SEOSSports Experience OS

SEOS Field Guide / Sailing / 2026–27

The world’s most distinctive sailing regattas.

Six events. Six different ways in which sport, place and hospitality become one experience.

A regatta is never only what happens between the start and finish lines. It is a temporary world: crews, coastlines, transport, hospitality, families, partners and spectators moving to the same rhythm.

From foiling AC40s in Naples to pre-war classics on the Clyde, these are the sailing events defining the 2026–27 calendar — and the experience-design challenge behind each one.

Explore the calendar

Last reviewed: 4 September 2026

A racing fleet crossing a coastal course under open sky, land visible on the horizon.

The calendar

2026–27, in order.

10 JUL 2027 — 38th America’s Cup Match begins, Naples, Italy (2027)

Understanding the race

Not every regatta is the same race.

Most regattas combine several races across a number of days. Consistency across the series can matter as much as winning a single start, while weather, geography and the type of yacht fundamentally change the competition.

Fleet racing

Many boats start and race on the same course. Positioning, clean air, mark roundings and consistency across the series become decisive.

Match racing

Two boats compete directly against each other. Speed matters, but controlling the opponent and forcing tactical errors can decide the result.

Coastal and offshore racing

The course uses coastlines, islands, tides and changing weather rather than only fixed racing marks. Navigation becomes part of the contest.

Two AC40 foiling yachts racing in the Bay of Naples with the coastline behind them.
01

America’s Cup

The future of sailing, in full view of a city.

Place
Naples, Italy
Dates
24–27 September 2026 · Main Match begins 10 July 2027
Racing
AC40 fleet racing and match final
Status
LIVE

The America’s Cup is sailing at its most compressed: design, software, weather interpretation and crew execution expressed in seconds.

Naples hosts the second preliminary regatta of the 38th cycle in September 2026, with equalised AC40 foilers contesting eight fleet races before the leading two teams meet in a final match race. The main America’s Cup Match begins on 10 July 2027.

The SEOS lens

Naples makes this more than a race course. The waterfront, race village, hospitality, team movements and live media must behave as one connected, city-scale experience.

Official event site ↗
Maxi yachts racing between granite islands near Porto Cervo.
02

Maxi Yacht Rolex Cup

Large yachts. Narrow channels. No room for approximation.

Place
Porto Cervo, Italy
Dates
6–12 September 2026
Racing
Maxi fleet racing — coastal and windward-leeward courses
Status
COMPLETED

Open to yachts and multihulls from 60 feet, the Maxi Yacht Rolex Cup sends some of sailing’s most advanced boats through the granite islands and shifting winds of the La Maddalena archipelago.

Scale is immediately visible, but precision decides the week. Starts, sail changes, coastal routing and crew coordination happen with remarkably little margin.

The SEOS lens

At this scale, owner hospitality, crew operations, tenders, safety, transport and shore programming cannot be designed as separate journeys. They must operate as one system without distracting from the racing.

Official event site ↗
A fleet of Swan sailing yachts racing in the waters near Porto Cervo.
03

Rolex Swan Cup

A fleet becomes a family.

Place
Porto Cervo, Italy
Dates
13–19 September 2026 · Biennial event
Racing
Multiple Swan classes
Status
COMPLETED

Held every two years since 1980, the Rolex Swan Cup brings the international Swan community back to Porto Cervo.

The 2026 edition marks Nautor Swan’s 60th anniversary and is set to assemble a record fleet, ranging from early Sparkman & Stephens designs to contemporary Swan Maxis and one-design racers.

The SEOS lens

Its defining challenge is community design. Owners, crews, families, designers and partners arrive with different priorities, but expect to feel part of the same story.

Official event site ↗
Classic and modern sailing yachts sharing the Gulf of Saint-Tropez.
04

Les Voiles de Saint-Tropez

When eras share the same horizon.

Place
Saint-Tropez, France
Dates
26 September–4 October 2026 · Approximately 250 boats
Racing
Classic yachts, modern racers and maxis
Status
LIVE

Les Voiles brings century-old classics, modern racing yachts and maxis onto the same water.

In 2026, the return of the J Class — Svea, Rainbow and Hanuman — adds three unmistakable silhouettes to a fleet expected to exceed 250 boats. The racing is only half of the identity: the harbour, crews and town create a public ritual that continues long after the boats dock.

The SEOS lens

The transition between competition and culture must feel effortless. Race viewing, harbour circulation, crew needs, partner activity and evening programming form one continuous participant journey.

Official event site ↗
Pre-war classic yachts racing under changing skies on the Firth of Clyde.
05

Richard Mille Cup

Classic yachts, raced rather than displayed.

Place
Firth of Clyde, Scotland
Dates
15–25 June 2026 · Invitation-only fleet
Racing
Classic yacht coastal and offshore racing
Status
COMPLETED

The Richard Mille Cup puts pre-1939 yachts and faithful replicas back into demanding competition rather than presenting them as static pieces of maritime history.

Its 2026 Scottish edition brought twelve yachts to the Firth of Clyde for eight races around islands, tides and rapidly changing weather. The 1935 sloop Sonny won the event overall.

The SEOS lens

Operational detail should disappear behind atmosphere. Heritage, safety, movement between ports and intimate hospitality all need to feel natural rather than staged.

Official event site ↗
Large sailing superyachts racing off Porto Cervo in Mediterranean light.
06

Giorgio Armani Superyacht Regatta

The Mediterranean season begins at scale.

Place
Porto Cervo, Italy
Dates
26–30 May 2026 · 17 yachts competed in 2026
Racing
ORCsy superyacht racing
Status
COMPLETED

The Giorgio Armani Superyacht Regatta opens Porto Cervo’s superyacht racing season with yachts whose scale makes every manoeuvre consequential.

Seventeen superyachts contested the 2026 edition. Moat and Liberty Squared secured the Silver Jubilee Cup in their respective classes, combining racing around the La Maddalena archipelago with an intentionally connected programme ashore.

The SEOS lens

The design problem is balance. Owner privacy, crew performance, sponsor visibility, guest movement and social programming must coexist without making the event feel over-produced.

Official event site ↗

The calendar at a glance

Six events. Six different operating environments.

  • America’s Cup
    Location
    Naples
    Dates
    24–27 September 2026
    Racing
    High-speed foiling
    Experience
    City-scale and technology-led
    Status
    LIVE
  • Maxi Yacht Rolex Cup
    Location
    Porto Cervo
    Dates
    6–12 September 2026
    Racing
    Maxi coastal racing
    Experience
    Precision, ownership and marine logistics
    Status
    COMPLETED
  • Rolex Swan Cup
    Location
    Porto Cervo
    Dates
    13–19 September 2026
    Racing
    Single-builder fleet
    Experience
    Community and brand heritage
    Status
    COMPLETED
  • Les Voiles de Saint-Tropez
    Location
    Saint-Tropez
    Dates
    26 September–4 October 2026
    Racing
    Classic, modern and maxi fleets
    Experience
    Public culture and harbour life
    Status
    LIVE
  • Richard Mille Cup
    Location
    Firth of Clyde
    Dates
    15–25 June 2026
    Racing
    Classic coastal and offshore racing
    Experience
    Heritage and intimate hospitality
    Status
    COMPLETED
  • Giorgio Armani Superyacht Regatta
    Location
    Porto Cervo
    Dates
    26–30 May 2026
    Racing
    ORCsy superyacht racing
    Experience
    Privacy, scale and social programming
    Status
    COMPLETED

Frequently asked

Sailing regattas: the essentials

What is a sailing regatta?

A regatta is an organised series of sailing races, commonly held over several days. Depending on the event, competitors may race as a fleet, directly against one opponent, or across longer coastal and offshore courses.

What is the difference between fleet racing and match racing?

Fleet racing places multiple boats on the course at the same time. Match racing is a direct contest between two boats, making control of the opponent as important as outright speed.

When is the next America’s Cup?

Naples hosts a preliminary regatta from 24 to 27 September 2026. The main Match of the 38th America’s Cup begins in Naples on 10 July 2027.

Which of these regattas take place in Porto Cervo?

The Giorgio Armani Superyacht Regatta, Maxi Yacht Rolex Cup and Rolex Swan Cup all take place in Porto Cervo, using courses around the La Maddalena archipelago.

SEOS / Sailing

A regatta lasts a week. The experience starts months earlier.

SEOS connects the operational detail around the race — arrivals, briefings, hospitality, family journeys, transport, communication and recovery — into one coherent experience.

Design the experienceBack to SEOS

SEOS is not affiliated with or endorsed by the events, yacht clubs or brands included in this guide. Dates, fleets and programmes may change. Consult the official organiser before making travel or attendance arrangements.

Information last reviewed on 4 September 2026.

Sources: official organiser websites for each event — America’s Cup, Maxi Yacht Rolex Cup, Rolex Swan Cup, Les Voiles de Saint-Tropez, Richard Mille Cup, Giorgio Armani Superyacht Regatta.