Conquer the Island 2026

Students from the Little Ship Club's Day Skipper and Yachtmaster shore-based courses can practice their skills on a sailing passage, tracing the route of the famous Round the Island Race.

This is a special opportunity for club members studying shore-based Day Skipper or Yachtmaster courses to apply their knowledge in an exciting 8 to 9-hour offshore sail, following in the footsteps of the famous Round the Island Race. Crews will be motivated to assist in planning the passage, reviewing tides and weather, and trying to chart the most efficient route around the Isle of Wight. Breaking from tradition, the crew will sail clockwise around the island. Begin your journey near No Mans Land Fort, heading south, through Bembridge Ledge. Proceed past Sandown towards Saint Catherine’s Point, where the iconic lighthouse has been a beacon for sailors returning home for generations. Finally, sail through the notorious Needles Channel to return to the protected waters of the Western Solent. Make no mistake, this is just as demanding as the actual race. We will face obstacles such as commercial traffic, tidal gates, and changing sea conditions.

The Draft Plan:

Week of April 15th, 2026 - April 19th, 2026

April 15th:

An evening safety briefing, team updates, and an introduction to the Skippers and First Mates.

April 17th:

In the afternoon, Skippers and First Mates will move the boats from their base at Port Solent to Gosport, a more convenient location for collecting crew and supplies.

April 18th:

An early start to catch the tide towards a transit just north of Cowes. For anyone wanting to hone their VHF skills, we will use CH 77 to ensure all boats stay in alignment. The journey will last 8 to 9 hours. We will have provisions on board for lunch and snacks, along with hot drinks to keep us energised. We can also mix things up with crew rotation, depending on how long we are out. Once we are back in Cowes, we will head to the Island Sailing Club for dinner and a small awards do, and if we are still feeling lively, maybe finish with a live band at the Anchor Inn.

April 19th:

We plan to enjoy a relaxed sail back to Gosport in the morning, where the crew can disembark. Afterwards, we will refuel and return to Port Solent to return the boats.

The Boats:

We are teaming up with Prometheus Sailing who are bringing along a fleet of matched Jeanneau Sun Odyssey 410s, modern, fast, and seriously fun 41-foot cruisers. This collaboration is built on a shared commitment, with Prometheus Sailing mirroring our dedication to excellence on the water. Their expertise and attention to detail make this partnership really unique. Together, we are not just putting on an event, we are inviting you to be a part of a sailing experience focused on exceptional performance, training opportunities, and pure fun on the water.

We have up to four yachts at our disposal, 20 spaces in total, so be sure to book early!

Jeanneau Sun Odyssey 410 Layout:

The Costs:

For those ready to take on the challenge and open the door to a life of high seas and adventure, there is an investment to get started. To reserve your spot on this amazing challenge, a fee of £255 per person is required, which is based on 8 people per charter boat. This covers your berth, provisions, fuel, and the Saturday evening meal. Any additional drinks or shoreside meals are for individuals to settle themselves.

Once your place is confirmed, you will receive a full kit list, details of a Q&A session, and all the other admin bits to get you properly prepped and ready to sail. This trip is organised by members for members of the Little Ship Club as a not-for-profit venture. This supports a key goal of the Club, as we are all dedicated to creating opportunities for people to get out on the water and enjoy the amazing experiences available.

Kit & Equipment

Life jackets and foul weather gear are provided.

You only need to bring non-marking shoes that you don't mind getting wet, a sleeping bag and a pillow!

A full suggested kit list will be published closer to the event.

Still Keen? Of course you are! Roll-up to your best adventure of 2026! Your skippers will have to balance the crews across the boats, so it's important when you book that you are honest about your skill on a sailboat. Please review the options below and select one when you go through the checkout:

Basic: You have little or no sailing experience and may only have been on a sailing boat once or twice.

You might still be getting familiar with how a yacht works, what the different control lines do, how the sails drive the boat, and how helming feels. Most of your experience so far may have been in calm or sheltered conditions. This level roughly aligns with the RYA Start Yachting Stage, where the focus is on getting comfortable on board and beginning to understand how a sailing yacht operates.

Intermediate: You have some sailing experience and have spent time as an active member of the crew on several sailing trips. You likely understand the main control lines and sails, can assist with hoisting and trimming sails, and may have helmed the boat for periods of time. You may also be familiar with basic buoyage and navigation marks, and have experienced sailing in moderate winds and changing conditions. This level broadly aligns with the RYA Competent Crew Course, where the aim is to become a capable and confident crew member.

Advanced: You are an experienced sailor and comfortable taking an active role in operating and navigating a yacht. You may sail regularly and might have skippered boats, chartered yachts, or owned your own boat. You are familiar with passage planning, tidal calculations, pilotage, and chart work, and have likely sailed in a wide range of weather conditions. This level broadly aligns with sailors who have completed RYA Day Skipper Theory or Practical Courses, or those progressing toward RYA Yachtmaster level.

Photography Credit: LSC Member Hugo Simpson