Cuba Multi-Country Holiday |

Begin in Havana

A multi-country holiday in February is a brilliant way to experience Cuba alongside another Caribbean destination, and Havana makes a memorable starting point. The city feels wonderfully alive, with classic American cars rolling past grand colonial buildings and music drifting from open doorways. Spend your first few days exploring the cobbled streets of Old Havana, where balconies, plazas and lively cafés create a real sense of place.

February usually brings warm, dry weather, making it comfortable to walk between the city’s highlights. Visit the impressive Castillo de la Real Fuerza, browse local art galleries and pause in Plaza Vieja for a coffee or a cold drink. In the evening, enjoy live son music or watch Havana’s famous sunset from the Malecón seawall.

Caribbean Holidays, Cuba Multi-Country Holiday, Tropical beach with calm turquoise water, palm trees and a small colourful fishing boat in Cuba

Relax in Varadero

After the energy of Havana, Varadero offers an easy change of pace. Its long sweep of pale sand and clear turquoise water is ideal for a few restful days, whether you want to swim, read beneath a palm tree or try a water sport. February is one of the most popular times to visit, thanks to pleasantly warm temperatures and low rainfall.

There is more to Varadero than its beach resorts. Take a trip to the nearby Ambrosio Cave, visit the peaceful Xanadú Mansion or join a boat excursion along the coast. The area is also a convenient place to enjoy Cuban seafood and sample the country’s famous rum in a relaxed setting.

Caribbean Holidays, Cuba Multi-Country Holiday, Colourful colonial street in Cartagena, Colombia, with balconies, flowers and warm evening light

Add Cartagena

Pairing Cuba with Colombia creates a varied Caribbean journey, and Cartagena is a natural second stop. The walled old town is packed with colourful façades, leafy squares and beautifully restored buildings. Wander through its lanes in the cooler morning, then take your time over lunch in a shaded courtyard.

Cartagena’s history is easy to discover, from the formidable Castillo San Felipe de Barajas to the city walls overlooking the sea. At sunset, the atmosphere becomes especially enjoyable, with musicians, street performers and locals gathering in the plazas. February is generally sunny and dry, so it is a reliable month for sightseeing and outdoor dining.

Caribbean Holidays, Cuba Multi-Country Holiday, Small Caribbean island beach with white sand, clear blue water and palm trees near Cartagena

Finish by the Sea

For a final few days, consider staying on the nearby Rosario Islands or choosing another Caribbean beach destination. The islands offer calm water, coral reefs and a slower rhythm after your city adventures. Snorkelling trips reveal bright marine life, while boat rides and quiet beaches make it easy to unwind.

A February multi-country holiday in Cuba can combine culture, history and beach time without feeling rushed. With carefully planned flights and transfers, you can enjoy Havana’s character, Varadero’s coast and Cartagena’s colourful charm in one rewarding trip. It is an excellent choice for travellers who want more than a single resort, while still having plenty of time to relax.