Welcome to Tomboy Sailing

Day sail, Skippered charter, sailing holiday with Tomboy Sailing and Gibraltar sailing.

Tomboy Sailing was founded in 2008 by David Campbell and Lucy Jones to introduce people to the joys of sailing regardless of their age, ability or expertise. We are now one of the foremost charter companies operating from Gibraltar.

Tomboy Sailing aim to give you the sailing holiday of your dreams! We provide a luxury skippered charter experience, enabling you to simply lay back and enjoy the sun, sail and sights. We also offer you the chance to be hands on, learning to sail the yacht yourselves.

With Gibraltar airport a stones throw away from the boat, it is possible to be on the water within an hour of landing. With our skippered charter service you can be assured the boat will be prepped and ready to sail on your arrival, so you can slip straight into holiday mode!

Gibraltar and its straits have some of the best sailing we have experienced. With its beautiful sunny days, warm evenings, tidal waters and consistent winds. Our Gibraltar Sailing holiday could not be better! With two continents and two seas right on our doorstep the possibilities are endless!

Tomboy Sailing offer a wide range of sailing packages to suit any clients specification Whether you are looking for simple day sail, a relaxed Skippered charter, or a fully packed adventure sailing holiday then Tomboy  Sailing has the package for you. With the ability to sleep up to 8 guests, feel free to bring along all your friends or charter the yacht solely for your own enjoyment.

Prices start from £60 per person for a day sail!

“Thanks for a wonderful trip, you gave me the confidence to do things I never thought I could do.” 
Ann, Chester