An Unrivalled Sailing Experience Aboard Ruby May

Welcome to Flagship Adventures – our premier range of high-end, exclusive sailing expeditions crafted for sailors seeking extraordinary journeys, deeper exploration, and uncompromised comfort.

Unlike our other adventure sailing trips, Flagship Adventures are hosted exclusively aboard Ruby May, our owners’ meticulously equipped, high-specification cruising yacht. Designed for serious coastal passage-making, she offers superior performance, advanced nav-tech, and luxurious living spaces.

To maintain an unhurried, intimate, and truly personalised experience, we strictly limit capacity to just 4 guest crew per voyage. With a low crew-to-skipper ratio, you’ll enjoy hands-on helm time, tailored instruction, and plenty of space above and below deck.

In 2027 we are excited to be offering two flagship expeditions; the Ultimate British Isles Explorer, and The Grand Infinity Odyssey.

Adventure Sailing Around Britain

  • Duration: 51 Days
  • Format: Full Expedition Only
  • Distance: ~2,500 Nautical Miles
  • Cost: £8,499 (3 Places Left)
  • To Book: Call 01634 890515 or email office@elitesailing.co.uk to book.

Step aboard Ruby May for an exclusive 51-day circumnavigation of the British Isles. Designed for an intimate crew of just four guests, this expedition offers a rare, luxurious home-from-home experience as you cover 2,500 nautical miles of breath-taking coastline. Setting sail from Chatham, your journey weaves through the Channel Islands, the rugged cliffs of Scilly and Skomer, vibrant Belfast, and the dramatic archipelagos of the Western Isles, Orkneys, and Shetlands. Unlike all other commercially-operated around Britain voyages this trip is only available to join for the complete circumnavigation and is not available to join in ‘legs’.  Unbound by fixed leg turnarounds, the itinerary offers significant flexibility to explore hidden coves, remote islands, and historic ports at the absolute best times, creating a truly tailored adventure.

This unbroken 51-day expedition allows a small, dedicated crew to come together as a team and master all elements of seamanship. From starry night passages off the Scottish headlands to quiet anchorages in the Helford River and Scillies, every day brings a new horizon paired with modern onboard comfort. Your package includes all food onboard, professional skipper guidance, safety equipment, and berth fees for £8,499 per person (running Friday 30th July to Sunday 19th September). Secure one of the four coveted berths on Ruby May and experience the definitive sea voyage around Great Britain.

The provisional itinerary is as follows: 

Chatham – Dover – Eastbourne– Channels Islands (Alderney – Guernsey -Sark – Herm) – Weymouth – Dartmouth – Salcombe – Fowey – Helford River – Penzance – Isles of Scilly – Milford Haven – Skomer Island  – Isle of Man  – Belfast – Campbeltown – Islay – Jura – Oban – Western Isles (Mull, Iona, Rhum, Skye and  more)  – Orkney – Shetland Islands – Wick –  Lossiemouth – Peterhead – Eyemouth – Farne Islands (Holy Island) – Sunderland – Whitby – Lowestoft – Southwold – Shotley – Burnham on Crouch – Chatham.

(Note: the itinerary is subject to change based on weather/tides and is only provisional)

Adventure Sailing Britain

  • Duration: 85 Days Total
  • Format: Available as individual legs or full expedition
  • Distance: ~2,900 Nautical Miles
  • Cost: £11,999 (full 85 day passage), or see individual prices of legs below

Covering 2,500 nautical miles of Britain’s most spectacular coastline, the West Meets East Expedition takes Ruby May from Chatham, along the South Coast via the Channel Islands, before continuing along the Devon and Cornish coasts, taking in the Scilly Isles before heading North to the Scottish Islands and through the majestic Caledonian Canal at Fort William, out to the wild beauty of the Orkneys and Shetlands for some bucket-list adventure sailing and exploration, over the top of Scotland, and back down the Irish Sea and along the South Coast to Chatham. This trip takes in all of the best bits of the British Coast – creating a ‘figure of 8’ or an ‘Infinity loop’, it really is the adventure of a lifetime.

Designed with a focus on immersive exploration, this expedition features extended 12 and 14-day legs. Longer legs mean you aren’t rushing between changeovers – you get more time ashore to explore remote islands, discover local culture, and sail at a natural, unhurried pace.

Grand Infinity Odyssey Legs:

Leg: Dates: Days:
Channel Islands
Adventure		 Weds 28th April – Mon 10th May 2027 12
Majestic Western
Explorer		 Tues 11th May – Mon 24th May 2027 13
Island Ascent Mon 24th May – Mon 31st May 2027 8
Caledonian Canal and Scottish Island Explorer Tues 1st June –  Sun 13th June 2027 12
Scotish Gems Discovery Sun 13th June – Sun 27th June 2027 14
Scotland & West Coast Island Adventure Sun 27th June – Mon 12th July 2027 14
South Coast Discovery Mon 12th July – Thurs 22nd July 2027 12

Elite Sailing FlagShip Sailing Adventures Around Britain

Format:

    • Join for a Leg: Choose one or more extended legs to experience iconic stretches like the Scottish Highlands or Northern Isles. Browse below for individual leg info and to book your place.
    • The Complete Journey: Join us for the full 85-day epic from start to finish. Cost: £11,999. Includes wet weather gear, all food onboard, professional skipper, all safety equipment, mooring fees and fuel. No hidden extras! Call 01634 890515 or email office@elitesailing.co.uk to book.

 

Why Choose A Flagship Adventure?

      • Maximum 4 Guest Crew: Unmatched personal space, comfort, and active helm time.
      • Our Premier Vessel: Sail aboard Ruby May, highly specified and meticulously maintained for long-distance cruising
      • Unrivalled Flexibility & Pace: Extended leg lengths and non-segmented itineraries mean incredible cruising and exploring

Ready to step aboard? Spaces are strictly limited to four crew . Contact us to discuss availability or reserve your berth on Ruby May.