Rupert Wakeley, Charter Broker | TJB Super Yachts

Rupert Wakeley

Charter Broker

My Contact Details

Telephone: +44 7511 176836

Languages: English

Position: Charter Broker

Location: United Kingdom

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How I got here

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My career as a Yacht Broker started when I was at university. Shortly after I graduated, I moved to London to work at the world’s leading Shipbroker, before leaving city life behind to return to yachting. As a qualified skipper, I have been lucky enough to cruise nearly every corner of the Mediterranean and have also sailed extensively in the Caribbean. I’ve explored many of the most beautiful corners of Europe and the Caribbean, and this knowledge gives me first-hand experience when it comes to giving advice on cruising destination and creating the best itineraries that are 100% customised to the clients.   

My passion for yachting eventually lured me back to London to become a Yacht Broker. My knowledge of yacht charters, both as a former skipper and a broker, means I create experiences for our clients based on my fairly unique depth of knowledge. I take great pride in helping our clients to travel the globe, ensuring they get the best value and experience in every destination they visit. 

Rupert Wakeley, TJB Charter Broker

My passions

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Outside of the office I love all things adventure and the great outdoors. From waterskiing and keeping fit, to slowly exploring first-hand every possible charter cruising destination there is! 

Rupert Wakeley


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TJB is an independent boutique brokerage with a small team of highly specialised brokers. We work together and combine our individual strengths to deliver the best yachting experiences for our clients. Our team is fuelled by energy and passion that I haven’t seen anywhere else in our industry.  


Top Tips For A First-Time Charterer

Charter Broker, Rupert Wakeley, shares his top tips with Superyacht Life for planning a first-time luxury yacht charter.

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Caribbean Charter: Cruising in Antigua and Barbuda

This guide offers essential information for superyacht enthusiasts and charterers looking to explore the enchanting islands of Antigua and Barbuda.


Turkey Oludeniz Beach Arabella

Top Superyacht Cruising Destinations in Turkey

Explore this curated list of coastal gems in this article from the SuperYacht Times about top superyacht cruising destinations in Turkey.

My favourite cruising destination

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For me it’s Greece and Croatia as it’s that ‘’island-hopping’’ experience that I find particularly special. To me the idea of a different island, town or anchorage is a particular pull. I recently fell back in love with Greece again, it’s the perfect destination for a first-time yacht charter. There is so much to see and do, you could charter there for 2-weeks every year and after 10-years, still have not seen every island!

I personally absolutely love Hydra in the Saronic! Think – no cars, gorgeous back alleys, some amazing boutique shops, and the most enchanting little harbour where everyone sits having a drink watching the local fishing boats come and go. This is where you will find the best restaurants in the Saronic Gulf and be completely blown away by a Greek island and town like no other you have seen before. Dinner at Sunset Restaurant is a must!


Superyacht charter and sale with TJB Super Yachts
Thank you, Rupert. It was great, the crew was amazing, and Captain Luigi is one of a kind, and the crew was amazing.


The trip was absolutely fantastic, and the crew were brilliant. Thanks for your help Rupert in organizing this trip on such a short notice!
JULY 2022

Rupert was absolutely amazing to work with. His feedback, follow-through, itinerary ideas and organization were an absolute 10. And, he is one of the nicest guys I’ve ever worked with on any project! The loveliest! My Yacht charter arranged with Rupert was absolute perfection. The boat, the Captain and crew, and the food were absolutely impeccable. On the boat, we felt completely cared for and were also able to have our privacy when we needed it. We loved that we could alter our itinerary at any point and visit coves and ports that our Captain recommended once on the boat. Behind the scenes, Rupert was in touch to make sure everything was going perfectly. He was an absolute pleasure to work with and we will definitively be working with Rupert again.

JUNE 2022