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Sailing Holidays

HomeSailing Holidays
join terry on a

sailing holiday

AN OVERVIEW

Terry has been conducting Sailing Holidays for over 40 years and while he has a number of favourite holiday areas, he’s always on the look-out for new destination experiences. He is very particular about the type of vessel he charters for these Holidays selecting modern 2-3 year old yachts, and while they may be able to accommodate up to 12 people, he rarely sails with more than 8 plus a qualified Skipper.

  • Open to any level of sailing experience, however Competent Crew is recommended so there is familiarity with sailing and conditions

  • Book by the Cabin which leaves you free to travel solo or bring a friend to share costs

  • 10 -14 days accommodation on a Chartered Yacht, including linen and towels

  • A variety of overnight stays, including marinas and remote anchorages

Flights and accommodation pre and post Sailing Holiday are not included and we recommend you do your own research or contact a travel agency. We do not offer any recommendations for flights or accommodation.
Tahiti
7-18 May 2026

Cruise around the beautiful islands of Tahiti - Raiatea, Huahine and Bora Bora, names and images which have become synonymous with paradise.
Dive into some of the most transparent, bluest water on earth, explore seaside villages and eat at local cafes/restaurants.
With a maximum 8 passengers plus Skipper, our luxury yachts offer plenty of space.

Find Out More
Croatia
September 2026

Details shortly

mauritius
Mauritius
2027

A work in progress

Greece, The Caribbean, Croatia, Thailand, Whitsundays, New Caledonia, Tahiti, Fiji, Tonga, Turkey

PREVIOUS SAILING HOLIDAY DESTINATIONS

“Fabulous sailing and brilliantly organised fun holiday adventures across the globe! I’ve done 4 – New Caledonia, Thailand, Caribbean, and Greece. Taking advantage of years of sailing experience and knowledge, Terry and Sarah mastermind, a wonderful balance of structure and flexibility ensuring everyone is engaged. You choose how much you want to improve your sailing, helming or navigation skills or relax, take it easy and chill. Highly recommend.”
TammyMultiple Trips
“For good company, the best fun, excellent sailing, great Greek food and wines Terry’s Pacific Sailing School Greek Islands sailing holiday ticks every box. Not to be missed if you can possibly do it. Definitely all 5 Star and highly recommended.”

We have made so many friends out on the water on their excellent range of boats with instructors Terry, Gardo, Phil and Damien – not to mention great introductions in the CYCA.  They have recently assisted with great advice as we purchased and renovated our Marten 49 cruiser-racer. Later in the year –  I need to come and do the theory for Coastal / Ocean Yachtmaster.
Jonathan B2018 Trip
“Where do I start…! The memories of sailing feel like it was just yesterday! Seamless transfers, an experienced and very knowledgeable crew made it a stress-free holiday filled with exploring ports, mixing with locals, many sunsets on board or in bars with a cocktail or two, and fun-filled inaugural yacht races in fancy dress. It was just magic! (Bed sheets came in handy… lol!) An experience you will hold onto for many years to come…! “
All of this wouldn't have been possible without my Aussie sailing family and friends through the advice, support, introductions, and generally making sailing so much fun. Thank you!! 😘
LeeStarted sailing with PSS in 2016

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