ssw 2019 rees leisure team

Southampton Sailing Week

Exciting racing, great team building! 

Following on from the success of 2019's regatta, this annual event, consisting of 5 individual cups, takes place during Southampton Boat Show. 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 Hampshire Cup - Monday, 14 Sept 2020

Southampton? Basingstoke? Portsmouth? Winchester? Which city will the 2020 Hampshire Cup be heading to after a day’s racing to determine the best city in the county! This brand new Cup for 2020 will see fierce rivalry between cities with a history of friendly competition.


Technology & Women’s Cup - Tuesday, 15 Sept 2020

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!


Dutton Gregory Property & Legal Cup - Wednesday, 16 Sept 2020

Property Cup

Our biggest Cup returns for 2020 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.

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 
  • Upt to 10 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

Download the 2020 regatta flyer 

SSW 2020 regatta flyer

To book

Yacht charter prices start from just £1979+VAT, with additional branding available. To reserve your place, contact [email protected] or call 02392 222 221.

Choose Sunsail

Stunning Sailing Destinations 
Flotilla routes
Types of yachts
44 yrs
Creating holidays
4 hr
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