Event Overview

Join us for a weekend of exhilarating adventure – 15 & 16 May 2027

The Clipper ‘City Challenge’ was established in 2007 as an industry sailing regatta, where companies from the financial services sector were invited to enter teams into a competitive, sociable weekend of racing on the Solent. In 2026 we open up this opportunity up to subsidiary sectors such as FinTech, Insurance and Wealth Management.

Having lost momentum due to COVID-19, the post-pandemic ‘hybrid’ working environment now places even more importance on getting employees, colleagues and clients together outside of work to enjoy a unique, in-person experience, and the Clipper City Challenge provides the platform to do just that.

The race itself will follow a similar format to previous editions, the two-day event will start with an informal breakfast at Gunwharf Quays, followed by two days of racing around The Solent with a race dinner and auction, and overnight stay in Cowes, Isle of Wight.

Sailing onboard a fleet of identical, 70-foot racing yachts*, each crew member will be under the guidance of a professional Skipper, First Mate, and Second Mate meaning that participants do not require any previous sailing experience to take part.

As an interactive, hands-on sailing experience, this provides a natural platform for team cohesion, encouraging crew members to work together to perform as a competitive racing team.

Earlybird Available until 31/01/2027 – £6,700 + VAT / £7,590 + VAT thereafter. Deposit required to secure team.
Min 6 pax, Max 12 pax

*We reserve the right to change the vessel type if necessary

PRICE

£6,700+VAT Earlybird / £7,590+VAT

PACKAGE HIGHLIGHTS

City Challenge Race Entry

All meals including Sat evening Shoreside Charity Function in Cowes, Isle of Wight

Training plus 4 races

Prize Giving

EVENT HIGHLIGHTS

  • Iconic Clipper racing experience on the Solent
  • Overnight stay in Cowes
  • Competitive but social event, no experience required
  • Teamwork, tactics & pure adrenaline

Itinerary

Please note this itinerary is indicative and correct at the time of posting and liable to change at any moment. If you have any questions surrounding the event and listed itinerary do get in touch with a member of the team.

  • Welcome breakfast at GunWharf Quays, Portsmouth.
  • Meet your crew mates and rival teams.
  • Safety brief on the boat and make way onto the Solent for a morning of training.
  • Lunch on board.
  • Complete race 1 and 2.
  • Arrive in Cowes, Isle of Wight for the evening.

  • Depart Cowes, Isle of Wight after an on board breakfast.
  • Complete race 3. Lunch followed by the final race 4 to end the day.
  • Return to GunWharf Quays, Portsmouth
  • Celebrate dockside with the prizegiving to crown the winners.

*Itinerary may change depending on weather conditions

What’s Included

This event includes the following items. If you would like further clarity on event inclusions please contact us.

  • Race a clipper yacht
  • Two days of competitive sailing on the Solent, including familiarisation and race training
  • Professional Skipper, First Mate and Second Mate on every yacht
  • Entry into the Clipper City Challenge aboard a Clipper 70 race yacht
  • All onboard safety equipment, berthing and Personal Accident Insurance (Musto BR2 wet-weather clothing and Spinlock lifejacket for use while sailing)

Who Can Enter

In order to take part in some sailing race events additional training and qualification events may need to be completed. Please make sure you meet the criteria listed within this section or contact the team for further information.

  • The Clipper City Challenge is open to all participants aged 18+.
  • No previous sailing experience is required.
  • Teams must have a minimum of 6 and maximum of 12 participants.
  • Teams can be made up of colleagues, clients or business partners. 
  • No discounts or rewards can be used in conjunction with this event.