Important Announcement Tomboy Sailing has closed down.
Thank you to all our regular customers and everyone who has sailed with us over the past 6 years.
Happy Sailing!

Welcome to Tomboy Sailing!

Come and sail the Straits of Gibraltar with us, enjoying the amazing marine wildlife and diversity of the Spanish and Moroccan cultures and cuisines.

Tomboy Sailing was founded in 2008 by David and Lucy. We are a family run business and our aim is to introduce people to the joys of sailing regardless of their age, ability or expertise.

We give you the sailing holiday of your dreams! Tomboy Sailing provides a luxury skippered charter experience. This means we enable you to simply lay back and enjoy the sun, sail and sights or you can be hands on and learn to sail the yacht yourselves.

Gibraltar and its straits have some of the best sailing Dave and Lucy have experienced; with its beautiful sunny days, warm evenings, tidal waters, consistent winds and amazing marine wild life. Our highly experienced skipper “Harley “ will be there to look after you

Special Offer!

New 2 hour Taster Sail, only £40 per person, including a snack and soft drinks!!
Contact us to book now

The sailing opportunities are endless from Gibraltar; you can sail East into the Mediterranean, West and head for the Atlantic or South down towards the Moroccan coasts, enjoying a truly diverse cultural and gastronomic experience.

I’ve used Tomboy Sailing numerous times for after work sunset sails, day trips, my hen party weekend, weekend onboard trips and overnighters to Ceuta over the last 3 years. I’ve personally recommended them to colleagues, friends and family and they’ve all been delighted. Fantastic hosts who are knowledgeable, informative and will even try and teach 10 girls full of cava how to sail – oh, and the food is always good too! Kellie 4th-5th July 2012

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Dave and Lucy offer a wide range of sailing packages to suit any clients’ specification. Whether you are looking for simple day sail, a relaxed short 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.

With Gibraltar airport a stone’s 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 yacht will be prepped and ready to sail on your arrival, so you can slip straight into the holiday mode.

Tomboy sailing is now the foremost charter company operating from Gibraltar.

Thank you for making my boyfriends birthday a fun one! we all had a great laugh and will be sailing with you again!
31st June 2012

Dave and Lucy, Thanks again for the most amazing time. Definitely the highlight of our holiday - and we`ve been doing some great things - But this comes top of my list. All the best for a wonderful life together...on the seas!!
Benny and Karl




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