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Sailing Holidays

Fifty years of doing one thing properly. Sailing Holidays effectively invented the British flotilla holiday and still runs it as a family business, which shows in the details: lead crews who know the anchorages rather than just the route, a fleet they own and maintain themselves, and a Share-a-Yacht programme that treats solo sailors as individuals rather than an awkward gap to fill. If you have just qualified and have nobody to sail with, this is the rare operator set up to take you anyway.

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See 4 trips
  • 4.9 from 128 reviews on Google
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Upcoming trips with Sailing Holidays

4 trips to choose from, with berths from £1,255.

  • October Half Term Corfu & Paxos - Share-a-Yacht — Sailing Holiday in Greece
    Open to all

    October Half Term Corfu & Paxos - Share-a-Yacht

    Greece · Europe

    Next: 25 October - 1 November 2026

    2 dates in 2026 & 2027


    £1,255£1,535

    -18%18% off

  • Highlights of the South Ionian - Share-a-Yacht — Sailing Holiday in Greece
    Open to all

    Highlights of the South Ionian - Share-a-Yacht

  • Skippered Highlights of the South Ionian - Share-a-Yacht — Sailing Holiday in Greece
    Open to all

    Skippered Highlights of the South Ionian - Share-a-Yacht

  • Corfu & Paxos - Share-a-Yacht — Sailing Holiday in Greece
    Open to all

    Corfu & Paxos - Share-a-Yacht

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Where you'll sail

The routes

See where each trip goes and when it next sails, then pick the one that fits your dates.

  • 1

    October Half Term Corfu & Paxos - Share-a-Yacht

    October Half Term Corfu & Paxos - Share-a-Yacht

    At the end of October the whole fleet returns to Corfu for the half term flotilla. Sail your own Beneteau 361 with a cabin each, visiting the fishing villages of Corfu and the…

    Route
    9 stops
    Next departure
    October 25 – November 1, 2026
    Berths from
    £1,255
    See dates and prices
  • 2

    Highlights of the South Ionian - Share-a-Yacht

    Highlights of the South Ionian - Share-a-Yacht

    Sail your own Beneteau 361 on a one week South Ionian flotilla, sharing the yacht with two other solo sailors.

    Route
    7 stops
    Next departure
    May 9 – 16, 2027
    Berths from
    £1,335
    See dates and prices
  • 3

    Skippered Highlights of the South Ionian - Share-a-Yacht

    Skippered Highlights of the South Ionian - Share-a-Yacht

    A week on a 15 metre Beneteau 50 with an experienced skipper aboard, sailing the South Ionian flotilla.

    Route
    7 stops
    Next departure
    May 9 – 16, 2027
    Berths from
    £1,585
    See dates and prices
  • 4

    Corfu & Paxos - Share-a-Yacht

    Corfu & Paxos - Share-a-Yacht

    Sail your own Beneteau 361 on a one week Paxos flotilla, sharing with two other solo sailors and a cabin each.

    Route
    7 stops
    Next departure
    May 9 – 16, 2027
    Berths from
    £1,335
    See dates and prices

About the operator

Meet Sailing Holidays

4.9 from 128 reviews on Google

Sailing Holidays is a family-run, British-owned flotilla specialist that has been putting people on boats in the Greek islands since 1976. Founded as the Flotilla Sailing Club and renamed in 1987, it is still owned and run by Barrie and Heidi Neilson, with offices in Corfu and London and a fleet of 120 yachts.

Their flotillas are built around unobtrusive support. You sail your own yacht, with a lead crew on hand when you want them and out of the way when you don't. The Greek islands make that easy: no significant tides, no cold water, and short scenic hops between harbours and tavernas. Holidays are ATOL protected, and flight-inclusive packages run from the UK with transfers included.

Fifty years in, a lot of their sailors come back year after year, which tells you most of what you need to know.

See their trips
Sailing Holidays

What it's like on board

Your home at sea

The boats you'll sail on

Where you'll sleep, eat and learn the ropes. Which one you sail on depends on the dates you pick.

    Beneteau 361 (Annabelle)

    Beneteau 361

    Type
    Sailing yacht
    Length
    36 ft (11.1 m)
    Built
    2001
    Flag
    Greece

    We consider these 3 cabin yachts perfect for family cruising with 4-6 people. They feature enhanced ventilation, a larger forepeak bed, and mainsail furling. Quality of life additions include an easy-to-use passerelle and modified anchor chain lockers. The spacious swimming platform and cockpit are ideal for relaxed lunches. A large bathroom with seperate shower area along with excellent build quality of the interiors really makes these yachts stand out in their class. Our classic family cruiser! All yachts have in-mast furling for easy handling by two people from the cockpit.

    Layout

    Beneteau 50 (Kassandra)

    Beneteau 50

    Type
    Sailing yacht
    Length
    51 ft (15.5 m)
    Built
    2013
    Flag
    Greece

    Our Beneteau Oceanis 50s are ideal for groups of couples or larger families, featuring four double ensuite cabins, a spacious saloon, and a separate skipper’s cabin. Designed for comfort and speed, they include an autopilot, bow thruster, in-mast furling mainsail, and roller furling headsail for easy handling. These yachts typically sail on flotilla but can also be independently chartered in the Ionian Islands. For those without qualifications seeking a larger boat experience, a professional skippered charter is available. All yachts have in-mast furling for easy handling by two people from the cockpit.

    Layout

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The SailTies community

From the logbooks

SailTies is the leading digital logbook and sailor network. These are stories from the sailors who use it.

All sailor stories
Three Volcanoes and a Cracked Shroud: Racing Offshore with Robert Šarić

Three Volcanoes and a Cracked Shroud: Racing Offshore with Robert Šarić

A cracked shroud 250 miles from the Rolex Middle Sea Race finish, three volcanoes in one campaign, and why Robert Šarić of Veruda Sailing School trains his crews on the Adriatic.

Read the story
Seven of Thirteen: Elouise Pemberton's Challenge Fleet Quest

Seven of Thirteen: Elouise Pemberton's Challenge Fleet Quest

A Tall Ships bursary put Elouise Pemberton to sea at 19. Twenty years on she is working through all thirteen Challenge yachts, logging every mile on SailTies.

Read the story
46 Legs Round Britain: Jenny Whelan's Voyage with Dogsail

46 Legs Round Britain: Jenny Whelan's Voyage with Dogsail

Jenny Whelan sailed 46 legs and 1,800 nautical miles around Britain with her partner Pete, their dog Svea, and an AI chatbot, logging every leg on SailTies.

Read the story

Questions people ask before booking a sailing trip

A sailor looking out from the foredeck
  • Can I book on my own?

    Yes, and most people do. Trips are sold by the berth, so you join a crew rather than needing to bring one. Cabins are shared with someone of the same sex unless you book a whole cabin.

  • Do I need sailing experience?

    It depends on the trip, and every listing says which level it is written for. Beginner trips assume you have never sailed; advanced trips assume you can stand a night watch without supervision.

  • What's included in the price?

    The berth, the skipper and crew, and the running of the boat. Flights, insurance and most meals ashore are not. Every trip page lists what is and is not included before you pay.

  • What happens if I need to cancel?

    The operator's cancellation terms are published on the trip page before you pay a deposit, so you can read them before you commit. They vary by operator and by how close to departure you cancel.

  • What if the weather is bad?

    The skipper decides the route, and changing it is normal seamanship rather than a problem. Trips are very rarely cancelled outright; when they are, the operator's terms say what happens.

  • Who are the operators?

    Independent charter businesses and skippers we either know personally or have been recommended by past customers. Their registered business details are available upon request. All trips are checked before they go live.

Ready to sail with Sailing Holidays?

Pick your trip, or ask a question first. We'll get you an answer before you book.

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    Greece · Europe

    Next: 9 - 16 May 2027

    10 dates in 2027


    £1,335

    Greece · Europe

    Next: 9 - 16 May 2027

    10 dates in 2027


    £1,585

    Greece · Europe

    Next: 9 - 16 May 2027

    10 dates in 2027


    £1,335

    Photos & videos from our sailing trips

    Taken by the people who were there, attached to the reviews they left.