Mediterranean Magic
Enjoy 20% off your Mediterranean sailing holiday this summer, including peak dates! View offer details
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Begin your sailing journey with Sunsail

Are you completely new to sailing and wondering if this type of holiday is worth trying? We can guarantee that there is no holiday quite like a sailing holiday, and once you have been, you will be hooked! With over 20 stunning destinations to choose from, covering the Mediterranean, Caribbean, Indian Ocean, Southeast Asia, and South Pacific, you will discover exhilarating adventures on the water, seeking out and exploring hidden gems, remote beaches, and uninhabited islands that can only be reached by boat. You can be certain that you will create wonderful memories that will last a lifetime.

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Skippered Sailing Holidays

Hiring a professional, knowledgeable skipper who will navigate your yacht during your sailing holiday is ideal for those who are new to sailing or aren’t comfortable going out on their own.  

You can still get as involved in the sailing as you want, or if you would rather relax and take in the beautiful scenery, you can be rest assured that your skipper will always be in complete control. Your skipper will also be an expert in your chosen destination and can provide tips on the best places to visit to help you get the most out of your itinerary. 

Skippered sailing holidays
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Flotilla Sailing Holidays

Sunsail invented the flotillas 50 years ago, and they have been popular among all levels of sailors ever since. Flotillas offer a more sociable sailing experience, where you will sail alongside other yachts on a planned route, with organised activities for the evenings, such as beach BBQs or punch parties, as well as the first morning breakfast and end-of-week regatta all included. One of the main advantages of a flotilla is that you will have the reassurance and support of a Sunsail lead crew, which includes a skipper, host, and technician. If you have children, Lefkas and Agana flotillas also have a kids activity coordinator. If you are not comfortable sailing the yacht by yourself, you can hire a skipper, or if you would like to learn, we have Flotilla Starter or Flotilla Hero courses in Croatia or Greece.

Flotilla Sailing Holidays

What sets Sunsail apart?

  • Firstly, and most importantly for additional peace of mind we are ABTA & ATOL protected, meaning if anything changes your holiday is in safe hands. 
  • We have our Book and Travel with Confidence policy which offers flexibility and insurance options.
  • We include more as standard in our pricing which includes; end of charter cleaning, dinghy and outboard engine (inclusive of fuel) and a 4-hour service commitment, plus much more so you can expect no hidden fees.
  • We can offer full travel services such as hotels, and transfers.
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Start your Sailing Journey with Sunsail
Sightseer45712203007 Antigua

“i have a group of sailing friends and we have been doing a bareboat charters around the world together each year for the last 20 years.
this year we went to Sunsail: Antigua
first let me talk about the base – nelson’s dock yard is a wonderful, protected landing and a nice place to start and end the journey – interesting things to see, easy access to stores to provision and buy souvenirs, lots of fun restaurants to try. the team at sunsail put the boat on and off the dock before handing the boat over (kind of like having a pilot coming into a major harbor), so while our crew may have enjoyed the challenge, we were also fine not having the drama of docking a boat we did not have a lot of experience with.
next antigua – plenty of great sailing detinations – the winds and weather did not disappoint. lots of easy to navigate to anchorages…..just easy and fun and interesting.
the boat – we had a Sunsail 44 with a 4 cabin layout. it was in good working order, clean, intelligently laid out and sailed very nicely. one of the nicest roomiest monohulls for its size.
the team at Sunsail – the team at the base were friendly and helpful and professional. there is a lot more paperwork and explicit focus on safety then in the old days. however the team was thorough in their boat and map briefing and didn’t rush it and took our followup questions and made us comfortable. we enjoyed their smile and enthusiasm seeing us start our charter and their smiles and help winding things up.
another great holiday – thanks Sunsail.”
skyehigh Agana

“We just came back from a week flotilla in Croatia. Our lead crew was amazing, Esme was on hand for bookings, Fraser welcomed us into every dock showing remarkable patience when the boys line throwing went wrong and Miha visited every night to check on all things technical”
Meander63970449191 Agana

“Huge thanks to Amy Smith for the fun and professional course with Sunsail Agana ! Amy is a very talented and thorough instructor. Her calm and patient approach certainly helped to get all Comp Crew and Skippers Ticket candidates across the line ! Thank you Amy ! You are a gem 😊”
K7070JAsimonj Agana

“We sailed as a family for a week with Rob from Sunsail. The children earned their RYA “Competent Crew”, my wife and I “Day Skipper”. We had a great time and learned a lot. Rob was great with the kids.”
Safari58349251535 Agana

“Thank you to Michael, Imogen, and Carraig for their support on our Krka flotilla. Lovely destinations and good times….”
OnAir18948491593 Agana

“Anja was our skipper,very well organized and neat.We were well informed of everything all the time.She even helped with restaurant reservations ect.The boat is very small and I would suggest 1 couple in the 3 room boat.”

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