Five Recommended Extremadura Tours

Extremadura doesn’t shout about itself the way the Costas or Catalonia does. That’s part of its charm but for travellers who are keen to dig deeper – whether that means bird-watching in Monfragüe, cycling through cork oak forests, or following the ghost of conquistadors – a good guide makes all the difference. Here's a run-down of five of the most recommended tour operators in the region, each ready to share Extremadura’s secrets with warmth, wit and colourful local anecdotes.

Destino Trujillo (destinotrujillo.com)

Best for contemporary rural life with a sense of fun

Rafa’s heart belongs to Trujillo, but you’ll also find him guiding travellers through the Roman riches of Mérida and the medieval lanes of Cáceres. Visitors might arrive for a ‘taste’ of the National Cheese Fair or the solemnity of Holy Week, yet what lingers is often something grander: tales of conquistadors, the discovery of the Americas, and Extremadura’s far-reaching past. Rafa’s multilingual tours move easily from the Jewish quarters of Cáceres to the nocturnal legends and whispered mysteries of his beloved hometown, always with the enthusiasm of someone who still sees wonder in the cobbles beneath his feet.

Association of Historian-Guides of Extremadura (guiashistoriadorex.com)

Best for history buffs

If you want absolute confidence in your facts, you can’t go wrong with the Association of Historian-Guides of Extremadura – a group of tour guides who also happen to be PhDs or history graduates. Their base is in Cáceres, but their reach stretches A to Z across the region - from Alcántara to Zafra. Topics are just as wide-ranging: one day you might be walking under Roman arches, the next learning about wartime Cáceres, cherry harvests, mining history, or the flavours of local gastronomy. And while the history is scrupulously researched, there are countless light-touches too such as the 'Legends of Cáceres' tours. (Contact the association to enquire about English-speaking guides.)

Martin Randall Travel (martinrandall.com)

Best for the perfect mix of rural and urban luxury

Step into the world of conquistadores and legionnaires on guided tours through Trujillo, Cáceres, Plasencia and Mérida. Track the elusive lynx in the Sierra de Gata and Sierra de Guadalupe, and sample the finest serrano ham in the seemingly endless dehesa. Evenings are indulgent too, with stays in historic paradores – from a 15th-century monastery to a castle of the same era – as well as elegant four-star hotels. This 10-day journey begins in Plasencia (via Madrid) and winds to a close in Seville, with prices starting at US$4,683 per person.

Expressions Holidays (expressionsholidays.co.uk)

Best for self-drive guided adventures

A guided self-drive tour gives you the freedom to pull over at sweeping viewpoints, wander through pueblos, and linger at those irresistible roadside eateries that make every Extremadura road trip feel like an adventure. This nine-night journey begins with two nights in Toledo (Castilla-La Mancha) – offering a chance to take in the land of Don Quixote before the drive onwards to Trujillo and the Extremadura section of your travels. From there, the route takes in Cáceres, Plasencia, Mérida, and the timeless orchards of the Jerte Valley, before looping back via Madrid. Expressions Holidays have been creating bespoke tours for 35 years and their well-prepared 10-day Extremadura History and Heritage Tour costs from US$2,195 per person.

The Natural Adventure (thenaturaladventure.com)

Best for two wheels and a sense of adventure 

Cycling through the gorgeous hill towns of Montánchez, Guadalupe and Monesterio, with nights spent at a mix of paradores, traditional casas rurales and guesthouses. You’ll pass through the steppes of Llanos de Belén and the mountain ridges of Sierras de las Villuercas. Averaging just under 50km/day, your two wheels will roll from Cáceres through Trujillo and Berzocana before finally exiting Extremadura near Navatrasierra to come to a stop finally at Talavera de la Reina (just over the provincial border in Castilla-La Mancha). For those who plan to take it easier E-bikes are available for rent. The 7-day tour has a starting price of US$1,062.