Joshua Todd, Cassandra Jennings


Sierra Retreats is a luxury bespoke tour operator. 'Sierra' referring to jagged mountain range and 'Retreats' to escape, we create and design the perfect unique holiday for you in those sought-after destinations. 

Founder and CEO Joshua Todd working closely with his partner Cassandra striving for perfection. Both with years of extensive hospitality and personal care experience, both very well-travelled and cultured bringing the very best service. 

The idea to start Sierra Retreats is to offer a distinctive professional service to clients that want a hassle-free holiday. Joshua has been a private chef for over 7 years previously at Blenheim Palace for the Duke & Duchess of Marlborough, before working for very affluent UHNW guests in luxury homes, estates, chalets, villas and onboard private yachts. Before this he has gained great knowledge in Michelin starred and other high-end establishments. 


The early part of this journey started in a chalet in Baqueira, Spain (the hidden gem as we refer to it) where Joshua knew he would return to one day. Setting up here is the starting point of much more to come for Sierra Retreats. 


Our HQ is currently based in the UK, Wiltshire. Joshua and Cassandra run and manage the company as well as the day to day operations, searching for perfection and directing the business forward. Personally, selecting and visiting all the accommodation featured, we can give our recommendations and expertise.

We have spent many years exploring and travelling the world from some of the most remote islands to the liveliest cities, taking part in many excursions and activities. We understand the importance and the aspects that make a great holiday. Our aim and statement 'Unique Luxury Getaways' is a combination of visiting a desirable undiscovered destination, our bespoke luxury service and exclusive touch. It will be a holiday you will remember for a life time.

With Joshua leading the business and team he really understands the importance of what our clients, their friends and families want to experience. Making sure that from enquiring, to after your holiday you are satisfied above and beyond expectations. 

We will go out of our way to give you a faultless service, ensuring all your needs are fulfilled, booking your every requirement.