ssw 2019 rees leisure team

Southampton Sailing Week

8th-9th July 2021

Exciting racing, great team building! 

The Southampton Sailing week is back for 2021! This annual event, consisting of 5 individual cups, usually takes place during Southampton Boat Show but next year will take place in the middle of spring. Join hundreds for this special annual regatta created to encourage networking, client hospitality and team building for both experienced and novice sailors alike. Everything is covered – you just need to turn up on the day with your team ready for an action-packed day on the water. We handle the rest! To find out more, visit the Sailing Week website

There are 5 cups throughout the week...

The Gallagher Cup - Thursday, 8th July 2021

Southampton? Basingstoke? Portsmouth? Winchester? Which city will the 2021 Hampshire Cup be heading to after a day’s racing to determine the best city in the county! This Cup for 2021 will see fierce rivalry between cities with a history of friendly competition.


Dutton Gregory Property & Legal Cup - Friday, 9th July 2021

Property Cup

Our biggest Cup returns for 2021 with property industry giants and smaller firms taking to Southampton Water.

Legal Cup

In a competitive industry, battle your way to the top of the leader board and showcase your superiority against rival legal firms.

Technology & Women’s Cup - TBC

Technology Cup

Calling all companies in the tech Industry! Come aboard for a day on the water to prove your dominance against other tech companies!

Women’s Cup

Then it's the ladies turn to get out on the water! If your team has adventurous women who want to try something new, why not join us on the water and compete against other female teams!

Race day programme

08:30 – Breakfast at Harbour Hotel’s Bow Room in Ocean Village - Southampton’s new 5-star hotel with stunning views overlooking the marina. Breakfast includes hot drinks, bacon sandwiches and a selection of pastries.

09:00 – Meet your crew and yacht orientation

09:30 – Head out onto the water for training and start of racing

12:30 – Racing lunches onboard

13:00 – Post lunch more racing

15:30 – Head back to Ocean Village

16:00 – Awards ceremony and networking drinks at Southampton Harbour Hotel

Included in your charter fee

  • BRAND NEW Sunsail 41.0 Yacht 
  • Up to 8 guests onboard
  • Professional skipper & mate
  • Breakfast at the Southampton Harbour Hotel
  • Lunch onboard
  • Wet weather gear & life jacket 
  • Awards ceremony and drinks post-racing

View the 2019 highlights video

View the 2021 regatta price list

To book

Yacht charter prices start from just £1979+VAT, with additional branding available.

To book or for more information, please email [email protected] or call us on 02394 350 505.

Choose Sunsail

Stunning Sailing Destinations 
Flotilla routes
Types of yachts
44 yrs
Creating holidays
4 hr
Service commitment
Consumer protection