  • Alternative accommodation at famed Royalton Cayo Santa Maria

  • Private adventures pre-booked, including sailing, diving and interacting with dolphins


Recommended minimum stay: 2-3 nights.

Luxury City and Beach Cuba Holidays by Captivating Cuba.
  • Private sightseeing transfer to Trinidad, via Santa Clara and through the mountains

  • Luxury stay at Iberostar Grand Hotel in Trinidad

  • Alternative accommodation in boutique casas Casona, Casa Tuti, or Casa De Trinidad

  • Dedicated guide service throughout your stay

  • Great choice of city, beach, or nature activities

For those looking for five-star luxury, the best possible experience in Cuba, we’ve hand-picked these four 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 or the Cayos. The unspoiled beaches of Cayo Santa Maria are increasingly popular. 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

  • Havana + Varadero
  • Havana + Trinidad

  • Havana + Trinidad + Cayo Santa Maria

  • Havana + Trinidad + Varadero

  • Havana + Varadero + Cayo Santa Maria + Trinidad

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 or Varadero  with our excellent  Premium Economy or Upper Class fares. Use your local airport in the UK and save the journey to  Gatwick and fly via Paris , Amsterdam or Madrid and enjoy our excellent fares in Premium Economy or Business Class. Why not take a short city break in these fascinating European cities on your way out to Cuba or on your return.

Combine Cuba with existing travel /business plans to  another destination by flying to various cities in the USA, Canada  or neighbouring Caribbean or Latin American countries and we can handle all your arrangements for you.

Arrive into Cuba and enjoy 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 .

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

Start your Cuba adventure right from the airport with a guided transfer to our recommended accommodation in the heart of Old Havana. Enjoy a unique experience by having a chauffeured Vintage 1950’s America Car journey to Old Havana.

Our recommended accommodation for you would include the newly opened Kempinski Manzana or the  Saratoga Hotel , both offering a choice of upgraded rooms  Or try the deluxe and intimate Loma Del Angel , boutique Casa Particular.  The Saratoga is considered by some the most sumptuous hotel in Havana. Ideally located in the heart of Old Havana and boasting a rooftop swimming pool with awe-inspiring views over the Capitol and Paseo del Prado, it is easy to see why this hotel is at the top of the list for luxury travellers. It’s reputation as a high-end hotel in Havana has been strengthen lately by a string of visits from international public figures, including US singers Beyonce and Madonna.

We suggest a three night stay in Havana and why not enjoy our dedicated guide service at your disposal to  show you around the city or our concierge service where one of our team will be on hand to be your  ” man in Havana”  to assist you throughout your stay. We can arrange any number of activities in Havana, including dinner reservations, cigar and rum tasting, ballet and opera performances, special interest tours tailor-made around the things you’d like to do, or perhaps a guided tour of Havana on board a vintage 1950’s American car. Take a look at some of our excursions, activities, and day trips in Havana for inspiration. Let us know if you see anything you’d like added to your itinerary, or tell us about your interest so we can build a tailor-made experience.

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

Luxury City and Beach Cuba Holiday

Experience Trinidad

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.

Stay 2 or 3 nights at the Iberostar Grand Hotel in the very centre of the small city or enjoy an authentic stay in pone of our highly recommended Deluxe Casa Particulars such as Casa Casona , Casa Tuti or Casa De Trindad

Enjoy your own dedicated guide service for your time in Trinidad and pre book your visits and restaurants

Head to the beach of your choice by travelling with your guide over the Escambray mountains , stopping at Revolutionary Santa Clara.

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 chauffeured 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 Royalton Hicacos and enjoy their upgraded rooms or dedicated Diamond Club.

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.
Luxury City and Beach Cuba Holiday

Idyllic Cayo Santa Maria

Head east on a private sightseeing transfer to Cayo Santa Maria  with your exclusive guide and stay at  the intimate, luxury  Melia Buenavista Hotel . Enjoy the chance to pre book your upgraded room and your butler will be on hand to look after you during your stay . Alternatively the  Royalton Cayo Santa Maria works really well for those of you that prefer a certain level of style .

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, Travel Designer